VP of Engineering

Type: Full-time / Permanent

Location: Toronto, ON

Location Type: On-site

Department: Technology

Salary: Salary range for this role does not meet the requirements for disclosure as per the ESA

Reports To: CEO

COMPANY OVERVIEW

50,000 athletes. 30+ locations. One app, every league night.

The technology group builds the Brodie app for Brodie Rec. League, supporting a rapidly growing sports brand operating across 30+ North American cities and serving more than 50,000 athletes.

Brodie League is more than a basketball league, it's a community. As one of North America's fastest-growing sports brands, Brodie League is redefining adult recreational basketball by delivering an elevated, professional-quality experience rooted in culture, competition, and community. Our mission is to make every league night the best night of the week for our athletes.

ROLE OVERVIEW

Every week, 50,000+ athletes in 30+ cities rely on Brodie's technology: the Brodie app, game-day reminders, stats, highlights, challenges and the notifications that bring them back between game nights. Behind that sit the internal tools and platforms our entire team relies on. That technology has grown as fast as the league has, and the next stage needs one leader across engineering and design.

The VP of Engineering is that leader. You'll lead Brodie's entire technology group. You own how we build and how well it runs, and you help shape what we build next. Your first job is an honest assessment of our infrastructure, codebase, security and AI infrastructure; then you decide what to keep, fix or rebuild, and get your hands dirty making it happen.

The reason this matters: athlete experience and scale. The product is where athletes see their stats, highlights and progress between game nights, and the tools behind it decide how fast we can launch and run a new city. Your job is to make the product fast, reliable and secure for every athlete, every week, in every city, and to build a platform that still works at twice the size.

You are not starting from scratch and you are not doing this alone. Brodie already has an app engineering team, a Product Design Director and a product athletes use every week. You'll be a player-coach: close enough to the code to review a pull request and ship a fix, and senior enough to set one direction for engineering, product and design. You'll work directly with our CEO and represent technology on the executive leadership team.

CORE RESPONSIBILITIES

Technology assessment and roadmap (primary focus)

Know exactly what we have before deciding what we build next.

- Run a full assessment of Brodie's technology in your first 90 days: infrastructure, codebase, architecture, data, security posture and AI infrastructure
- Map tech debt, single points of failure and scaling risks, and rank them by their impact on athletes and the business
- Turn the assessment into a 12-month technology roadmap with clear calls on what we keep, fix, rebuild, buy or retire
- Own security end to end: access control, secrets management, vendor risk, incident response, and the protection of athletes' personal data
- Set Brodie's AI infrastructure strategy: which models, platforms and vendors we build on, how we evaluate them, what they cost and how AI features ship safely
- Own the technology budget, including cloud spend, software and vendor contracts, and technology headcount

Hands-on engineering

A player-coach who still ships.

- Write production code, review pull requests and pair with engineers on the hardest problems
- Make the final call on architecture and major technical decisions, and document the reasoning
- Set the engineering standard: code review, testing, CI/CD, observability, documentation and release management
- Own reliability and performance, especially at peak moments like registration openings, game nights and season launches
- Build an on-call and incident process so problems are caught and fixed before athletes feel them
- Make AI-assisted development part of how the team works every day, from coding and code review to testing and documentation

Product development and product management

Help decide what gets built. Own how it ships.

- Partner with the CEO and leadership on the product roadmap: what we build, in what order, and what we say no to
- Bring technical judgment to every product decision: scope, effort, trade-offs, sequencing and risk
- Run a product development process that takes features from problem to spec to shipped in fast cycles, timed to the league calendar: Slasher Season, Coldest Winter, Bracket Season and Brodie Summer
- Scale the Brodie app's engagement and retention features, including progression, challenges and notifications, with our Growth and lifecycle/CRM teams
- Make every release measurable, with product analytics, experimentation and dashboards that show what athletes actually do

Efficiency, internal tools and platforms

Make the whole company faster, not just the app.

- Audit the tools and platforms Brodie runs on across Operations, Growth, Content and the rest of the business, and find where manual work, duplicate tools and broken handoffs slow teams down
- Decide what to build, buy, integrate or retire, and consolidate the stack where tools overlap
- Build internal tools and automation that let us run 30+ markets, and then twice that, without headcount growing at the same rate
- Own the data foundation: connected, trustworthy data on athletes, teams, leagues and revenue that every team can use
- Bring AI and automation to the rest of the company: find the repetitive workflows, ship the fixes and give non-technical teams tools they can use safely

Leading the technology group

One technology team, one standard.

- Lead engineering, product and design as one group, with clear goals, clear ownership and an operating rhythm the rest of the company can rely on
- Hire, coach and grow the team, and set the hiring bar, career paths and performance expectations
- Decide the right mix of in-house engineers, contractors and agencies, and hold external partners to the same standard
- Represent technology on the leadership team and explain technical trade-offs in plain language
- Report on delivery, reliability, security and spend with a point of view, not just a dashboard
- Partner with our Product Design Director to hold design quality and accessibility to the same bar as code

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REQUIREMENTS

- 10+ years in software engineering, including 5+ years building and leading engineering teams. You are senior enough to own Brodie's entire technology function on your own accountability
- You have personally inherited an existing platform, assessed it honestly and modernized it without stopping the business, and you can speak to what you kept, what you rebuilt and the results it drove
- You still write code: strong hands-on depth across mobile, backend services and APIs, and cloud infrastructure (AWS, GCP), enough to review a pull request as confidently as a roadmap
- A security-first track record: you have owned application and cloud security, access management and the protection of customers' personal data, with working knowledge of Canadian and US privacy requirements
- Hands-on experience with AI infrastructure: you have shipped LLM-powered features or AI tooling in production and can evaluate models and vendors on quality, cost and risk
- Strong product judgment. You have partnered closely with, or led, product management and can make scope and priority calls with the business
- A track record of building and scaling teams: hiring, coaching and managing a mix of in-house engineers
- Proof that you make teams faster: shorter release cycles, fewer incidents and less manual work, with the numbers to show for it
- You have built process and structure in a fast-scaling company without slowing it down
- You explain technical trade-offs in plain language to non-technical leaders, and you write well
- AI-Native Mindset: You actively use AI to accelerate development, code review, testing, documentation and operations, including working with tools such as Claude Code, Cursor, GitHub Copilot and emerging AI-powered engineering workflows. You constantly look for ways to automate repetitive work and increase speed without compromising quality
- 5 days in office at our Toronto HQ - Brodie has thrived due to a culture of collaboration and teamwork in office

Strongly Preferred

- You have been the first or most senior technology leader at a startup (Head of Engineering, VP of Engineering or CTO) through a period of fast growth, ideally with product or design reporting to you
- Experience with consumer mobile apps built around community, sports, fitness, gaming or live events
- Experience with registration, scheduling, payments or membership platforms
- You have built engagement systems at scale: real-time scores and stats, push notifications, gamification or loyalty
- Experience with a modern data stack and product analytics (Mixpanel, Amplitude or similar)
- You hoop, or you understand why someone gets off the couch on a Tuesday night to play

COMPENSATION

The expected annual compensation range for this role is above the ESA requirements for disclosure. Compensation is based on skills, experience, qualifications, internal equity, and business needs. The compensation range may be adjusted in the future.

WHY JOIN BRODIE LEAGUE

- Comprehensive health and wellness plan
- Access to a yearly Brodie takeover of the Toronto Raptors court
- Growth and mentorship opportunities
- Professional development budget

ARTIFICIAL INTELLIGENCE DISCLOSURE

Artificial intelligence may be used in the recruitment and selection process, including to screen, transcribe interviews, assess, or evaluate applicants.

POSITION STATUS

This job posting is for:

a new position at Brodie League

APPLICATION PROCESS

Interested candidates should apply by submitting their resume through the designated application platform.

COMMITMENT TO INCLUSION

We know through experience that different ideas, perspectives, and backgrounds foster stronger and more creative teams. We strive to create organizations that reflect the communities we serve and where everyone feels empowered to bring their full, authentic selves to Brodie Rec Leagues.