In this episode of Thoughts on Selling, I sit down with Mike Baron — longtime sales leader, mentor, and operator who has lived the startup, PE, and enterprise trenches. Our conversation is part playbook, part reality check, and packed with practical wisdom for anyone leading or enabling sales teams.
We dive right into a “what if” scenario: if Mike were CRO and I were head of sales enablement at a security startup, what would we do first? Mike breaks it down with clarity:
Start with comp plans. Keep them simple, transparent, and behavior-driving. A clear plan motivates, while a 65-page manual kills performance.
Talk to customers — and closed-lost deals. Understand where you win, where you lose, and why. The gold is in the feedback loop.
Assess the tech stack. Too many tools = administrivia. Too few = inefficiency. The goal: help reps spend more time selling.
From there, we cover the importance of defining an ICP that’s not just a “total addressable market” (because “anyone between 200 and 2,500 employees” isn’t a strategy). We talk about how to apply the “hive mind” to big deals by letting reps present stuck opportunities for group problem-solving.
We also dig into value selling: moving past feature talk to true business outcomes — revenue growth, OPEX reduction, market expansion. Mike shares how coaching, role play, and peer-led conversations shift reps into those business-focused dialogues.
A few key takeaways:
Comp drives behavior. A well-built plan aligns sellers, customers, and company goals.
Feedback is fuel. Win/loss analysis and customer conversations sharpen the value prop.
Simplify to amplify. Tech should serve sellers, not bury them.
Deliberate practice matters. Just like athletes, reps need repetition and coaching to build muscle memory.
Celebrate the whole team. SEs, rev ops, legal — reward them too, not just quota carriers.
This is a fun, wide-ranging conversation full of actionable ideas. If you’re leading a team, building enablement, or just want to sharpen your own selling, you’ll take something useful away.
🎧 Tune in — and let me know what resonates most.
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