Founding Sales Masterclass with Collin Stewart
Finding your first customers is one of the most daunting and defining parts of building a startup.
The messy, uncertain stage where conversations matter more than funnels, and learning happens one prospect at a time. The challenge isn’t just selling; it’s sequencing your way from problem-solution fit to your first revenue engine.
Join Collin Stewart (author of The Terrifying Art of Finding Customers and founder/CEO of Predictable Revenue) and Lightfield for an evening workshop designed to help founders master the earliest stages of go-to-market: finding customers, validating demand, and closing those critical first deals.
In this hands-on session, you’ll learn:
How to measure and strengthen your product-market fit signal
How to run discovery the right way and actually listen to prospective customers
How to identify your first repeatable customer segments
How to land your first paying customers with clarity and structure
How to build the early scaffolding for a scalable revenue engine
Whether you're working toward your first 10 customers or building the bridge from founder-led hustle to a repeatable sales motion, you’ll walk away with clear milestones, practical benchmarks, and step-by-step methods you can apply immediately.
Agenda
6:00 PM - Check-in, networking & light bites
6:15 PM - Welcome (Lightfield)
6:30 PM - Founding Sales Masterclass with Collin Stewart
7:15 PM - Q&A
7:30 PM - Closing & networking
About the speaker
Collin Stewart is the founder and CEO of Predictable Revenue, where he helps B2B companies grow faster and achieve consistent, predictable results. With more than a decade of building sales development teams for companies like Uber, Toptal, and Vox Media, Collin has seen firsthand the patterns that stop most startups from getting to market - and the techniques that actually work.
He’s co-founded both a CRM that nobody wanted (voltageCRM) and a revenue platform that rocketed from $0 to $1M in months (Carb.io), giving him a uniquely honest view of what finding customers really takes. Collin also hosts the long-running Predictable Revenue Podcast, one of the most widely followed shows in B2B sales. He lives in Vancouver, Canada.
About the book
The Terrifying Art of Finding Customers
From one of North America’s top sales development leaders comes a practical, step-by-step blueprint for guiding startups to lasting revenue.
A straight-talking guide for founders, the book breaks the early GTM journey into three clear stages:
Finding product–market fit
Closing your first customers
Building a scalable revenue engine
Stewart offers real stories, practical milestones, and sequence-based advice to help founders avoid common traps, learn from mistakes, and build a commercial engine that endures. It starts with the uncommon art of deeply listening to customers — and ends with the systems that let a startup scale with confidence.
Hosted by Lightfield
Lightfield: An AI-native CRM that remembers everything, then acts on it. It automatically captures and organizes every customer conversation across email, meetings, and notes, creating your team’s collective customer memory. Backed by Greylock, Lightspeed, and Coatue, Lightfield helps founders learn from every interaction and move faster toward repeatable growth.