The 25% nobody's underwriting - by Monica - on paper
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The 25% nobody's underwriting<br>AI-native services are betting on automation. The hard part is everything left over.
Monica<br>Jul 29, 2026
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Everyone’s excited to use a chatbot. Ask the same team to change their workflows, double their throughput, or spend half their day selling, and many professionals start to bristle .<br>That gap is the entire investment case for AI-native services, and it’s the part nobody’s underwriting .<br>The history here is well covered: Atrium, WeWork, Opendoor, Compass — VC-backed services companies that raised like tech companies and ultimately got priced as something else. Opendoor and Compass now trade around 1x forward revenue, against 5-8x for public software. It has always been hard to deliver a service consistently and economically while growing fast, and growing fast is exactly what everyone who took venture money signed up for.<br>The bet now is that automation fixes both by addressing call it 75% of the job.<br>But if 75% of the job goes away, the job doesn’t just get faster. It gets redefined.
A role that used to contain 10+ kinds of work collapses into two residual pillars. Judgment — the license, the signature, the authority to apply known rules and be accountable for the answer, the way a lawyer, a CPA, or a radiologist is. And the relationship — account management, selling, upselling, knowing the client well enough to keep them.<br>So you want a fundamentally different person in the seat than you wanted just two years ago . They need to spike on one or both of those pillars, not on the tasks that used to fill their days and shaped how they were trained.<br>Which leaves two options, both difficult . Hire people already suited to the new version of the job. In practice, these hires are exceedingly rare, which means committing to training new grads over time. Or take people trained one way over a long career and ask them to work in a whole new way that feels, at first, like their expertise is being compressed.<br>The latter is more actionable now. So what actually works? Incremental changes introduced continuously? Formal training sessions? Embedding a SEAL team of AI-native builders, or maybe picking a small group of professionals that want to prove it out and letting their numbers do the convincing?<br>Automation won’t be the hard part this time.
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Hi! I'm Monica, a former venture investor turned operator. Currently advising, investing, and writing On Paper about what building companies looks like from both sides of the table.
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