Senior Applied AI Engineering Lead

Headstart AI; Toronto; Remote; CAD 363,000 - 491,000; Full time

Benefits offered by this job

401k with employer match

Medical, dental, vision insurance

Wellness stipend

Parental leave

Job summary

Headstart AI is seeking a Senior Engineering Manager to lead engineers, shape architecture, and drive staffing across client engagements in the US and Canada. You'll start on a client engagement to learn the work, then build and lead a team as we grow.

You’ll own recruiting, staffing, and partnerships with product and client stakeholders, guiding technical strategy and ensuring delivery in production AI systems.

Qualifications

• 4+ years managing engineers, 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.

Responsibilities

• Lead your team with direct, actionable feedback to hold a high bar and grow engineers.
• Provide technical leadership: review architecture, agent, prompt, and eval design; handle production regressions and unclear requirements.
• Close the loop across engagements by turning patterns into standing practice and reference implementations.
• Shape staffing: determine who works on which engagement and plan transitions; flag risks early.
• Run hiring for your team from sourcing to onboarding; you define the bar.
• Partner with product, client partners, and client stakeholders so each engagement lands.

Skills

People management

Software engineering

Python

Client delivery

AI tooling

System design

Job description

Headstart AI is seeking a Senior Engineering Manager to lead engineers, shape architecture, and drive staffing across client engagements in the US and Canada. You'll start on a client engagement to learn the work, then build and lead a team as we grow.

You’ll own recruiting, staffing, and partnerships with product and client stakeholders, guiding technical strategy and ensuring delivery in production AI systems.