The Drafting Table

Jess Lin
  • 5.0 (1)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY
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.

  1. 19H AGO

    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

    55 min

  2. JUN 10

    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

    44 min

  3. JUN 3

    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.

    48 min

  4. MAY 28

    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.

    46 min

  5. MAY 13

    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.

    58 min

  6. MAY 6

    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.

    59 min

  7. APR 30

    Conferences Aren’t a Vibe. They’re a Sales Channel. How to Actually Make Them Worth It, with Amy Holtzman, CMO at CHEQ

    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. 🎙️ Covered live in this episode: How to decide which conferences are worth it Creative ways to show up if you don’t have a booth How to book meetings before the event even starts Why most teams get the conference pitch totally wrong Swag ideas that actually cut through the noise How to follow up after the event and land real meetings Why your conference ROI is made or broken before the event even begins — with real examples of prep docs and playbooks🛠️ BONUS tactical playbook (shared after recording): After our recording, Amy shared even more detailed tactical advice that her teams follow at every conference: Set clear activity goals for the on-site team — or scans and meetings will fall flat: 🔹 100 booth scans per day 🔹 25 on-site demos per day 🔹 5 REAL trial requests per day Use lead scanner questions to balance quantity and quality: Customize your lead scanner with key qualifiers (e.g., “Did they see a demo?” “Which product were they most interested in?” “Did they ask for a trial?”) to prioritize post-event outreach. Scan everyone you talk to — even if they’re a customer, partner, or competitor: Having a full record helps track engagement across audiences, makes reporting easier the next year, and avoids missing hidden opportunities.Don’t trust memory — demand detailed real-time notes: Every attendee interaction should have notes logged immediately, or you’ll forget who you met after a whirlwind 3-day event.Post-event success starts pre-event: Prep the team on how to take notes, set daily performance targets, and treat the scanner like gold — not an afterthought.Persistence matters after the event ends: Personalized, thoughtful follow-up — even weeks after the conference — is what converts conversations into real deals.Mentality matters: Without daily goals and a scanning plan, “the drift” happens. Activity drops. Set expectations early and rally the team on-site to hit their numbers. If you’re betting on in-person marketing this year, this is the episode to listen to first. 📍 For early-stage B2B founders building go-to-market 📍 Hosted by Jessica Lin, General Partner at Work-Bench Timestamps: 0:00 Intro 3:00 What founders get wrong about conferences 6:45 Conference prep templates + why 37 slides isn’t crazy 10:30 How to pick the right conference 14:00 Hacks to attend without breaking the bank 20:15 What to say in your outreach before the event 24:00 Nailing your 3-second pitch at the booth 26:30 Swag ideas that actually work 32:00 Why follow-up is where the real value is 39:00 Amy’s #1 rule: Don’t go if you’re not going all in

    56 min

  8. APR 22

    What Founders Don’t Know About QBRs, with Rose Kozar, VP of Client Solutions at Courier Health

    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 turn champions into megaphones. We cover: What a QBR actually is (and why most teams get it wrong) How to prep QBRs like a Broadway production What to say when things aren’t going well How post-sales teams should think like revenue teams (because they are) Whether you’re a founder still managing accounts yourself or building out your first customer success function, this is a masterclass in driving long-term enterprise growth. Post-sales isn’t a cost center. It’s the engine.

    57 min
See All (13)

About

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.

Information

  • Creator
    Jess Lin
  • Years Active
    2K
  • Episodes
    13
  • Rating
    Explicit
  • Copyright
    © Jess Lin
  • Show Website
    The Drafting Table

You Might Also Like

To listen to explicit episodes, sign in.

Stay up to date with this show

Sign in or sign up to follow shows, save episodes, and get the latest updates.
Select a country or region

Africa, Middle East, and India

Asia Pacific

Europe

Latin America and the Caribbean

The United States and Canada