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Kastle is building AI agents for regulated finance, working with major US banks and mortgage lenders to scale contact center and compliance operations. The company has processed over $2 billion in transactions, is backed by Insight Partners and Y Combinator, and just raised a $24M Series A.
You will be Kastle's first dedicated Head of Talent, reporting directly to the CEO. This is a strategic leadership role responsible for scaling the people function from foundational to mature as the company grows 4x over the next year.
Key responsibilities include:
- Building and managing the recruiting team, owning sourcing strategy and interview process improvements across engineering, product, GTM, deployments, and operations
- Designing and implementing people strategy including performance management frameworks, compensation structures, employee development programs, and career pathways
- Partnering with leadership on organizational design, headcount planning, and critical talent decisions
- Evolving HR infrastructure: refining policies, ensuring compliance across all locations, and optimizing benefits programs
- Leading compensation strategy including pay band equity, equity grant management, and market benchmarking
- Driving culture and engagement initiatives including values definition, employee feedback loops, team events, and DEI programs
- Ensuring compliance with employment laws and regulations
The role requires someone who can build strategic HR infrastructure while maintaining a business partner mentality—advising leadership on talent strategy, not just executing transactional HR tasks. You'll work in a fast-paced environment where sprints and major launches move quickly. The team typically works around 70 hours per week, with five days in-person collaboration at the San Francisco office, beginning at 8:00 AM.
Benefits include medical, dental, and vision coverage, 401(k), and catered lunches and dinners.
REQUIREMENTS:
- 5-8+ years in People/HR roles at high-growth startups, with at least 2 years in a leadership capacity
- Demonstrated experience scaling people functions at early-stage companies (50-200 employees)
- Track record designing and implementing people processes (performance management, compensation, onboarding, career frameworks)
- Business partner mentality—advising leadership on strategic decisions, not just executing HR tasks
- AI native: strong experience working with Claude Code, Cursor, or similar tools to build sourcing agents
- Strong coaching skills to develop managers and help them navigate people challenges
- Comfort with ambiguity and ability to build infrastructure without waiting for perfect clarity
- Excellent judgment on sensitive employee matters
NICE-TO-HAVE:
- Experience in fintech, lending, or regulated industries
- Background in AI/ML or technical product companies
- Previous experience scaling a company through hyper-growth (20→200+ employees)
- Knowledge of multi-state employment compliance
