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Crossing the Enterprise Chasm
Michael Grinich
31 episodes
5 months ago
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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Entrepreneurship
Business
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All content for Crossing the Enterprise Chasm is the property of Michael Grinich and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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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Entrepreneurship
Business
Episodes (20/31)
Crossing the Enterprise Chasm
Avoiding the PLG Trap: Strategies for Scaling to Enterprise

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. 

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9 months ago
25 minutes

Crossing the Enterprise Chasm
How to Make B2B Marketing for Developers Actually Helpful

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.

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1 year ago
26 minutes

Crossing the Enterprise Chasm
Maintaining a Developer-centric Focus with Product-led Sales


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.

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1 year ago
33 minutes

Crossing the Enterprise Chasm
The Importance of Complementing PLG with SLG

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.

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1 year ago
24 minutes

Crossing the Enterprise Chasm
The Power of Developer Evangelism, Authentic Content, and Simple Messaging

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.


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1 year ago
22 minutes

Crossing the Enterprise Chasm
The 7 Go-to-market Principles for Developer Products

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

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1 year ago
24 minutes

Crossing the Enterprise Chasm
The Art of Balancing Strategy and Emotion in Platform Marketing

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

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1 year ago
21 minutes

Crossing the Enterprise Chasm
Unpacking DevRel: Responsibilities, Metrics, and the Importance of Community

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

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1 year ago
20 minutes

Crossing the Enterprise Chasm
Maintaining Developer Trust While Scaling Upmarket

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

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1 year ago
24 minutes

Crossing the Enterprise Chasm
Driving Growth through DevRel

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


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1 year ago
27 minutes

Crossing the Enterprise Chasm
Successfully Scaling Developer Products with Customer-Led Sales

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. 

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2 years ago
25 minutes

Crossing the Enterprise Chasm
Achieving the First $100M in Revenue Without a Sales 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. 

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2 years ago
26 minutes

Crossing the Enterprise Chasm
The Crucial Role of Customer Feedback when Building Developer Products

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. 

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2 years ago
20 minutes

Crossing the Enterprise Chasm
Harnessing Down Market Constraints for Up Market 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.

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2 years ago
24 minutes

Crossing the Enterprise Chasm
Building Successful Developer Products in a Crowded Landscape

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. 

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2 years ago
23 minutes

Crossing the Enterprise Chasm
Adapting Open Source Developer Products for Commercial Enterprise

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.

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2 years ago
23 minutes

Crossing the Enterprise Chasm
Balancing Self-serve and Sales-lead Outbound for Developer Products

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.

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2 years ago
20 minutes

Crossing the Enterprise Chasm
The Critical Role the Developer Plays in Winning Enterprise Deals

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.

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2 years ago
20 minutes

Crossing the Enterprise Chasm
Shaping Product for Enterprise

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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2 years ago
25 minutes

Crossing the Enterprise Chasm
Scaling Teams for D2D: Developer-to-Developer Tools

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. 

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2 years ago
21 minutes

Crossing the Enterprise Chasm
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.