Stop Guessing. Start Growing.
The First Sales Hire Playbook
Why 90% Fail (And What to Build So Yours Succeeds)
90% of first sales hires fail within 12 months. Not because they're bad at sales—because there's no system for them to execute. This playbook shows you the 5 frameworks to build before you hire, so your first rep walks into infrastructure designed for them to win.
Inside the Sample Playbook
Section 1: The $150K Mistake Most Founders Make​
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Why 90% of first sales hires fail within 12 months—and the infrastructure difference that makes the 10% succeed. Learn the pattern: hire without system → rep struggles → founder jumps back in → rep exits → $150K+ poorer.
Section 2: What Customers Actually Want​
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The 3 levels of WHO most founders miss. Why Level 1 (title) and Level 2 (context) aren't enough. How Level 3 thinking (mindset & politics) tells you what to say, when to say it, and who else is involved in the decision.
Section 3: The 5 Frameworks to Build Before You Hire​
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WHO/WHAT/WHY Positioning - Clear target, outcome language, timing triggers
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Messaging Matrix - Persona-specific pain points and discovery questions
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Trigger-Based Prospecting - 8-15% response rates vs. 1-2% cold blasting
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Discovery Framework - 45-minute structure that qualifies and positions
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Give-Get Scorecard - Objective qualification (stop chasing garbage deals)
Section 4: First Hire Readiness Self-Assessment​
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20-point checklist across positioning, prospecting, discovery, sales process, and onboarding. If 4+ boxes are unchecked, you're not ready yet. Build infrastructure first, then hire.
Section 5: The Access Question​
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It's not "who should we sell to?"—it's "who can we actually REACH and WIN?" Why focusing on access vs. budget size 3x'd Fresh Tilled Soil's close rate.
Section 6: Three Ways to Work Together​
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First Hire Readiness Diagnostic ($5,000, 2 weeks) • First Hire Growth Playbook ($18,000, 8 weeks) • Fractional CRO ($10,000/month, 3-12 months)
What You'll Learn
Why 90% of first sales hires fail — and the infrastructure difference that makes the 10% succeed
The 3 levels of WHO — why most founders stop at Level 1 (title) when Level 3 (mindset & politics) wins deals
The 5 frameworks to build before you hire — positioning, messaging, prospecting, discovery, qualification scorecards
First hire readiness self-assessment — 20-point checklist to know if you should hire or build infrastructure first
Trigger-based prospecting — how to get 8-15% response rates vs. 1-2% from random cold outreach
The Access Question — why "who can we reach?" matters more than "who has the biggest budget?"
A Proven Trackrecord
20+
Years Building B2B Revenue Engines
$20M+
New Revenue Generated for Clients
$100K → $5M
ARR Growth (Fresh Tilled Soil)
200+
Enterprise Demos Generated
EXPERTISE SPANNING
Digital Product & UX Agencies | Enterprise Technology Platforms | Strategic Consulting Firms | Marketing Technology Providers
