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

1. 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

2. 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

3. 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.
• Communicate at the right level for the situation. A vibe-coded prototype is great, but so are detailed security requirements for it. 
• Close the loop on what shipped, what worked, and what didn't, and use this insight to help shape how the product and engineering functions evolve

4. GTM Partnership

• Own the feedback loop between field conversations and the product roadmap, making sure what customers and prospects are saying in sales cycles is structured, documented, and traceable to product decisions
• Partner with marketing on positioning and messaging, bringing enough product depth to pressure test how we're describing what we build against what practitioners actually care about
• Support launch strategy for new product surfaces, from how we sequence rollout to how we arm the GTM team to have the right conversations
• Develop and maintain the training and enablement materials that keep the product marketing team current: what shipped, what changed, what it means for how we position, and what questions they should expect in the field
• Work closely with the founding AE and channel partners to understand how deals are won and lost, and feed that signal back into how we build and prioritize
• Serve as the internal authority on what the product does, what it doesn't do, and where it's going, so that GTM always has a credible and current answer
• Sit between product and business development, supporting the GTM team to land new deals, expand existing opportunities, and gain signal on new product surfaces to pursue

What We're Looking For

Required

• 7+ years as a PM, including meaningful experience at a fast growing early stage company
• Deep domain expertise in application security and/or product security, either as a practitioner who moved into product or a Product Manager who has spent years embedded in the space
• Enough technical fluency to hold your own in security design conversations and write specs that engineers understand and respect 
• Direct experience shipping AI or ML powered products in production, not just prototyping or evaluating them
• Demonstrable product taste - show us screens, flows, or specs you're proud of
• Writing that compresses complexity. You can turn a messy customer conversation into one paragraph that changes how the team thinks
• High bias toward talking to customers over reading reports about them, and a track record of decisions made from that fieldwork
• Comfort with ambiguity and a track record of making good decisions without complete information
• "Unreasonable Hospitality" energy - you take care of the people you build for in detail, beyond what the job strictly requires

Strongly Preferred

• Deep domain expertise in application security and/or product security, either as a practitioner who moved into product or a Product Manager who has spent years embedded in the space
• Product design fluency - you can wireframe a flow, make UX calls, and own the experience without waiting for a designer
• Shipped to enterprise security buyers (CISO org, AppSec, GRC, privacy)
• Opinions on where AI is genuinely useful in security workflows and where it falls short, backed by real experience building in that space

How success is measured (first 6 months)

• Can articulate why we win, why we lose, and where the biggest product gaps are - informed by real customer and market exposure, not inherited assumptions
• Roadmap is set, communicated, and updated on a regular cadence that the whole company and our customers trust
• Key product metrics (adoption, retention, expansion, revenue impact) are baselined and trending in the right direction, driven by product decisions you can point to
• Core product processes are stood up and running: discovery cadence, spec workflow, prioritization framework, and a plan for how product grows
• AI output quality metrics are defined, baselined, and on a documented improvement trajectory within the first two quarters
• Customer discovery runs on a consistent weekly cadence, with findings documented and traceable to product decisions
• Customers understand where their asks sit on our roadmap, and trust how we're making prioritization decisions - even when the answer is "not yet"

Why Join Clearly AI

• Own product at a company with real customers, real revenue, and real urgency
• Work directly with technical founders who've done the work and respect the craft
• Build the AI product playbook for an entire enterprise category
• RSAC 2026 Innovation Sandbox Top 10 Finalist, backed by $8.4M in seed funding
• Operate at the intersection of frontier AI and enterprise security
• Competitive salary, meaningful equity, and benefits
• Direct path to product leadership as the company scales