Engineering Manager, Applied AI
Role Overview
The Engineering Manager, Applied AI combines hands-on client engagement work, engineering leadership, and staffing responsibilities.
The manager leads engineers across engagements, develops team capability, and reports to the Head of Engineering.
Key Skills for This Role
Full Job Posting
About Headstart
Headstart builds production AI systems for enterprise clients and is developing a platform for agentic systems.
Engagements involve varied industries, high-stakes problems, and unclear initial requirements.
Role overview
The Engineering Manager, Applied AI combines hands-on client engagement work, engineering leadership, and staffing responsibilities.
The manager leads engineers across engagements, develops team capability, and reports to the Head of Engineering.
What you’ll own
- Manage and develop engineers up to senior level through direct feedback, coaching, and performance standards.
- Review architecture, agent, prompt, and evaluation designs; resolve difficult technical and client issues and raise risks early.
- Lead engagement-level client and stakeholder relationships with product and client partners.
- Plan team transitions and staffing, identify risks, and escalate cross-engagement conflicts.
- Interview, calibrate, close, and onboard engineers.
- Apply and improve team practices and share useful patterns across the organization.
Background
- 3+ years managing engineers and developing people.
- 5+ years of software engineering experience, with depth to review designs and challenge approaches.
- Hands-on Python experience and experience delivering software in client environments.
- Curiosity about agents, evaluations, and multi-agent systems and how to judge their reliability.
- Fluency with AI coding tools.
- Consulting, services, or forward-deployed engineering management, or building a team or practice from zero to one, is a bonus.
How the team works
The team emphasizes high trust, agency, low ego, candid feedback, and sharing lessons.
AI agents write much of the client code; people review outputs and remain accountable.
The manager is expected to participate in technical decisions and bring a point of view.
Interview process
The process includes a recruiting screen, a practical coding screen, a hiring manager interview, coding and systems design interviews, and a live case discussion.
Candidates may use AI tools in the coding interview; no preparation is needed for the case study.
Compensation
- The posting states a base salary of CAD 285,000 USD and a compensation range of CAD 285K, creating a currency and amount inconsistency.
- The posting does not state a salary cadence.
Workplace
- The posting describes hybrid work in NYC and fully remote candidates in the US or Canada.
- The stored job location is Toronto, Canada, which conflicts with the posting’s NYC and remote-location description.
Benefits
- Benefits include competitive equity, a 401(k) with 4.5% employer match, medical, dental, and vision premiums, and a monthly wellness stipend.
- Other listed benefits include Citi Bike, pre-tax commuter benefits, 12 weeks of parental leave, and an optional four-week ramp-up at 50%.
- The posting mentions a Soho office with lunch and snacks.
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