How do you sell security software to buyers who distrust vendors?

Lead with proof of value rather than positioning. Arjun’s approach is to demonstrate a narrow, verifiable result rather than make a broad claim, on the basis that the market has already learned to discount confident messaging.

Is Y Combinator worth it for an enterprise security startup?

Arjun’s answer is yes, but for reasons other than funding. The value was credibility with enterprise buyers at a point when the company had no track record, plus leverage when recruiting against established employers.

What does product-market fit look like for an enterprise security startup?

Arjun gives a practical definition built around repeatable use cases: the same problem, described the same way, by multiple customers who are willing to build alongside you rather than wait for a finished product.

How do you plan a roadmap when the technology changes every quarter?

By anchoring on the customer problem rather than the current capability. Overwatch plans around repeatable use cases, which survive a model upgrade, instead of around features, which often do not.

Building Overwatch: AI Agents for Threat Intelligence at Attacker Speed

Phill Keaney-Bolland· Co-founder and Designer, YayaFebruary 25, 20262 min read

With Arjun Bisen, Co-founder and CEO, Overwatch Data

Listen on Spotify Listen on Apple Podcasts

Key takeaways

Proof of value outperforms polished messaging when buyers have been burned before.
Y Combinator mattered less for capital than for enterprise credibility and recruiting.
Repeatable use cases produced traction faster than breadth did.
Roadmaps need a different shape when the underlying technology shifts every quarter.
The human side of building is what founders consistently underestimate.

From diplomacy to threat intelligence
Selling honestly into a burned market
What Y Combinator was actually worth
Roadmapping when the ground moves every quarter

From diplomacy to threat intelligence#

Arjun’s route into cybersecurity did not run through a security operations center. It ran through diplomacy, then Google, then Stripe, each of which gave him a view of how risk and intelligence work were actually handled inside large organizations. What he saw was manual, fragmented and slow relative to the people it was defending against.

Selling honestly into a burned market#

The most useful part of this episode for any founder is Arjun on honesty in the sales conversation. Security buyers have been overpromised to for years and have adapted by discounting confident claims. His response is to lead with proof of value rather than positioning, and to let a narrow, demonstrable result do the persuading.

This matches what CISOs tell us directly. They are suspicious that they are being sold snake oil, and the fastest way past that suspicion is a specific mechanism and a result they can verify.

What Y Combinator was actually worth#

Arjun is precise about what YC did and did not provide. The value was not primarily the money. It was enterprise credibility at a stage when Overwatch had none to trade on, and leverage in recruiting against much larger employers.

Roadmapping when the ground moves every quarter#

Overwatch is building on a technology base that changes faster than an annual planning cycle can absorb. Arjun describes an early moment that set the company’s direction, and how the team plans when a capability that was impossible last quarter is commodity this one.

Phill Keaney-Bolland

Co-founder and Designer, Yaya

Co-founder and designer at Yaya, and host of the Cult Products podcast. Fifteen years designing products, brands and UX across multiple industries before narrowing to cybersecurity, and lectures on design at Imperial. Works with cybersecurity founders on positioning, strategy and the website that has to carry a launch, across identity, cloud security, AI agents and software supply chain, including Twine out of stealth and Geordie AI, which won the RSA Innovation Sandbox in 2026.