Chief of Staff

Chief of Staff – Wagepoint – Toronto, Canada

At Wagepoint, we’re authentic, diverse, and proud to bring the best versions of ourselves together to create payroll magic for thousands of small business owners across Canada. We’re growing fast and looking for people who share our commitment to our customers and our belief that the consequences of payroll mistakes can be dire.

We’re looking for a talented Chief of Staff who thrives in fast‑paced environments and has a knack for turning big ideas into actionable plans. You’ll serve as the right‑hand to our CEO and a strategic partner to the Executive Leadership Team, ensuring that priorities are executed smoothly and that the entire organization stays aligned and on track.

• Drive the execution of high‑priority, cross‑functional strategic initiatives directly sponsored by the CEO.
• Translate the CEO’s vision into concrete, actionable plans with owners, timelines, and follow‑through.
• Co‑lead the company’s strategic planning processes, partnering with Finance, Ops, and People Ops.
• Own the rhythm and outcomes of executive meetings—including ELT, SMT, quarterly business reviews, and off‑sites.
• Act as a strategic advisor and sounding board to the CEO, helping to identify risks, pressure‑test decisions, and provide honest counsel.
• Lead special projects that span departments or require senior oversight, focusing on business operations and continuous improvement.
• Support executive communications—internal memos, announcements, board updates, and investor‑facing content.

• 7+ years of progressive experience in strategy, operations, consulting, or general management—preferably in a tech or SaaS company.
• Experience working directly with C‑level executives in an operational leadership or strategic advisory capacity.
• Proven ability to lead and drive cross‑functional initiatives from start to finish.
• Strong project management skills and comfort navigating fast‑moving, ambiguous environments.
• Experience supporting executive‑level communications (e.g., board decks, internal announcements, or investor updates).
• Strategic thinker with strong data literacy—able to interpret, synthesize, and present data that drives decision‑making.
• Executive presence with excellent judgment, discretion, and a bias for action.
• Experience at a high‑growth SaaS or tech company.
• Experience with OKRs or strategic planning frameworks.
• Has helped shape or scale business operations.
• Prior Chief of Staff experience or experience reporting directly into a CEO.

Impact:
Roll up your sleeves and directly contribute to the growth and success of Wagepoint by shaping our workforce.

Culture:
The opportunity to work with the world’s friendliest team, solving interesting problems together with an endless amount of laughter. We work hard, but we always have time for a bad joke or two, and we are always learning with a growth‑oriented mindset.

Innovation:
Work in an environment that encourages creativity and new ideas.

Remote:
Wagepoint is a remote company, so you can work from home, forever! More time with your pets is always a bonus.

If this role sounds like the right fit for you, send us your updated resume and a few lines on what excites you about the job. If we believe you’re a good match, someone from our team will reach out to schedule a call.

Wagepoint is an equal‑opportunity employer. We welcome and appreciate all applicants with diverse backgrounds, races, religions, genders, identities, ages, and experiences. We are committed to making our workplace safe and inclusive for everyone and to ensuring our recruitment process reflects that. If you require any special accommodation during our recruitment process, please let us know—we are more than happy to assist.