Chief of Staff

Who We Are:

At Wagepoint, we’re good people. Sure, maybe we’re biased. But that’s only because Wage pointers bring the best versions of ourselves to do some of the best work in our careers.

We’re an authentic team who bring our diverse backgrounds, ideas, experiences and cultures together to make payroll magic. Speaking of, we “pull rabbits out of hats” for thousands of small business owners across Canada who rely on our payroll software to pay their employees and process their payroll taxes. And we’re just getting started.

We’re growing and looking for more awesome people to join our merry band of misfits. We are looking for people who share our understanding that when it comes to our commitment to our customers: we mean business. Especially given that the consequences of getting payroll wrong can sometimes be dire.

If you are the kind of person who has always wanted to make a difference and be heard at work, Wagepoint will give you plenty of opportunity to do just that.

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. You’ll report directly to the CEO.

• Drive the execution of high-priority, cross-functional strategic initiatives that are directly sponsored by the CEO.
• Translate the CEO’s vision into concrete, actionable plans with owners, timelines, and follow-through.
• Co-lead our company’s strategic planning processes, partnering with key functions like Finance, Ops, and People Ops.
• Own the rhythm and outcomes of executive meetings — from ELT and SMT meetings to quarterly business reviews and offsites.
• 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 fall between departments or require senior oversight, with a focus on business operations and continuous improvement.
• Support executive communications — from internal memos and announcements to 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.

• You’ve worked at a high-growth SaaS or tech company.
• You have experience with OKRs or strategic planning frameworks.
• You’ve helped shape or scale business operations.
• You have prior Chief of Staff experience or experience reporting into a CEO.

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:
Opportunities for professional development and career advancement - we are always, always learning with a growth oriented mindset.

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

Remote:
The ability to work from home, forever! Wagepoint is a remote company, so you don’t have to worry about commuting to an office. Plus, more time with your pets is always a bonus!

Ready to embark on an exciting journey with us? Apply now and help us build the future of Wagepoint!

Wagepoint is a…