Explore every episode of the podcast Crossing the Enterprise Chasm

WorkOS CEO, Michael Grinich, and former Asana CRO Oliver Jay discuss insights on the benefits of targeting outbound to existing customers, international expansion, and the challenges and strategies of scaling from product-led growth (PLG) to enterprise sales while avoiding the PLG trap. 

WorkOS CEO, Michael Grinich, and Augment Code Acting CMO, Francois Dufour, discuss the enterprise shift during Francois’ time at Twilio, B2B marketing that is actually helpful for developers, and early signals that indicate the right time to build for the enterprise.

WorkOS CEO, Michael Grinich, and Sanity CEO, Magnus Hillestad, discuss the evolution of Sanity, starting with its origins as a PLG company focused on developer advocacy and open source, and transitioning to a product-led sales strategy that better serves enterprise customers.

WorkOS CEO, Michael Grinich, and Timescale CEO, Ajay Kulkarni, dive into Timescale’s own journey to becoming Enterprise Ready. They discuss the limitations of relying solely on PLG and why you must layer in sales, the importance of saying no to certain customer requests, and the risks of relying too heavily on past relevant experiences when hiring.

WorkOS CEO, Michael Grinich, and Datadog CMO, Sarah Varni, discuss learnings from Twilio’s growth from $400 million to $2.8 billion in revenue, the importance of developer evangelism as a function, and the nuances of marketing a broad platform like Datadog.

In this episode, WorkOS CEO, Michael Grinich, and Partner at Calyx Consulting and former director of platform marketing at Slack, Ceci Stallsmith, discuss the tactics of building successful ecosystems, the importance of founder-led brand experience, and the seven principles of developer GTM.
 Watch the full episode here:https://youtu.be/ArxOC9JG6W4

In this episode, WorkOS CEO, Michael Grinich, and former CEO at Vimeo, Adam Gross, discuss the evolution of platform marketing and what it means to balance between strategic and emotive elements in building successful products. They also dive into the distinct challenges and strategies involved in marketing developer-focused platforms. 

Check out the talk that Adam mentions in the episode here: https://www.youtube.com/watch?v=za7PbKZcnos

In this episode, WorkOS CEO, Michael Grinich, and Director of Developer Relations at Pinecone, Bear Douglas, explore the definition and importance of DevRel including its interplay with product and marketing. They also dive into the metrics for success, the role of community, and advice for startups considering their first DevRel hire. Watch the full episode here: https://youtu.be/c83NYZ2eUj4

In this episode, WorkOS CEO, Michael Grinich, and Co-founder of Phenomenal Ventures and former Head of Marketing at Plaid, Helen Min, discuss the importance of maintaining developer trust, hiring smart generalists as first marketing hires, and maintaining a robust relationship between marketing and sales. For additional insights, be sure to check out Helen’s blog here: https://helenmin.com/blog

In this episode, WorkOS CEO Michael Grinich and co-founder of HyperGrowth Partners Martin Gontovnikas discuss tactics around building community engagement and how to stand out from the crowd. Watch the full episode here: https://www.youtube.com/watch?v=8SqYzDD7JZ4

In this episode, WorkOS CEO Michael Grinich and former Head of Revenue at Plaid Paul Williamson discuss the power of an intense focus on the success of the Developer, the importance of a seamless end-user experience, and what candidate profile to look for when building out your go-to-market team. 

In this episode, WorkOS CEO Michael Grinich and Atlassian Chief Revenue Officer Cameron Deatsch discuss Atlassian’s unconventional approach to sales, focusing on self-serve sales to successfully scale, and Atlassian’s transition into the enterprise market. 

In this episode, WorkOS CEO Michael Grinich and LaunchDarkly Co-Founder and Executive Chair Edith Harbaugh discuss the importance of personal interaction when selling new technology, early founder-led sales, and the long road to success. 

In this episode, WorkOS CEO Michael Grinich and Cloudflare Co-Founder, President and COO Michelle Zatlyn discuss how the early constraint in building easy-to-integrate and financially viable product for small businesses became an asset when selling to enterprise, and how important the sharing of future roadmap with customers is to staying relevant and warding off the competition.

In this episode, WorkOS CEO Michael Grinich and Cockroach Labs Co-Founder and CEO Spencer Kimball discuss the importance of execution over ideas, the need for exploratory sales in early GTM teams, and leveraging technical content to target developers. 

In this episode, WorkOS CEO Michael Grinich and HashiCorp Co-Founder and CTO Armon Dadgar discuss open core strategy, the challenges surrounding cloud-based product adoption for traditional enterprise, and the evolution of enterprise commercial structure.

In this episode, WorkOS CEO Michael Grinich and former CRO at Segment Joe Morrissey discuss how to layer in an outbound sales motion on-top of a self-serve motion for developer products, the advantages of leveraging an early sales team in product development, and usage-based vs. pre-bought consumption pricing.

In this episode, WorkOS CEO Michael Grinich and Flatfile CEO and David Boskovic discuss how to foster the developer champion, the critical role they play in winning enterprise deals and how building “hero features” changes the enterprise buying cycle.

In this episode, WorkOS CEO Michael Grinich and former GitHub VP of Worldwide Sales Paul St. John cover how the GitHub sales team lead the open source software to enterprise sales. They also talk about how social coding changes workflows for the better, and how a sales team can be instrumental in driving product market fit. 

In this episode, WorkOS CEO Michael Grinich and former Stripe COO and and author of 'Scaling People' Claire Hughes Johnson cover how the early Stripe team navigated explosive growth, both from a product and people perspective. 

In this episode, WorkOS CEO Michael Grinich and Drata's CTO Daniel Marashlian talk about security, compliance, and startup growth.

In this episode, WorkOS CEO Michael Grinich and Vinay Hiremath who's the Co-Founder, CTO, and VP of People at Loom, talk about Loom's journey. They discuss how it started out as a tool that empowered individuals and small teams to being a part of large companies' cultures. They go over what went well and what could've been done differently.

In this episode, WorkOS CEO Michael Grinich and PlanetScale's CEO Sam Lambert discuss how to build an exceptional Developer experience that enables Software Development teams of all sizes. And how to do it in a way that a developer who is at the absolute bleeding edge, hottest startup can use the same technologies as someone who is at a hundred-year-old company that is revolutionizing their technology. 

In this episode, WorkOS CEO Michael Grinich and Netlify Co-founder, chief strategy, and creative officer Chris Bach cover balancing between building for developers and building for Enterprise customers.

In this episode, WorkOS CEO Michael Grinich and Notion CRO Olivia Nottebohm cover how businesses can create engines of community-led growth for their products. They also talk about customer advisory boards, cultivating an ecosystem, and customer communication.

In this episode, WorkOS CEO Michael Grinich and Superhuman CEO Rahul Vohra cover what happens after a company finds product-market fit: getting enterprise ready. They also talk about when to hire a sales team, how to scale up high touch onboarding, and the philosophy driving a product that hundreds of thousands of people are on a waitlist for.

In this episode, WorkOS CEO Michael Grinich and Ramp CEO Eric Glyman cover how to choose the right customers to serve. They also talk about organizational speed, why sales and support need to stay connected, and how Ramp expanded from corporate cards into a financial automation platform.

Michael Grinich (00:02):

Welcome to Crossing the Enterprise Chasm, a podcast about software startups and their journey, moving upmarket to serving enterprise customers. I'm your host, Michael Greenwich. I'm the founder of WorkOS, which is a platform that helps developers quickly ship common enterprise features like Single Sign-On. On this podcast cast, you'll hear directly from founders, product leaders and early stage operators who have navigated building great products for enterprise customers. In every episode, you'll find strategies, tactics, and real world advice for ways to make your app enterprise ready and take your business to the next level.

Michael Grinich (00:38):

Today I'm joined by Ilan Frank VP of Enterprise Product at Slack. Slack is of course used by lots of small and medium size companies. But over the last several years, the product has also been adopted by very large organizations like Walmart, Nike, News Corp, and IBM. Along the way this meant Slack needed to become enterprise ready and build lots of new features and functionality for IT admins. We're going to dig into all this and more, and talk about the way Slack was able to move up market and cross the enterprise chasm. Ilan, let's get started by going back in time. Tell us about back when you joined Slack five years ago, what was the state of the enterprise business and product for those customers?

Ilan Frank (01:18):

It's actually been almost six years. It's crazy, time really flies by. So in early 2016, when I joined we had enterprise customers, but for the most part there were 20 people that were called account managers and we were taking orders. If the people didn't want to pay with credit card, if they were large organizations and they wanted to have some type of enterprise wide license agreement. Those 20 people would basically take down their information and really kind of work with them to structure some type of invoicing rather than credit card transaction. But that was kind of the state of our enterprise world. We really didn't have a sales team, certainly not a customer success team. And the product itself was also very immature from an enterprise perspective. The only thing that we had at that time from what we call enterprise features was SSO. That was the first feature that we developed. And that was about all we had at that point.

Michael Grinich (02:10):

Was that developed before you joined? Were you part of that, the SSO Feature?

Ilan Frank (02:13):

It was, the SSO feature was developed just before I joined that's right. In 2015, we launched SSO.

Michael Grinich (02:19):

Do you remember what folks were asking for at that time? You only had SSO. The buying motion was opposite, this is kind of an entire separate thing. Sales maturity around selling enterprise, but from a product functionality perspective, what we're folks asking for? Where was Slack maybe not up to par from there? What they needed?

Ilan Frank (02:36):

Quite a few things. I mean the first thing which doesn't necessarily relate to WorkOS, but Slack in general, is just reliability. I don't know if anyone has read any articles about 2015 in Slack, but if you had a team of larger than 5,000 or so people. Slack was not the most reliable platform to be on at that point. So that's the first thing is customers like IBM came to us and said, "Okay, we can't even hit 5,000 people. How are we going to get 400,000 people on this thing?"

Ilan Frank (03:02):

So that was one of our main focuses initially on the enterprise side is okay, "How do we actually re architect Slack?" Because it was built as a team tool, for a hundred people, the initial pitch deck was there's going to be teams of a hundred. And if you want more than that, you go create another team. But now how do we scale that from that to 400,000 people at IBM, all in one channel together for announcements or anything like that. So scalability was job one initially.

Ilan Frank (03:26):

And then I joked that in 2016, I said the word table stakes, or heard it more than any other time in my career. The tables stakes feature from enterprise were obviously expanding some of the SSO, so supporting other IDPs, we had to support SCIM for provisioning and de provisioning. So that was something that we developed in 2016 so that you can do that. We had to do all kinds of things around compliance. So everything from eDiscovery to DLP, data protection at data exports, anything like that was basically 2016 and that's when we started really that effort. And then finally some administration features basic administration features around users, permissions things like that. Those were kind of the table stakes features that people wanted that first year.

Michael Grinich (04:13):

How did you build intuition to know what to built here, or not even intuition, but how did you actually know what to build? Was it coming from the sales team, you connecting with IT, walk us through. I think many people listening are either at that similar spot or about to be at that spot. How do you assess what features to build? Or how did you build your roadmap around that?

Ilan Frank (04:33):

So a couple ways. Certainly we had a product gaps type of process where sales people and SEs could report what they're hearing as show stoppers from the field. And so we wanted to pay attention to that, but we actually, from a product perspective, we actually did our own TAM analysis. And looked at the market and looked at these features around compliance and security as ways to really unlock TAM. And so the basic ones were basically we're at multiple organizations, almost any public organization is going to need the features that I just spoke about. From SSO to provisioning and de provisioning, specifically, some type of device management to the ability to manage devices. And so there's like a basic level of kind of Maslow's hierarchy that you just need to meet in order to really be taken seriously in the enterprise.

Ilan Frank (05:25):

And then there are other features that you have to be careful about because they sound enterprisey, but they really are pertaining to a specific geography or a specific industry. And those are the ones that you have to be careful not to rush off and do right away. I would hold those off into later years. So for example, we have a lot of requirements around FINRA and financial services. Regulation around compliance, data archiving, legal holds, different types of formats of data export. Which financial services companies like Goldman Sachs will say, "This is a must have." And they're probably right. It is a must have, but it is a must have for the financial service's industry, not for every single organization.

Ilan Frank (06:05):

So you have to really think, what is this going to open up for me as an organization? Are we ready to take on financial services or healthcare? The same thing with healthcare? I advise companies that I work with who look at obviously high tech first then after that media, companies like the Netflix's, HBOS, CBS, Hulu, Disney. These are going to be companies that are usually forward looking then the professional services type organizations. Or organizations that provide a service and only fourth is financial services. So the Capital Ones, American Expresses they're going to be forward looking for financial services. But they're not forward looking compared to all of the other companies that are going to come before it, on those other industries.

Speaker 3 (06:52):

Is that kind of just TAM analysis as you're talking to that?

Ilan Frank (06:53):

...

In this episode, WorkOS CEO Michael Grinich and Webflow CTO Bryant Chou cover an enterprise go-to-market strategy for product-led growth SaaS companies. They also talk about product-market fit, discerning between consumer customers and enterprise customers, and experimenting with the enterprise sales motion.

In this episode, WorkOS CEO Michael Grinich and Vercel CEO Guillermo Rauch cover how developer-focused businesses can get enterprise ready. They also talk about enterprise sales, customer success, and security.

In this podcast, WorkOS CEO Michael Grinich and Vanta CEO Christina Cacioppo cover how businesses can unlock new markets and accelerate deals with SOC 2 compliance. They also talk about bug bounties, security practices, and enterprise sales.