The League
Steve Founder exec
Four exits behind him, and a decade of getting B2B SaaS founders past pricing, enterprise security and the deal itself.
Start with a Top 3 Problem you have, then set me to work 1-3 months ahead of the rest of the day-to-day business.
Executive · GTM · Exits · CTO · CISO
01 · Who I am
The short version.
The short version, in blocks — because nobody reads the long version.
Started as
A developer
Then architect, then CTO. I have built the thing I am now asking you to build.
Exits
4
Two of my own, two alongside founders I coached through diligence.
Hats worn
CTO · CISO · CRO
Which is why I can sit in any of those seats on your team.
Based
Global
My primary regions are North Carolina, Texas, Toronto and Calgary — and when I am not there, you will likely find me in South America.
Founders coached
100+
Pre-seed through to acquisition.
Plays written
40+
Everything I teach is a play somebody has already run and won with.
02 · What I’m known for
Call me about these.
What founders come to me for, when to call, and what I get up to when I am not working.
Top 3 I’m known for
- 01ExitsPlanning one from day one, running the process, and holding the terms through diligence.
- 026-Figure DealsPricing that scales to enterprise, and the security posture that gets you past their review.
- 03Profitable GrowthPipeline and unit economics, so the next round is a choice rather than a rescue.
Call me when…
- 01You're working on the biggest deal you've had.
- 02You want to know your exit options long before you get there.
- 03You need a big push forward, but without that win you're limited in cash.
Outside it
Kiwanis — board member and treasurer
My favourite part was wrapping the hundreds of gifts we hand-picked each year, making Christmas packs for the youth.
Working globally
When I am not in North America you will find me living abroad — usually Colombia, Argentina or Mexico.
03 · Big wins
Mine, and the ones I got for other people.
Twenty years in the seat before the studio, and a few hundred founders since.
Big 3 Personal Wins
In non-startup markets.
8-figure strategic exit
2018 — 2019 · ScribbleLive
- What I apply to startups today
- Going through an exit forces you to rethink how you would start at the beginning again. It is not a VC round — any historical mistake will be used against you.
$30M run rate in 3 years
2016 — 2018 · Slalom
- What I apply to startups today
- Slalom taught me pipeline and unit economics, and how to scale a business profitably with limited investment cash.
API-first rollout across 8 bank divisions
2014 — 2016 · TD Bank
- What I apply to startups today
- If you want to sell 6-7 figure deals, you need to know the internal mechanics of big enterprises.
Big 3 Wins for Founders
How I helped startup founders win.
04 · Learn from me
Free, and in my own words.
Short ones for the commute, longer ones for the night before the board meeting.
One-minute tips
Longer sessions
05 · How to work with me
Four ways in.
Start small. Most founders start at one and work down the list.
01
1:1 advisor call
$500
60 minutes
One problem, on the table, with a straight answer at the end of it.
- ✓Pick the problem in advance
- ✓Written summary and next steps
- ✓Credited if you go further
02
1-month play
$5,000
1 month
One play from the playbook, run end to end with your team.
- ✓Pricing, security, or enterprise sales
- ✓Weekly working session
- ✓You keep the artefacts
03
3-month gameplan
$5,000/mo
3 months
A quarter of plays in sequence, with the outcome defined on day one.
- ✓Gameplan written up front
- ✓Three plays, one a month
- ✓Monthly executive reporting
04
Fractional C-suite
From $5,000/mo
Ongoing
A seat on your team — CTO, CISO or CRO — in your org chart and in the room.
- ✓Hands-on, not advisory
- ✓Can show on your org chart
- ✓Expert bench behind me
Want this coach in your corner?
Two calls. Free 12 month GTM Gameplan.