The Drafting Table

Jess Lin
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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.

  1. 08/05/2025

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

    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 actually speaks for itself ✅ The playbooks Grafana borrowed and rewrote, from DigitalOcean ✅ How to balance top-down sales with bottom-up adoption ✅ The biggest mistakes founders make with community and activation ✅ Why the best growth strategies still start with talking to your users David gets into the brass tacks of funnel segmentation, onboarding personalization, nurture strategies, and building champions in the enterprise. If you’re trying to build a self-serve motion without losing sight of your end user, this one’s packed with lessons you’ll want to revisit. 🎧 Subscribe for more conversations like these. #ProductLedGrowth #GoToMarket #SaaSFounders #DeveloperMarketing #OpenSourceGrowth

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  2. 07/30/2025

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

    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 early-stage founders. 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 and why finding the fun might just be your biggest advantage. Whether you’re pre-idea, pre-seed, or scaling your first customers, this episode is packed with battle-tested advice and frameworks to help you build with more clarity, confidence, and grit. — ⏱️ Timestamps 00:00 – Intro + Thank you for this Season 00:35 – How do I know if my idea is good enough? 01:56 – What does “venture scale” really mean? 02:39 – How much traction do I need to raise VC? 04:32 – Should I build a prototype or MVP before fundraising? 05:34 – Do I need a co-founder? What to look for 07:46 – What do investors want to see at seed stage? 09:14 – How do I find and approach investors? 10:24 – How do I get my first 10 customers? 12:37 – How important is picking a specific vertical early on? 15:33 – How do I hire early employees without capital? 18:16 – What’s the hardest part of being a founder? 20:27 – How can I prep for being a founder before I make the leap? 22:13 – When should I hire a sales rep vs doing founder-led sales? 24:24 – What does product-market fit really feel like? 26:25 – Can I go enterprise-first? Or start with SMB? 30:33 – Why enterprise sales is all about change management 33:15 – 90% of enterprise sales happen when you’re not in the room 35:13 – How many leads do I really need? A smarter approach to B2B marketing 38:11 – Wrap: What Work-Bench looks for in founders 41:05 – Why unique perspectives and contrarian views stand out 43:03 – Final advice: Find the fun, it’s a long journey—🎧 Subscribe for more conversations like these#startupadvice #venturecapital #founderplaybook #seedstage #startuplife #b2bsales #workbench #thedraftingtableshow

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  3. 07/17/2025

    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

    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 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. This is not a highlight reel. It's the real stuff: tough pivots, million-dollar mistakes, and why early-stage execution matters more than perfect strategy.—⏱️ Timestamps00:00 – Intro: Meet the founders and the Work-Bench team 07:12 – Meet Akash (Adonis) and Trey (Tennr) 10:28 – How both founders stumbled into their ideas via personal pain points 12:59 – First-time vs second-time founders: what actually gets easier 14:20 – How they really found product-market fit 17:01 – The danger of building compound products too early 20:22 – Cutting early revenue to focus: painful but necessary 23:43 – Why focus too early can also be a trap 25:06 – Why healthcare integrations are brutal and where founders get it wrong 28:40 – Go-to-market: who pays, how to choose, and landing early customers 30:55 – Pitching ROI when your product replaces headcount 33:00 – Pricing lessons: subscriptions + usage models 36:10 – Selling into healthcare: make it fun, not performative 38:20 – Your first customers should feel like your only customers 40:07 – What they’d do differently starting from scratch 42:10 – Hiring with industry context vs generalists 43:58 – How they manage long sales + implementation cycles 47:07 – Selling to PE-backed provider groups: lessons and myths 49:58 – Moats in healthcare: what actually matters 54:10 – AI in healthtech: team impact and realistic expectations 58:51 – The biggest bets they’re making this year Subscribe for more conversations like these—#healthtech #startups #productmarketfit #gtmstrategy #venturecapital #workbench #adonis #tennr #b2bsaas #founderstory #startupmistakes #healthcareinnovation #beyondthecore

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  4. 06/10/2025

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

    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 selling to startups 13:30 – Rebuilding go-to-market: hiring new CRO and team 18:00 – Rethinking B2B marketing beyond LinkedIn vibes 27:00 – Sales decks, POCs, and what actually closes enterprise deals 30:00 – AI in engineering: why founders should still code 38:00 – Pricing power and enterprise vs startup sales 42:00 – Fundraising and founder-VC dynamics #b2bsales #enterprisesaas #startupfundraising #venturecapital #startuptips #merge

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  5. 06/03/2025

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

    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 founder faces between building what customers want and maintaining a healthy, high-functioning product team. Together with Work-Bench General Partner Jessica Lin, Danielle shares tactical frameworks on: How to prioritize feature work vs. internal tooling Ways to avoid the “feature treadmill” while still closing deals How to use support tickets as early product health signals When to invest in design, implementation tooling, and debt paydown Why fast doesn’t always mean better and what to track instead How to build product that customers love without killing your roadmapThis episode is a must-watch for early-stage founders, engineering leaders, and PMs navigating the messy middle between MVP and maturity. — ⏱ Timestamps 00:00 – Why “watching users struggle” is the best form of discovery 03:00 – Ruthless prioritization: building what users will pay for 09:00 – Feature parity vs. product identity 12:30 – What Twilio got right about customer empathy 17:00 – When internal tooling should take priority 22:00 – Why engineering estimates always go wrong (and how to fix it) - Also check out this blog post for more on this: https://www.rubick.com/steel-threads/ 26:30 – How FireHydrant ties engineering effort to company goals 34:00 – How to align your whole team around cost-consciousness 37:00 – Implementation, margins, and the myth of “free” customers 40:00 – Where AI tools are helping and where they still fall short 44:00 – The one question Danielle asks every founder she advises — 📌 For early-stage B2B founders, engineering leaders, and PMs building sustainable product roadmaps. Hosted by Jessica Lin, General Partner at Work-Bench.

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  6. 05/28/2025

    How Do You Find Product-Market Fit When No One Cares Yet? With Kevin Wang, Chief Product Officer at Braze

    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 feels like—and why most early teams get it wrong. Together, they break down: The difference between polite interest and real buyer urgency What not to build when selling to enterprise customers How “cool ideas” derail early product roadmaps Why great support tickets are a PMF signal And the one metric that matters post-PMF: product velocity If you’re in the dark forest trying to find real traction, this is your flashlight. No fluff. No theory. Just hard-won lessons from a builder who’s seen it all. — 📌 Highlights: 00:00 – Why “Wouldn’t it be cool if…” is a red flag 02:00 – Product-market fit is not a vibe—it’s obvious when it’s real 06:00 – When to pivot, and when to wait for the market to catch up 09:00 – B2B PMF ≠ consumer PMF 13:00 – How Braze’s first 10 customers shaped the roadmap 17:00 – Why product velocity is everything post-PMF 22:00 – Pricing models, regret, and reversibility 25:00 – Why being shameless is a competitive advantage — 🎙️ The Drafting Table is hosted by Jessica Lin, General Partner at Work-Bench. Subscribe for tactical conversations with top enterprise builders.

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  7. 05/13/2025

    12 Years, 12 Lessons: The Unfiltered Playbook for Emerging VCs, with Jonathan Lehr, Co-Founder/GP at Work-Bench

    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, and often hilarious moments that shaped Work-Bench along the way. From getting cold-shouldered by LPs to standing by a tea table just to get a pitch in (yes, that happened), this episode is a no-BS masterclass for emerging managers and anyone dreaming of building a lasting VC franchise. We cover: What actually moves an LP through the funnel The “slot strategy” that helps create urgency when closing Why your data room is probably too thin What fund management really looks like behind the scenes Why staying disciplined—especially in hype cycles—is your biggest moat How to build in public (and let LPs “lurk”) Why GP-GP references matter more than you think The infamous “tea pitch” and what it taught us about shameless hustle What it means to build a fund, a team, and a franchise for the long haul 📍 Whether you’re raising your first $10M fund or scaling your third, this one’s for you. Hosted by Jessica Lin (General Partner, Work-Bench) 🎧 Listen wherever you get your podcasts.

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  8. 05/06/2025

    How Great Startups Build Pipeline From Day One, with Alex Rosemblat, Advisor and Former CMO at Datadog

    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 Datadog thought about scoping, focus, and qualifying customers out What kinds of marketing campaigns actually worked — and which failed A simple formula any founder can use to figure out how much pipeline they actually need The biggest mistake technical founders make when trying to build go-to-market How Datadog transitioned from PLG to enterprise — and the hidden lessons they learned Whether you’re just getting your first users or trying to scale to your first million in ARR, this episode will leave you with practical, non-obvious insights on how to build pipeline the right way. Subscribe to The Drafting Table for more tactical conversations with operators, founders, and GTM leaders.

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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.

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