What's Inside the Playbook
Not theory. Not a framework from a conference stage. These are the exact 10 systems I built and used at Whip Around — from first hire to $100M exit. I now install this same playbook for B2B SaaS companies stuck between $1M and $10M ARR.
Build the System Before You Scale the Team
Why process beats talent — and what to document before your first sales hire.
Discovery Is the Whole Game
The 5 diagnostic questions that transformed our win rate in one quarter.
Clean Your Pipeline or It Will Kill You
How to separate real opportunities from wishful thinking. The Monday audit.
Coach Weekly or Don't Bother
The 80-minute weekly cadence that drove 2.3x quota attainment in coached reps.
Founder-Led Sales First — Always
Why you must close 50 deals yourself before you hire anyone. No exceptions.
The Hiring Framework That Actually Works
The $200K VP of Sales is the most expensive mistake at $1–3M ARR. Here's what to do instead.
Outbound Wins
Why waiting for inbound is a losing strategy. The 3-touch sequence that drove 40% of new business.
The Metrics That Matter (And the Ones That Lie)
Pipeline coverage ratio, stage conversion, win rate by source. What to actually track.
Compensation: How to Structure It So Reps Stay and Win
Make it easy to earn, hard to coast. The comp structure we used at Whip Around.
How to Know When You're Ready for a Full-Time VP
The 4-criteria test. Most founders hire too early — and pay for it.
"We were 4 people in a WeWork with zero revenue, zero brand, and zero clients. Everything in this playbook was built in the trenches — not in a strategy session. These are the systems that made the $100M exit possible."— Michael Flournoy, Founder of GSD Associates
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"This is the clearest breakdown of early-stage sales systems I've seen. Practical, specific, no BS."
— SaaS founder, Series A