About DealCounsel
Built by people who have been in the room.
Not consultants. Not theorists. Operators who have personally closed deals from seven figures to hundreds of millions in ARR — and now bring that pattern recognition to your pipeline.
Our philosophy.
Enterprise deals are won or lost on strategy, not effort. Most sales teams work hard. The ones that win consistently have a clear picture of the deal — who the real decision-makers are, where the risk lives, and exactly what needs to happen next.
That clarity is rare. It comes from having seen hundreds of deals at every stage, in every industry, at every deal size. It comes from knowing what a stalled deal looks like six months before it dies. And it comes from being willing to tell founders and sales leaders the truth, even when it's uncomfortable.
That's what DealCounsel is built to do. We're not here to validate your pipeline. We're here to help you win.
The track record behind the coaching.
Our advisors have closed, led, or coached deals across some of the most competitive enterprise sales environments in the world.
$100M+
in enterprise ARR closed directly
200+
enterprise deals coached and reviewed
$50k–$10M
deal size range we work across
Who we are.
Deal Strategy & Coaching
Senior Enterprise Advisor
Sixteen years closing enterprise software deals at customers ranging in size from $1B to $130B of annual revenues. Personally closed hundreds of deals, including $10M+ in ARR. Specializes in complex multi-stakeholder deals and procurement navigation.
CRM Analysis & Risk Identification
Deal Intelligence Lead
Expert in Python and LLM utilization to generate insights from data, call logs, and your own assets and value props. Skilled at converting technical value props to business value.
Founder & Executive Coaching
Strategic Coaching Advisor
Coached hundreds of deals and mentored dozens of AE's at one of the largest software companies in the world. Specializes in helping technical founders navigate enterprise buying processes and build champion relationships at the executive level.
What makes us different.
01
We've done it, not just studied it.
Every advisor at DealCounsel has personally closed or led enterprise deals. We don't teach frameworks we read about. We teach patterns we've lived.
02
We tell you what you need to hear.
If your deal is in trouble, we'll tell you — and we'll tell you why. We're not here to make you feel good about a deal that isn't going to close. We're here to help you fix it.
03
We work at the deal level.
We don't do pipeline reviews. We do deal reviews. Every session is focused on specific deals, specific stakeholders, and specific actions. No generic advice.
Ready to bring us a deal?
Start with your hardest one. We'll show you what we see.
Get a Free Deal Audit