Vice President of Engineering

VP of EngineeringLocation: Toronto, ON (Hybrid preferred) Reports to: Co-Founder & CEO Build the future of healthcare.Blair is building the operating system for the next generation of healthcare, closing specialist gaps while enabling proactive, preventative care. We build LLM-powered clinical infrastructure that enables licensed healthcare providers to deliver specialist-level care at scale. Today, Blair supports patients across Canada and the United States through our menopause, women’s health, urology, and clinical nutrition programs, while partnering with employers to improve access to specialist care. Today, we support patients across Canada and the United States across menopause, women’s health, urology, and clinical nutrition, while partnering with employers to improve access to high-quality care. We’re entering an exciting new phase of growth and are looking for an exceptional engineering leader to help build the technology that will define Blair’s future. About the RoleThis is the most senior engineering role at Blair. Reporting directly to our Co-Founder & CEO, you’ll partner with the founding team to define our technical vision, build the engineering organization, and architect the platform that powers the next generation of healthcare. This is not a traditional VP of Engineering role. We’re looking for a technical builder first, and a leader second. You won’t inherit a large engineering organization. You’ll build it. You’ll make foundational architectural decisions, establish engineering standards, recruit exceptional engineers, and work alongside the founders to solve some of healthcare’s hardest technical challenges. Most importantly, this is a hands-on role. You should expect to spend a significant portion of your time designing systems, reviewing architecture, and writing production code. While you’ll recruit and mentor engineers as we grow, we’re looking for someone who leads by building, not someone who has stepped away from engineering. If your ideal day includes designing distributed systems, shipping production code, collaborating directly with founders, and solving problems that improve patient care, we’d love to meet you. As Blair grows, this role is expected to evolve into the company’s executive technology leader. What You’ll DoYou will: Own Blair’s overall technical vision, architecture, and engineering strategy.Design, build, and ship production-quality software every week.Build scalable LLM-powered clinical infrastructure that enables licensed healthcare providers to deliver specialist-level care.Partner directly with the Co-Founder & CEO and clinical leadership to shape product strategy and technical direction.Design secure, reliable, and highly available systems capable of supporting rapid growth across multiple healthcare specialties and jurisdictions.Lead architecture reviews and make key technical decisions that will shape the company for years to come.Continuously improve engineering processes, developer productivity, deployment pipelines, security, observability, and operational excellence.Build and maintain a high-performing engineering culture centered around ownership, speed, accountability, and continuous improvement.Recruit, mentor, and develop an exceptional engineering team.Balance long-term architectural thinking with rapid product delivery.Help define what world-class engineering looks like at Blair.What We’re Looking ForWe’re looking for someone who has built products from the ground up and enjoys solving difficult technical problems. You likely have: Significant experience building and scaling modern software platforms.Strong backend engineering experience using technologies such as TypeScript, Python, or Go.Experience designing distributed systems and cloud-native architectures.Experience building products powered by LLMs and modern AI infrastructure.Strong product intuition and the ability to make pragmatic engineering decisions.Excellent communication skills and the ability to work closely with technical and non-technical teams.Experience mentoring engineers through technical leadership.A strong bias toward ownership, execution, and shipping.Bonus points if you’ve worked with: React or Next.jsPostgreSQLDocker and KubernetesAzure or AWSRetrieval-Augmented Generation (RAG)Agentic AI systemsHealthcare technologyClinical decision supportPHIPA or HIPAA environmentsThis Role Is for You If…You love building products and solving hard technical problems.You still enjoy writing production code.You believe engineering leadership means leading by example.You want to build an engineering organization from the ground up.You care about architecture, but you care just as much about shipping.You believe speed is a competitive advantage.You enjoy improving engineering systems, developer productivity, and operational excellence.You thrive in fast-moving environments with ambitious goals.You want to build a company, not simply work for one.This Role Is Probably Not for You If…You’re primarily a people manager and no longer enjoy hands-on software development.You haven’t written meaningful production code in recent years.You prefer managing teams over solving technical problems.You enjoy maintaining mature systems more than building new ones.You believe process is more important than progress.Engineering metrics, operational excellence, and continuous improvement don’t interest you.You need perfect information before making decisions.You’re uncomfortable taking calculated risks.You prefer highly structured environments over the pace and ambiguity of an early-stage company.You’re looking for a role where someone else defines the roadmap.Why Blair?Healthcare is one of the world’s largest industries, yet access to specialist care continues to become more challenging. We’re building the clinical infrastructure that enables specialist knowledge to scale beyond the specialist workforce itself. This isn’t another AI application. We’re building the technology that enables licensed healthcare providers to deliver specialist-level care across multiple medical specialties, helping patients access expert care faster, wherever they live. If we’re successful, we’ll fundamentally change how healthcare is delivered. You’ll work directly with the founding team, have enormous influence over our technical direction, recruit an exceptional engineering team, and help shape the future of the company from an early stage. What We OfferCompetitive compensation.Meaningful equity ownership.Comprehensive health benefits.Flexible hybrid work environment.The opportunity to build one of Canada’s most ambitious healthcare technology companies.Interested?If you’re excited about building category-defining technology, working directly with founders, remaining deeply hands-on, and helping redefine how healthcare is delivered, we’d love to hear from you. Email careers@blairhealth.ca or apply directly on LinkedIn.