Engineering Manager, AI

About the company

Founded in 2019, the company is a digital healthcare company that puts the patient in control of their own health and wellbeing. We’re passionate about building technology and beautiful customer experiences to make healthcare more accessible (and more enjoyable) for all Canadians.

The company is Canada's first end-to-end healthcare experience, providing online treatment, prescription delivery and ongoing care. We deliver care across a growing range of daily health categories such as weight loss, birth control, menopause, erectile dysfunction, acne, longevity and more.

Website: [link for members]

The Role

Our AI team builds applied AI products at the company – LLM-powered experiences for patients, and the systems behind them that let a small team serve a growing patient base. As an Engineering Manager on the AI team, you will lead a team shipping AI into a regulated healthcare environment, where accuracy, safety and auditability matter as much as speed. You'll be responsible for delivering on and helping define the AI roadmap, partnering closely with Product, CX, Clinical and Pharmacy to decide where AI creates real leverage.

You will

• Lead and grow a team of engineers building AI-powered features and platform capabilities across the patient and operations experience

• Define, build, and optimize the systems behind our AI products; evaluation, prompt and model management, retrieval, guardrails, and monitoring

• Set the bar for how we measure AI quality, and build the evaluation practices that let us ship changes with confidence

• Own the operational side of running AI in production: model upgrades, cost and latency tradeoffs, and the observability to catch degradation before patients do

• Partner with Clinical, Pharmacy and CX teams to keep humans appropriately in the loop, and to make sure what we build holds up to clinical and regulatory scrutiny

• Lead team ceremonies and planning alongside product

• Brainstorm features and initiatives with product and designers, helping set and guide the AI roadmap

• Take part in all engineering-related and business-related decisions, with the expectation that you'll grow as a leader and engineer

• Mentor and be mentored by other engineers

You have

• 3+ years as an engineering leader or manager

• Hands-on experience shipping LLM-based or ML-driven products to production, not just prototypes

• Real opinions about evaluation: how to measure quality, and how to avoid shipping on vibes

• Strong judgement on where AI is the right tool

• Leadership skills in unblocking and leading development teams

• Clear communication around technical concepts and ability to collaborate with Product

• Familiarity with evaluation, observability and experimentation tooling

• Experience with both front-end and back-end technologies

• Nice to have: experience in a regulated domain such as healthcare, fintech or insurance

Benefits

• Full medical, dental and vision benefits

• Maternity/paternity policy

• 4 weeks vacation (3 weeks anytime + 1 week during the holidays)

• Competitive compensation

• Stock option grant

• Remote first, work from anywhere in Canada

• Incredible culture powered by a highly collaborative and high-performing team

• Large impact at an early-stage technology company

• Professional development opportunities, working closely with founders and the senior leadership team

Open vacancy: This posting is for existing vacancies at the company.

Location: Toronto, Remote (Canada). We have an office in Toronto, but are currently working remotely and open to candidates from anywhere in Canada.

Our commitment to an inclusive team culture means embracing diversity and offering equitable access to opportunities and resources for people who might otherwise be excluded. During our recruitment process, we provide accommodations at any stage. Candidates can communicate their accommodation needs to the hiring manager directly or by emailing [link for members]

Recruitment Fraud Alert

Please note: We have been made aware of fraudulent recruiting activities where individuals pose as the company representatives.

• Communication: We will only ever contact you from an official [link for members] [link for members] email address.

• Interviews: All interviews are conducted via Google Meet; we never interview via text-only platforms (like Telegram or WhatsApp).

• Payments: We will never ask for credit card information, bank details, or payments for "equipment" or "onboarding" during the application process.