Head of Strategy & Operations

Midnite is a next-generation sports betting and gaming platform built for a new wave of players.

We combine sharp product thinking, bold brand, and fast execution to create experiences that feel modern, intuitive, and built for how people actually play today.

Over 400,000 players have already made the move, and we’re only just getting started.

We’re a high-performance team operating at pace. High ownership. Constant iteration. No hiding behind processes. We move quickly, test relentlessly, and turn ambitious ideas into real impact. If you’re driven, creative, and thrive in fast-moving environments where you can shape meaningful outcomes - keep reading.

Not your grandad’s bookie.

👀 The Role

Head of Strategy & Operations

Location: Toronto - in office

Midnite is preparing to launch and scale its Canadian business. We are looking for a Head of Strategy & Operations to partner directly with the Canada GM, drive the launch program, build the operating model, and become the steward of the Canada strategy, P&L, priorities, and budget once we go live. This leader will ensure that priorities are clear and that cross-functional teams and plans are aligned toward a common outcome.

As a member of the Canadian leadership team, the Head of S&O will support the GM in launching, operating, and scaling the business. They will work closely with Canada's Growth and Product leads, as well as with central teams, to shape the market strategy, go-to-market approach, and long-term plan, with the aim of delivering an exceptional, locally relevant experience for Canadian customers.

This is a hands-on leadership role for an exceptional operator who is committed to winning with integrity, building a strong brand, developing a high-performing team, and executing with excellence.

You will:

• Serve on Midnite’s Canada leadership team and a strategic partner to the GM, helping launch the market, steward the strategy, priorities, budget, and P&L, and ensuring cross functional plans support sustainable revenue growth, profitability, and responsible business practices.

• Lead the development and delivery of the Canadian strategy, operating plan, budget, and performance review while adopting central performance standards.

• Build and manage the Canadian operating cadence, including business reviews, leadership meetings, performance reviews, forecasting, and strategic planning sessions.

• Lead cross-functional alignment and execution against P&L, working closely with CA Growth, Product, Ops leads and Central teams to influence and build coherent go-to-market plans.

• Maintain a clear view of performance against plan, identifying opportunities to accelerate when the business is ahead and mobilizing the team to close gaps when it is behind.

• Build trusted relationships with UK central leaders while ensuring Canadian market needs are represented.

The next Midniter:

• You are an exceptional operator with experience owning strategy, planning, forecasting, P&L performance, and cross-functional execution.

• You have a track record of translating strategy into execution and driving cross-functional teams to deliver against a shared plan.

• You have a strong track record of delivering results, taking on increasing responsibility, and progressions throughout your career.

• You bring strong financial and analytical judgment and understand the drivers of revenue growth, customer value, retention, margin, media and promotional efficiency, and profitability.

• You can move confidently between long-term planning and day-to-day execution, using data to identify opportunities, diagnose performance gaps, and drive action.

• You have experience building operating cadences that create accountability, support fast decision-making, and keep teams aligned.

• You have experience building and developing high-performing teams across multiple commercial or analytical disciplines.

• You are comfortable building a new function in an entrepreneurial environment where the local business and operating model are still taking shape.

• Ideally combines strategy or commercial experience combined with meaningful end-to-end operating ownership.

• Experience in gaming is useful but not essential; fintech or another regulated technology environment is highly relevant.

💰 Winnings

• 24 days off, with Canadian national holidays counted separately.

• 3% RRSP match from day one — we start investing in your future immediately.

• Full Manulife health benefits including dental, vision, life insurance, income protection, and an EAP, from day one

• We're early in Canada, and our benefits will keep getting better as we scale.

At Midnite, we’re committed to creating equal opportunities for everyone. We actively strive to build balanced teams that reflect the diversity of our communities, including ethnic minorities, people with disabilities, the LGBTQIA+ community, and all genders.

We aim to provide an inclusive and supportive interview experience for all candidates. If you require any reasonable adjustments, please let us know in advance so we can ensure you feel comfortable and set up for success.