Tag: napkins

I was talking with a friend about the overlaps I see between dating apps and job platforms. We’d just heard a pitch from a founder building AI-powered skill assessments for hiring. Good solution to a real problem, but I felt a bit deflated watching another startup cater to the hirers’ triaging workflows.

I think there’s a lot being left on the table regarding the emotional space of people seeking. The problems around how to represent yourself/how to signal your appeal or X-factor feel more profound to me than problems about managing huge applicant pools. And there’s something civically motivating about how the same problem shows up on both sides of seeking/accepting dynamics: How can I enable the right people to find me? and How can I make myself known to the right people?

You sometimes see job descriptions that list out all their qualifiers—8 years of experience and such—and then say something like “…if you don’t meet any of this, still reach out anyway.” They say that because they know criteria only help up to a point. We lean on metrics and static signifiers in lieu of more dynamic ways to convey value through matching systems.

Metrics and hard requirements are proxies for something harder to articulate. You might want to date tall people because you want the sense of capability you associate with height. You might want an artist or a poet, though the underlying qualities that draw you to them aren’t exclusive to those people. By filtering for tall poets or for job applicants who’ve already done the exact thing you’re hiring for, you miss richer ways people could meet your needs. Traditional systems force a shape-fitting paradigm¹ (reducing complex qualities to flat attributes), which pressures people to self-present in ways that don’t guarantee actual fit.

After qualifications and criteria are cleared, any matching decision ultimately comes down to vibes… the fuzzier, harder-to-articulate signals that the criteria only sketched around.² The hiring manager or the dater needs someone who fills a particular gap and creates a particular feeling. Current matching systems don’t really touch this emotional space, but it’s where real compatibility lives and struggles to express itself.

Moving beyond shape-fitting

AI matching using sophisticated vector embeddings holds some promise, but it risks being a more complex form of shape-fitting; you’d plug in keywords, and the system finds things closer to those keywords. A more novel direction might bypass the keyword step entirely: matching signal to signal, letting the fuzzy things find each other directly without forcing them through structured descriptions first. A better north star might be curiosity-driven connection rather than just “better matching” (finding the shape faster). Instead of assuming the seeker knows exactly what they want, a more curiosity-driven system would allow for emergent fit, acknowledging that:

• We tend to think of shapes first, then look for people to match them. Shapes are lossy at best and reductive at worst.
• The “perfect match” can change your understanding of what you needed in the first place. Discovery can shift criteria.
• Moving toward signal-based matching also shifts incentives away from pressuring people to fit themselves into static shapes.

What could power this? I keep thinking about ambient signals, something like digital pheromones that allow for serendipitous stumbles into people with compatible vibes. Or matching that values the energy of someone’s interests over the content—because connection often stems from sharing one’s world, not just overlapping taste.