Crossing the Enterprise Chasm is a podcast on how high-growth startups prepare to build with enterprises and Fortune 500 companies. Each week WorkOS founder Michael Grinich is joined by founders, early-stage team members, and product leaders who lead the charge to go upmarket. In every episode, you'll find tactics, strategies, and actions on how to successfully sell to and serve your crucial early enterprise customers.
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Avoiding the PLG Trap: Strategies for Scaling to Enterprise
25:28
25:28
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25:28WorkOS 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.By Michael Grinich
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How to Make B2B Marketing for Developers Actually Helpful
26:18
26:18
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26:18WorkOS 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.By Michael Grinich
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Maintaining a Developer-centric Focus with Product-led Sales
33:46
33:46
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33:46WorkOS 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.By Michael Grinich
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The Importance of Complementing PLG with SLG
24:18
24:18
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24:18WorkOS 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.…
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The Power of Developer Evangelism, Authentic Content, and Simple Messaging
22:28
22:28
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22:28WorkOS 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.By Michael Grinich
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The 7 Go-to-market Principles for Developer Products
24:53
24:53
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24:53In 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…
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The Art of Balancing Strategy and Emotion in Platform Marketing
21:33
21:33
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21:33In 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 th…
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Unpacking DevRel: Responsibilities, Metrics, and the Importance of Community
20:56
20:56
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20:56In 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 fu…
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Maintaining Developer Trust While Scaling Upmarket
24:32
24:32
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24:32In 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 o…
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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=8SqYzDD7JZ4By Michael Grinich
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Successfully Scaling Developer Products with Customer-Led Sales
25:07
25:07
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25:07In 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.By Michael Grinich
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Achieving the First $100M in Revenue Without a Sales Team
26:08
26:08
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26:08In 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.By Michael Grinich
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The Crucial Role of Customer Feedback when Building Developer Products
20:37
20:37
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20:37In 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.By Michael Grinich
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Harnessing Down Market Constraints for Up Market Success
24:35
24:35
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24:35In 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 …
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Building Successful Developer Products in a Crowded Landscape
23:43
23:43
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23:43In 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.By Michael Grinich
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Adapting Open Source Developer Products for Commercial Enterprise
23:05
23:05
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23:05In 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.By Michael Grinich
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Balancing Self-serve and Sales-lead Outbound for Developer Products
20:09
20:09
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20:09In 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.…
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The Critical Role the Developer Plays in Winning Enterprise Deals
20:41
20:41
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20:41In 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.By Michael Grinich
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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.…
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Scaling Teams for D2D: Developer-to-Developer Tools
21:48
21:48
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21:48In 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.By Michael Grinich
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How compliance and customer trust will grow your business
27:11
27:11
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27:11In this episode, WorkOS CEO Michael Grinich and Drata's CTO Daniel Marashlian talk about security, compliance, and startup growth.By Michael Grinich
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How focusing your efforts on the correct buyer persona will scale your business
28:02
28:02
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28:02In 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.…
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Building the Next Generation of Developer Tools
27:26
27:26
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27:26In 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-yea…
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What is good for the Developer IS good for Enterprise
25:46
25:46
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25:46In 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.By Michael Grinich
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Grow Your Business Through Community, with Notion CRO Olivia Nottebohm
25:35
25:35
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25:35In 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.By Michael Grinich
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Prepare to Sell to Enterprises After Finding Product-Market Fit, with Superhuman CEO Rahul Vohra
23:04
23:04
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23:04In 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.…
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Identifying the Right Customers to Serve, with Ramp CEO Eric Glyman
22:32
22:32
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22:32In 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.By Michael Grinich
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Understanding Users and Choosers through Customer Advisory Boards, with Slack VP Ilan Frank
27:32
27:32
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27:32Michael 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 c…
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Dive Deep Into Go-to-Market Strategy With Webflow CTO Bryant Chou
24:34
24:34
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24:34In 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.…
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Blend Developer Experience and Enterprise Sales, with Vercel CEO Guillermo Rauch
26:42
26:42
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26:42In 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.By Michael Grinich
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1
Breeze Through SOC 2 Compliance with Vanta CEO Christina Cacioppo
22:39
22:39
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22:39In 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.By Michael Grinich
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