The Drafting Table

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. In this episode, Jessica Lin and David break down: ✅ Why great PLG starts with a product that actual...

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? 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 ear...

What does it really take to build a fast-growing healthtech startup in one of the most complex industries in the world? 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. They talk about the brutal realit...

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. ⏱️ Timestamps 3:00 – Merge's origin story and why they wish they started with enterprise sooner 8:34 – The case for starting enterprise-first vs sell...

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. 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. We dive into the practical tradeoffs every founde...

Most founders think they’ve hit product-market fit. Kevin Wang wants you to prove it. As Chief Product Officer at Braze (NYSE: BRZE), Kevin joined the team in 2012 as an early engineer and helped build the company from near-zero to 2,200+ customers and $500M+ in revenue. In this episode of The Drafting Table , he sits down with Jessica Lin to unpack the messy, unsexy reality of what PMF actually f...

What does it really take to raise and run a venture fund from scratch? In this special episode of The Drafting Table , Work-Bench co-founders Jessica Lin and Jon Lehr pull back the curtain on their 12-year journey building one of New York’s most respected enterprise seed funds. They share the lessons they wish someone had told them before they ever raised their first fund—and the painful, tactical...

Most founders think if they build a great product, the pipeline will magically appear. It won’t. In this episode of The Drafting Table, Alex Rosemblat (Advisor and Former CMO at Datadog ) joins us for a tactical breakdown of how startups should actually think about marketing — especially in the early days. We cover: Why “knowing your customer” is a cliché…until you realize you really don’t How Dat...

Most founders don’t realize it, but they could be wasting thousands of dollars attending conferences — and getting very little pipeline to show for it. In this episode of The Drafting Table , Amy Holtzman (CMO at CHEQ and former marketing leader at Splash, AlphaSense, and Conductor) breaks down the exact prep, playbook, and post-event tactics her team uses to turn conferences into real revenue. 🎙️...

Most founders think the sale ends with a signed contract. But according to Rose Kozar, that’s just the beginning. In this episode of The Drafting Table, Rose Kozar —VP of Client Solutions at Courier Health —makes the case that post-sales is the most overlooked growth lever in SaaS. She breaks down how to run high-impact QBRs (Quarterly Business Reviews) that retain customers, unlock expansion, and...

In this episode of The Drafting Table, Jess sits down with her teammate, Work-Bench investor Daniel Chesley for a rare behind-the-scenes look at how early-stage VC decisions actually get made. If you’re a pre-seed or seed-stage founder, this is the real talk you’ve been craving—but rarely get from investors. We break down: What separates a great wedge from a forgettable one Why your “champagne pro...

Most founders want to hire an SDR as soon as they’ve closed a few deals. Alexandra Kane (VP of Revenue at Chalk) says that’s a massive mistake. In this episode of The Drafting Table, we dive into the tactical truths no one tells you about early-stage sales: how founders should approach cold outbound, when to actually hire an SDR, and why your cold email probably sucks. Alexandra has led GTM at B2B...

Most seed-stage enterprise software founders obsess over topline growth. But the smartest ones? They dig deeper. In this episode of The Drafting Table, Jessica Lin sits down with Michaela Lehr , seasoned CFO and startup finance leader, for a tactical breakdown of the non-obvious SaaS metrics that actually matter. Whether you’re building your first model, navigating messy margins, or just trying to...

Most SaaS founders get product launches wrong. They think it’s about blasting their features everywhere on Day 1—but the best launches don’t happen in just one day. In this episode of The Drafting Table, I sit down with Natalie Marcotullio, Head of Growth and Product Marketing at Navattic, to break down how to run a product launch that actually works. We cover:✅ Why you shouldn’t launch the day y...

Your startup’s biggest risk isn’t running out of money—it’s running out of alignment. In this episode of The Drafting Table, I sit down with David Politis, founder of BetterCloud, to unpack one of the most underrated yet critical skills every founder needs: building an effective operating rhythm. We cover:✅ Why every startup needs a structured operating rhythm (even at 5 people!)✅ How to run all...