Head of Engineering @ Callidus AI

About Callidus

We are entering the golden era of AI. Over the next 5-10 years, breakthroughs will drive a completely new world. Callidus is on a mission to transform the $1T global legal market and we’re well on our way.

Callidus is the most advanced legal generative AI platform on the market today. We offer a uniquely powerful platform, enabling lawyers (as one example) to draft a full 30‑page legal brief in ~10 minutes—saving about a week of effort. We are an engineering‑led organization that empowers talent to build collaboratively toward our mission.

More than 1,000 paying lawyers rely on Callidus today, and ARR is growing >20% MoM, putting us in the top 1% of funded startups at this level. We’re ready to scale and are looking to triple the size of our team.

We work hard, ship fast, and win together. 

About The Role

The Head of Engineering will lead the development of the most advanced legal AI platform on the market as a 50% strategist/coach, 50% hands-on coder. Improve our ability to scale reliably while preserving our trademark shipping velocity. Competitive cash + meaningful equity. High-intensity, outcome-obsessed culture. San Francisco.

• 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

• 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

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

• 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