Founding Head of Product

About Clearly AI

Clearly AI automates the most painful bottleneck in the enterprise: security and privacy reviews. We help security teams complete high-quality threat models, privacy impact assessments, and vendor risk evaluations in minutes instead of weeks.

We’re live with Fortune 500s and global brands including Rivian, Ericsson, HID Global, Affirm, Webflow, and Okta. We’ve reviewed thousands of security-critical products, from badge scanners to stablecoin platforms to autonomous driving features.

Backed by Y Combinator, Basis Set Ventures, Crosspoint Capital, Argon Ventures, and Ritual Capital. Selected as a Top 10 Finalist for the RSAC 2026 Innovation Sandbox Contest. Advised by former CISOs of Amplitude and OKX, the former CEO of Reddit, and the former CPO of Brex.

We are early. We are deeply technical. We are building alongside real practitioners, and we want a real practitioner who loves working with customers to help. We need a founding Product Manager who will own product the way a founder does.

Why This Role Exists

We’re hiring a Head of Product to own Clearly AI’s roadmap end-to-end, working with our founders to align product strategy against many competing needs from our enterprise customers and set the long-term vision.

You’ll lead design, discovery, experimentation, and delivery across a repeatable product lifecycle that you will be designing and implementing - partnering closely with Engineering, security SMEs, and the GTM team to translate the feedback from our customers into real, production-level value that solve their problems. At this stage, product and GTM/distribution are not separate problems; we need to figure out what to build, at the right time, in such a way that we continue to hold strong product-market-fit and a vision we can confidently grow towards.

We're a team of 10 with no product function today. You'd be building it from scratch.

What You'll Own

• Product Vision & Leadership

Set the full product roadmap, aligning with the GTM and founding team to build things that matter

Develop and own the framework for how we justify what is and isn't on roadmap, how it's resourced, and how we measure success of those investments and their impact on the business

Establish scalable, repeatable product processes that grow with Clearly - this is the first product hire and comfort defining how to build things well is a must

You've shipped AI that practitioners deeply love - you know how to design trust into the product, build guardrails from day one, make the call on when humans stay in the loop, and categorize LLM failure modes to target improvements

You've set early product process and hired or grown product development teams

• Customer Discovery

A customer-first mindset - you’d rather talk to a customer than read a report, and you have experience building feedback loops that identify opportunities across multiple customers

Run weekly conversations with security practitioners at our customers and prospects

Aggregate feedback across every customer touchpoint, from support tickets to implementation calls.

Embed in real review workflows  sit in on threat models, observe DPIA reviews, watch how the Jira ticket actually gets written

Turn that fieldwork into crisp written product specs backed by "we asked five customers and they said X".

Figure out what success means: through sales metrics, customer conversations, user usage, AI success/failure modes, etc.

Develop training materials and serve as the internal authority on the product (what it does, what’s coming, what launched)

You’ve found creative ways to get enterprise pilots off the ground, defined what success looks like, and turned early wins into a case for going broader or deeper

• Engineering Partnership

Write specs that engineers want to read

Enough technical fluency to hold your own - you've owned technical products, have experience in ML/AI, and/or can talk to engineers without a translator. Engineering, Comp Sci, or related degree is a bonus.