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
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.
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⏱️ 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
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
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
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:
This episode is a must-watch for early-stage founders, engineering leaders, and PMs navigating the messy middle between MVP and maturity.
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⏱ 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
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📌 For early-stage B2B founders, engineering leaders, and PMs building sustainable product roadmaps.
Hosted by Jessica Lin, General Partner at Work-Bench.
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:
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.
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📌 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
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🎙️ The Drafting Table is hosted by Jessica Lin, General Partner at Work-Bench.
Subscribe for tactical conversations with top enterprise builders.
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:
📍 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.
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:
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.
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:
🛠️ 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:
Use lead scanner questions to balance quantity and quality:
Scan everyone you talk to — even if they’re a customer, partner, or competitor:
Don’t trust memory — demand detailed real-time notes:
Post-event success starts pre-event:
Persistence matters after the event ends:
Mentality matters:
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
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:
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.
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:
Plus: Our favorite tactics for breaking into legacy markets, why “thesis-driven VC” is mostly BS, and the one thing every founder should include in their intro blurbs.
Whether you’re about to raise or just sketching out your first idea—this one’s packed with tactical gems.
🔍 For more on all things GTM, fundraising, and SaaS strategy, check out our newsletter and events at work-bench.com.
🎧 Listen to the full pod wherever you get your episodes.
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 startups across cybersecurity, infra, and dev tools—and she’s seen firsthand what separates real pipeline from vanity metrics.
We cover:
If you’re a founder thinking about building your sales org—or wondering why your outbound isn’t working—this one is for you.
Chapters:
0:00 Intro
2:00 What most founders get wrong about sales
4:57 When not to hire an SDR
6:00 Why founder-led sales is non-transferable
7:10 The myth of scaling cold outbound
9:40 Cold calling, LinkedIn, and real data on what works
13:00 Why SDRs need to write better emails (with examples)
16:00 How to onboard and coach SDRs the right way
24:00 Personalization that actually works
29:00 Measuring success beyond meetings booked
34:30 Building an SDR team that scales
46:00 TL;DR: Start simple, test everything, and stay patient
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 understand what your numbers are really telling you—this is the financial playbook every founder needs.
We cover:
✅ Why termination-for-convenience clauses can quietly kill your valuation
✅ The difference between product vs. services revenue (and why M&A buyers treat them differently)
✅ How to think about gross margin, CAC payback, and unit economics—the right way
✅ Why collections (yes, just getting paid) is one of the most overlooked issues in early-stage startups
✅ How to use funnel conversion and sales cycle data to underwrite your own top line
✅ What “great” looks like in retention—and how it ties into upsell, pricing, and packaging
Michaela doesn’t just explain the numbers—she explains the strategy behind them. This is SaaS finance demystified.
🎧 Perfect for:
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 your product is released✅ How to build momentum with a multi-week launch strategy✅ The right way to test messaging before launch day(s)✅ Why your launch should focus on end users, not just buyers✅ Tactical plays that drive awareness and long-term adoptionNatalie shares real-world examples from her work leading growth at Navattic and consulting with top B2B SaaS companies. Whether you’re launching your first product or looking to refine your go-to-market motion, this episode is packed with highly tactical advice.
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-hands meetings that actually keep teams aligned✅ The CEO’s job as the Chief Repeat Officer and why repetition matters✅ Why investor communication should happen every 2 weeks—not just at board meetings✅ How a single company-wide goal (“100 Customers”) transformed BetterCloud’s growthWhether you’re leading a team of five or scaling past 500, these battle-tested frameworks will help you build an operating rhythm that keeps everyone aligned, motivated, and moving in the same direction.
