Vice President of Software Engineering

Eagle Search; Toronto; On-site; CAD 180,000 - 300,000; Full time

Job summary

Eagle Search is partnering with a rapidly scaling healthcare technology company to appoint a Vice President of Development (AI-First Engineering) to lead the next phase of its AI-driven platform transformation in Canada.

As the first senior engineering hire in Canada, the VP will establish the Toronto office, shape culture, hire world-class talent, and create a centre of excellence for AI-first product development, embedding AI across design, development, testing and operations.

Qualifications

• Extensive leadership of large engineering teams in AI/ML.
• Proven track record delivering AI/ML products at scale.
• Experience with LLM-based apps and agentic systems.
• Healthcare or regulated environments preferred.
• Strong strategic tech leadership with execution.

Responsibilities

• Define AI-first engineering strategy across the portfolio.
• Establish and scale the Toronto engineering hub and culture.
• Recruit and develop world-class AI and software talent.
• Oversee end-to-end software delivery from design to operations.
• Partner with Product, Clinical, Data Science, Security and Compliance.
• Establish governance and responsible AI frameworks.

Skills

AI leadership

Engineering leadership

AI/ML product delivery

Stakeholder management

Education

Bachelor’s degree in CS/Engineering

Tools

LLM platforms

MLOps

Cloud infrastructure

Job description

Eagle Search are proud to be partnered with a rapidly scaling healthcare technology company to appoint a Vice President of Development (AI-First Engineering) to lead the next phase of their AI-driven platform transformation.

This is a rare opportunity to join a business at the intersection of artificial intelligence, healthcare, and large-scale clinical data, with a mandate to redefine how software is built, deployed, and operated in an AI-first world.

As the company's first senior engineering hire in Canada, this individual will be responsible for establishing and leading the Toronto engineering office, building high-performing teams from the ground up, shaping the culture, and creating a centre of excellence for AI-first product development.

The organisation has already established itself as a market leader within radiology technology, combining advanced AI, clinical workflows, and large-scale healthcare datasets to transform how clinicians work and make decisions.

The role:

The Vice President of Development will own the end-to-end engineering organisation and lead the transition towards an AI-native operating model.

In addition to driving the company's AI-first engineering strategy, this leader will establish and scale the Toronto engineering hub, hiring and developing world-class engineering talent while creating the culture, processes, and operating model that will support the next phase of growth.

The successful candidate will be responsible for embedding AI into every aspect of software delivery, from product design and development through to testing, deployment, and operations.

This is a role for an Agentic AI thinker, to build and lead the Software Engineering function in Toronto.

Responsibilities include:

• Define and execute an AI-first engineering strategy across the entire development portfolio, driving measurable improvements in productivity, quality, and delivery speed.
• Re-architect the software development lifecycle so that AI agents, copilots, and autonomous workflows become core components of design, development, testing, deployment, and operations.
• Lead the design and delivery of AI-native products, including LLM-based applications, multimodal AI solutions, and workflow automation capabilities.
• Build and scale the platforms required to support AI workloads, including model training, evaluation, observability, governance, and deployment.
• Build, retain, and develop a high-performing engineering organisation, recruiting world-class AI and software engineering talent while fostering an AI-first culture.
• Partner closely with Product, Clinical, Data Science, Security, and Compliance teams to deliver trusted AI solutions in a highly regulated environment.
• Establish robust evaluation, governance, and responsible AI frameworks to ensure quality, safety, and regulatory compliance.
• Manage key technology partnerships and make strategic build-versus-buy decisions across AI platforms, infrastructure, and tooling.
• Own engineering financials, balancing innovation, scalability, and operational efficiency.
• Act as a visible technology leader, influencing executive stakeholders, shaping technology strategy, and driving organisational transformation.
• Lead the establishment and growth of the Toronto engineering office, building a high-performing team and creating a centre of excellence for AI-first product development.

What we're looking for:

• 12+ years of software engineering experience, including significant experience leading large engineering organisations and AI/ML-focused teams.
• Proven track record of delivering AI/ML products at scale, ideally including LLM-based applications, agentic systems, computer vision, or multimodal AI solutions.
• Strong understanding of modern AI technologies, including foundation models, generative AI, agent frameworks, MLOps, and AI infrastructure.
• Experience embedding AI-assisted development tools and workflows into engineering organisations, driving measurable improvements in productivity and quality.
• Healthcare experience is strongly preferred, although experience within other highly regulated environments will also be considered.
• Ability to balance strategic technology leadership with a strong understanding of product, architecture, and engineering execution.
• Strong commercial and financial acumen, with experience managing technology investments, infrastructure costs, and vendor relationships.
• Exceptional people leadership, with a track record of hiring, developing, and scaling high-performing engineering and AI teams.