The Drafting Table

After a decade of investing in enterprise software, I've noticed something fascinating: While everyone talks about becoming a founder someday, almost no one discusses the tactical skills you need to master before making that leap. That's why I'm launching "The Drafting Table" – a podcast and content series dedicated to uncovering the tactical skills that separate successful operators and founders from those stuck in the dreaming phase.

The Drafting Table is a business podcast hosted by Jess Lin, with 15 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Jess Lin hosts The Drafting Table, a business show with 15 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  The Drafting Table

  The Truth About Product-Led Growth and How This Company Got It Right, with David Dorman VP Growth at Grafana Labs

  Aug 5, 202559 minS0

  <p>Product-led growth (PLG) isn’t just a switch you flip, it’s a strategy that only works when layered with thoughtful go-to-market. David Dorman VP Growth / Self-Service at Grafana Labs, joins The Drafting Table to share what it really takes to scale Product-Led Growth inside a modern SaaS company.</p><p><br></p><p>In this episode, Jessica Lin and David break down:</p><p><br></p><p>✅ Why great PLG starts with a product that actually speaks for itself</p><p><br></p><p>✅ The playbooks Grafana borrowed and rewrote, from DigitalOcean</p><p><br></p><p>✅ How to balance...

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  The Drafting Table

  What Every First-Time Startup Founder Needs to Know, According to Jessica Lin of Work-Bench

  Jul 30, 202539 minS0

  <p>How do you know if your idea is strong enough to build a company? When is the right time to raise funding, or hire your first employee? And what actually matters most at the seed stage?</p><p>In this episode of The Drafting Table, Jessica Lin, co-founder and general partner at Work-Bench, an early stage enterprise software & Saas VC firm in NYC, answers the most frequently asked questions from early-stage founders.</p><p>From figuring out if you need a co-founder, to founder-led sales, to when to build a prototype, Jessica shares the unfiltered realities of startup life...

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  The Drafting Table

  What does it really take to build and scale a modern healthcare startup in 2025? | Akash Magoon – CEO and Co-founder of Adonis, Trey Holterman – CEO and Co-founder of Tennr

  Jul 17, 202555 minS0

  <p>What does it really take to build a fast-growing healthtech startup in one of the most complex industries in the world?</p><p>In this episode of The Drafting Table, Jessica Lin sits down with Akash Magoon (Co-founder & CEO of Adonis) and Trey Holterman (Co-founder & CEO of Tennr) to unpack the early journeys of two of NYC’s fastest-growing healthcare startups.</p><p>They talk about the brutal reality of finding product-market fit in healthcare, navigating buyer resistance, building through messy integrations, choosing the right go-to-market strategy, and why saying "yes" too often nearly killed their early momentum.</p><p>...

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  The Drafting Table

  How Merge Landed the World’s Biggest Bank, with Shensi Ding, Co-Founder of Merge

  Jun 10, 202544 minS0

  <p>Can a startup go straight to enterprise and survive? Shensi Ding, Co-Founder at Merge, shares how they scaled from zero to 25,000+ customers by starting enterprise-first, rebuilding their go-to-market team, and why founders should skip SMBs entirely.</p><p><br /></p><p>⏱️ Timestamps</p><p><br /></p><p>3:00 – Merge's origin story and why they wish they started with enterprise sooner</p><p><br /></p><p>8:34 – The case for starting enterprise-first vs selling to startups</p><p><br /></p><p>13:30 – Rebuilding go-to-market: hiring new CRO and team</p><p><br /></p><p>18:00 – Rethinking B2B marketing beyond LinkedIn vibes</p><p><br /></p><p>...

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  The Drafting Table

  The Hidden Cost of Shipping Fast: How to Prioritize Without Burning Out Your Team

  Jun 3, 202548 minS0

  <p>It’s easy to keep saying yes to new features. It’s a lot harder to say no, especially when the customer is dangling a big contract.</p><p><br /></p><p>In this episode of The Drafting Table, Danielle Leong (CTO at FireHydrant and former engineering leader at Twilio and GitHub) breaks down how to scale product and engineering without running your team into the ground.</p><p><br /></p><p>We dive into the practical tradeoffs every founder faces between building what customers want and maintaining a healthy, high-functioning product team.</p><p><br /></p><p>Together with...

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