Chief of Staff

SharpStakesOntario, Canada

4 days ago

Job type

Full-time

Job description

Chief of Staff

Location : Remote / Hybrid Toronto

Type : Full-Time

Reports to : CEO

Start Date : asap

About SharpStakes

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.

The Role

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.

What You’ll Do

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 Might Be a Fit If…

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.

Requirements

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

Bonus (Nice to Have)

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

Why this role is awesome

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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Chief Of Staff • Ontario, Canada