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The cheapest hire you'll make this year is going to find $74,000 you didn't know you were spending.

You're not going to find it yourself. You can't. Your founder chair was built so you couldn't.

A founder I've been working with for two months found his $74,000 the same way every operator I've ever watched find one. He sat in someone else's seat for a couple of weeks, watched a workflow he'd never seen up close, and walked out with two pages of notes about money routing into a wall.

He didn't go looking. His head of customer success went on parental leave in April and his senior CSM was on PTO the same week. He had to cover the renewal inbox himself for 14 days. He told me on a Friday, with the kind of laugh that wasn't a laugh, that he'd learned more about his company in those two weeks than in the previous nine months of dashboards.

The piece this week is about the chair.

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What he found, in order

I'll spare you the full inventory. The headlines were enough to get my attention.

Three customers had been re-submitting their integration credentials every quarter because the API token rotated and nobody had documented the renewal step. Each one of those tickets ate two hours of his senior CSM's time and ended with the customer apologizing for being confused. The workflow was broken in a place no dashboard he owned looked.

Five accounts were paying for licenses they hadn't activated in more than six months. His billing dashboard counted what they bought and never checked what they used. Those customers were going to notice on the next renewal call and pull the unused seats out of the contract. About $38,000 a year of soft revenue, already gone, still showing up on his ARR slide.

One AE was sending a 14-page onboarding doc to every new customer. The CSM had built it 18 months earlier when the product had a different shape. Nobody read it. Nobody told the AE to stop sending it. The AE kept sending it because it was on his welcome-sequence checklist.

A $4,200-a-month vendor invoice was hitting his card for a CRM enrichment tool that his head of revops had canceled in January. The cancellation had gone through inside the tool's dashboard. The credit card line item had not. The vendor's renewal email had been routing to the inbox of a CSM who had left the company. Nine months of invoices, paid on autopilot, for a service nobody was using.

That's $74,000 of leaks in a single CSM queue, and that's only the part he could find by sitting there. He's at $4.2M ARR. He thought his big problem was top-of-funnel demand.

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