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Brodie Sports Group is a rapidly growing North American recreational sports brand operating 30+ locations and serving 50,000+ athletes. The company has built a mobile app and platform ecosystem that powers league management, athlete engagement, stats, highlights and community features across multiple cities.
As VP of Engineering, you will lead Brodie's entire technology function, including engineering, product design and internal platforms. This is a hands-on player-coach role where you'll own strategy, execution and team leadership simultaneously.
Your primary focus in the first 90 days is a comprehensive technology assessment: infrastructure, codebase, architecture, data, security posture and AI infrastructure. You'll map tech debt, scaling risks and single points of failure, then translate findings into a 12-month roadmap with clear decisions on what to keep, fix, rebuild, buy or retire.
Key responsibilities include:
**Technology & Infrastructure**: Own the complete technology stack assessment, security end-to-end (access control, secrets management, vendor risk, incident response, athlete data protection), and set Brodie's AI infrastructure strategy including model selection, platform evaluation, cost management and safe feature deployment.
**Hands-On Engineering**: Write production code, review pull requests, pair on hard problems, set engineering standards (code review, testing, CI/CD, observability, documentation), own reliability and performance at peak moments (registration, game nights, season launches), and build on-call and incident processes. Integrate AI-assisted development into daily workflows.
**Product Development**: Partner with CEO and leadership on product roadmap, bring technical judgment to scope and sequencing decisions, run fast product cycles aligned to league calendar (Slasher Season, Coldest Winter, Bracket Season, Brodie Summer), scale engagement features with Growth and CRM teams, and establish measurable releases with analytics and experimentation.
**Internal Tools & Platforms**: Audit tools across Operations, Growth, Content and other departments; consolidate overlapping systems; build automation and internal tools to scale operations across 30+ markets; own the data foundation for athletes, teams, leagues and revenue; bring AI and automation to non-technical teams.
**Team Leadership**: Lead engineering, product and design as one unified group with clear goals and operating rhythm. Hire, coach and grow the team; set hiring bar and career paths; manage mix of in-house engineers, contractors and agencies; represent technology on executive leadership team; partner with Product Design Director on quality and accessibility standards.
You'll report directly to the CEO and work from Brodie's Toronto headquarters 5 days per week.
**Requirements:**
- 10+ years in software engineering, including 5+ years building and leading engineering teams
- Proven experience inheriting and modernizing an existing platform without stopping the business; ability to articulate what was kept, rebuilt and results achieved
- Strong hands-on technical depth: mobile, backend services, APIs, cloud infrastructure (AWS, GCP); capable of confidently reviewing pull requests and architecture decisions
- Security-first track record: owned application and cloud security, access management, customer data protection; working knowledge of Canadian and US privacy requirements
- Hands-on AI infrastructure experience: shipped LLM-powered features or AI tooling in production; can evaluate models and vendors on quality, cost and risk
- Strong product judgment; experience partnering with or leading product management; ability to make scope and priority calls with business stakeholders
- Proven track record building and scaling teams: hiring, coaching, managing mix of in-house engineers
- Demonstrated ability to make teams faster: shorter release cycles, fewer incidents, less manual work, with measurable results
- Experience building process and structure in fast-scaling companies without slowing growth
- Ability to explain technical trade-offs in plain language to non-technical leaders; strong writing skills
- AI-native mindset: actively use AI tools (Claude Code, Cursor, GitHub Copilot, etc.) to accelerate development, code review, testing, documentation and operations; constantly seek ways to automate repetitive work while maintaining quality
- Commitment to 5 days in-office at Toronto HQ
**Strongly Preferred:**
- First or most senior technology leader at a startup (Head of Engineering, VP of Engineering or CTO) through fast growth period, ideally with product or design reporting to you
- Experience with consumer mobile apps in community, sports, fitness, gaming or live events
- Experience with registration, scheduling, payments or membership platforms
- Built engagement systems at scale: real-time scores/stats, push notifications, gamification, loyalty
- Experience with modern data stack and product analytics (Mixpanel, Amplitude, etc.)
- Personal connection to sports or understanding of recreational sports culture
