Head of Engineering (Hybrid, Toronto).

What we’re looking for

• This is a net new, foundational leadership role. We are hiring our first Head of Engineering to own and evolve Leo Berwick’s software development function.
• Today, all development resources are outsourced and off-shored, and you will manage those teams with full ownership of execution and outcomes. Over time, you will shape a hybrid operating model which should include our own employees.
• In parallel, this role will shape how Leo Berwick responsibly enables non‑technical internal teams to build tools using AI‑assisted coding platforms and low-code tools. As AI lowers the barrier to software creation, we see this as an opportunity to define how modern technology leaders empower non‑engineers while maintaining appropriate standards around security, architecture, and maintainability.

You’re the right fit for this role if you –

• Have owned end‑to‑end engineering delivery and are accountable for outcomes, not just technical decisions
• Are comfortable building structure in ambiguous, growth‑stage environments
• Have experience leading outsourced or offshore engineering teams to high delivery standards
• Believe engineering should enable the business, including responsibly supporting AI‑assisted or low‑code development
• Can clearly translate technical complexity into practical insight for senior leaders

This role is based in the Greater Toronto Area (GTA) and follows a hybrid work model, which requires 2 days per week in the office.

What you'll do

Own core software development and delivery 

• Own end-to-end delivery of Leo Berwick’s software platforms.
• Lead and govern outsourced development teams.
• Design and evolve the engineering operating model.
• Establish technical standards and delivery metrics.
• Incorporate state-of-the-state AI tools and processes into our software development lifecycle.

Enable AI‑assisted development by non‑technical users 

• Define guardrails, patterns, and tooling that allow non‑technical teams to safely build internal tools using AI coding assistants and low-code tools.
• Establish standards for when AI‑assisted solutions are appropriate versus when formal engineering involvement is required.
• Partner with IT, Security, and Data leaders to ensure AI‑enabled development aligns with firm‑wide controls, data protection, and audit expectations.
• Act as an internal thought leader on how AI changes the relationship between engineering teams and business users.
• Create leverage by enabling the broader organization to solve small, local problems without consuming core engineering capacity.

What you bring

• 5-7+ years of software engineering experience with senior leadership responsibilities.
• Direct experience managing outsourced and offshore engineering teams.
• Comfort building structure in ambiguous environments.
• Have enabled or governed AI-assisted or low-code development responsibly.
• Have strong communication skills and can synthesize information to various stakeholders.
• Experience working in a professional services or consulting environment would be advantageous.

What Success Looks Like

• You’ve built outsourced engineering teams that deliver like an internal function. Delivery is predictable and scalable, engineering stays focused on the highest‑leverage work, and non‑technical teams are safely empowered to build tools using AI without compromising standards. 

Benefits & Perks North America

• Unlimited paid time off including 2 weeks of disconnected time each year
• Flexible working arrangements – remote and location flexibility
• Tuition reimbursement
• Attractive medical, dental insurance
• Pension & retirement contributions
• Monthly fringe benefit stipend (up to $400)
• Additional benefits to support your physical and mental wellness

Compensation:

This is a permanent full-time role offering a base salary range of $150,000–$200,000 CAD, commensurate with skills, experience, and alignment with the requirements of the role. Placement within this range will be determined based on experience relevant to this role and scope of responsibility.

Vacancy Statement:

This posting reflects a new vacancy.

Use of Artificial Intelligence in Hiring:

The firm uses artificial intelligence tools to screen candidates for this role.

Equal Opportunity Statement

Leo Berwick provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type with regard to race, age, ancestry, color, creed, disability status (physical or mental), gender, marital status, legally-protected medical condition (including pregnancy), national origin, religion, gender identity or expression, genetic information, sexual orientation, military, protected veteran status, or any other characteristic protected by applicable federal, state, or local laws.