Job Description

. Chief of Staff

Location: Remote / Hybrid Toronto

Type: Full-Time

Reports to: CEO

Start Date: asap

SharpStakes is on a mission to rewire how the next generation experiences sports. We’re building the most engaging and data-powered sports betting ecosystem — from tools that help users make smarter bets to content that empowers sports fans. We're growing fast, backed by top-tier investors and loved by a passionate Gen Z audience who crave connection, competition, and culture.

As Chief of Staff, you’ll be the right hand to the CEO — an execution machine, thought partner, and strategic operator who helps the company move faster, smarter, and more effectively. You’ll sit across every function — from growth and ops to product and fundraising — solving bottlenecks, managing special projects, and amplifying the impact of the CEO and leadership team.

This is not a “keep the trains running” role. This is a build a high-speed rail system role.

We’re looking for an A-player : high IQ, high EQ, obsessed with execution, allergic to mediocrity. You’ll thrive if you’re ambitious, adaptable, wildly resourceful, and care deeply about building something that matters.

• CEO Extension : Be in lockstep with the CEO, helping prioritize time, drive key meetings, and keep the company focused on what matters most.
• Special Projects : Lead high-priority projects across product, ops, marketing, partnerships, or hiring — whatever moves the needle most.
• Company-Wide Alignment : Ensure everyone is rowing in the same direction. Help set OKRs, run weekly check-ins, and hold teams accountable.
• Internal Ops & Systems : Build and streamline internal processes to scale execution — from Notion systems to meeting cadences and internal comms.
• Hiring & Culture : Help find and retain top talent. Shape a culture of speed, ownership, and obsession with the user.
• Investor & Partner Support : Support fundraising efforts, prep materials, manage comms, and help grow strategic partnerships.
• Right-Hand Problem Solver : When the CEO says “We need to figure this out,” you're the one who figures it out — and fast.

• You’ve crushed it in high-performance environments (startups, consulting, investing, hypergrowth ops).
• You’re a clear thinker and a bias-to-action doer . You don’t wait to be told — you take initiative.
• You’re organized and can juggle chaos without dropping the ball.
• You understand how to communicate with execs, investors, and 20-year-old brand ambassadors — and make them all feel seen.
• You have the humility to do the dirty work and the ambition to own the big picture.
• You care about product, people, and making things actually work .
• You're excited by building the most fun, engaging, and community-driven betting experience in the world.

• 2–5+ years of experience in startups, consulting, VC, banking, or a similar high-performance environment
• Proven track record of owning and executing complex projects
• Strategic mindset with a detail-oriented operator's brain
• Excellent written and verbal communication
• Comfortable working directly with founders and senior stakeholders
• A deep desire to build — and to win

• Experience in consumer tech, sports, or betting
• Background in product management or operations
• Worked closely with a founder or C-suite before
• Comfortable with technology like powerpoint

• You’ll work directly with the CEO on high-impact initiatives
• You'll help define how we scale from scrappy to sharp
• You’ll get an inside look at fundraising, product, growth, and hiring — and level up fast
• You’ll be part of a movement changing the way Gen Z interacts with sports
• Competitive Pay
• Real start up experience
• Awesome PTO policy

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