Head of Engineering

AI Fund

8+ Years | San Francisco, California, United States (Hybrid) | Full Time | 4 months ago

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Job Summary

Callidus AI is seeking a Head of Engineering to lead the development of its advanced legal generative AI platform. This role involves 50% strategy and coaching, and 50% hands-on coding, focusing on scaling the system reliably while maintaining a high shipping velocity. The company is experiencing rapid growth with over 1,000 paying legal clients and ARR increasing by over 20% month-over-month. The Head of Engineering will be responsible for architectural decisions, system scaling, enhancing reliability and observability, and mentoring a high-performance engineering team. Key responsibilities include driving technical excellence, improving engineering velocity and quality through CI/CD and testing, and acting as a strategic partner to translate technical concepts into business value. The role also involves making critical trade-offs between speed, robustness, and cost, with a focus on user impact, and strategizing on roadmaps and SOC 2 Type II compliance.

Must Have

8+ years engineering experience
3+ years leading teams in high-growth B2B-SaaS
Proficiency in React/Next.js, Python/FastAPI, Postgres, Redis, Docker/K8s
Proven system scaling and observability experience
Deep expertise in building products on AI APIs
Significant personal AI use for development
Startup experience
Engineering degree

Good to Have

Legal or LegalTech experience
Strong DevOps skills on Azure

Perks & Benefits

Massive impact
Velocity
Mission
Strong fundamentals
Modern stack + AI frontier
Competitive cash + meaningful equity

Job Description

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.

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