This is a full time remote role based in Canada. THE OPPORTUNITY We are looking for a Director, Software Engineering to own the end-to-end software development process and lead our engineering squads. You will be responsible for delivery cadence, team development, process discipline, and agile health across a 12-person development organization spanning 4-5 squads. You will report directly to the CTO and work closely with product leadership to keep delivery moving at startup velocity inside a HIPAA-regulated and FDA targeted environment. You will own the operating rhythm that keeps the squads aligned, unblocked, and shipping. You will be translating engineering strategy into squad-level execution with discipline and consistency. This is an inward-facing leadership role: your key output will be a high-performing team, a predictable delivery cadence, and a culture of craft and accountability. You will build the systems and processes the team runs on, develop the engineers within it, and scale the organization as we grow. WHAT YOU'LL OWN Delivery Owner. Orchestrate with tech leads sprint planning, retrospectives and other agile processes across the squads in the organization. Identify and resolve delivery blockers before they become missed commitments, using data and delivery metrics to drive decisions and surface risks early. People Leader. Run structured 1:1s, performance conversations, and career development plans for developers and QA across all squads. Partner with tech leads to build squad-level capability and culture. Own hiring and onboarding for development roles. Process Architect. Establish and maintain engineering process standards: coding standards, definition of done, PR review policies, defect triage, and change management. Own QA and release coordination in partnership with the QA manager. Drive compliance-aware engineering practices that keep SOC2 Type 2 policies intact. Champion responsible adoption of AI coding tools across squads, establishing norms for how they are used without eroding code quality or compliance standards. Cross Functional Execution. Partner with product management and design to align priorities, sequence work across squads, and keep delivery moving at a startup velocity. Own the translation of product requirements into engineering commitments. Identify and resolve cross functional blockers. Represent engineering in cross-functional forums where delivery timelines and trade-offs are the agenda. Technical Direction. Partner with the CTO and Director of Architecture on technical road mapping and long-term technical strategy. Translate architectural decisions and strategic direction into squad-level execution plans. MUST HAVE 5+ years of engineering leadership experience, including direct management of multiple teams or squads simultaneously.Track record of improving delivery predictability and team health in a fast-moving product environment.Experience managing tech leads and senior engineers, not just individual contributors.Experience adopting/scaling AI-assisted development practices; familiarity with tools like Cursor or Claude Code, and a point of view on how they change team workflows, output quality, and delivery expectations.Comfort operating in a regulated or compliance-adjacent environment (HIPAA, SOC2, or equivalent).Strong process instincts: you know when to add structure and when structure is the problemExcellent written and verbal communication: you can run a difficult 1:1, write a clear post-mortem, and present a delivery update to a board member with equal confidence.Familiarity with modern engineering tooling: GitHub, JIRA or equivalent, CI/CD pipelines, and observability stacks. NICE TO HAVE Experience in a health tech or regulated SaaS environment (HIPAA, FDA SaMD, or similar).Background in scaling engineering teams from 10–25 people.Familiarity with NestJS, React Native, NX monorepo, or AWS-based infrastructure.Experience with SR&ED, IRAP, or other R&D funding programs (Canadian context a plus).Prior work in a product company targeting the U.S. healthcare market. WHO YOU ARE A people-first leader: You are energized by growing engineers, not by shipping code yourself. Your fingerprints are on the team, not the codebase.A process pragmatist: You build just enough structure to create predictability, then get out of the way. You know the difference between process that serves the team and process that serves itself.Mission-aware: You understand that the software this team ships affects real patients managing chronic conditions. That context informs how you lead.Calm under pressure: Startups are noisy. You stabilize the team when things are uncertain rather than adding to the noise.