Senior Engineering Manager, Applied AI

Headstart is built for people who want to think like founders. The company works inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. The role is part player, part coach, part staffing lead, part hiring engine. You'll start on a client engagement to learn the work and where engineers get stuck, then build and lead a team and help shape the company as it grows. How we work: high trust, high agency, low ego. We are our first client, running our coding agent Friday and our knowledge infrastructure Statum on ourselves. AI-first, human-accountable. Partners, not a vendor. Breadth that compounds. Weekends are yours. Pay is transparent. Interview process: initial screen (30 min) with recruiting partner; technical screen (30 min) coding exercise with an engineer; hiring manager interview (45 min); technical interviews (2.5 hrs, two sessions) covering coding and systems design, where AI tools may be used; case study (75 min) on staffing, feedback, technical review, and closing the loop.

Responsibilities

Lead your team: hold a high bar and grow each engineer through direct, actionable feedback; develop senior engineers into staff; give clear priorities and expectations; Technical leadership: review architecture, agent prompts and structure, and eval design; step into the hardest technical and client situations, like production regressions and unclear requirements, and make the call; flag trouble early; Closing the loop: spot patterns across engagements and turn them into standing practice, reference implementations, and platform capabilities; check that the next engagement is faster because of it; Staffing: shape who works on which engagement, plan transitions ahead, and flag risks before they reach a client; Hiring: run hiring for your team, from sourcing to onboarding; define the bar; Partnerships: work closely with product, client partners, and client stakeholders so each engagement lands

Requirements

4+ years managing engineers and managers, including senior and staff, with real experience hiring and developing them; 8+ years in software engineering, deep enough to review designs and challenge the team's approach; Hands-on with Python; Experience delivering software in real client environments and taking something from zero to one, whether a team, a practice, or a hiring process; Curious about agents, evals, and multi-agent systems, with a sense of where they're reliable and where a person needs to take the wheel; Fluent with AI coding tools; Depth matters more than prior title

Nice to have

Management experience in a consulting, services, or forward deployed engineering organization

Benefits

Base salary of $300,000 USD, plus competitive equity; 401k with 4.5% employer match; fully covered medical, dental, and vision premiums; Monthly wellness stipend; Citi Bike; pre-tax commuter benefits; 12 weeks parental leave, with an optional 4-week ramp-up at 50%; Loft office in Soho with lunch and snacks