Explore every episode of the podcast SaaS Backwards - Reverse Engineering SaaS Success
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Ep. 187 - Your SaaS Isn’t Broken—Your Execution Is
Why SaaS companies stall at $10M, how execution breaks down, and what founders must change to scale
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Guest: Mark Abbott, Founder & CEO at Ninety
Most SaaS companies don’t hit a wall because demand dries up — they hit it because execution doesn’t keep pace with growth.
In this episode of SaaS Backwards, Mark Abbott, Founder and CEO of ninety.io, explains why SaaS companies predictably stall as they grow and how founders underestimate the leadership and operational shifts required at each stage. Drawing on decades as an operator, investor, and board member, Mark walks through the five unavoidable stages of company growth and why stage three is where most companies get stuck.
The conversation explores why speed becomes a liability, why leadership requirements change as teams scale, and how operating discipline and culture quietly determine whether a SaaS company breaks through its ceiling or plateaus indefinitely.
Mark also unpacks the Entrepreneurial Operating System (EOS), the mindset shift from lifestyle entrepreneur to long-game founder, and why operational systems are not overhead — they’re a competitive advantage. This conversation is essential listening for SaaS founders navigating product-market fit, team scaling, and leadership complexity.
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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup.
Guest: Lara Shackelford, SVP of Growth Marketing at iCapital
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Most SaaS companies are investing heavily in AI, yet many struggle to see meaningful ROI. In this episode of SaaS Backwards, Lara Shackelford—SVP of Growth Marketing, MarTech, and CRM at iCapital—breaks down why AI initiatives fail without the right systems, governance, and change management.
Lara explains how AI-powered revenue systems should be designed across the full customer lifecycle, from demand generation through customer success. She introduces the concept of “agent sprawl,” outlines why AI readiness assessments are critical before scaling automation, and shares practical examples of signal-based marketing and sales automation that actually work.
This conversation is essential listening for SaaS CROs, CMOs, and RevOps leaders looking to align AI strategy, revenue operations, and go-to-market execution.
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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup.
Guest: Braydan Young, Co-Founder and CEO at SlashExperts
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Buyers don’t want another “book a demo” button—they want proof from people like them.
In this episode, Braydan Young, Co-Founder and CEO of SlashExperts (and previously co-founder of Sendoso), joins host Ken Lempit to share how buyer-led growth is reshaping SaaS sales and why the old way of running references at the end of the deal cycle is broken.
Key insights from this episode:
Why moving customer references earlier can shorten sales cycles by 4–6 weeks
How authentic peer conversations double conversion rates compared to demos
What CROs can learn from Sendoso’s hypergrowth—and its “we grew too fast” moment
Why handwritten notes and simple gifts outperform flashy, expensive ones
How to turn the “dark funnel” into a competitive advantage
If you’re a B2B SaaS CMO or CRO looking to accelerate pipeline, increase deal size, and close faster with fewer wasted demos, this episode is a must-listen.
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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup.
The B2B world is different today, and (unfortunately) there’s no one formula that works across the board. It’s not outbound versus inbound. It’s not advertising versus content.
Every organization has a unique formula that will consistently drive meaningful conversations with targeted prospects.
Therefore, you'll never see a productive organization where there's a lot of animosity between marketing and sales leadership.
In this episode, Ben Page-Fort, who works with early and growth stage FinTechs to develop and execute go-to-market strategy, talks about how sales and marketing alignment is no longer a goal—it’s a must have.
And it’s all hands on deck to find the right formula because we’re all in the same boat.
Key Takeaways:
Hiring for today (their skillsets match the current needs of the organization) and not by trying to anticipate future needs.
The importance of setting qualitative goals and key performance indicators with all revenue growth stakeholders committing to driving results.
When joining a new organization as a marketing or sales leader, it's important to understand and respect what is already working and avoid making drastic changes without fully understanding the existing strategies and successes.
There’s nothing like an economic slow-down to thin the herd. Companies take longer to buy, consolidate resources, and rethink their go-to-market strategy.
So why are companies doubling down on yesterday’s strategies?
Normally the host of SaaS Backwards, Ken Lempit, President of Austin Lawrence, sits in the guest seat this week to answer questions about how SaaS leaders need to approach marketing to engage today’s buyer.
Key Takeaways from this episode:
Demand generation involves both demand capture (or lead generation), which is a short-term focus, and demand creation, where you’re creating relationships over the long term with potential customers not yet in a buying motion.
Creativity is back. With the proliferation of content and generative AI, it’s the creatives that are going to figure out how to stand out from the crowd.
Why all B2B SaaS marketers should read "The Challenger Customer" if they’re using thought leadership content.
When a company starts out, verticalization may not be the best thing. In fact, today’s guest Corey Quinn, fractional CMO and GTM strategist prefers to work with companies who went broad first, since there’s value in exploring different verticals and learning the nuances in the different markets.
But at a certain point, verticalization becomes necessary to scale. It reduces complexity, improves marketing, and helps to differentiate from the competition.
In this episode, host Ken Lempit and Quinn discuss how to narrow down and exploit areas of specialization.
Key Takeaways:
Understanding your best fit customer by conducting qualitative and quantitative analyses of your business.
The role of thought leadership content and the importance of ensuring subject matter expertise within the chosen vertical.
Ensuring that your marketing efforts align with your sales process and provide valuable insights to potential customers during sales conversations.
It’s never been harder for marketers generate an audience where you can have impact than it is today.
The media landscape has exploded and the number of choices we have as marketers has never been more varied.
In many ways, we’re now paying for the sins automating a process of building trust and relationships.
In this episode, Anthony Kennada, Co-Founder and CEO of Audience Plus talks with Ken about how the marketing pendulum is swinging back from marketing automation, inbound, and maximizing SEO to its original intent—creating value for an audience in a more authentic way.
Key takeaways:
How to create the authentic content that B2B buyers care about today.
Why first party data will be crucial to personalize content and prove impact in the face of changing data privacy regulations and the decline of third-party cookies.
How the shift towards owned media will help marketers regain control over their lead-to-revenue process and reduce reliance on third-party platforms and algorithms.
As martech SaaS founder, Steve McDonald acknowledges the tendency to believe that their product is so exceptional that customers will naturally flock to it.
But then reality sets in and you realize that maybe Shoeless Joe Jackson wasn’t whispering in your ear after all.
There’s a lot of risk for customers to invest in something new, and content marketing is the obvious way to build trust. But with the volume of noise out there today, your development process must be strategic, methodical, and efficient.
In this episode, Ken and Steve geek out on the role that content plays for today’s SaaS and how thought leadership actually works to spark conversations with prospective customers.
Key takeaways:
Why podcasting is still an effective way to create thought leadership content efficiently and effectively.
Marketers should consider creating themed podcast series that focus on specific topics or industry challenges.
Why it's important to invest in thought leadership that delivers customer insights early on to establish the company as an expert to spark conversations with prospects.
When joining MadKudu as a Marketing VP, Shannon Curran knew they were so much more than a predictive lead scoring platform.
She wanted to shift the conversation from product-led growth (PLG) to a focus on hybrid funnels and revenue generation. And because it would be a huge challenge to cut through the noise in the MarTech/RevTech space, they engaged an external consultant to conduct research and help with the positioning process.
They explored the competitive landscape, market trends, and the company’s unique value proposition.
Through testing and feedback, they arrived at the positioning as a revenue automation intelligence engine, emphasizing the company's ability to predict and prioritize revenue-generating actions, automate revenue intelligence, and provide data-driven insights for go-to-market teams.
The repositioning efforts showed a 2X increase in demo conversions.
In this episode, Curran talks about:
The importance of positioning before messaging and branding, as it provides a solid foundation for effective communication and differentiation in a crowded market.
Vetting new job opportunities: funding, understanding their key metrics (CAC, LTV, churn), board involvement, and the experience of the founders.
Using a test and learn approach to their messaging change by conducting bi-weekly tests on their website, paid advertising, and other channels to gather data and feedback.
Outbound selling is here to stay—but to make it work, efficiency is key.
Of course, the task at hand isn’t lost on Salesintel.io CEO Manoj Ramnani, who’s tools are designed to do just that. Salesintel.io is a go-to-market intelligence platform that helps marketing, sales, and revenue operations teams research prospective accounts and find contact information.
Ramnani is most excited about “Predictive AI” where it has the potential to predict future intent based on historical data so that sales teams can target the right prospects and tailor their outreach accordingly.
For example, if a company has recently purchased Salesforce and is using it for CRM and HubSpot for marketing, and you have six BDRs and AEs, it is highly likely that they would be interested in purchasing a sales cadence software.
In addition, Ramnani and host Ken Lempit discuss:
How the sales process is shifting towards a demand generation approach and what it takes to build efficient pipelines and generating meaningful conversations with potential customers.
The role of AI and machine learning in enhancing account intelligence and making it more actionable.
Outbound sales efforts are still essential, but sales leaders need to embrace the changing sales landscape, leverage AI and account intelligence to drive efficiency, and prioritize personalized and value-driven outbound sales efforts.
But what if you could hire one on an hourly basis?
That’s what Jason Shapiro, CEO and founder of 82i talks about in this episode. 82i is a strategic growth services firm that serves as “a co-founder for hire” to help with growth functions such as raising capital and hiring so founders can keep their eye on what truly matters--revenue.
Key takeaways:
The dynamic nature of investability and the importance of building on a solid business foundation while remaining open to creative solutions to attract investors.
How and why a founder may need to “let go” of certain things to build an appropriate team for growth.
Why an overconfident founder could scare investors away
In this episode, guest host Jason Myers interviews Alex George, the head of marketing at Hint Health--a platform that is redefining healthcare by providing back-end software for the direct primary care market.
Alex shares insights into Hint Health's go-to-market strategy and how they enable the growth of the direct pay model in the healthcare industry. The company adopted a HubSpot-like model for educating its client practices resulting in 90 percent of client acquisition being inbound.
Key Takeaways:
How to use educational content as a key driver of business success.
Aligning content with the buyer journey and how to ensure they can find what they need with minimal resistance.
Leveraging agencies to and collective members to deliver superior marketing results.
Last year, the report focused on the self-serve economy—they want product information readily available without talking to sales and then they would validate customer proof points.
All of that still holds, and the good news for vendors is that companies are still spending on technology.
The bad news is that with the changes in the economic climate, it’s all about consolidation, time and cost savings, third-party validations, and in many cases, adding the CFO to the buying committee…
Yuck.
That all translates to some significant changes for most B2B vendors’ go-to-market strategies if they want to align with today’s buyer.
For example:
Because the content noise volume confuses buyers, they’re relying more on their own past experiences and ability to research proof. That goes way beyond what vendors are used to providing in their content.
If you’re not transparent in your pricing, buyers will find it, potentially from your competitor.
More than ever, buyers are resistant to talking to sales until they’re way down the funnel. And if they easily can’t get the information they’re looking for…
This is a must-listen episode for all B2B marketers that want to stay ahead of the competition.
Guest: Courtney Hiller, Founder of All Points Agency --
You wouldn’t hire one person to build your product, sell it, and run support. So why are B2B SaaS companies still expecting one marketer to manage a million-dollar media budget?
In this episode, Courtney Hiller, founder of All Points Agency, joins host Ken Lempit to break down how to build a modern media engine that actually performs—and why yesterday’s paid strategy won’t cut it in 2025.
Key insights from this episode:
Why splitting strategy, creative, and media buying unlocks performance
What most in-house teams get wrong about channel mix and audience targeting
How to fix attribution when your sales cycle is 6–12 months
Why creative volume—not just creative quality—is the new growth lever
How to use Reddit, Meta, and programmatic without wasting your budget
If you’re a B2B SaaS CMO or CRO managing six-or seven-figure ad spend, this episode will help you rethink your team structure, channel strategy, and ROI expectations.
Why are some SaaS companies raising significant funds while others struggle to find their first customers or determine what to build?
We caught up with Sanjit Singh Dang, the Chairman and Co-founder of U First Capital, at the Ascent conference and he shares his insights as a VC evaluating startups—most notably how VCs now require more proof points on the customer side and ask the crucial question of "why now?" to evaluate product market fit with startup opportunities.
He also discusses effective pitch tactics, such as showcasing customer feedback and engaging in whiteboard sessions to understand the entrepreneur's passion and clarity of thought.
Check out this episode for valuable insights into today’s world of SaaS and AI investments.
We talk a lot with our customers about the 97%. The people who have problems you solve, but don’t know there’s a solution and certainly don’t know about you.
That’s what we talked about with Olgo Noha, CMO of SplitMetrics at the recent Ascent Conference in San Francisco.
Split Metrics is in a relatively new market with little competition—but there is little solution-awareness.
Therefore, their strategy has focused on education. And when you have a complex product that requires education—customer creation is the name of the game.
Also in this episode:
Looking for the pivot in terms of go to market or your product or even operational side of things.
How SplitMetrics restructured their sales teams to focus on a single portfolio of products.
Does anyone really understand their health benefits?
Most of us have experienced going to HR with a benefits question, only to be redirected to a call center just to sit on hold and maybe get answers.
Guy Benjamin, CEO and co-founder of Healthee, developed a way to simplify this age-old problem with a platform that lets employees easily navigate their health and wellness benefits, and even helps choose the best plan for them.
In just two years, Healthee has managed to raise $26 million dollars. But it hasn’t been simple or easy. Benjamin declares that starting Healthee has been his toughest challenge yet - even more challenging his prior experience as an Israeli fighter pilot.
He shares his experience as a founder, and other key takeaways including:
The perks of outsourcing the R&D team from Israel (and spoiler, they are not all financial)
How AI boosts customer experience and gives key insights to employers
Hiring the right experts to fill in your knowledge gaps
Finding the champion in the organization you’re selling to - in this case it’s HR
When Stacey Epstein became the CMO of Freshworks a few years ago, their PLG motion was doing okay. But approaching marketing from her success with other enterprise SaaS startups, Epstein expanded the marketing and sales motion to include more traditional demand gen tactics—direct sales, events, Account-Based Marketing.
Now they can fully meet the buyer where they’re at—calling it Buyer Led Growth.
In this episode recorded live at the Ascent Conference in San Francisco, Epstein shares her expertise including:
How the PLG motion is different and should be treated.
Dealing with churn in the early years
Freshworks incorporation of AI and why you might not want to share everything with ChatGPT.
What are you trying to do in your forecasting process that you're not getting from your CRM?
That’s the question Aviso set out to answer for its clients by leveraging advanced analytics. Their software helps sales teams optimize their strategies, identify trends, and make data-driven decisions to improve their sales outcomes.
At the recent Ascent Conference in San Francisco, we sat down to talk with their chief marketing officer Amit Pande who shared how they found their product-market fit during the pandemic, the ability to adapt to changing market dynamics, and the significance of building a strong brand.
Key takeaways:
Leading with pain points instead of demoing features.
Investing where others aren’t in a cost-efficient way.
Chip House has had a long career in SaaS with companies such as ExactTarget, Salesforce, and SharpSpring.
Now as the CMO at Insightly, we caught up with Chip at the Ascent Conference in San Francisco and got him to share his experiences with all things B2B marketing, including:
Most of us can sniff out a sales email in a split second--the headline is cheesy, it’s about them, and it’s completely irrelevant. Obviously, sellers haven’t done their homework.
That’s the opportunity we discussed in my interview with Lavender AI’sJen Allen-Knuth and Will Aitken at the Ascent Conference in San Francisco. Their tool helps sellers write better emails—or as Aitken says, “stop them from writing such bad ones.”
Using AI to comb through millions of sales emails, Lavender has solid data on what works and what doesn’t to coach your sales team before they hit send, giving them the best opportunity for engagement.
Key Takeaways from this episode:
The best structure for sales emails that you’re probably not doing.
Why emails under 50 words and boring subject lines get the best replies.
The most overlooked thing by sellers. (Hint: it’s about them and not about you).
People just don’t pick up the phone like they used to, and as a result, outbound call response rates are few and far between.
A rep that makes 100 calls a day may only get a handful of connects. It’s such a grueling and inefficient process that many companies have abandoned the phone altogether.
The problem is that sales ultimately is based on having valuable conversations. And if you’re not having them, your pipeline will suffer.
So, what if you could improve the connection rate and have more conversations?
That’s what Orum’s VP of Sales Colin Specter talked to us about live at the Ascent Conference in San Francisco.
Their product claims to be the most efficient way to generate human-to-human conversations on the phone by using AI to drive more live conversations and bring back the buzz of a sales floor—even when reps are virtual.
Key takeaways from this episode:
The importance of product-market fit to scale.
The addition of long-term demand generation after succeeding with short-term sales KPIs.
The importance of finding the champion that will do the hard selling internally for you.
Why can a person with an iPhone in their bedroom with no budget create videos that get millions of views, while B2B companies that hire professionals can’t seem to get a fraction of that engagement?
That’s the problem Michael Hoffman set out to solve with his company Gather Voices.
Traditional agency production processes are expensive, slow, and don't scale well, which hinders B2B companies from creating video content for various channels like social media and websites.
When you look at consumer videos, it’s the funny, interesting, and fantastic stories that go viral—and it has little to do with the production value.
Hoffman proposes that B2B companies think differently about their brand and how they produce more “authentic” video content and find what resonates.
Key Takeaways from this episode:
To scale video production efficiently, companies should prioritize capturing genuine stories from customers, employees, and partners, avoiding overproduction, and focusing on delivering authentic content that resonates with their audience.
How to tap into user-generated content by actively encouraging users to share their experiences through video.
Hoffman’s perspective on when, how, and why to take investment and the importance of finding investors who share your vision.
In this episode, fractional CMO Andrew Bolis shares how owning a pipeline number and being responsible for specific revenue-related targets not only helps sales and marketing teams work towards common goals, but also provides leverage in conversations with the CFO.
Other Key Insights from this episode include:
Bringing in the right fractional CMO for your situation.
Working with agencies to fill in skill gaps and drive faster results.
AI isn’t just generating ad copy—it’s reshaping the entire performance marketing playbook for B2B SaaS.
In this episode, Hikari Senju, founder and CEO of Omneky, shares how the platform evolved from an enterprise solution to a self-serve powerhouse—and why smart creative strategy matters more than big budgets.
How ad performance data can directly inform GTM messaging
Why brand inconsistency across platforms kills trust and conversion
How AI-powered ads are becoming core to revenue strategy
If you’re a B2B SaaS CMO or CRO looking to improve ROAS, scale faster with fewer resources, or make AI actually work for your GTM team, this episode is a must-listen.
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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup.
You’ve probably heard the criticisms of B2B marketing—it’s boring and lacks creativity.
And besides, it’s way too expensive to produce ads like B2C companies.
In this episode, Melissa Rosenthal, Chief Creative Officer at ClickUp shares her approach to creating remarkable content without breaking the bank.
Coming from B2C powerhouses like Buzzfeed and Cheddar, Rosenthal immediately saw the blue-ocean opportunity in B2B to differentiate. So, she built an in-house creative agency at ClickUp by investing in the right people and equipment to produce Madison Avenue quality content at a fraction of the cost.
As a result, they’ve taken on the gorillas in its crowded space, growing from 60 to over 1000 employees in under three years.
Key takeaways from this episode:
The portfolio approach to creative that enables ClickUp to create hundreds of pieces of content cost-effectively instead of betting the farm on a singular campaign.
Why you should treat your entire content strategy as an evergreen campaign
Why securing leadership buy-in from the beginning is crucial in fostering a culture of creativity.
Working at Google’s mapping team, Steve Benson thought that field salespeople needed a lot more functionality to adequately plan their routes.
So, in 2012 founded Badger Maps and set out to build a tool where field sales teams could not only build routes, but also visualize their customers on a map on their mobile device that automatically connected with their CRM.
To ensure product/market fit, Benson personally talked to hundreds of field salespeople to ensure that this was a problem worth paying for and not just a nice-to-have.
Key takeaways from this episode:
When and what skills/background to look for when hiring the first salesperson.
The importance of founder involvement in early product management.
Debt vs. equity financing and how Badger Maps used debt most effectively.
The role that thought leadership content played in building their reputation.
When Susan Peich joined Monitaur AI as their head of marketing earlier this year, the power (and dangers) of AI was still mostly talk amongst data scientists.
How quickly things change.
With the rise of ChatGPT in recent months, AI's power (and danger) are now at the forefront causing companies to scramble to figure out how to handle its governance.
That’s where Monitaur.ai comes in. They help companies in highly regulated environments such as insurance, healthcare and financial to not only leverage the potential of AI and ML but also to mitigate risks.
In this episode, Peich talks with host Ken Lempit about what companies should be thinking about today with AI Governance including:
What investments in AI and ML are right for the business
What are responsible and ethical uses of AI and ML and developing governance models
Generating supervised inputs and outputs to generate evidence-based reports for compliance.
If we’re being honest, there's a big difference between the imagined buyer's journey that marketers invent and what’s happening in reality.
But then, we’ve always made those assumptions because it’s nearly impossible to track.
Or is it?
That’s what Molly St. Louis, Head of Marketing at DealTale talks about in this episode - applying AI to track the previously un-trackable journey.
DealTale is a SaaS that leverages causal machine learning methods to track buyers while they’re still anonymous (by IP address) and then backfill their information later when they fill out a form—even when it’s months (or years) later so they can see what is transpiring and then replicate it in future campaigns.
With their innovative ChatGPT-like interface, campaign analytics become accessible to all marketers, not just those in large companies with data analysts.
Key Takeaways from this episode:
The importance of understanding causality for mapping customer journeys.
How AI can go deep on attribution, customer journey mapping and causality.
Remember that marketing is fun, and not to worry about always “getting it right.”
In this episode, Matt Trifiro, CEO of Vapor.io, joins host Ken Lempit to discuss the insidious tyranny of artificial Key Performance Indicators (KPIs) and how to fight back against their oppressive hold on SaaS marketing.
Long gone are the days when early adopters of advertising platforms could easily dominate their market niche, as the law of diminishing returns has caught up with all forms of marketing, leaving SaaS marketers struggling to find innovative ways to attract and retain customers.
But with CFOs and CEOs demanding increased results on yesterday’s KPIs, how can SaaS marketers break free from the shackles of convention and embrace experimentation and agility?
Find out in this enlightening conversation, where Trifiro and Lempit explore topics such as:
Establishing a culture that’s tolerant of experimentation and agility by constantly testing and iterating.
How investing in customer retention is the real determination of lifetime value.
Why you should always be asking, “what could I be doing with that money?” Is there a better way to spend it than on 10 BDRs or $100K tools?
Despite building a great product and amassing close to 1000 customers, LiquidPlanner struggled to continue on the same growth trajectory.
Customers expected broader capabilities. Competitors had more money. And as access to capital tightened, the board decided to look for a partner.
They found Tempo, a complimentary business that will help deliver better portfolio management capabilities as well as its connectivity to Atlassian’s Jira–something their customers are looking forward to.
Even though the acquisition happened a few weeks ago, the focus is squarely on delivering better portfolio management capabilities and confidence to project teams than anyone else in the market.
In this episode, LiquidPlanner CEO Ted Hawksford talks about the salesmanship involved with internal stakeholders–and while it’s not the 10X valuation that most startups hope for, it’s the best outcome for everyone involved.
Key takeaways:
The challenges and concerns that arise when the two development teams are asked to work together before the deal is consummated.
Communications with customers about an impending acquisition and providing assurances about the future of product development.
The importance of having clean books before entering an acquisition and preparing for every detail to be scrutinized.
For marketers, breaking through the trust gap is getting harder. Prospective buyers won’t believe it without some third-party validation.
So, how can you break through that trust gap in a new and innovative way?
That’s the problem Jeff Ernst set out to solve as the founder of SlapFive, a customer marketing solution that makes it simple to engage and mobilize customers to drive growth.
In over 2000 interviews with CMOs during his tenure at Forrester, Ernst notes that overwhelmingly, the number one thing that buyers trust and seek out is what their friends and colleagues think and what your other customers’ experiences are.
“They want a crystal ball into the life of a customer. They know it’s not perfect and don’t expect it to be--and they can only get that from your current customers.”
In this episode, Ernst talks about his journey as an entrepreneur and shares his advice on:
How to leverage customers in ways beyond case studies, testimonials, and referrals.
How to find an unmet need in the marketplace and ensure product/market fit.
And most importantly, what marketers should be doing today to build trust with both current and prospective clients.
Having spent a decade growing a retail mortgage origination business, Jason Doshi noticed that the movement of funds surrounding the real estate transaction was still very antiquated.
A few years later, he built Payments.io, a SaaS digital platform that allows title companies and real estate brokerages to send and receive digital money transfers, saving everyone money and time while reducing the risk of fraud.
Doshi recently raised $3 Million and he talks in this episode about their challenges and opportunities such as:
White labeling as a strategic initiative
Providing a competitive advantage to customers in a challenged market
Soliciting the customer’s input in establishing your business model
Starting his career as a research scientist, Harsha Rajasimha became interested in addressing the issue of clinical trial recruitment after realizing that many promising drugs were not making it to market due to recruitment delays.
To better understand the problem, he conducted interviews with 3,000 stakeholders of clinical trials, including patients, physicians, and pharmaceutical companies and found that 85% of those delays were because of recruitment issues.
Rajasimha created Jeeva Informatics, a platform that uses artificial intelligence and machine learning to identify potential candidates for clinical trials based on their medical records and other data. The platform also helps to match patients with clinical trials that are appropriate for them.
The company has had success in improving clinical trial recruitment rates, with some trials seeing a 50% increase in enrollment. Jeeva Informatics is also working to expand its platform to include a wider range of data sources and to improve the user experience for patients and physicians.
Key takeaways:
Conducting research and gathering insights from stakeholders before building a product is critical in finding product/market fit
Technology, such as artificial intelligence and machine learning, can play a role in addressing complex problems and improving processes.
Creating a product that is easy to use and meets the needs of users is important for adoption and success.
There’s a tendency for entrepreneurs to believe that the motivations for starting a company is the fame and fortune.
But as Aseem Chandra, co-founder and CEO of Immersa explains, “That's the absolute wrong reason. You get into a startup because you love the problem, and you can't wait to see what that solution's going to turn out to be, and you're willing to give 10 years of your life to it.”
Knowing that the two biggest reasons for startup failure (they run out of money and irreconcilable differences amongst the founders) Chandra first made sure that they had the disagreement piece solved before starting. He chose a co-founder that he trusted and could establish a process for working through disagreements positively.
The money piece is a bit trickier, especially coming from big company background where many work habits don’t apply in startup world.
In his transition from big companies into startup world, Chandra operated as an entrepreneur in residence with Global VC Fund Mayfield to take the time needed to “unlearn and re-learn” how to run a startup.
Today, Immersa has raised over $10M in series A funding, and with a relatively small staff, they’re positioned well for growth.
Key takeaways from this episode:
Choosing the right partners and executive team and how to operate on trust
How an “entrepreneur-in-residence” might be a good path
The customer research involved in ensuring product-market fit
The go-to-market playbook for AI SaaS is being rewritten in real-time, and those who cling to old models risk being left behind.
In this episode, Adir Ben-Yehuda, founder and CEO of Autonomy AI, joins host Ken Lempit to share how his team went from zero to 70 customers in months by ditching outdated frameworks and building a brand buyers can trust.
We unpack: ✅ Why “Crossing the Chasm” no longer applies in the age of ChatGPT ✅ How brand marketing now beats lead gen in AI go-to-market ✅ What it really takes to convert skeptical enterprise buyers ✅ The shift from SEO to “share of response” in AI search platforms ✅ Why every SaaS GTM leader must become an orchestrator—not just a doer
Adir also breaks down the sales motion that helped Autonomy scale so quickly—and shares how his team leverages live demos and social proof to close deals in a single call.
If you’re a B2B SaaS CMO or CRO navigating AI adoption, rethinking pipeline strategy, or looking for a more effective way to win technical buyers, this episode is your cheat code.
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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup.
While working for a large manufacturer in the film and broadcast industry and visiting over 200 Film and TV studios, David Kaszycki spotted a big problem.
Engineers had to stay up to date with updates, critical security patches, general maintenance and accessing manuals and documents for over 10,000 different pieces of technology.
With his partner, Kaszycki started Beam Dynamics to build a common interface platform that would bring all of it together. Engineers can upload or connect their inventory list and access the data on thousands of manufacturers.
Now with incredible potential to expand in multiple industries such as stadiums and arenas, hospitals and houses of worship, Kaszycki has opted for the profitability path instead of pressured expansion from VCs.
Key takeaways from this episode:
The unforeseen advantages of building a startup in a smaller city.
The difficulties of defining a new category where there isn’t a competitive offering.
The importance of building a strong team and keeping everyone aligned.
Working with large system integrators and resellers as partner channels.
Why do 90 percent of acquisitions fail for the buyer?
According to Ari Kahn, President and CEO of Bridgeline, a big reason is because they’re not leveraging the customer base to create greater lifetime value (LTV), so they don’t adequately recover the original customer acquisition costs (CAC).
Bridgline Digital has acquired its way to a suite of SaaS solutions that bridge the gaps between marketing, content, commerce, social and insights to grow online revenue for its customers.
Kahn’s secret acquisition sauce comes in evaluating targets that make sense both from a selling perspective (getting new logos) and by enhancing customer lifetime value for its existing customers by bringing appealing new technologies.
In this episode, Kahn shares his stories and specific methodologies for bringing companies into the fold, including:
His first acquisition during the dot com bust
Understanding the CAC to LTV ratio
Strategies for dealing with “the cash flow trough”
How providing multiple paths for customer solutions leads to greater LTV
Like most SaaS companies, Brandon Metcalf, CEO & Founder of Place struggled with the outbound sales model.
Out of necessity, they started looking at why companies weren’t buying their products. They found that over half bought nothing.
In other words, no decision.
So they decided to flip the script and educate prospective buyers on what could happen instead of finding the people whose arm they could twist a sales conversation.
They put a lot of work into messaging, revamped their website to let buyers self-serve, they started a podcast, and focused heavily on LinkedIn content.
Less than a year later, they saw a flurry of inbound activity, and for the first time had more revenue from it than any other source.
If you’re struggling with the outbound sales model and don’t know how to fix it, this episode is a must listen.
Other interesting topics include:
Building products on Salesforce – the pros and cons
Recruiting the right people by getting specific on the ask
How to use podcasting to stay in touch with your customers
There’s a lot of hype with Product-Led Growth (PLG) with the promise of low-cost customer acquisition and streamlined expansion.
But as Peter Zawistowicz, Pace’s head of marketing says that when you introduce a PLG motion into an organization with an existing direct sales motion, you get an interesting set of problems.
Most notably, sellers in a PLG motion are almost always left in the dark while still trying to hit their numbers.
Intercede too early and it could artificially inflate price points.
On the flip side, self-serve customers that lack proper guidance when problems arise could leave money on the table and lead to churn.
That’s the problem that Pace is tackling with a new set of tools that are built for customer facing roles that allows them to focus on the users that really need their attention and eliminating the rest of the noise.
In this episode, Zawistowicz draws on his (and the founders’) background with companies like Gremlin and MongoDB that successfully implemented PLG motions to help Pace customers to find enlightenment—the right mix of sales and customer service intervention to maximize growth.
Other notable topics include:
What to do when you don’t have product-marketing fit
Not getting beat by hype cycles
Getting the DIY champion on your side
How to provide salespeople with actionable insights vs letting them self-serve
It’s estimated that 40 percent of all warehouse worker movement is wasteful. A simple example is a worker having to walk through and assemble 12 items that need to be shipped to a customer. What’s the optimal order of items to minimize the steps
That’s the problem Yosh Eisbart, CEO of Fullfilld is tackling with their warehouse management orchestration platform. Their system paints a “digital twin” of the physical warehouse, digitizes it, and ingests all that data into the software.
So instead of a static image (which doesn’t communicate any data about optimal flow), they’re able to use AI and ML to capture data around the entire buzz happening in the warehouse beehive, analyze the data and calculate the optimal workflow.
As compelling as this solution potentially is for warehouses, Fulfilld must overcome problem awareness issues and status quo bias to penetrate new accounts.
How are they doing it?
Eisbart shares his learnings about crossing that chasm including:
Getting those first five customers to demonstrate product-market fit
How they vetted “smart money” that could impact business development from the beginning.
Overcoming “problem awareness” by launching smaller components and expanding based on use cases.
Their strategy for scaling through channel partners.
As fans of the Challenger Sale methodology, we know that getting prospects to move off their status quo to make a change is paramount to winning a new deal.
But as Tim Riesterer Chief Visionary for B2B Decision Labs (and self-professed “research nerd”) talks about in his new book The Expansion Sale, growth for a vast majority of companies comes in retention and expansion.
Because most deals start out too small, underpriced, and overserviced, the question is how to keep and grow those customers when it comes to renewal time? (Oh, by the way, the price is going up.)
In many ways, renewing isn’t just renewing. And upselling isn’t just upselling. It’s all reselling.
Therefore, challenging their status quo won’t help you—you are the status quo, and you want to leverage that.
And there’s more commercial activities in that existing customer interaction and engagement that you need to be savvy about, such as:
How to defend your position as the status quo bias
Transitioning from the decider to the doer and setting up the business case
The four must-win commercial moments of the client relationship
The framework and content choreography for having the renewal conversation
Documenting mutual investment so they view change as a loss and view the new vendor as “risky business.”
Today’s B2B tech buyer has a much greater expectation and appreciation for self-service—they don’t want to have to jump through hoops or talk to a sales rep to find out what the business does.
But what to do about it?
It’s a difficult shift for traditional marketers and sellers—to be more buyer-centric--which is why we talked with Tyler Lessard, vice president of marketing at Vidyard, a video technology company that provides marketers and sales teams with custom video messaging and analytical tools.
Lessard provides an action-packed 30 minutes of tangible advice…stuff you can do right now to have a greater impact such as creating a library of on-demand demo videos (and how to sell it to the hyper-competitive leadership crowd).
And, rethinking the “Get a Demo” button that most of you have in the hero image.
He challenges you to think about what customers want when they come to your website:
They want to see what you do
They want to see the products in action so they can really understand how it works.
They want to learn about your pricing.
They want to understand how you compare to others.
And then…they’ll want to talk to sales or do a live demo.
“It’s not about selling better, it’s about helping customers buy better,” he says.
Maximize those things, and you’ll be WAY ahead of the pack.
If you want to make good on the promises you made to investors and grow the company the single most important thing the C-suite needs to get right is hiring.
That’s why we spoke with Michael Bertoni, CEO of PhillyTech.co—a hiring agency dedicated to SaaS.
Most startups have no idea how to hire people and build high-performing teams. They think they can do themselves and find out quickly where the mines are buried.
With a background in sales and lead generation, Bertoni has developed a method that is 100 steps deep. They’re hunting talent by hyper-targeting, and that specialization, combined with his prowess for lead generation, is what makes them so successful.
In this episode, Bertoni shares some of the ingredients to his secret sauce including:
Finding SaaS specialized help that understand how the business operates and the roles and responsibilities required
Must focus on hypertargeting – much like Account Based Marketing (ABM)
How to optimize the hiring process and provide the candidate a great experience
Why the best candidates aren’t on the market, and how to attract them.
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At the 2019 Ascent Conference in New York, Aptiv.io’s CEO Guy Mounier recalls their informal poll about how well their demand generation programs were working.
Two-thirds of respondents said, “we’re fine” or “we’re good.”
Fast forward to the same conference in November 2022 and almost everyone was struggling to cut through the noise to generate qualified leads. Even those with good results were still getting pressure from boards and investors to produce more leads at a lower cost.
Effective demand generation has become like Moore’s Law in reverse – you have to double down on marketing spend every year to maintain the same number of leads.
To solve this conundrum, companies have gravitated towards AI platforms that identify buyer intent signals to prioritize account focus—a space Mounier calls “Revenue AI” where AI platforms can identify buyer intent signals for accounts potentially entering a buying window.
Only a third of the survey respondents knew about the potential of these platforms though—and 90 percent of them said they couldn’t afford it--the value for the money and the complexity didn’t make sense to deploy.
The game changer according to Mounier is to have a 360-degree approach to intent signals (versus the siloed approaches that exist today) and do it a quarter of the cost.
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Guest: Ray Meiring, Co-Founder & CEO at QorusDocs --
Scaling a SaaS business from consultancy roots to enterprise success requires more than just great tech—it takes ruthless focus, smart go-to-market choices, and a deep understanding of your buyer.
In this episode, Ray Meiring, co-founder and CEO of QorusDocs, joins host Ken Lempit to share the lessons learned on his journey from South Africa to the U.S. market and how QorusDocs carved out a winning niche in AI-powered proposal automation.
We unpack: ✅ Why founder-led sales can’t scale—and how to move beyond it ✅ The trap of chasing SMBs after funding (and what to do instead) ✅ How QorusDocs found product-market fit through one anchor customer ✅ What every SaaS CRO and CMO should know about RFP response teams ✅ The critical role of marketing in driving pipeline (not just sales)
Ray also shares the moment venture funding pushed them off course—and how doubling down on their ideal customer profile helped them reset, rebuild, and grow more efficiently.
If you're a SaaS CMO or CRO scaling into enterprise, navigating founder-to-function transitions, or wondering where AI really moves the needle, this episode is packed with firsthand insight.
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With market uncertainty, and the average CMO tenure at 40 months (2020), conducting an executive level job search at some point is inevitable.
While most trade off past relationships, Justin Schmidt, VP of Marketing at Compt.io suggests that “something really magical” happens by putting on the candidate hat and interviewing again as somebody off the street.
By taking interview opportunities that he ultimately didn’t think he would be interested in, Schmidt found value in “the batting practice” - honing his interviewing skills, asking better questions, and “getting the jitters out” for the right opportunity.
Added to Compt’s leadership team in August, Schmidt passes along advice from his recent job search experience including:
How he found the right opportunity (and the right CEO)
Interviewing for the first time; exerting control of the content and narrative, and having the right mindset
Getting proper help on resume writing, career coaching and questions to ask.
Building a new team leveraging past experience, but not beholden to it.
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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup.
At the kickoff of their recent user conference, Dave Becker, CEO of CampusESP told the story of the person he first approached with his company idea for a SaaS that enables parent involvement in higher education.
She told him that “parent involvement is a fad, and I don’t think you have a company here.”
Nine years later, the company has gone from fad, to nice-to-have, to need-to have with over 260 schools representing over four million parents using the platform.
So, how do you pull off category creation?
Certainly not with VC money, although, not for lack of trying.
“It’s a long journey of educating people on the problem, educating them on a solution, and then educating on your solution.”
In fact, Becker shares with fellow entrepreneurs that however long you think it’s going to take, double it.
In this episode, Becker shares key learnings such as:
How difficult it is to get those first few customers.
How they used extensive market and customer research to build a foundation for client acquisition.
Why they had to abandon branding and positioning that didn’t serve the value proposition.
Why it’s important to find the right support network early.
In his bathroom at home is a hole in the door that Becker refuses to fix. “It’s a reminder of how hard this is, and it keeps me grounded.”
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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup.
If you’ve had the experience working with a large company, day one consists of paperwork--lots of it--and it contributes to a poor first impression.
Simply increasing the percentage of people that accept offers and actually start work would have a massive bottom-line impact.
And it’s not just day one. Research shows that what happens in the first 90 days of an employee’s tenure plays a big role in retention.
It’s hard for the all-in-one HR software behemoths to be experts at every component an HR team must solve, but so is getting traction as a best-of-breed startup.
That’s the situation CEO Mike Ehrle walked into a year ago at Click Boarding, a SaaS that’s an employee experience platform and provides modern compliant HR solutions to impact higher growth and retention rates.
In this episode, Ehrle sheds some light on his experience with:
Fixing internal issues and transforming to a collaborative culture
Dealing with unforeseen issues he missed in his due diligence (like development staff located in Ukraine prior to Russia’s invasion)
The need for product and business expertise to build key relationships in target accounts.
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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup.