You’ve seen the gap between your top rep and everyone else, and you’ve decided what to do: hire a VP of Sales. It’s the most expensive mistake you can make - not because VPs are bad, but because you’re asking them to run a system that doesn’t exist.
From the archive
You understand the problem. You see the gap. And you’ve already decided: "We need to hire a VP of Sales." I’m going to tell you why that’s the most expensive mistake you can make.
$8M company, founder still closing 60% of deals personally, six reps producing inconsistently. The CEO’s diagnosis: "we need a real sales leader." VP #1 - scaled a company from $5M to $40M - ran a 90-day listening tour, built a beautiful strategy deck, changed things. Six months later, close rates unchanged. "Wrong culture fit." VP #2 restructured territories and built a new CRM workflow. Eight months later, same close rates, two good reps quit. "Needed someone more hands-on." VP #3 did ride-alongs and worked 60-hour weeks on willpower. Four months later: burned out and gone.
Finally: "Maybe the problem isn’t the VP." It was never the VP.
You think you’re hiring someone to run your sales system. They think they’re being hired to run your sales system. But there is no system - there’s a founder who closes on instinct, a top rep who keeps it in her head, and a CRM full of stages that mean different things to different people. That’s not a system. That’s chaos with a Salesforce license. And you just hired someone to optimize it.
The VP walks in and has two choices: build the infrastructure from scratch (a 12-18 month project they weren’t hired for) or coach their way through it. The best VPs read a broken system in the interview - they ask about close-rate consistency, ramp time, the playbook - and when the answers are "it varies," "about a year," and "we don’t really have one," they walk. You’re left with the desperate or the inexperienced.
Most CEOs: identify the revenue problem → hire a VP to fix it → watch them fail → blame them → repeat. The sequence that works: identify the problem → run a 5-day diagnostic → build infrastructure in 3 weeks → hire a VP to scale what’s working. Hire a VP into infrastructure and they spend their first 90 days accelerating, not excavating.
So before you post the job, answer one question honestly: are you hiring someone to build your revenue infrastructure, or to run it? If build - you’re not ready for a VP; you need an architect first. If run - make sure the infrastructure actually exists, documented and transferable, before they arrive. Every VP who failed didn’t fail because they weren’t good enough. They failed because nobody built them something worth running.
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