Welcome To The Drafting Table
👋 Hey there, Jess Lin here.
I’m a Co-Founder and General Partner at Work-Bench, an early-stage enterprise software VC fund based in New York City. For the past 10 years, I’ve been investing in and supporting the next generation of SaaS and infrastructure startups, with a deep focus on helping founders go from 0 to 1 in GTM. At Work-Bench, I lead investments across mental health, customer success, financial data management, recruiting, sales, and beyond, with a portfolio that includes Spring Health, Catalyst, RippleMatch, Leapfin, Courier Health, ZippedScript, ShiftRx, GovWell, and more.
I’ve always believed that investing isn’t just about writing checks—it’s about helping founders land enterprise customers, develop real go-to-market motions, and scale from early traction to category leadership. Too many investors focus only on product, when in reality, the difference between success and failure often comes down to distribution, positioning, and execution.
That’s why I launched The Drafting Table—a podcast and content series dedicated to uncovering the tactical skills that separate successful founders from those who never make the leap. Over the years, I’ve worked with hundreds of operators and founders and have noticed a clear pattern: the best founders didn’t just wake up one day and start a company. They spent years deliberately building specific capabilities that became their unfair advantage—whether it was learning how to sell before they had a product, mastering the art of positioning, or developing a repeatable execution playbook before they even hired a team.
On The Drafting Table, I sit down with the industry’s best founders, operators, and leaders to break down these critical but often overlooked skills. Each episode delivers a step-by-step playbook for a specific capability—running high-stakes sales meetings, building systems that scale beyond yourself, turning domain expertise into a founder advantage, and developing GTM strategies that actually work in the real world. The goal isn’t just to share high-level insights but to provide detailed, tactical guidance that ambitious operators can implement immediately.
Before Work-Bench, I worked at Cisco Systems, where I led Agile software transformation efforts, and spent time supporting student startups from Harvard University in South Africa. Outside of venture, I’m deeply passionate about workforce development and adult education and have spent over 15 years as a GED instructor. I also write an enterprise SaaS newsletter packed with sales tips, GTM hacks, and tactical lessons from the field—subscribe here: https://jerseejess.substack.com.
For founders and operators looking to sharpen their skills before making the leap, The Drafting Table is the ultimate playbook for becoming a stronger, more prepared founder. Whether you’re a VP of Sales dreaming of your own company, a Head of Product planning your founder journey, or an engineering leader plotting your path to founding, this is where you’ll find the insights and frameworks to make it happen.
Welcome to The Drafting Table. Let’s get you ready to build.
