The Drafting Table

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 problem” might not be a real market

• How to package your pitch to stand out in a saturated category

• The #1 data room mistake most founders make

• Why storytelling isn’t optional (even if you’re technical)

• The true test of grit we look for in early-stage teams

• And how the best founders accelerate learning through fast experiments

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:

• The actual milestones you need before hiring an SDR

• Why most founders get messaging completely wrong

• A play-by-play on onboarding and coaching junior reps

• How her team drives pipeline from LinkedIn (yes, even with technical buyers)

• Why cold calling isn’t dead

• And what every SDR should send on their fifth day

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:

• Seed & Series A enterprise software founders

• First-time CEOs

• Anyone building (or breaking) a financial model

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.