Head of Product

What SkillBench does SkillBench is the measurement and transformation layer for AI-augmented knowledge work. We measure how developers actually use AI tools — not what they report, but what the telemetry shows — and translate that into two outputs: private skill coaching for individual developers and workforce architecture intelligence for CXOs. Microsoft (63K developers) and CommBank are paying customers. We just signed one of the top financial services firms in the world as our ARR customer. We’re a team of 13 across the US, Korea, and Taiwan, with Reid Hoffman, Jeff Wilke, and Anu Bharadwaj (outgoing Atlassian President) as advisors, and our founding team combines deep research roots (MIT, KAIST, NeurIPS keynote, UN AI Panel) with an obsession with shipping. Why this role, why now We’re at an inflection point. A major platform partnership is creating simultaneous deployment targets (100K+ developers), an enterprise assessment pipeline ($5M+ active), and a B2C freemium funnel (5M developer community). The founders — one CEO/research, one CTO/engineering — need a product leader who can translate this velocity into disciplined execution, and who has the design instinct to make every screen, every interaction, and every onboarding step feel like it was built by people who care about craft. What you’d do Own product execution week over week. Make sure what 11 engineers and application scientists are building aligns with the highest-priority deployment target of the moment — which changes as enterprise deals, platform partnerships, and B2C traction evolve. Define and track the product metrics that connect shipping activity to business outcomes. Partner with the CEO and CTO on product strategy. You’re the third voice in the room when we’re deciding between shipping a feature for a $50K assessment customer vs. building the self-service onboarding that unlocks 100K users. Player-coach. We have a junior PM. You mentor them, establish a lightweight process, and build the product function from one person to a small team as we grow through the seed round. Navigate dual tracks. The enterprise product (CXO dashboards, organizational recomposition, telemetry reports) and the developer-facing product (free profiles, skill marketplace, coaching exchange) share an engine but serve different users. You keep both coherent. Drive sprint priorities across US and Korea time zones. The engineering team is distributed. You need to be comfortable with async coordination and know when synchronous time matters. Set the bar on product quality. You have opinions about spacing, hierarchy, and interaction patterns — and you’ve shipped products where those opinions were visible in every screen. Our backend is world-class. You make the frontend match. What you bring 5+ years as a product manager, at least 2 of those managing other PMs or product designers. You’ve shipped a product that developers chose to use voluntarily — not one that was mandated by their CTO. You understand what makes developer tools sticky: effortless onboarding, value in the first 30 seconds, interactions that feel considered. Technical enough to read a PR, understand a data pipeline architecture, and have a credible opinion on build‑vs‑buy decisions. You don’t need to write code, but you need to know when the engineers are solving the right problem. Design sensibility. Not “you’re a designer” — but you notice when something is 4px off, and you care. Comfort with ambiguity. We have paying customers, a production system, and a growing pipeline — but we’re also a 13-person startup where the product roadmap changes when a CEO of a $1.5B company calls with a new deployment target. Strong written communication. Specs, briefs, and async updates are how this team operates. If you need a meeting to make a decision, this isn’t the right pace. If you’ve shipped at or been shaped by companies like Notion, Linear, Vercel, Figma, Datadog, or Stripe — you know what bar we’re aiming for. Nice to have Experience with AI agents, LLMs, or the emerging AI tooling ecosystem — not as a buzzword, but because you’ve thought about how AI changes product surface area and user expectations. Familiarity with workforce analytics, skills platforms, or learning technology. Experience at a company navigating the seed-to-Series A transition — you know how to build process that helps without slowing things down. What you don’t need A PhD or academic research background. We have two MIT PhDs already. We need someone who ships. Enterprise sales experience. We have that covered. You need to understand what enterprise customers need from the product, not how to close them. Prior startup founding experience. Helpful, not required. What matters is that you can operate at the speed and ambiguity level of a company that went from 0 to $5M pipeline in 6 weeks. Compensation Competitive salary + meaningful equity. This is a co-builder role, not a hired-hand role. The equity reflects that. Location San Francisco Bay Area strongly preferred. The timezone overlap with our Korea-based engineering team matters, and the cultural proximity to the agentic developer tools ecosystem (Claude Code, Cursor, Codex, etc.) matters more. Periodic travel to NYC for customer meetings. #J-18808-Ljbffr SkillBench