Engineering Manager, Applied AI

Headstart; Toronto; Remote; CAD 345,000 - 467,000; Full time

Benefits offered by this job

$285k USD base salary

401k with match

Medical, dental, and vision coverage

Wellness stipend

Parental leave (12 weeks)

Office in Soho

Hybrid/Remote in US or Canada

Job summary

Headstart seeks an experienced engineering leader to manage a team of engineers across client engagements and to drive technical delivery of AI-powered solutions.

You will guide architecture reviews, oversee staffing and coaching, and partner with clients, product teams, and engineers to land engagements with impact. This role blends leadership with hands-on involvement in complex technical work.

Qualifications

• 3+ years managing engineers and giving feedback to grow talent.
• 5+ years in software engineering with design review experience.
• Hands-on Python experience and client delivery exposure.
• Interest in agents, evals, and multi-agent systems; AI tooling familiarity.

Responsibilities

• Manage engineers up to senior level, set a high bar, provide actionable feedback.
• Provide technical leadership: review architecture, agent, eval design, and decisions.
• Run engagement-level relationships with clients, product, and stakeholders.
• Oversee staffing, transitions, and risk management across engagements.
• Lead hiring, calibration, and onboarding to uphold engineering standards.
• Contribute to practice development and spread effective patterns.

Skills

People management

Software engineering

Code review

Python

Client delivery

Multi-agent systems

AI tooling

Architectural insight

Education

Bachelor's degree in CS or related field

Tools

Python

AI coding tools

Job description

About the company

Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to deliver truly agentic systems.

Why join us

Enterprise clients bring us messy, high-stakes problems, often with no clear picture of what the AI system should be. Our engineers work out what to build, build it, and run it in production. Most of the time, they're the experts in the room.

This role is part player, part coach, part staffing partner. Most of your time stays on a client engagement, hands-on, close to the work and to where engineers get stuck. You'll manage a group of engineers across a few engagements and grow with the team as we do.

Level: Reports to the Head of Engineering. You run a team inside our system: you apply the bar, keep your engineers growing, and stay close to the work.

What you'll own

• Your engineers. Manage engineers up to senior, hold a high bar, and give direct, actionable feedback. Coach on execution and help strong engineers step up toward tech lead.

• Technical leadership. Review architecture, agent, prompt, and eval design on your engagements. Step into hard technical and client situations, like production regressions and unclear requirements, and make the call. Raise trouble early, while it's cheap to fix.

• Engagement delivery. Run the engagement-level relationship with clients and their stakeholders, alongside product and client partners, so each engagement lands.

• Staffing. Manage transitions on your team, plan ahead, and flag risks before they reach a client. Escalate conflicts across engagements to the Head of Engineering.

• Hiring. Interview, calibrate, close, and onboard new engineers against the bar the Head of Engineering sets.

• Practice. Follow the team's practices and tell us what isn't working. Bring patterns you see to the wider team so they can become standing practice, and make sure your engineers use what exists.

Your background

• 3+ years managing engineers, with real experience giving feedback and developing people.

• 5+ 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.

• 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.

Bonus: management experience in a consulting, services, or forward deployed engineering organization, or experience taking a team or practice from zero to one.

How we work

High trust, high agency, low ego. We push back when something isn't right and share what we learn, so good instincts spread fast.

• We are our first client. We built Friday, our coding agent, and Statum, our knowledge infrastructure, and we run them on ourselves.

• AI-first, human-accountable. Agents write nearly all our client code. Every output is reviewed, and the person is accountable.

• Partners, not a vendor. You're in the room when hard calls get made, and you're expected to have a point of view.

• Breadth that compounds. You'll see more industries and problems in a year than most people see in a career.

• Weekends are yours. Pay is transparent, and we don't confuse long hours with good work.

What to expect

1. Initial screen (30 min): with our recruiting partner.

2. Technical screen (30 min): a short, real-world coding exercise with an engineer.

3. Hiring manager interview (45 min): behavioral and past work.

4. Technical interviews (2.5 hrs, two sessions): coding and systems design. Use AI tools in the coding interview, since it reflects how we work.

5. Case study (75 min): a live, scenario-based discussion covering staffing, feedback, technical review, and closing the loop. No prep needed.

What we offer

• Base salary of $285,000 USD plus competitive equity

• 401k with 4.5% employer match, and fully covered medical, dental, and vision premiums

• Monthly wellness stipend, Citi Bike, and 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

• Hybrid in NYC. We're open to fully remote candidates in the US or Canada.