Head of Engineering

We're looking for a Head of Engineering who will:

• Leads by example— set the standard for technical excellence, code daily, conduct thoughtful code reviews
• Architects for the future and delivers for the present— lead the scaling of our system to support 10x users, while increasing reliability and observability
• Is a master of applied AI engineering—architecting sophisticated systems on top of modern AI APIs to solve complex legal problems with high reliability and performance
• Guides a high-performance team— drive hiring, onboarding, and developing our engineering talent, fostering a culture of ownership, intensity, and collaboration to attract and retain top performers
• Systematically improves engineering velocity and quality— mature our CI/CD pipelines, increase test coverage, and improve release processes, without bogging the team down in bureaucracy
• Is a strategic business partner— translate complex technical concepts and trade-offs into clear business implications for founders, product leads, and GTM teams, ensuring technical strategy is always aligned with customer value and company goals
• Makes difficult trade-offs between speed, robustness, and cost, always prioritizing user impact
• Helps strategize & lead on roadmap, tech choices, and SOC 2 Type II compliance.
• Communicates crisply with founders, PMs, design, and GTM to keep everyone rowing one direction
• Finds ways to leverage AI to maximally improve the development process

Core Requirements:

• 8+ yrs engineering experience, incl. 3+ yrs leading teams in high-growth B2B-SaaS companies
• Fluency in our stack (React/Next.js, Python/FastAPI, Postgres, Redis, Docker/K8s)
• Proven record of scaling systems to thousands of concurrent users and introducing observability
• Deep, applied expertise in building sophisticated products on top of modern AI APIs (RAG, eval frameworks, agents, etc.)
• Significant personal use of AI for development (Cursor, Replit, Windsurf, Claude Code, etc.) and ability to reimagine end-to-end systems with AI
• Significant startup experience
• Engineering degree, ideally from a top institution

Nice to Have:

• Legal or LegalTech experience
• Strong DevOps skills on Azure (or AWS/GCP with quick ramp‑up)

Why join Callidus AI:

• Massive impact — shape architecture as we 10× usage
• Velocity — no bureaucracy; great shipping culture
• Mission — completely transform an entire industry
• Strong fundamentals — paying customers, soaring ARR
• Modern stack + AI frontier — work daily with the most interesting cutting-edge technology ever