Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2018. After spending 9 years building the company, Eoghan left Intercom in 2020, but he’s since returned, reshaping Intercom and pioneering its pivot to an AI-first service. This episode highlights his unabashed takes on leaning into your intuition as a founder, and his perspectives on the critical junctures in company building. – In today’s episode, we also discuss: Eoghan's reflections since leaving Intercom The value of intuition and first-principles thinking The changes Eoghan made upon returning to Intercom How Eoghan increased Intercom's productivity by 41% Tactical advice on hiring top talent Why you can't make small improvements in big categories Crafting a culture of ruthless honesty and transparency Why software branding is in crisis – Referenced: 37signals: https://37signals.com Basecamp: https://basecamp.com Brian Halligan (HubSpot): https://www.linkedin.com/in/brianhalligan David Heinemeier Hansson (37signals, Basecamp): https://www.linkedin.com/in/david-heinemeier-hansson-374b18221 Intercom: https://www.intercom.com Jason Fried (37signals, Basecamp): https://www.linkedin.com/in/jason-fried Salesforce: https://www.salesforce.com Marc Benioff (Salesforce): https://www.linkedin.com/in/marcbenioff Zendesk: https://www.zendesk.com – Where to find Eoghan: LinkedIn: https://www.linkedin.com/in/eoghanmccabe/ Twitter/X: https://x.com/eoghan – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps 0:00:00 - Founder intuition vs. standard practice 0:25:00 - Silicon Valley knowledge loops 0:28:13 - Building an executive team 0:36:38 - Eoghan’s return to Intercom 0:42:02 - Transparent and honest leadership 0:46:42 - Changing Intercom’s strategy 0:54:22 - AI and category disruption 1:03:17 - How Intercom thinks about brand 1:10:40 - Eoghan’s inspirations

Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox. – In today’s episode, we discuss: Marketing lessons from OpenAI, Stripe, and Retool The 3 pillars of Stripe’s approach to brand How to manage resource allocation as a marketer Adapting marketing strategy to different business models Advice for early marketing hires – Referenced: Coca-Cola AI-generated wish card campaign: https://theprint.in/ani-press-releases/coca-cola-ignites-diwali-celebrations-with-unique-personalized-ai-generated-wish-cards/1840093/ Cristina Cordova: https://www.linkedin.com/in/cristinajcordova/ Gong: https://www.gong.io/ Greg Brockman: https://www.linkedin.com/in/thegdb/ Kenzo Fong: https://www.linkedin.com/in/kenzofong/ Retool: https://retool.com/ Stripe’s “Capture the Flag” campaign: https://techcrunch.com/2012/08/22/stripes-capture-the-flag-2-0-a-hands-on-contest-for-app-developers-to-test-their-security-know-how/ Stripe Press: https://press.stripe.com/ Stripe Sigma: https://stripe.com/us/sigma Tanya Khakbaz: https://www.linkedin.com/in/tanya-khakbaz-a725732/ – Where to find Krithika Muthukumar: LinkedIn: https://www.linkedin.com/in/krithix/ Twitter/X: https://x.com/krithix – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Timestamps: (00:00) Intro (02:43) Getting involved in Stripe (05:37) Evaluating success in product marketing (06:35) The 3 pillars of Stripe's approach to brand (12:10) Managing resource allocation as Stripe grew (17:22) How Stripe scaled taste (21:30) Were Stripe reviews micromanaging? (24:16) Marketing under founders with strong marketing skills (26:44) Advice for early marketing hires (31:52) Marketing at Retool vs Stripe (33:59) Marketing to mid-market vs SMB vs enterprise (37:02) Marketing programs that had an outsized impact (39:59) Marketing horizontal vs vertical products (43:20) Lessons from OpenAI (52:22) Inside OpenAI’s recent website relaunch (55:57) How OpenAI’s marketers use OpenAI tooling (59:53) When to start hiring marketers (61:34) How to screen early marketing hires (66:39) The biggest influences on Krithika's career (67:52) Outro

May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant. —  In today’s episode, we discuss: Advice for AI founders in 2024 Why it’s difficult to scale AI products for enterprise The secret to finding champions Signs of a healthy co-founder relationship The future of agentic AI —  Referenced: Accenture: https://www.accenture.com ChatGPT: https://chat.openai.com/ Dropbox: https://www.dropbox.com Goldman Sachs: https://www.goldmansachs.com/ Grammarly: https://www.grammarly.com Jill Kramer: https://www.linkedin.com/in/jill-kramer-64230840/ L’Oreal: https://www.loreal.com/ Northwestern Mutual: https://www.northwesternmutual.com/ Palmyra: https://writer.com/blog/palmyra/ Retrieved Augmented Generation: https://blogs.nvidia.com/blog/what-is-retrieval-augmented-generation/ United Healthcare: https://www.uhc.com/ Vanguard: https://global.vanguard.com/ Waseem Alshikh: https://www.linkedin.com/in/waseemalshikh/ Writer: https://writer.com/ —  Where to find May Habib: LinkedIn: https://www.linkedin.com/in/may-habib/ Twitter/X: https://twitter.com/may_habib —  Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:34) Writer’s origin story (06:30) Building a full-stack generative AI platform for enterprise (11:56) The #1 challenge building Writer (15:41) Writer’s approach to finding champion customers (20:29) How Writer is winning the enterprise space (27:11) Signs Writer found product-market-fit (29:26) Scaling LLMs for specific use cases (31:53) Writer’s goals for 2024 (33:57) Advice for 0 to 1 founders (35:53) Creating a culture of “connect, challenge, and own”

Today’s episode is with Jane Davis, the Director of UX Research and UX Writing at Zoom. She previously led UX Research and Content Design at Zapier, and managed the growth research team at Dropbox. Throughout the episode, Jane tackles the thorniest customer development questions and walks us through the end-to-end research process in incredible detail, covering everything from clarifying your goals and asking the right questions, to selecting participants and synthesizing insights.     We start by going through how she applies her playbook in the early-stage startup context — when you’re shipping the first version of your product and don’t yet have the resources to invest in a full research team. We also dig into challenges such as deeply understanding the problem you’re solving, taking on a competitive or a greenfield market, and figuring out willingness to pay. We also get into best practices for prototyping and iterating, as well as some of the common roadblocks startups face later on, including how to build for multiple users and what to do when people aren’t excited about your product or using it frequently. Whether you’re talking to potential customers before you start a company, or are looking to get better feedback from your current users, there’s tons of insights in here for founders, product-builders, and design folks alike. Here’s the book Jane mentioned in the episode: Just Enough Research by Erica Hall. We also recommend checking out Jane’s recent article: What’s the point of a UX research team? You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Alex Buder Shapiro, the Chief People Officer at Flatiron Health, a company that focuses on accelerating cancer research and improving patient care.   Alex first joined Flatiron back in 2016, after an 8-year stint on Google’s People Operations team. Before her promotion to Flatiron’s executive team this past March, Alex previously ran the HR business partner and employee relations team as the startup rapidly scaled.   We kicked things off by talking about resolving conflict at work. Alex talks us through the patterns she’s seen across her career and her advice for troubleshooting, including why she loves borrowing techniques from the world of couples therapy.   We also touch on the challenge of getting employees to stick around long-term at startups. From hiring your own boss to navigating tough career conversations, Alex shares helpful tips, as well as more about her own journey rising through the ranks from IC to exec at Flatiron.   Her experiences mean that she’s also seen the growing pains that come with scaling first hand — things like the challenge of “selling” your new role with an elevator pitch when you first join, or the danger of locking into people processes and frameworks too early.   This episode explores so many different facets of what it means to be both a people leader and a long-tenured employee at a fast-growing startup, meaning there are plenty of lessons for managers and leaders in any function.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Ryan Glasgow, the founder and CEO of UserLeap, a product research platform that helps PMs, user researchers, and growth marketers launch microsurveys to uncover customer insights faster. Before founding UserLeap in 2018, Ryan was a PM and early team member at Weebly (which was acquired by Square) and Vurb (which was acquired by Snapchat).    We start by rewinding the clock back to the 6-month period before Ryan started the company — when he was validating his idea and assessing the crowded market. From how he approached segmentation and early customer conversations, to common product/market fit mistakes, there’s so much advice in here for aspiring entrepreneurs.   We also get into what the first version of the product looked like, how they think about adding new features, and how UserLeap’s 3 product principles are used day-to-day. We also dig into how this self-described “product guy” taught himself founder-led sales, including the specific tactics that made the biggest difference and how he’s refined his approach into a repeatable playbook.   From the question he always asks in customer meetings, to the books that have had the biggest impact on his development, there’s tons of really tactical nuggets in here for founders and product leaders alike.   Here are the books Ryan mentioned in the episode: What Customers Want: Using Outcome-Driven Innovation to Create Breakthrough Products and Services by Anthony Ulwick You Can't Teach a Kid to Ride a Bike at a Seminar by David Sandler User Story Mapping: Discover the Whole Story, Build the Right Product by Jeff Patton   You can follow Ryan on Twitter at @ryanglasgow.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Nick Caldwell, VP of Engineering at Twitter. Previously, Nick was at Microsoft for 15 years, eventually becoming GM of Power BI. Nick has also held roles as Reddit’s VP of Engineering and Looker’s Chief Product and Engineering Officer.   Between Microsoft, Reddit, Looker, and now Twitter, Nick’s worked for companies with vastly different cultures. And in today’s conversations, we comb through the biggest lessons from each of these orgs.    With Microsoft, we unpack what Nick believes is a massively underrated approach to organizational design. He explains the company’s rigorously approach to regular pruning and shaping the org chart. He also gives us an inside look at their management training and talent development, as well as what Nick calls the fairest performance review system he’s seen.   As Nick tells it, there was a steep learning curve when he pivoted from 15 years at Microsoft to Reddit. He doles out advice for other folks getting their bearings after a big career move. He also explains how Reddit’s mission-driven culture informs his approach to leadership at Twitter.    Finally, with Looker, Nick unpacks his biggest lessons from leading both the product and engineering teams, which offered him a unique perspective on how these two orgs that are often at odds can properly team up.   It’s an incredibly wide-reaching conversation, so there’s something for pretty much everyone. Whether you’re interested in the cultural practices that power some of the world’s biggest companies, or you’re a manager looking to level up, or you’re an engineer with goals to take on leadership, Nick’s got plenty of advice and insider stories to share.    You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Sam Taylor, VP of Sales and Success at Loom. Previously, Sam was Dropbox’s first enterprise sales rep, and also served as Quip’s first sales leader. In today’s conversation, we dig into the key learnings from each stop in Sam’s career so far. Starting with his earliest experience at Dropbox, he walks us through his aha moment that sales is an insight driver — which includes his lessons on pricing and packaging, as well as plotting the feature roadmap as Dropbox moved up market. Next, he reflects on his time at Quip, including what sticks with him from working closely with its CEO Bret Taylor and COO Molly Graham. He also digs into his tested tactics for selling in a competitive market where you’re going up against plenty of established players, like Google and Microsoft. We then turn our attention to his current role at Loom, and how he’s threading all of those experiences together. He pays particular attention to his partnership with Loom’s product leaders, and how they’re teaming up to achieve what he jokingly calls “total Loom domination.” If you’re in sales, you won’t want to miss Sam’s insights he’s picked up over the course of multiple startup success stories. And folks that work for other functions at product-led growth companies will come away with a greater understanding and appreciation for how sales fits in. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with McKenna Quint, who was most recently the Head of People at Plaid and also built and led the people team at Cruise Automation. Currently, she’s co-founder and general partner at Quint Capital, a seed-stage fund.   In today’s conversation, we focus on the people challenges that inevitably crop up when you’re going from a couple dozen employees to a couple thousand. We start by discussing when startups should draw from established playbooks in the people space versus when to start from first principles. She also dives into the details of bringing her data mindset to the people space, including designing a sophisticated attrition model.   Next, she tackles some of the questions she most often gets from startup founders, including whether the company should introduce levels, what to look for in your first people leadership hire, and how to approach performance reviews.   Finally, we dive into a larger conversation about the roles that companies play in today’s employee experience. From the company cultures that most inspire her, to the evolution of uncomfortable conversations in the workplace, and what pieces of the Google cultural revolution she’s ready to leave behind.   Today’s conversation is a must-listen for HR leaders of course, but also for folks at startups across the org chart that want an inside look at what’s top of mind for people leaders today — and the systems behind the scenes that powers startups to reach new heights.   Let My People Go Surfing: https://www.amazon.com/Let-People-Surfing-Education-Businessman/dp/0143037838   Management Lessons from the Mayo Clinic: https://www.amazon.com/Management-Lessons-Mayo-Clinic-Organizations/dp/1260011836   Let’s Not Kill Performance Evaluations Yet: https://hbr.org/2016/11/lets-not-kill-performance-evaluations-yet   You can follow McKenna on Twitter at @mckmoreau   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Waseem Daher, co-founder and CEO of Pilot, a company that specializes in bookkeeping, tax prep, and CFO services for high-growth startups. In addition to Pilot, Waseem co-founded two other startups with the same group of co-founders, including Ksplice, which was acquired by Oracle in 2011, and Zulip, which was acquired by Dropbox in 2014.    In today’s conversation, we pay particular attention to the earliest days of Pilot. Waseem takes us behind the scenes of the ideation stage for what would eventually become Pilot, and how the founding team gained conviction to actually start building. He also explains why Pilot landed on its human plus machine model, with a software component in addition to employing full-time accountants and tax preparers to partner with customers.     Next, we talk about building out Pilot’s ICP, and how he started getting the product into the hands of paying customers. He’s got some great tips for framing conversations with potential customers to make sure you’re building a must-have product that solves hair-on-fire problems, not a nice-to-have. Finally, he looks out to the horizon and shares how he prioritizes which offerings to add to Pilot’s product suite.    Today’s conversation is an absolute must-listen for founders and folks that have goals to one day become founders. Product pros also won’t want to miss learning from Waseem’s playbook honed over the course of building three companies.    You can follow Waseem on Twitter at @waseem. For more startup real talk from Waseem, you can subscribe to his Substack: https://waseem.substack.com/    You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Today’s episode is with Shannon Brayton, a Silicon Valley veteran with more than two decades of experience shaping corporate narratives and leading teams at companies like LinkedIn, OpenTable, eBay, Yahoo!, and Intuit. She recently joined Bessemer as the venture capital firm’s first-ever CMO.   In today’s conversation, Shannon shares the comms and leadership lessons she’s picked up along the way. In addition to sharing her broader philosophy around the role of comms and her thoughts on why it’s one of the more underappreciated functions, Shannon gets into the tactical weeds on everything from killing stories and creating new categories, to her frameworks for building relationships with reporters. There’s plenty of career advice as well, from how she approaches selecting companies to work for, to what the transition from head of comms to CMO was like, to what she’s learned from mentors and bosses like Jeff Weiner.   Here’s the reverse mentoring post Shannon mentioned on how she approached taking on the CMO role: https://www.linkedin.com/pulse/how-i-tackled-first-100-days-my-new-role-reverse-brayton/    You can follow Shannon on Twitter at @sstubo.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson

Today’s episode is with Colleen McCreary, the Chief People Officer at Credit Karma.    With more than 20 years of experience in HR, operations, recruiting and M&A, Colleen has headed up the people function at companies such as Vevo, The Climate Corporation, and Zynga. She’s also seen the early-stages and scaled through multiple IPOs and acquisitions, which means she has a great perspective on the people problems founders tend to run into as their businesses grow.   We kick this conversation off with Colleen’s explanation of why she designs for the 80% and focuses on clarity, context, and consistency when building people organizations and crafting culture. She walks us through some really tactical examples of that work, including how her team approaches compensation at Credit Karma and the reason they do promotions quarterly.   Colleen also shares why she views the Chief People Officer not as the CEO of culture, but rather the product manager of the systems and tools that run the company. She gives a detailed look at how she approaches many of those systems, from how rewards and recognition were incredibly different at Zynga and Credit Karma, to why career growth isn’t just about a promotion. Colleen also shares her take on whether we should double down on strengths or focus on correcting weaknesses when it comes to performance.   Given her experience as a 4X Chief People Officer, today’s episode is a must-listen for first-time founders and early people leaders looking for a roadmap as their startups scale.   You can follow Colleen on Twitter at @Chiefpplofficer, and you can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Irving Fain, founder and CEO of Bowery Farming. Bowery is a modern farming company that grows produce indoors, free from pollutants and using significantly less water and space. Just this week, the company announced a $300 million Series C round, the largest private fundraise to date for an indoor farming company.   Bowery’s mission to democratize access to fresh, locally grown food. It’s no doubt an extremely complex problem, so it might surprise you that its founder, Irving, didn’t have any background in agriculture before starting Bowery. He was previously the CEO and founder of CrowdTwist, a loyalty and analytics solution that was eventually acquired by Oracle, and helped build iHeartRadio.    But looking back on the early days of Bowery, Irving believes his naivety was in fact an asset. Coming in with no preconceived notions about how to solve the problem, he committed to approaching agriculture with a wide aperture and going unreasonably deep. In today’s conversation, he walks us through his multi-pronged approach to developing the idea for what would become Bowery, which includes paying just as much attention to the doubters as to the folks who believed in the vision.      Next we switch gears and talk about assembling Bowery’s small-but-mighty team of five, which Irving kept deliberately small and sought out folks that didn’t have vast agriculture experience and could approach problems from first principles. Whether you’re a founder yourself or have long-term career goals to make the leap, today’s episode is packed with equal parts inspiration and tactical takeaways.    You can follow Irving on Twitter at @ifain   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Bowery Farming and its most recent fundraise, https://techcrunch.com/2021/05/25/indoor-farming-company-bowery-raises-300m/amp/

Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy. — In today’s episode, we discuss: How AI is reshaping the software landscape Bridging the gap between ideas and software Why YC almost rejected Replit four times Replit’s fundraising difficulties, and how Paul Graham helped The secret lever Replit pulled to scale ahead of its competition Replit’s impressive distribution engine — Referenced: 7 Powers: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319/ Codecademy: https://www.codecademy.com/ Hacker News: https://news.ycombinator.com/ I Am a Strange Loop: https://www.amazon.com/Am-Strange-Loop-Douglas-Hofstadter/dp/0465030793 Mythical Man-Month: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959 On the Naturalness of Software: https://people.inf.ethz.ch/suz/publications/natural.pdf OpenAI: https://openai.com/ Paul Graham: https://twitter.com/paulg Python: https://www.python.org/ Read Write Own: https://www.amazon.com/Read-Write-Own-Building-Internet/dp/0593731387/ Replit: https://replit.com/ Roy Bahat: https://www.linkedin.com/in/roybahat/ Sam Altman: https://twitter.com/sama The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780/ The Little Schemer: https://www.amazon.com/Little-Schemer-Daniel-P-Friedman/dp/0262560992/ Y Combinator: https://www.ycombinator.com/ — Where to find Amjad Masad: LinkedIn: https://www.linkedin.com/in/amjadmasad Twitter/X: https://twitter.com/amasad — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:31) Replit’s origin story (08:24) Starting Facebook’s JavaScript infrastructure team (10:36) Amjad’s unique path to entrepreneurship (16:04) How Replit got its early users (17:00) Replit’s fundraising difficulties (17:54) Why YC almost rejected Replit four times (20:23) Building Replit’s distribution engine (22:08) Drivers of Replit’s growth (27:41) What Silicon Valley gets wrong (30:09) Replit’s monetization strategy (32:29) Integrating AI into the platform (36:18) The impact of AI on software engineering (39:40) Defining the new “software creator” role (41:43) How to keep up with developments in AI (46:24) Replit’s goals for 2024 (48:11) Advice for founders: defy conventional wisdom (51:12) Amjad’s 4 favorite books

Today’s episode is with Kelly Watkins, CEO of Abstract, a platform for structure and transparency in the design process. In joining Abstract last year, Kelly is one of very few folks from a marketing background to take on the CEO seat. She brings a wealth of experience leading incredibly high-performing marketing teams for Slack, Github, and Bugsnag.   In today’s conversation, we start by reflecting on her first year as CEO. She shares her alternative to yearly planning, borrowing from famed military strategist John Boyd. Kelly also walks us through Abstract’s most recent product launch, and how it clearly crystallized her leadership point of view to constantly optimize for trade-offs, rather than clear-cut right and wrong.    Next we switch gears to talk about some of the lessons from her storied marketing career. She unpacks her jobs-to-be-done approach for crafting a product story when there’s loads of competition. She also takes us behind the scenes in developing Slack’s “where work happens” tagline, and crossing the chasm from a passionate early adopter customer base to the ubiquitous product it is today.    Today’s conversation is a must-listen for marketing folks, who will surely appreciate the peek behind the curtain. But all sorts of leaders with goals to more effectively collaborate with the org will come away with a deeper understanding of marketing’s art and science.    You can follow Kelly on Twitter at @_kcwatkins   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Kelly’s advice on hiring your first head of marketing, read her Medium article: https://medium.com/hackernoon/how-to-hire-your-first-head-of-marketing-67c43dd2cd73 For more on the jobs-to-be-done framework, check out this article on the Review: https://review.firstround.com/build-products-that-solve-real-problems-with-this-lightweight-jtbd-framework

Today’s episode is with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital.  Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto. In today’s conversation, one theme stands out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, Rick brings this mindset to every aspect of running Persona.  From hiring lessons to go-to-market strategies, Rick offers up some counterintuitive thinking, including why his engineers sell and cold-email prospects, and why he doesn’t try to convince candidates that Persona is a company that will change the world. Today’s episode holds tons of insights for anyone who’s a founder or thinking about starting a company one day, but there’s also plenty in here for engineering leaders and hiring managers. You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.com/  You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Eric Berg, CEO of Fauna, which is an adaptive operational database platform. In joining Fauna as its CEO in the summer of 2020, he brought a wealth of experience as a product leader. Most recently, he was the Chief Product Officer at Okta, scaling the company from 10 employees and zero customers to its eventual IPO in 2017. He started his career in product at Intel, working under the legendary Andy Grove, as well as a five-year stint as a product leader at Microsoft.   In today’s conversation, he opens up his executive playbook as he weaves together each of those experiences — and covers a lot of ground along the way. He starts by talking about early go-to-market lessons and the keys to honing in on an ICP to get Okta off the ground. He also dives into the often-maligned “messy middle,” particularly when it comes to moving upmarket and developing a pricing and packaging model that, when done well, takes a company to new heights.         We then switch gears and discuss more broadly about team building and company building — particularly the cultural lessons that stick with him from his tenure at each stop in his career. His biggest learnings include hiring folks up and down the org chart with the right ego to talent ratio and the tactical steps he takes to implement a “disagree and commit’ value so it’s not just a long-forgotten team motto. Finally, we touch on the biggest surprises as he approaches one year of sitting in the CEO seat.    Today’s conversation is a must-listen particularly for product folks, as well as others who want to more deeply understand the trade-offs that nearly every great company faces on the path to scale.    You can follow Eric on Twitter at @ericberg.   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s conversation is with Elliot Shmukler, founder and CEO of Anomalo, which is a platform that validates and documents all of your data. Elliot founded Anomalo after a storied career as a product and growth leader at some of the most interesting companies around. Most recently, he was Instacart’s Chief Growth Officer, driving fast and profitable growth and geographic expansion. His jam-packed resume also includes stops at Wealthfront as the VP of Product and Growth and as a product leader at LinkedIn and eBay.    In today’s conversation, we pull on threads from his newest role as a founder of a startup going from zero to one, including his biggest surprises in the transition from executive to CEO. We also touch on how he prioritizes his time at a startup still in the earliest stages of company-building, and how to avoid wasting your time on prospects that are not all that interested in actually buying.    Next, we turn our attention to his history of picking incredible companies to work for — from the questions he asks as a candidate to the decision-making frameworks he borrows from his poker playing. Finally, we end with his biggest lessons from the best CEOs he’s worked with, including habits that set the best communicators apart from the pack, and the tactics for keeping office politics at bay so the best ideas are able to surface.    All sorts of folks will find something worthwhile in today’s conversation — whether you’re a founder still in the early phases of customer discovery, an executive with long-term goals to start your own company, or someone earlier in their career that wants to get better at spotting the next unicorn.    You can follow Elliot on Twitter at @eshmu.   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson   To learn more about how Elliot uses A/B testing as a management framework, check out this article on First Round Review: https://review.firstround.com/how-a-b-testing-at-linkedin-wealthfront-and-ebay-made-me-a-better-manager   And check out “The Goal,” which Elliot cited as the most influential management book he’s ever read: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951

Today’s episode is with Kate Taylor, who recently joined Notion as their Head of Customer Experience. Previously, Kate spent 8 years at Dropbox, leading their SMB revenue and scaled sales operation before leaving in 2020. Prior to that, she started her career as a sales rep at Salesforce.   In today’s conversation, Kate shares a wealth of advice for building out product-led growth and self-serve motions. She shares tons of nuances around going up market, competing with sales and product planning, offering up tactical advice that any founder, product or go-to-market leader can learn from.   Kate also gives us a detailed look at how they approach product prioritization at Notion, including their system of 700 tags and examples of tradeoffs they’ve had to navigate. We also get into pricing and packaging, from specific experiments at Dropbox to why interestingly Notion’s trial isn’t time based.    We also chat about how to handle a wide range of use cases, as well as the “front door” customer experience her team is trying to build. From why customer service shouldn’t be focused on getting customers off the phone faster, to the questions she asks to find more signal in their product feedback, Kate shares some counterintuitive thoughts here.   Finally, we wrap up by talking about her approach to leading teams, including why she hires for curiosity, how she tries to teach her team to ride the ups and downs of startup life, and how working for three very different CEOs — Marc Benioff, Drew Houston and Ivan Zhao — has impacted her own leadership style.   Kate isn’t on Twitter, but you can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Today’s episode is with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School. Previously, Mark served as the Chief People Officer at both InVision and Return Path. He also ran his own leadership development consultancy and taught on HR topics as an adjunct professor.   Mark has an invaluable perspective and tons of advice to share after setting up several people orgs in a range of different companies. In this conversation, Mark shares his approach to the CPO role and his philosophy around the function more generally, including why he thinks at its core, it’s a data and analytical function and how to match the employee experience to your company’s competitive positioning.   He also gets incredibly tactical on a wide range of topics, from how to hire with empathy and advice for approaching skip-levels, to gathering employee feedback and driving career conversations.   Today’s conversation is a must-listen for both founders and early-stage people leaders trying to thoughtfully scale this function, as well as for current and aspiring managers hoping to hone their leadership and development chops.   You can follow Mark on Twitter at @freintime, and you can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Marco Zappacosta, co-founder and CEO of Thumbtack. He’s spent the last 13 years building the company into a billion-dollar business  — and it’s his first and only job after graduating college.   In today’s conversation, Marco dives into the company milestones that require a return to first principles versus pulling from a tested playbook, and the mental models he leans on when parsing through the mountains of advice he gets as a first-time founder and CEO. He connects these dots to how he manages Thumbtack’s board so those quarterly meetings are a critical resource, not just a time suck — and why he shares the board deck with the entire company.   He also candidly reflects on Thumbtack’s COVID-related layoff last year, and what he specifically did as CEO to make sure the folks that remained still had confidence in the company and his leadership moving forward.    Finally, he opens up his playbook for choosing what to spend his time on as a busy CEO with only so many hours in the day — and perhaps more importantly, how he stays accountable for these priorities.   Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats.    To learn more about how Marco and Thumbtack approach executive hiring, check out the article on First Round Review: https://review.firstround.com/assembling-an-executive-leadership-team-is-daunting-let-thumbtacks-ceo-help   You can follow Marco on Twitter at @mlz.   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Today’s episode is with Tido Carriero, the Chief Product Officer at Segment, a customer data platform which was recently acquired by Twilio. Before that, he built out the engineering teams that worked on the core product and the initial business product at Dropbox. Tido started out his career in 2008 as an early member of the Facebook ads engineering team, and went on to become an eng manager on the Pages team, a transition from IC to leadership that he talks about in this episode.    In today’s conversation, we dig into his career lessons from building engineering orgs and launching new product lines at several different top tech companies. From the pros and cons of single threaded leadership to his black box analogy for assessing a team’s performance, there are tons of tactics in here on how leaders can think differently about org design, planning and execution. He also shares several gems of advice for new engineering managers and new managers-of-managers.   We also chat about the path to product/market fit, especially for multi-product strategies. Tido shares his advice for going from zero to one in a new product, including the simple milestone his teams have to hit before he’ll greenlight a new project, why he prefers iterative approaches over “big bang launches,” and his thoughts on why Dropbox struggled here. (Tido shares more of his thoughts on finding product/market fit in the context of multi-product strategies here in this blog post: https://segment.com/blog/finding-product-market-fit-again/)   Tido isn’t on Twitter, but you can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Russ Laraway. After starting out in the Marine Corps, Russ made his way into the world of startups, joining Google in 2005 where he led teams for 7 years and was recognized as one of the company’s best managers. Russ then went to Twitter, where he founded and ran the SMB advertising business. Afterwards, he teamed up with Kim Scott to co-found Candor, Inc to help people implement the concepts from Radical Candor and have better relationships at work.    In 2018, he joined Qualtrics as the Chief People Officer, a position he stepped away from this past January to focus on helping the company’s customers think differently about employee experience. Russ also has a book on this topic coming out soon — and we can’t wait to read it.   In today’s conversation, we dig into how startups can drive employee engagement and develop high-quality managers. Russ reaches across his career to serve up some incredible wisdom, whether you’re a first-time manager or a seasoned leader.   He starts by sharing his direction-coaching-career framework, along with his thoughts on where companies go wrong on OKRs. He also gets really tactical, sharing the typical phrases he relies on when delivering feedback, his go-to questions for soliciting what folks on his team really think, and underrated questions to include in employment engagement surveys. Finally, Russ gives us 13 recommendations for leadership reads for managers.   For more of his thinking on talent development, we recommend reading his article from a few years ago in the First Round Review: https://review.firstround.com/three-powerful-conversations-managers-must-have-to-develop-their-people    You can follow Russ on Twitter at @ral1 and you can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Jeff Lawson, co-founder and CEO of Twilio. He’s spent the last 13 years building and running the company, including leading through a successful IPO in 2016.    In today’s conversation, Jeff looks back on some of the peaks and valleys in Twilio’s journey, and his own evolution as the CEO. He dives into some of the initial wins, like going against conventional wisdom to launch a second product in the early days of Twilio. He’s equally game to unpack some of the mistakes along Twilio’s path — like when one of their biggest customers, Uber, significantly scaled back their investment in Twilio’s products.    Jeff also opens up the pages from the playbook he pulled from his time at Amazon, chiefly Twilio’s “write it down” company value, and makes his case for why PowerPoint is a terrible decision-making tool. He takes us inside Twilio’s C-suite, including why they do post-mortems when things go right — not just when they go wrong. He also sketches out his “aha” moment that his executive team needed to argue more.    Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats.    Jeff’s new book is titled “Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century.” https://www.amazon.com/Ask-Your-Developer-Software-Developers/dp/0063018292   To learn more about how Twilio approaches company values, check out this article on First Round Review: https://review.firstround.com/draw-the-owl-and-other-company-values-you-didnt-know-you-should-have   You can follow Jeff on Twitter at @jeffiel.   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor. — In today’s episode, we discuss: Key product strategies used by Square and Gusto The pros and cons of building for SMBs How to build horizontal after creating a wedge The catch with building vertical SaaS How product teams can move faster Developing product sense and intuition — Referenced: Alyssa Henry: https://www.linkedin.com/in/alyssa-henry-0905692/ Copilot: https://copilot.microsoft.com/ Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/ Gusto: https://gusto.com/ High Output Management: https://amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 Marty Cagan: https://www.linkedin.com/in/cagan/ Opendoor: https://www.opendoor.com/ Silicon Valley Product Group: https://www.svpg.com/ Square: https://squareup.com/ The Three Horizons Model: https://www.mckinsey.com/enduring-ideas-the-three-horizons-of-growth Toast: https://pos.toasttab.com/ — Where to find Michael Cieri: LinkedIn: https://www.linkedin.com/in/michaelcieri/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:41) Why SMBs require unique software solutions (05:58) The level of specificity required when building for SMBs (08:47) Finding Square’s form-fitting solution (11:48) Building vertical versus horizontal SaaS (14:34) Inside Square and Gusto’s decision making framework (16:15) How to build horizontally from a wedge product (23:00) Using the Three Horizons Model (25:29) How to craft a compelling vision for products (28:51) How to assess Horizon 3 bets (32:08) How to give employees the freedom to try things (34:24) Creating a risk-taking culture (37:27) Essential advice for new PMs (40:27) Common thread with bad product pitches (42:29) Applying the Horizon framework at Gusto (44:46) Developing good product sense (47:43) 5 signs of great product sense (49:03) Why product sense is like athletic ability (51:43) How to ship faster without increasing headcount (56:10) People who had an outsized impact on Michael

Today’s episode is with Leah Sutton, SVP of Global HR at Elastic. Leah’s been in the HR space for over 20 years, and now leads everything from HR operations to recruiting and employee engagement for Elastic’s fully-distributed employee base, which includes over 2,000 spread across 40 countries and 48 states.  In today’s conversation, we look closely under the hood of what Leah calls Elastic’s “distributed by design” company DNA. She walks us through her learnings tackling challenges companies now are paying close attention to — including how to interview for leaders that can manage well remotely — and even dives into the nitty-gritty details about payroll and compensation across regions. She also outlines a few of the tactics Elastic has leaned on to smooth over some of the language and cultural barriers that often trip up global leadership teams. Leah zooms out even further to discuss Elastic’s source code, which she describes as not so much a traditional list of values but more the things that make Elastic, Elastic. Finally, she sketches out her pitch for why companies should talk about operational debt as much as they do technical debt. Today’s conversation is a must-listen for HR leaders and founders — and for folks on the hunt for a more systematic approach to the new challenges of distributed work.   Learn more about Elastic’s source code here: https://www.elastic.co/about/our-source-code   You can follow Leah on Twitter at @leahesutton   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Kevin Fishner, Chief of Staff at HashiCorp. As the first business hire at the cloud infrastructure automation company, he previously built out the sales, marketing and product management teams. Now as chief of staff, he’s focused on building a strong foundation of company-wide systems, now that the team has grown to over 1000 people. In today’s conversation, Kevin shares a detailed look at how they run meetings, set and track progress toward goals, and make decisions through writing at HashiCorp.  He also shares incredibly tactical advice for making annual planning more effective, including the unique business simulation they run, their scorecard system, and the weekly and quarterly meetings that help them stay focused on important KPIs. While today’s episode is clearly a must-listen for fellow chiefs of staff and founders spinning up a company from scratch, managers and leaders of all kinds will walk away with several takeaways on how to make their teams more effective. Because so much of what he shared is so detailed, we’ll be sharing some templates and visuals to go along with Kevin’s interview over on the First Round Review, so be sure to check that out.  You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with David Lieb, the Director of Google Photos. Previously, he was the founder/CEO of Bump, an app that allowed users to swap contact information by physically bumping phones. Bump was acquired by Google in 2013, and formed the basis for the design of Google Photos, which launched in 2015 and passed the 1 billion users mark in 2019. In today’s conversation, David takes us through that journey of building a consumer product from scratch and scaling it to over a billion users in just four years. He shares the mistakes they made while building Bump, what he learned from navigating big company politics at Google, and how they pinpointed the problem in the photo-sharing space. From the precise questions they asked in user interviews, to how they stack ranked for the canonical users, there’s tons of wisdom in here for early product builders. There’s also lessons from operating at Google’s scale as well, including how his approach to planning and org design have evolved. Learn more about the Spotify “squads’ model that David mentioned in the org design section here: https://medium.com/pm101/spotify-squad-framework-part-i-8f74bcfcd761    You can follow David on Twitter at @dflieb, and you can learn more about his approach to building products on First Round Review: https://firstround.com/review/cognitive-overhead-is-your-products-overlord-topple-it-with-these-tips/    You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Bill Carr and Colin Bryar, two long-time Amazon executives who just published a new book, “Working Backwards,” which provides an inside look at how the leadership principles and business processes that have made the company so successful. Bill started at Amazon in 1999, and went on to launch and run the Prime Video, Amazon Studios, and Amazon Music businesses before he left the company in 2014. Colin joined Amazon in 1998, as the Director for Amazon Associates and Amazon Web Services Programs. He also spent two years as Jeff Bezos’ technical advisor or “shadow,” and later served as the COO for IMDb.com.  In today’s conversation, Bill and Colin take us through Amazon’s culture of innovation and the origin stories of the Kindle, AWS, and Prime businesses. From granular details about the “working backwards” process, to an inside look at how players like Jeff Bezos and incoming CEO Andy Jassy operated up close, they share invaluable insights on diving deep and operational excellence. Whether it’s their lessons on why innovation can’t be a part-time job, or the perils of taking a “skills-forward” approach to exploring new opportunities, or why mechanisms are more important than good intentions, there’s lots of food for thought in here for founders and startup leaders. Learn more about “Working Backwards” here You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  

Today’s episode is with Anne Raimondi, Chief Customer Officer at Guru, and independent board member at Asana, Gusto and Patreon. Previously, she was part of the founding team at Blue Nile, spent five years in product marketing at eBay, and led marketing as an early employee at SurveyMonkey, before pivoting to operations as an SVP at Zendesk.  In today’s conversation, Anne pulls on threads from across her impressive career as a founder, operator, executive and board member to deliver spot-on advice for folks with an eye for the C-suite. From what enables the best executives to scale up, to how she’s approached her own 30, 60, 90-day plans as a brand-new hire — she doles out plenty of prescriptions for getting this critical transition right and avoiding common traps. She also opens up her playbook for approaching executive recruiting, interviewing and hiring, and when to mine executive talent internally rather than defaulting to external hires. Finally, she opens up about her board work, sharing the essential ingredients for productive, impactful boards across every growth stage.  Today’s conversation is a must-listen for executives, founders and board members looking to level up their leadership frameworks — and for folks who someday hope to step into these same shoes. You can follow Anne on Twitter at @anneraimondi and you can learn more about her approach to diagnosing and repairing team trust on First Round Review: https://firstround.com/review/use-this-equation-to-determine-diagnose-and-repair-trust/ You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Jean-Denis Grèze, Head of Engineering at Plaid, which securely connects your bank to your apps. Before joining Plaid, Jean-Denis served as Director of Engineering at Dropbox, and even had a stint in law school and one year as a lawyer under his belt before diving deep into the world of CS.  While he says becoming a lawyer was a “four-year detour he probably didn’t need,” there’s a lot to be said for how it’s shaped his engineering career and management philosophy. As he puts it, he strongly favors pragmatism over perfection, and it’s something he hammers home within his engineering teams. In today’s conversation, Jean-Denis pulls on threads from across his career to weave together a modern playbook for engineering leadership — and the hard-won lessons that stick with him. He also shares his insights on why his engineering org doesn’t have titles, the one question he asks every engineering manager candidate, and how his team prioritizes technical debt and keeping the lights on versus sexy, brand-new projects. Today’s conversation is a must-listen for technical leaders or those who are eyeing the engineering leadership track. From motivating a team to tracking the right KPIs, Jean-Denis has got tons of great tactics and stories from his time at Plaid and Dropbox for you to learn from. You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. Before founding Upstart, Dave was President of Google Enterprise, and spent 8 years building Google's billion dollar cloud apps business. Here at First Round, we first came to know Dave when we invested in Upstart’s seed round back in 2012, and we’ve found him to be one of the most tenacious and focused founders we’ve ever backed. In today’s conversation, Dave gives us an inside look at how the business was built and what other startups can learn from its early days. In addition to unpacking the initial idea and subsequent business model pivot, Dave gets into what it felt like flying under the radar of Silicon Valley, why he “sucked at fundraising,” and how he and his co-founders have stuck together for almost a decade.  From his “Are you Airbnb or Paypal?” test and why you should look at your career in landscape mode, to the three mental models he leans on to manage his psychology as a founder, Dave shares helpful frameworks that any startup leader can learn from. We also dive into his “management by exception” philosophy, what he learned from Google, how he runs his leadership team, and why he leans on references, not interviews, when hiring execs.   You can follow Dave on Twitter at @davegirouard and you can read his First Round Review articles that we mentioned in the episode here:  https://firstround.com/review/speed-as-a-habit/  https://firstround.com/review/how-does-your-leadership-team-rate/  https://firstround.com/review/a-founders-guide-to-writing-well/    You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Jay Simons, who’s currently a partner at Bond and serves on the boards of Hubspot and Zapier. But before that, he had a long run as the President of Atlassian, which develops software collaboration tools like Jira, Confluence and Trello. In today’s conversation, Jay dives into Atlassian’s growth story, from what’s misunderstood or not talked about enough, to the strategic choices that went against the grain. He shares an inside look at how Atlassian built a product that can sell itself and deferred short-term openings for more durable long-term opportunity. In addition to unpacking what he calls their “three-legged stool” of self-service, a global network of channel partners, and eventual enterprise upselling, Jay gives us a deep dive into their pricing strategy and how they thought about exploring adjacent product areas. From spinning the flywheels of a remarkable product and a high-velocity self-service funnel, to building a culture that focuses on first principles, there’s tons of great advice in here — not only for go-to-market and revenue leaders, but for anyone who works at a startup. This blog post from Intercom has the flywheel graphic that Jay mentioned in the episode. https://www.intercom.com/blog/podcasts/scale-how-atlassian-built-a-20-billion-dollar-company-with-no-sales-team/  You can follow Jay on Twitter at @jaysimons. You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Cristina Cordova, Notion’s Head of Platform & Partnerships. Previously, she was the 28th employee and the first partnerships hire at Stripe, where she cultivated partnerships with companies like Shopify, Squarespace and Apple, built out the BD org, and led their new Corporate Card effort.  After a decade in partnerships, Cristina has bagged big deals, honed her negotiation skills, built out teams — and made plenty of mistakes she hopes others can learn from. In today’s conversation, Cristina pulls from across her career to share the inside scoop on deals that had an unexpected outsized impact — as well as the ones that went sideways.  She also shares her playbook for being a startup’s first partnership hire, including the three critical areas to focus on first, and the common traps to avoid. It’s also full of actionable tactics on everything from dealing with partners trying to push you around, to how to hire for partnerships roles and structure the org chart. Today’s conversation is a must-listen of course for folks currently in or hoping to break into partnerships, platform or BD roles, but Cristina also shares great tactics for getting better at negotiating, as well as some fascinating stories of how Stripe and Notion scaled — meaning there’s tons to learn here for everyone. You can follow Cristina on Twitter at @cjc. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels. In today’s conversation, David unpacks those lessons and tells us why he’s so focused on storytelling these days as the co-founder and CEO of Drift, a conversational marketing and sales platform. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift. He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication. It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills.   You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom”  For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg.  To learn more about how Drift approaches storytelling, check out this article David wrote for Inc: https://www.inc.com/david-cancel/five-storytelling-tips-to-better-communicate-your-brand-message.html  To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: https://fs.blog/2013/10/inversion/ You can email us questions directly at review@firstround.com or follow us on Twitter @firstround (twitter.com/firstround) and @brettberson (twitter.com/brettberson) 

Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages. — In this episode, we discuss: Common customer success mistakes Creating a world-class customer success org Tactics for hiring exceptional talent How to structure compensation packages Where customer success fits into the wider org Key early-stage customer success metrics and rituals Successful strategies from Box, Medallia, and LinkedIn — Referenced: Aaron Levie: https://www.linkedin.com/in/boxaaron/ Box: https://www.box.com/ David Love: https://www.linkedin.com/in/david-s-love/ Gainsight: https://www.gainsight.com/ Jon Herstein: https://www.linkedin.com/in/jonherstein/ Jonathan Lister: https://www.linkedin.com/in/jonathanlister/ Ken Fine: https://www.linkedin.com/in/kmfine/ Medallia: https://www.medallia.com/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Opower: https://www.oracle.com/utilities/opower-energy-efficiency/ — Where to find Stephanie Berner: LinkedIn: https://www.linkedin.com/in/stephanieberner/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:21) Formalizing customer success at a startup (05:01) Hiring ICs before CSMs (06:22) Tactics for hiring standout talent (11:39) 3 questions to ask candidates (15:38) Fail-case patterns among customer success hires (17:49) Considering candidates with non-traditional backgrounds (21:21) Indexing toward a bias for action (24:17) What v1 of customer success looks like (26:03) Key early-stage customer success metrics (28:21) Whether customer success or sales should own renewals (30:40) Where customer success fits into the org (32:14) Why customer success doesn’t report to an executive (33:48) Distinguishing a product problem from a customer success one (35:18) Simple way to deal with customer churn (39:21) Tactics to get customers to give honest feedback (40:58) What happens when customer success and product teams collaborate (44:14) Rituals for zero-to-one customer success (48:23) How to structure an early customer success team (52:01) Structuring compensation packages (54:35) Aligning customer success with the business model (60:14) The role of customer success in B2B software (62:17) Common customer success mistakes (67:44) People who had an outsized impact on Stephanie

Our third episode is with Steve El-Hage, co-founder and CEO of Drop, an electronics company that creates products powered by feedback by a massive community of enthusiasts and experts. Reflecting on his 8-year, heads-down grind since becoming a first-time founder at 22, Steve shares the lessons that he figured out the hard way, from revenue dropping off a cliff and painful pivots, to hiring blunders and severe burnout.

Our second episode is with Ayo Omojola, VP of Product at Carbon Health. Previously, he was the founding product manager on the banking team for Cash App at Square, where he co-created the Cash Card and helped build out Square’s technical banking infrastructure. He’s also a former founder of a Y Combinator-backed startup and an active angel investor, which gives him a unique lens into finding and evaluating startup ideas. Tapping into Ayo’s experience working in the heavily regulated spaces of healthcare and financial services, we dive into how he untangles regulations to find “the opportunities where it’s easy to stop” and goes “unreasonably deep” when building early products. Ayo thinks a lot about problem selection and makes the case for putting more effort into choosing what to work on. It’s a must-listen for anyone who’s thinking about starting a company someday, or a product leader who hopes to help a new product take shape. But even if those aren’t goals of yours, there’s still tons to learn. Ayo shares the individuals he learned the most from during his time at Square and the frameworks he picked up from them, such as on how to get better at process, setting context, and “optimizing for the outstanding.” Last but not least, we get into his management and hiring philosophy, including why he loves to hire former founders. You can follow Ayo on Twitter at @ay_o. For reference, the leaders he gave a shout out to in the episode include Robert Andersen (the founding designer at Square), Dhanji Prasanna (who led engineering for Cash App), Jim Esposito (Operations Lead for Cash App) and Emily Chiu (who led strategic development efforts for Cash App). You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Our first episode is with Molly Graham, a seasoned exec and builder who particularly excels at helping startups to go not from 0 to 1, but from 1 to 2. We’ve interviewed her four times on First Round Review — which might be a record — because the advice she has to share and the experiences she can draw from are unbelievably helpful to founders and startup leaders. She helped build and scale Facebook, Quip, The Chan Zuckerberg Initiative in their early days, and is now the COO of Lambda School. While on The Review she’s shared advice on everything from managing your emotions and struggling with scaling, to codifying your culture and setting up your first comp system, today’s conversation is focused on a different topic — management.  This is a topic Molly has strong opinions on—she’s seen time and time again across her career how so many startup mistakes come down to general management issues. We cover everything from the traps that are easy to fall into, to why you should be spending more time with your highest—not your lowest—performers, to the managers she’s learned the most from, so there’s tons of insightful advice and practical tactics for both first-time managers and seasoned leaders alike. You can read more about Molly’s approach to scaling startups on First Round Review. We particularly recommend following her advice to ‘give away your Legos’ https://firstround.com/review/give-away-your-legos-and-other-commandments-for-scaling-startups/ And here’s the article on compensation that Molly mentioned in the interview: https://firstround.com/review/A-Counterintuitive-System-for-Startup-Compensation/    You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson 

Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. We’ll cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. I hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com

Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership. — In today’s episode, we discuss: Lopp’s “utopia” — where engineers have time to create and invent What makes an excellent engineering leader The flexibility required for managerial roles in different contexts Navigating internal dynamics between design, engineering, and product How to build and grow effective engineering orgs The importance of understanding individual motivations Key lessons from over 30 years in the industry — Referenced: AOL: https://aol.com Apple: https://www.apple.com Borland: https://en.wikipedia.org/wiki/Borland Netscape: https://en.wikipedia.org/wiki/Netscape Palantir: https://www.palantir.com/ Phillipe Kahn: https://www.linkedin.com/in/philippekahn/ Pinterest: https://www.pinterest.com/ Slack: https://slack.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Tom Paquin: https://www.linkedin.com/in/tom-paquin-240b4b2/ — Where to find Michael Lopp: Blog: https://randsinrepose.com/ LinkedIn: https://www.linkedin.com/in/michaellopp/ Twitter/X: https://twitter.com/rands — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Beginning career at Borland (05:41) The difficulty with shipping software at scale (07:52) Why it’s harder to ship today than ever before (09:42) What makes a startup operationally sound (11:23) Why engineers should have concrete time to invent (19:42) How PMs can improve engineering culture (21:35) An engineer’s perspective on good product management (23:36) The role of product compared to design and engineering (26:38) How micromanagement kills creativity (29:35) Fostering a debate culture in an org (31:26) Declarative versus prescriptive leadership (36:09) 3 ideas on leadership from Lopp’s upcoming book (38:29) Understanding employee motivation (42:28) Advice on discovering what motivates people (46:06) Why teams should reorg every 6 months (48:32) One thing all successful leaders do (52:22) Why sound judgment is crucial for decision-making (53:45) Crystallized lessons from working at software giants (56:19) Why Lopp is afraid of becoming irrelevant (57:58) The number one leadership lesson from Lopp’s career (59:32) What Lopp has changed his mind on over time (61:12) People who had an outsized impact on Lopp

Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012. — In today’s episode, we discuss: Creating a community of power users How to stay ruthlessly focused and make decisions faster Clay’s principles for finding product-market-fit Why a company is the reflection of its founder’s personality Aligning your own psychology with the business The mindset change from a first to second-time founder — Referenced: Airtable: https://www.airtable.com/ Clay: https://www.clay.com/ Figma: https://www.figma.com/ Internal Family Systems: https://ifs-institute.com/ NetSuite: https://www.netsuite.com/ Notion: https://www.notion.com Sailthru: https://www.sailthru.com/ — Where to find Kareem Amin: LinkedIn: https://www.linkedin.com/in/kareemamin/ Twitter/X: https://twitter.com/kareemamin — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:36) Clay’s origin story (05:54) Building for a specific customer (10:42) Knowing when to build for a broader customer-base (12:46) The life spiral framework (15:52) How founders can make better decisions (18:57) Kareem’s principles for product-market-fit (25:36) Clay’s customer journey (30:04) Interesting tactic to find power users (34:00) How to know you have product-market-fit (37:11) The impact of founder psychology on the business (39:41) Mastering commitment to sprints (40:47) How Kareem’s own personality affected his company (43:31) Actionable advice to understand founder psychology (46:25) Why focus is misunderstood (47:09) The mindset shift from a first to second-time founder (50:28) What’s next for Clay (52:14) The best piece of advice Kareem has actioned

Kyle Parrish, Figma’s first sales hire, built the company’s zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York. — In today’s episode, we discuss: The right time to build a sales function Hiring and scaling a successful sales org Building a unique sales culture Career advice for ambitious salespeople Figma’s early sales motion How to integrate your first sales hire Navigating the founder/Head of Sales relationship — Referenced: Amanda Kleha: https://www.linkedin.com/in/amanda-kleha-015599/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Claire Butler: https://www.linkedin.com/in/clairetbutler/ Dropbox: https://www.dropbox.com/ Dylan Field: https://www.linkedin.com/in/dylanfield/ FigJam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Kevin Egan: https://www.linkedin.com/in/kevin-egan-59719/ Oliver Jay: https://www.linkedin.com/in/oliverjayleadership/ Praveer Melwani: https://www.linkedin.com/in/praveer-melwani/ Salesforce: https://www.salesforce.com/ Slack: https://www.slack.com/ — Where to find Kyle Parrish: LinkedIn: https://www.linkedin.com/in/kparrish8/ Twitter/X: https://twitter.com/KyleHParrish — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:10) What founders need to figure out before hiring salespeople (03:48) Who to hire as your first salesperson (05:34) Transitioning away from founder-led sales (07:07) Tactics for hiring great salespeople (12:50) The ideal experience sales candidates should have (13:49) Common traits of successful salespeople (18:45) What it was like being Figma’s first sales hire (19:59) Interesting tactic to integrate the first sales hire (21:16) How Figma executed its early sales motion (32:27) Why Figma changed its customer narrative (34:03) Building outbound sales strategy at Figma (36:17) Segmented pricing and no discounts (41:55) Kyle’s transition from Dropbox to Figma (47:25) Creating a world-class sales culture (51:46) How Figma does sales differently (54:02) Building the initial sales team around a passion for the product (57:12) Figma’s unique hiring process for salespeople (60:40) Advice for founders hiring their first salesperson (63:18) The secret to Dylan Field’s success (64:33) How to scale yourself as an early hire (66:25) Oliver Jay’s impact on Kyle

Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses. — In today’s episode, we discuss: Common mistakes PLG companies make The “PLG trap” and how to avoid it The playbook for transitioning into enterprise How and when to build an enterprise sales team How PLG companies can break $10 billion market cap Why it’s difficult to emulate Atlassian, Slack or Salesforce — Referenced: Airtable: https://www.airtable.com/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Bitbucket: https://bitbucket.org/product/ Confluent: https://www.confluent.io/ Daniel Shapero: https://www.linkedin.com/in/dshapero/ Datadog: https://www.datadoghq.com/ Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/ Dropbox: https://www.dropbox.com/ Dustin Moskovitz: https://www.linkedin.com/in/dmoskov/ Jay Simons: https://www.linkedin.com/in/jaysimons/ Jira: https://www.atlassian.com/software/jira Justin Rosenstein: https://www.linkedin.com/in/justinrosenstein/ Kim Scott: https://www.linkedin.com/in/kimm4/ Salesforce: https://www.salesforce.com/ Slack: https://slack.com/ The PLG Trap: https://www.linkedin.com/pulse/plg-trap-oliver-jay/ The seed, land, and expand framework: https://www.endgame.io/blog/seed-land-expand-framework Zendesk: https://www.zendesk.com/ — Where to find Oliver Jay: LinkedIn: https://www.linkedin.com/in/oliverjayleadership/ Website: https://www.oliverjayleadership.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:23) Differences between PLG and enterprise companies (05:56) Avoiding the “PLG trap” (07:39) Transitioning to enterprise feels like building two companies (10:57) Thinking about user value versus company value (13:58) The relationship between OKRs and executive champions (14:59) Dropbox had almost no company value (15:33) The strategy PLG companies should avoid (18:30) Why Dropbox is worth $10b, not $50b (19:41) The story of Asana’s expansion (21:16) Asana’s unique customer success team (23:27) How product strategy relates to finding champions (25:03) How Asana structured its GTM org (27:11) What Oliver would have done differently with Asana’s GTM (29:45) Getting executive-level buy-in (31:49) Asana’s concept of “selling clarity” (33:18) An inside look at Asana’s transition into enterprise (37:59) The champion tree framework (40:43) Structuring Asana’s early enterprise sales team (44:27) The impact of company size on GTM (47:20) Common sales mistake (48:29) The seed, land, and expand framework (51:43) Oliver’s advice to founders (54:13) Why building horizontally may be a mistake (55:32) Common challenges faced by PLG companies (58:30) How PLG companies can break the $10b market cap (60:17) Why emulating Atlassian’s playbook is difficult (63:21) People who had an outsized impact on Oliver

Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve’s career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned author of The Four Steps to the Epiphany and The Startup Owner’s Manual. — In today’s episode, we discuss: Why there aren’t more successful startups How to improve entrepreneurship in the USA Misunderstood aspects of the Lean Startup methodology Common traits shared by outlier founders Why successful entrepreneurs are irrational (and need to be) How founders can transition to CEOs Why some second-time founders fail Building in existing versus new markets The Four Steps to the Epiphany in 2023 — Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder Allen Michels: https://en.wikipedia.org/wiki/Allen_Michels Ben Wegbreit, Co-founder of E.piphany: https://www.linkedin.com/in/ben-wegbreit-22192/ Convergent Technologies: https://en.wikipedia.org/wiki/Convergent_Technologies Eric Ries: https://www.linkedin.com/in/eries/ Gordon Bell: https://www.linkedin.com/in/gordon-bell-3035b43/ JB Straubel: https://www.linkedin.com/in/jb-straubel-b694981/ Kathy Eisenhardt: https://www.linkedin.com/in/kathleen-eisenhardt-5642247/ Roger Siboni, former CEO of E.piphany: https://theorg.com/org/coupa-software/org-chart/roger-siboni Satya Nadella: https://www.linkedin.com/in/satyanadella/ Steve Ballmer: https://www.linkedin.com/in/steve-ballmer-7087a8157/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The semiconductor industry - explained: https://steveblank.com/2022/01/25/the-semiconductor-ecosystem/ The three pillars of world class corporate innovation: https://steveblank.com/2022/11/11/the-three-pillars-of-world-class-corporate-innovation/ Tina Seelig: https://www.linkedin.com/in/tinaseelig/ Tom Mueller, Ex-SpaceX Propulsion CTO: https://www.linkedin.com/in/thomas-mueller-2094513b/ Why corporate entrepreneurs are extraordinary: https://steveblank.com/2015/08/25/why-corporate-entrepreneurs-are-extraordinary-the-rebel-alliance/ Why entrepreneurs start companies rather than join them: https://steveblank.com/2018/04/11/why-entrepreneurs-start-companies-rather-than-join-them/ — Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Why there aren’t more successful startups (06:07) Outlier founders have similar childhoods (10:34) How to be a successful founder CEO (12:00) Why entrepreneurship should be taught in schools (16:39) The importance of curiosity (19:57) The role of instincts in entrepreneurship (22:31) Having profound beliefs in a vision (24:17) Building in existing versus new markets (29:09) What second-time founders can get wrong (33:49) Why founders need to be irrational (39:28) Common traits shared by outlier founders (45:05) Evaluating what makes a startup successful (49:44) Steve’s assessment of Satya Nadella at Microsoft (52:26) What it takes to build an incredible company (60:45) The Four Steps to the Epiphany in 2023 (64:36) The origins of The Four Steps to the Epiphany

Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes’ list of “America’s Richest Self-Made Women 2023” with an estimated net worth of $520m. — In today’s episode we discuss: The origins of Confluent, Kafka, and Oscilar How to become a successful second-time founder Advice for monetizing open source product Neha’s unique GTM strategies How Confluent ran two businesses within one company Neha’s path to founder market fit — Referenced: Apache Kafka: https://kafka.apache.org/ Confluent: https://www.confluent.io/ Confluent Cloud: https://www.confluent.io/confluent-cloud/ Jay Kreps, co-founder at Confluent: https://www.linkedin.com/in/jaykreps/ Jun Rao, co-founder at Confluent: https://www.linkedin.com/in/junrao/ MongoDB: https://www.mongodb.com/ Oscilar: https://oscilar.com/ — Where to find Neha: LinkedIn: https://www.linkedin.com/in/nehanarkhede/ Twitter/X: https://twitter.com/nehanarkhede Website: https://www.nehanarkhede.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14)The origin story of Kafka (05:24) Co-creating Kafka at LinkedIn (07:31) Why open sourcing Kafka was a masterstroke (11:04) The unique nature of Confluent's Zero to One phase (16:35) Building for a specific customer early on (18:42) Inside Confluent’s successful launch (20:12) Establishing Confluent as an enterprise company (22:00) The role of developer evangelism in Confluent’s success (23:49) Using developer evangelism in category creation (26:41) Navigating early co-founder dynamics (30:06) Leveraging complementary founder skills (31:56) Advice for future founders (32:45) Building Confluent with monetization in mind (34:38) Monetizing open source products (36:05) GTM for subscription Saas versus consumption SaaS (39:48) The importance of founder-led GTM sales (40:58) Neha’s order of operations for GTM sales (42:33) When to build out outbound sales (45:28) Adding SaaS to a software business (49:48) Choosing what to license and what to open source (53:32) How Confluent’s co-founders decided on SaaS offering (57:58) Neha’s journey as a second-time founder (59:48) Building Oscilar differently to Confluent (64:15) Going from speculation to product realization (70:00) Solving problems people are willing to pay for (72:07) Neha’s “proactive research sprint” tactic (73:48) How Neha has applied this tactic

Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs. – In today’s episode, we discuss: Sam’s advice for future engineers What’s next for AI How to develop technical taste The importance of asking “what if” questions Lessons on market timing Scaling a software company in 2024 – Referenced: Amazon: https://amazon.com Box: https://www.box.com/ Elon Musk: https://twitter.com/elonmusk Google Docs: https://docs.google.com Itzhak Perlman: https://itzhakperlman.com/ Microsoft: https://www.microsoft.com Netflix: https://www.netflix.com Tesla: https://www.tesla.com/ The Innovator’s Dilemma: https://www.amazon.com.au/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 TurboTax: https://turbotax.intuit.com/ Uber: https://www.uber.com/ Walmart: https://www.walmart.com/ Workday: https://www.workday.com/ Writely: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/ – Where to find Sam Schillace: LinkedIn: https://www.linkedin.com/in/schillace/ Newsletter: https://sundaylettersfromsam.substack.com/ Twitter/X: https://twitter.com/sschillace – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:54) Lessons on market timing (07:30) Developing technical taste (09:51) Asking “what if” questions (14:03) Building Google Docs (19:32) The decline of Google apps (20:57) The Innovator’s Dilemma facing Microsoft (22:53) The differences between Google and Microsoft (24:42) How to build a winning product (27:46) Becoming an optimist (29:12) Why engineering teams aren’t smaller (32:00) Sam’s prediction about AI (34:11) Capturing the value of AI (37:43) How you should think about AI (45:33) Advice for future engineers (48:18) What makes a great engineer (49:45) One thing the best engineers do (51:37) Microsoft’s new leverage (56:01) Scaling software in 2024 (59:50) The future of AI across several sectors (64:28) What Sam and a violinist have in common

Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google’s collaborative, conversational, and experimental AI tool that’s bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to inquire about and summarize YouTube videos. — In today’s episode, we discuss: Key lessons from Bard’s development process Ethics in AI How Bard shipped fast What separates Bard from competitors The future of LLM, Generative AI, and AGI Advice for aspiring AI developers — Referenced: Bard: https://bard.google.com/ ChatGPT: https://chat.openai.com/ Duet AI: https://cloud.google.com/duet-ai Free courses on machine learning by Andrew Ng: https://www.andrewng.org/courses/ Google Assistant: https://assistant.google.com/ Introducing Google Assistant to Bard: https://blog.google/products/assistant/google-assistant-bard-generative-ai/ Large Language Model (LLM): https://en.wikipedia.org/wiki/Large_language_model Meena: https://blog.research.google/2020/01/towards-conversational-agent-that-can.html Sissie Hsiao (GM at Bard): https://www.linkedin.com/in/sissie-hsiao-b24243/ Steve Stoute: https://www.linkedin.com/in/stevestoute/ UnitedMasters: https://unitedmasters.com/ — Where to find Jack Krawczyk: Twitter/X: https://twitter.com/JackK LinkedIn: https://www.linkedin.com/in/jack--k — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:17) Bard’s origin story (03:54) Deciding on the application of Bard (05:59) The ethical considerations around building Bard (10:19) Why Bard launched to the public so early (13:30) Risk-taking at big companies versus smaller ones (16:20) Bard’s early user research (21:21) Bard versus ChatGPT (25:01) The cultural and product principles behind Bard (30:56) Insight into Bard’s impressive development speed (35:17) Deciding when to ship Bard (41:41) Why Bard is different from other products Jack has built (46:30) Evaluating Bard’s original spec (48:02) Insight into Bard's product roadmap (56:00) The toughest challenges Bard has faced (57:50) What’s special about team-building at Bard (62:54) Addressing Bard’s negative press (67:49) Advice for aspiring LLM companies (69:15) Advice for non-LLM companies (71:05) The biggest barriers to advancing AI (75:45) How product people can use or build with AI (77:24) How AI is changing product leadership (79:20) People who had an outsized impact on Jack

Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Puzzle. — In today’s episode we discuss: How to form an engineering strategy Common engineering management mistakes, and how to avoid them Advice for explaining, measuring, and optimizing engineering velocity Will’s nuanced approach to organizational policies Why it’s sometimes counterproductive to tell someone not to micromanage — Referenced: Accelerate (book): https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 Calm: https://www.calm.com/ Carta: https://www.carta.com/ DORA: https://dora.dev/ Good Strategy, Bad Strategy (book): https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 JavaScript: https://www.javascript.com/ KAFKA: https://kafka.apache.org/ Minto Pyramid (framework): https://untools.co/minto-pyramid Ruby on Rails: https://rubyonrails.org/ SPACE (framework): https://queue.acm.org/detail.cfm Stripe: https://www.stripe.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Will Larson: Twitter/X: https://twitter.com/lethain LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/ Personal website/blog: https://lethain.com/ An Elegant Puzzle (book): https://www.amazon.com/Elegant-Puzzle-Systems-Engineering-Management/dp/1732265186 Staff Engineer (book): https://staffeng.com/book — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) The nuances of taking lessons from old companies (14:28) The value of writing down engineering principles (17:03) How to structure a strategy document (18:48) The 2 parts of any engineering strategy (21:08) Advice for turning strategy into action (23:44) Carta's unique "navigator" model (24:50) The Hidden Variable Problem (29:59) Explaining, measuring, and optimizing velocity (35:28) Useful metrics for engineering orgs (39:08) The balance between micromanagement and understanding details (43:03) Management anti-patterns (45:49) How to execute policies whilst managing their exceptions (47:56) What an excellent engineering executive looks like (53:53) How Will has evolved as an engineering executive (56:56) How to communicate with executives (63:18) Things that derail meetings (66:10) How to approach presentation feedback (67:30) A bad sign when working with direct reports (69:13) Advice for growing as an early-career engineer (71:11) Will's model for developing engineering teams (74:33) Sources of inspiration for Will's views on engineering management

Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine’s “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online. — In today’s episode we discuss: The origins of Runway The limitations of being “customer-driven” when building in AI How Runway balances research development with product development How goal-setting and planning is different for AI products Advice for early-stage AI founders — Referenced: Containerization: https://aws.amazon.com/what-is/containerization/ Docker: https://www.docker.com/ Green screen tool by Runway: https://runwayml.com/green-screen/ Hugging Face: https://huggingface.co/ Hugging Face Spaces: https://huggingface.co/spaces Hugging Face Model Hub: https://huggingface.co/docs/hub/models-the-hub Replicate: https://replicate.com/ Runway Gen-1: https://research.runwayml.com/gen1 Runway Gen-2: https://research.runwayml.com/gen2 Runway’s 30 AI Magic Tools: https://runwayml.com/ai-magic-tools/ — Where to find Anastasis Germanidis: Twitter/X: https://twitter.com/agermanidis LinkedIn: https://www.linkedin.com/in/agermanidis Personal website: https://agermanidis.com/ Personal blog: https://blog.agermanidis.com/ — Where to find Todd Jackson: Twitter/X: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:23) The unique story of how Runway's co-founders met (08:27) The origins of Runway (09:28) Forming the initial product (13:55) Turning Runway into a company (14:41)Approach to initial market segments (18:53) Early-adopters (21:20) The limitations of being “customer-driven” (25:54) Forming a vocal community (27:08) Fostering community (29:05) The progression of Runway's tech and use-cases (33:08) How they picked users for early release (34:00) Expanding past the first 100 users of Gen-2 (35:33) Runway’s approach to safety and content moderation (36:44) Balancing product development and research development (43:51) Runway's org structure (45:08) Goal-setting amidst constant change in AI (46:50) Why Runway doesn't plan very far ahead (50:26) Advice to early-stage AI founders (53:11) Will AI replace video editors? (55:04) When Runway had the most momentum (56:49) Anastasis' #1 piece of advice