Helping startups scale since 2010

According to Peter Thiel, going from 0-1 in software is the greatest leap possible. But in my experience, scaling from $1M to $10M in ARR is just as hard, if not harder. Before that milestone is achieved, founders often have a lot of questions around what I call the three P’s-

Process. Am I running this deal right? How can I close it faster or at a higher price? What could I be doing better?

People. Who should I hire and when? What kind of background is right for our business, and what level of seniority?

Performance. Are my IC’s good, great, or terrible? What do I look for, and how do we build a sales culture of excellence?

From 0 to 1, and subsequently 1 to 10, is where I’ve spent the last 28,000 hours of my career across three category-creating companies: WePay (acquired by JP Morgan Chase for $400M), Segment (acquired by Twilio for $3.2B), and Monte Carlo Data ($1.6B valuation). I joined all three as a founding AE and soon jumped into leadership, intimately learning what it takes to go from nothing to tens of millions in ARR in less than 5 years.

Now I help founders navigate these stages through a combination of hands-on coaching & advisory.

  • "Stephen is the best sales person I've personally worked with. After joining MC, he singlehandedly doubled the size of our company. He's also one of my favorite human beings."

    -Barr Moses, Founder & CEO of Monte Carlo Data

  • "There are few people that know how to sell (and coach how to sell) a technical saas as well as Stephen. He was instrumental in coaching our sales team to 5x+ ARR in a single year. "

    -Tejas Manohar, Founder of Hightouch Data

  • "Stephen is in the trenches with us – he's the most hands-on advisor I've worked with."

    Graham Neray, Founder & CEO of Oso

  • "Stephen was our best enterprise rep at Segment. If you're an early stage founder with traction and want to uplevel your sales motion, talk to Stephen."

    Calvin French-Owen, Founder and CTO of Segment

  • "Steve's bar of excellence and results are second to none. He joined as our first non-technical hire and changed the trajectory of our business within weeks of coming on board."

    - Rich Aberman, Founder of WePay