Senior Engineering Manager, Applied AI
Role Overview
The role combines hands-on client engagement work, engineering team leadership, staffing, and hiring.
The manager will begin on a client engagement, then build and lead a team and help shape the growing company.
Key Skills for This Role
Full Job Posting
About Headstart
Headstart builds production AI systems for enterprises and is developing its own platform for agentic systems.
The company describes itself as bootstrapped, cash-flow positive, and growing.
Role overview
The role combines hands-on client engagement work, engineering team leadership, staffing, and hiring.
The manager will begin on a client engagement, then build and lead a team and help shape the growing company.
Team and technical leadership
- Provide direct, actionable feedback, grow engineers, and develop senior engineers into tech leads.
- Set clear priorities and expectations without adding process before the problem is understood.
- Review architecture, agent, prompt, and evaluation designs.
- Step into difficult technical and client situations, including production regressions and unclear requirements, and make decisions.
- Raise trouble early while it is inexpensive to address.
Delivery, staffing, and hiring
- Identify patterns across engagements and turn them into standing practices, reference implementations, and platform capabilities.
- Check that improvements make future engagements faster.
- Plan staffing across engagements, prepare transitions, and flag risks before they reach clients.
- Lead hiring for the team from sourcing through onboarding and define the hiring bar.
- Work with product, client partners, and client stakeholders so engagements succeed.
Background
- At least 4 years managing engineers, including senior and staff engineers, with experience hiring and developing them.
- At least 8 years in software engineering, with depth to review designs and challenge the team’s approach.
- Hands-on experience with Python.
- Experience delivering software in real client environments.
- Experience taking something from zero to one, such as a team, practice, or hiring process.
- Curiosity about agents, evaluations, and multi-agent systems, including judgment about reliability and human oversight.
- Fluency with AI coding tools.
- Consulting, services, or forward deployed engineering management experience is a bonus.
How the company works
The company emphasizes high trust, high agency, low ego, shared learning, and raising concerns when needed.
The company uses its own coding agent, Friday, and knowledge infrastructure, Statum.
Agents write most client code, but every output is reviewed and a person remains accountable.
The role is expected to contribute a point of view as a partner to clients.
Hiring process
- The process includes a recruiting screen, a technical coding exercise, a hiring manager interview, technical interviews covering coding and systems design, and a live case study.
Benefits
- Compensation is listed as CAD 300,000 plus competitive equity; a separate compensation range is listed as CAD 300K.
- Benefits include a 4.5% employer 401(k) match, covered medical, dental, and vision premiums, wellness and commuter benefits, 12 weeks of parental leave, and an optional four-week ramp-up at 50%.
- The company lists a Soho office and says work is hybrid in NYC and fully remote in the rest of the US and Canada.
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