OPEN CAREER OPPORTUNITIES
Chief of Staff
Description
At Chexy, we’re reshaping the way money moves - making payments smarter, faster, and more rewarding. We started by being the first in Canada to let people pay their biggest and most painful bills with credit cards and earn rewards on money they had to spend anyway. Now, we’re on a much bigger mission: to build a super app that acts as your co-pilot for all your money—helping you get more value from every dollar you spend.
As a high-growth fintech startup, we’re at the forefront of payments innovation, and we’re looking for hungry, ambitious people to help us scale. If you thrive in a fast-moving, high-energy environment and want to be part of something big, we’d love to work with you.
The Role
As Chief of Staff, you will be the CEO’s strategic partner and operational force multiplier. You’ll have a direct hand in the highest-leverage decisions at the company — from growth strategy and fundraising to investor relations and organizational design — while ensuring the
operational engine runs smoothly behind the scenes.
This is a high-trust, high-access role with extraordinary breadth. You’ll represent the CEO in rooms when she can’t be there, own the preparation and storytelling behind our most important stakeholder communications, and lead the special projects that will define Chexy’s next chapter. The best day might be pressure-testing a new market entry strategy in the morning and pulling together a flawless team offsite by the afternoon.
We see this as a 2–3 year tour of duty that positions you for a senior leadership role — whether that’s a VP/GM seat at Chexy or your next venture. If you’re looking for the fastest way to learn what it takes to build and scale a company, this is it.
What You'll Own
Strategic Initiatives & Special Projects
- Co-own the CEO’s most critical priorities — the projects designed to step-change the business over the next year
- Lead cross-functional initiatives end-to-end, from problem framing and analysis through execution and measurement
- Serve as the voice of the CEO in meetings, ensuring decisions move forward and context flows back with precision
- Develop briefing materials, strategic recommendations, and talking points for key internal and external engagements
Investor & Stakeholder Communications
- Own investor reporting, board materials, and partner updates — both the substance and the narrative
- Track and communicate company milestones, KPIs, and strategic progress to stakeholders
- Support fundraising processes and investor communications as needed
Organizational Performance
- Build and maintain company-wide KPI frameworks and dashboards that keep the leadership team aligned and accountable
- Drive operational cadences — leadership meetings, quarterly planning, OKR cycles — to keep execution tight
- Monitor organizational health, flag emerging issues early, and drive resolution
Operational Excellence
- Ensure the company’s operational backbone runs smoothly — office environment, vendor relationships, team logistics, and workplace experience
- Lead planning and execution of team events, offsites, and key cultural moments
- Step in wherever there’s a gap; no part of the business is outside your remit
What You Bring
- 5+ years of experience in management consulting, investment banking, private equity, or a similarly rigorous, high-performance environment
- The ability to structure ambiguous problems, build conviction around a path forward, and execute with minimal direction
- Exceptional communication skills — you can draft an investor memo and present it to a boardroom with equal confidence
- Strong financial and analytical acumen; fluency with models, data, and performance metrics
- High EQ and executive presence — you can credibly represent the CEO to investors, partners, and the full team
- Startup experience or a deep passion for fintech is a strong plus
Who You Are
- Ambitious. You see this as a launchpad into senior leadership. You want proximity to the hardest decisions, the most important relationships, and the messiest problems — and you’re ready to earn it every day.
- Versatile and low-ego. You move seamlessly between strategy and execution. You care more about the company winning than about your title or job description.
- Relentlessly reliable. You have impeccable judgment about what matters, you follow through on everything, and the CEO never has to check your work twice.
- Discreet. You’ll have access to sensitive information across every dimension of the business. Trust is the foundation of this role.
Why Chexy
- We are building the next category-defining payments company that will shape how money moves in Canada for generations.
- We are a high-performance team that actually likes each other. We’re fast, we’re ambitious, and we have zero tolerance for "corporate boredom." If you want to work with people who are as witty as they are technical, you’ve found your home.
- You will have a clear trajectory into senior leadership as the company scales and a seat at the table for every major strategy decision at a company in hyper growth stage.
- In two years, you will have a chance to look back and say you build something that mattered.