Matthew Bellows founded Yesware, a Boston-based B2B SaaS company, with a product that genuinely solved a real problem. He had paying customers and real momentum. So he did what most founders do at that stage - he hired a sales team.

It didn't work. The team struggled to convert. Deals were handled differently by every rep. There were no clear next steps after calls, no defined process for moving a prospect through a buying decision, and no documented foundation for anyone to learn from. Matthew eventually made the difficult decision to let the entire team go. The Harvard Business School wrote a case study about it.

I joined Yesware shortly after that, as one of the first reps brought in to rebuild. And what I experienced in those early days stayed with me for the rest of my career.

When I arrived, leads were coming in and we were largely winging it. Each conversation was handled a little differently. We were figuring things out as we went, which sounds manageable until you realize how much uncertainty that creates - for the rep and for the prospect.

A rep named Paul Hlatky, who had joined from BU, cracked the code. He figured out what actually worked and, more importantly, he documented it. He defined a repeatable sales process that another rep could learn and follow. Clear stages. Clear next steps. A way to guide a prospect through the buying journey with certainty rather than improvisation.

That was the unlock. Once the foundation existed, everything else compounded. We figured out the demand motion, aligned it to the process, and started scaling. We grew the sales team from 2 reps to 30 and took the company from $1 million to $15 million in ARR in three and a half years. The same company that had to fire its entire sales team became a case study in how to build a repeatable sales engine.

I watched that transformation from every angle. I started as a rep learning the process Paul built. Then I became a sales manager and hired a team of seven AEs. Then Director of Sales, overseeing two teams. Then VP of Sales, owning the full org - AEs, SDRs, sales ops. And eventually VP of Sales and Marketing.

As the business scaled, Joel Stevenson joined Yesware as CEO. Joel came from Wayfair, where he had built and led one of the largest B2B sales organizations in e-commerce. He brought a level of operational rigor I hadn't experienced before - data-driven decision making, relentless attention to unit economics, conversion rates, deal sizes, margins, CAC, LTV. Every decision was grounded in the numbers.

Joel trusted me to run the sales and marketing organization, and that trust shaped how I approached the role. I wanted to represent him well. That meant building systems that were defensible, documented, and visible - not just performing well in the moment, but making the entire operation legible to anyone who looked closely at it.

I began my career in investment banking, advising technology companies on M&A and helping founders understand what made their business worth acquiring. Years later, I found myself on the other side of that table - sitting through diligence as the VP of Sales and Marketing at a company being acquired by Vendasta, an 800-person AI software company doing $100 million in revenue.

I'll be honest: I had doubts. Vendasta was a much bigger company with a much more experienced executive team, and I wasn't sure I was good enough to earn a seat at that table. I also didn't want to let Joel down after everything he had invested in preparing us for this moment.

In the year following the acquisition, I ran sales and marketing for Vendasta's portfolio of four direct brands. After that, I moved into my current role leading demand generation for the company. I manage a 13-person team of marketers whose job is to generate leads that convert into qualified opportunities, pipeline, and new closed-won billings for our 60-plus person sales organization.

Vendasta's founder and CEO, Brendan King, has built a culture around a simple principle: AI does the work, humans orchestrate. That philosophy has shaped how I operate every day - and it's central to how I deliver for clients at StoryForm Labs.

My early career in investment banking taught me how to analyze what makes a business transferable. My years at Yesware taught me how to build the systems that make it so. And my work at Vendasta taught me how to apply AI to compress timelines and eliminate the overhead that makes premium consulting inaccessible to most early-stage companies.

That combination is what StoryForm Labs is built on. I work with B2B founders between $500K and $2M in ARR who are approaching their first sales hire. My job is to build the system before the hire - the narrative, the process, the playbook, the hiring criteria, and the onboarding structure - so that the rep has something real to work from on day one. Because I use AI to do the heavy lifting, I can deliver McKinsey-caliber work at a price point that makes sense for founders who are still building, not founders who are already backed by institutional capital.

My hope is that this work saves you from the experience Matthew had at Yesware - and gives you the foundation to build a sales team that compounds rather than one you eventually have to let go.

Hiring a sales rep without the right system in place is how founders lose $150,000 and six months. The rep fails. The deals don't close. You end up back at zero, except now you're behind.

After years of building sales systems for B2B companies, I've identified the 10 criteria that have to be in place before a first sales hire makes sense. This is the same framework I use to assess every company that engages me. I've made it available as a free download so you can run the evaluation yourself.

Ten minutes. Ten criteria. You'll finish knowing exactly where you stand and what to fix before you make the hire.