Head of Engineering

Mason • San Francisco, CA

8d • Onsite

About The Position

Mason is hiring a Head of Engineering to lead engineering while remaining hands-on. The role works directly with the CTO to make technical decisions, drive delivery, and help a small team handle increasingly complex enterprise AI deployments. Initially, the role is expected to be approximately 70–80% hands-on engineering and 20–30% leadership, with that balance evolving as the team grows. The position involves writing and reviewing code, designing systems, solving difficult implementation problems, setting priorities, identifying risks, giving direct feedback, and helping engineers deliver accountable, high-quality work. The role is full-time and based in New York City or San Francisco, with direct customer interaction and onsite engagements when engineering leadership is needed.

Requirements

• Substantial recent experience designing, building, and operating production software, grounded in at least four years of engineering work.
• Demonstrated leadership of engineers or a substantial technical initiative involving multiple contributors.
• Strong system-design judgment and the ability to work with code and implementation details.
• Evidence of setting priorities, making tradeoffs, and delivering through uncertainty.
• Ability to give direct feedback, handle difficult conversations, and improve team effectiveness.
• Clear communication with founders, engineers, and customer stakeholders.
• High ownership and ability to run engineering work independently.
• Comfort working directly with customers and joining onsite engagements when engineering leadership is needed.

Nice To Haves

• Strong architecture and engineering judgment in backend, data, infrastructure, or production AI systems.
• A record of making engineers more effective and maintaining a high standard for delivery.
• Founder experience building from an unclear starting point, making consequential decisions, and owning the result.
• Experience translating demanding customer requirements into dependable systems.
• Experience with Python, TypeScript, Node.js, SQL, PostgreSQL, Snowflake, Databricks, AWS, AI model APIs and agent SDKs, workflow orchestration, or containerized infrastructure; comparable technologies are welcome.
• A prior Head of Engineering title is optional; staff engineers and technical leads with project leadership, as well as founders and managers who remain deeply involved in building software, are welcome.

Responsibilities

• Build and review the backend, data, and AI systems that power enterprise deployments.
• Own engineering architecture and make system-design, vendor, and build-versus-buy decisions.
• Translate company and customer priorities into clear engineering goals, plans, and ownership.
• Keep delivery moving across projects, identify risks early, and resolve technical or organizational blockers.
• Coach engineers, give candid feedback, and hold people accountable for outcomes.
• Set practical standards for correctness, security, testing, observability, and operating production systems.
• Work with the deployment team to make customer commitments realistic and turn repeated needs into shared infrastructure.
• Help hire and develop the team as engineering needs grow.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed