President's Club
President's Club is a single-operator firm for B2B SaaS founders with real pipeline coverage and a procurement bottleneck. Stephen takes each enterprise deal end-to-end: discovery, procurement, security review, signature, onboarding. And stays to close the next ones and renew the first.
Multiple successful exits and fundraising events led by Stephen. $15M+ in direct enterprise software sold for seed and Series A startups.
Send Stephen a stuck deal →60 minutes. No charge, no pitch.
"I've been able to call Stephen with a new hire, when I think they're a good fit but I want another opinion, and he's always happy to jump on a screening call and ensure that we are making the right decisions. One of these reps brought on 42 new customers in the past year."
David Abell · CEO, AM Transport Services
"I was most impressed by the amount of depth that was provided. It was clear that we were getting a consultative approach, not just a one-size-fits-all approach, something that was very much tailored to our business."
Bobby Narang · Co-Founder, Opensense
"Stephen was helpful for us to learn how to have a structured process. I appreciate the work we did together to learn about sales as an early stage company and put the first level of structure in place."
Including the ones that ended in acquisition. He builds the version that actually gets used, not the version that looks good in a demo. The CRM is configured to your motion. The playbook is written in your voice. Both are built into your company from day one.
The contract isn't the result. What the contract makes possible is the result.
Stephen has led sales at multiple startups that exited to category-leading acquirers. At Data Advantage Group, metadata management and governance sold into Fortune 100 banks and healthcare, he ran sales and marketing for seven years, driving $10M+ in direct enterprise sales. The motion ended in DAG's acquisition by Sequoia-backed Bigeye. A similar pattern played out at Datacoral, which exited to Cloudera. Build the enterprise sales motion. Get bought. That's the pattern.
Joined pre-revenue. Built the CRM and pipeline from zero. Closed the first enterprise contracts, including a top-5 automotive supplier, paid out as the next round of funding led by Index Ventures.
At Data Advantage Group, Stephen repeatedly won enterprise evaluations against the category incumbents — Informatica and Collibra — public companies with 10× the marketing budgets and the brand recognition buyers default to when nothing else convinces them otherwise. The startup operator beat the public-company incumbent, again and again. Founders weighing whether their product can win against the safer choice: it can. The motion just has to be built for the buyer's procurement team, not for the founder's deck.
"It comes down to being scrappy, but also being smart. Hustle culture is important at startups, but you want to make sure you're hustling on the right thing, not just being busy to look busy."
3× President's Club at FullFunnel
Sandler & Costigan trained
10+ years selling enterprise data infrastructure
Most founders are losing winnable enterprise deals, not because their product is wrong, but because nothing about how they're running the close is built for the procurement side of the table. I've sat on both sides of that table for a decade.
Every demo, every follow-up, every close, your calendar. The product is real. The motion isn't proven yet.
Not a deck on a shelf. The actual ability to look at your pipeline and tell anyone — your board, your investors, yourself — exactly who is buying each deal, what problem they're solving, why your product is the one to solve it, and how their procurement will get it signed.
When you're ready to bring on a full-time AE or SDR, Stephen sources, vets, and helps onboard the hire, making sure whoever joins can actually run on the rails you've built together.
Each one loses to a different aspect of how we work — for different reasons, at different stages.
The right move once the motion is proven. Before that, you're hiring against a hypothesis, and if the hypothesis is wrong, you've spent eighteen months and a six-figure base learning that. Stephen proves the hypothesis first. Then he helps you hire against the proof.
Consultancies sell hours and leave. Stephen builds the deal motion, closes your first enterprise contracts, and runs it as you scale. The CRM, the playbook, the procurement motion — built into your company on day one, not rented from somebody else's firm.
You built the technology and you can pitch the technology. But enterprise procurement, security review, and compliance run on a different playbook, and that's where most first enterprise deals stall. The math gets paid back the moment your first enterprise contract closes.
These aren't separate services. They're the infrastructure Stephen builds while he closes your first deals — and keeps running as the team scales.
Implemented and tuned to your motion — Salesforce or HubSpot, your call. Configured the way the people using it will actually use it, not the way the demo looked.
The ICP, the message, the discovery questions, the demo flow, the objection answers, the procurement playbook — written down, in your voice, so your next hire ramps in weeks instead of quarters.
Why "President's Club"? The award sales orgs give their #1 performer — usually locked up at large companies. President's Club, LLC exists to put that talent inside earlier-stage companies for the months when it matters most.
Stephen is a strategic enterprise sales leader with over a decade of experience driving complex, high-value software deals in large, regulated organizations. He has translated deep technical capabilities into business outcomes for two companies that exited under his sales leadership, Data Advantage Group (acquired by Bigeye) and Datacoral (acquired by Cloudera), and led the sales motion behind a $25M Series B at an AI/electronics SaaS startup backed by Index Ventures.
And outside of work? A decorated water polo player who still competes at the masters level. Golfer. Father, husband, and the housemate to two beagles who have strong opinions about most things.
Your pipeline coverage is thin. Your POCs are stalling at procurement. Your board has told you what to fix. You don't need another deck — you need someone who has closed these deals before to look at why yours aren't closing.
Pick the enterprise deal that's costing you the most sleep — the one that died in security review, stalled at procurement, or has been "two weeks from signature" since last quarter. Stephen will work it back end-to-end with you: where it broke, what was missing, what your next deal needs to do differently. You'll leave with a post-mortem you can take to your board.
60 minutes. No charge, no pitch, no follow-up sequence. If after the post-mortem you want Stephen to run your next deal, you'll tell him.
Stephen reads everything personally. He'll be in touch within one business day.
If it's time-sensitive, his direct line is [email protected].