Crossing the Enterprise Chasm

Michael Grinich
  • 5.0 (4)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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.

  1. Avoiding the PLG Trap: Strategies for Scaling to Enterprise

    02/04/2025

    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.

    25 min
  2. How to Make B2B Marketing for Developers Actually Helpful

    10/24/2024

    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.

    26 min
  3. Maintaining a Developer-centric Focus with Product-led Sales

    09/27/2024

    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.

    34 min
  4. The Importance of Complementing PLG with SLG

    08/27/2024

    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.

    24 min
  5. The Power of Developer Evangelism, Authentic Content, and Simple Messaging

    08/13/2024

    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.

    22 min
  6. The 7 Go-to-market Principles for Developer Products

    07/30/2024

    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

    25 min
  7. The Art of Balancing Strategy and Emotion in Platform Marketing

    07/16/2024

    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

    22 min
  8. Unpacking DevRel: Responsibilities, Metrics, and the Importance of Community

    07/02/2024

    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

    21 min
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Ratings & Reviews

5
out of 5
4 Ratings

About

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.

Information

  • Creator
    Michael Grinich
  • Years Active
    2021 - 2025
  • Episodes
    31
  • Rating
    Clean
  • Copyright
    © WorkOS, Inc.