Engineering Manager (Player-Coach) – AI, React, TypeScript, AWS

Position Details -Job Title: Engineering Manager -Employment Type: Full-Time -Location: Remote (Canada & United States) -Reports To: Chief Technology Officer (CTO) -Start Date: Early August 2026 (Mid-July preferred) Compensation Canada: CAD $63–65/hour United States: USD $55–60/hour About the Role: This is an execution and people leadership role reporting to the CTO. The team comprises approximately 7 engineers — a mix of full-time staff and embedded external developers — split across two workstreams: the existing Builder product and the AI Builder. The successful candidate will: -Unify a currently fragmented Landing Page Builder group into one coherent unit with a shared sprint board and delivery cadence -Bring real Scrum discipline to delivery — story sizing, sprint commitments, burndowns, and retrospectives -Manage a hybrid team of engineers and embedded vendor developers through a legacy-to-AI-native product transition, including clean vendor offboarding and knowledge transfer -Balance parallel workstreams — maintaining the existing Builder while shipping the AI Builder — without starving either -Lead the team's adoption of agentic engineering workflows and tooling -Partner with the CTO, VP of Product, peer Engineering Managers, and the Director of Data & AI/ML Engineering to keep engineering a credible voice in roadmap conversations What We Need to See in Candidates: -5–8 years of engineering experience, with 3+ years managing teams of 8 or more in a SaaS environment -Proven experience leading a team through a legacy-to-modern product transition — parallel workstreams, deprecation planning, shipping new product alongside active maintenance -Demonstrated experience shipping AI-powered or agentic features that are actually in production (not just POCs) -Experience managing hybrid teams of full-time staff and embedded vendor or contractor developers, with accountability for standards, knowledge transfer, and clean offboarding -Solid technical depth — this is a hands-on "player coach" role, with 30–40% of time spent on feature delivery, code review, and pairing with the team -Hands-on experience with the stack: React, Tailwind, GraphQL, AWS, Postgres, DynamoDB, TypeScript (Python, GrapesJS, MySQL, Ruby, Java, Clojure, OpenTofu, and Radix are valuable pluses) -Modern engineering discipline: CI/CD maturity, code review culture, observable velocity, and delivery predictability. Comfortable working alongside a CTO in a clear division of responsibilities — executing on direction, and pushing back credibly when needed -A genuine track record of developing senior engineers into technical leaders Culture Fit We are looking for someone who: -Moves with urgency and doesn't wait for permission -Treats AI as a real capability multiplier rather than a buzzword -Measures success by how much they unblock and upskill others -Builds momentum without leaving people behind -Stays calm under uncertainty — the roadmap and team composition are still being shaped, and this candidate thrives in that environment -Is decisive on people and process without requiring consensus Submission Requirements: Please include the following for every candidate: Full resume A short 2–3-minute video introduction covering the candidate’s relevant experience and response to the pre-screening question: "Tell me about a time you led an engineering team through a legacy-to-modern product transition while managing a hybrid team of full-time and vendor developers. How did you split attention between keeping the legacy product stable and shipping the new one, and what is an AI-powered or agentic feature you helped get into production?" Please add the link under Additional Background Material on the submission. Important Note: The candidate must be in the US and Canada. Proposals without a Loom video will not be considered.