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Founder Strategy Council
Strategy Chair · advisory brief
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Question
We have eight months of runway and an unproven B2B product. Do we double down on enterprise sales or pivot to self-serve?
Recommended call: run a six-week self-serve experiment without abandoning the enterprise pipeline. The bet — your real constraint is reachability, not willingness to pay. Load-bearing risks: self-serve cannibalizing high-touch deals, and a payback period your runway can't absorb. First move this week: instrument the three steps where trials stall, and put a price page live behind a waitlist.
Choose the motion that gives the team a measurable learning loop inside six weeks. Enterprise can remain a pipeline, but self-serve must prove activation and payback before it earns the next quarter.
Buyers are not asking for a category decision; they are asking whether the product removes a painful job quickly. Self-serve is the fastest way to hear that without a sales narrative filtering every signal.
The model dies if CAC payback runs past your runway — prove a sub-90-day payback before you commit a quarter to either motion.
Do not build a second product for self-serve. Strip the path to one job, one proof point, and one measurable activation event; the experiment should be smaller than the debate around it.
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