Many leaders will happily talk for 45 minutes about their product… and struggle to talk for two about their prospecting engine. In this episode of Why Did It Fail?, Gabe Lullo, CEO of Alleyoop, joins Shivan to unpack why that gap quietly kills startups and stalls growth in mid-market and enterprise sales teams.

Gabe shares stories from decades in the trenches: SDRs who couldn’t make it past lunch, weeks of zeros on the whiteboard, clients who raised millions and still ran out of runway, and what changes when you treat prospecting with the same seriousness as product. He breaks down how Alleyoop makes over a million dials a month and how his team uses AI as a sparring partner to prepare reps for the only 9-10 objections that really matter.

Gabe offers a clear challenge: if you obsess over building the product but take a casual approach to go-to-market, you’re betting the company on hope. He explains when it makes sense to outsource SDR, how to instrument your sales engine like an F1 car, and why the founders who win are the ones who own the front end of the funnel.