Head of Engineering

Mason • New York City, NY

2d

About The Position

Mason is hiring a Head of Engineering to lead engineering while remaining actively involved in building its enterprise AI systems. The role works directly with the CTO on technical decisions, delivery, and increasingly complex enterprise deployments. Initially, the work is expected to be approximately 70–80% hands-on engineering and 20–30% leadership, with the balance evolving as the team grows.

The Head of Engineering will build and review backend, data, and AI systems; own engineering architecture and key technical decisions; translate company and customer priorities into clear plans; and help a small team deliver dependable systems. The role also involves coaching engineers, supporting customer deployments, and helping grow the engineering team.

The position is full-time and based in New York City or San Francisco. The successful candidate should be comfortable working directly with customers and joining 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 in 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 the 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 holding 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 relevant technologies such as Python, TypeScript, Node.js, SQL, PostgreSQL, Snowflake, Databricks, AWS, AI model APIs, agent SDKs, workflow orchestration, and containerized infrastructure; comparable technologies are welcome.
• A prior Head of Engineering title is optional; staff engineers, technical leads with project leadership, founders, and managers who remain deeply involved in software building 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