It’s a cold, drizzly Seattle morning in late 2016, and I’m in a boardroom staring at a dashboard that looks like a Christmas tree — if Christmas trees were decorated exclusively with red warning lights. I’m running Customer Success at a B2B SaaS startup and my CEO is across from me, frowning softly at the screen, waiting for an explanation I’m not sure I can give.
“What’s going on?” he asks, his tone more curious than accusatory, which somehow makes it worse. “Why are we seeing these big customers three, four, even six months into their subscription but yet to deploy?”
I’d been asking myself the same question for months.
When you’re working at a scrappy startup (the kind where beer-on-tap is considered a legitimate employee benefit), big sales wins are events. I’m talking bell rings, high-fives, and yes, those ceremonial cold ones pulled from the tap. Six and seven-figure ACVs deserved the fanfare. But celebrations… well… they end. And when the last ‘cheers’ and clink of beer glasses echoes through the office, you’re left with the reality of actually delivering on those promises.
