Senior Engineering Manager & Talent Architect (Remote)

Headstart; Toronto; Hybrid; CAD 370,000 - 484,000; Full time

Benefits offered by this job

Salary + equity

401k + benefits

Wellness stipend

Parental leave 12 weeks

Office in Soho

Hybrid/Remote

Job summary

Headstart is building production AI systems for real enterprises with a strong emphasis on leadership and engineering excellence. You will lead a talented team, grow engineers into tech leads, and define priorities across engagements while maintaining a high bar for quality and delivery.

You will balance hands-on architectural review with staffing decisions, work closely with product teams and client partners, and help shape the company’s growth as it scales its AI platform and delivery practice.

Qualifications

• 4+ years managing engineers, including senior and staff.
• 8+ years in software engineering, hands-on with Python.
• Experience delivering software in real client environments.
• Curious about agents, evals, and multi-agent systems; depth matters over title.

Responsibilities

• Lead and grow engineers, set priorities and expectations.
• Review architecture, agent, prompt, and eval design.
• Handle production challenges and unclear requirements with decisive calls.
• Shape staffing and hiring for engagements, and plan transitions.
• Collaborate with product and client stakeholders to land engagements.

Skills

People management

Python

Engineering leadership

Hiring

AI tooling

Tools

AI coding tools

Job description

Headstart is building production AI systems for real enterprises with a strong emphasis on leadership and engineering excellence. You will lead a talented team, grow engineers into tech leads, and define priorities across engagements while maintaining a high bar for quality and delivery.

You will balance hands-on architectural review with staffing decisions, work closely with product teams and client partners, and help shape the company’s growth as it scales its AI platform and delivery practice.