Director, Managed Payroll and Compliance

Rise to the challenge

Rise is Canada's complete people management solution that gives employers everything they need to build loyal and productive teams—all in one place. We collaborate and co-create to build solutions that completely change how companies of all shapes and sizes manage their payroll, scheduling, time tracking, group benefits, recruitment, onboarding, and more.

In partnership with some of Canada's most innovative insurance carriers, Rise Health offers Canada's only fully integrated digital employee group benefits solution, offering the most delightful one-stop-shop experience, from plan design to self-enrolment and administration to billing and collection of premiums.

At Rise, we're changing how work happens and how people work. We'd love for you to join us and experience the most positive, challenging, and transformative part of your career.

About the role

Thousands of Canadian companies trust Rise to run their payroll and stay onside with the rules that govern it. When a client hands us their payroll to manage end-to-end, they're trusting us with the thing their people care about most: getting paid correctly and on time. Compliance sits right beside that promise, spanning every offering we sell.

That's where you come in. As Director of Managed Payroll and Compliance, you'll own our fully managed payroll service and all client compliance across the Rise platform. You'll lead the team that processes and safeguards client payrolls, and you'll set the standard for how Rise interprets and applies payroll and regulatory requirements everywhere they touch a client. You'll partner closely with our Client Experience leadership so that managed payroll, support, and onboarding feel like one seamless service to the customer.

This is a builder's seat on the leadership team, reporting to the CEO. You'll shape how a growing service scales, decide where process ends and judgment begins, and make Rise the partner clients turn to when payroll gets complicated.

The day-to-day

• Lead the fully managed payroll team, owning service quality, accuracy, and timeliness for every client payroll Rise runs on their behalf.

• Own client compliance across all Rise offerings, setting the policies and controls that keep clients onside with payroll and regulatory requirements.

• Build the processes, controls, and quality checks that let managed payroll scale without losing accuracy as the client base grows.

• Partner with Client Experience leadership to connect managed payroll, onboarding, and support into one coherent client journey.

• Coach and grow the managed payroll and compliance teams, hiring for the roles the service needs next and developing the people already in them.

• Serve as the senior escalation point for complex payroll and compliance questions, guiding clients through the situations that don't have a textbook answer.

• Work with Product and Engineering to turn what your team learns on the front line into a stronger platform.

About you

• 8+ years in payroll, with several years running full-cycle Canadian payroll at scale.

• Experience leading and growing a team, with a track record of developing people and lifting service quality.

• Deep knowledge of Canadian payroll legislation and compliance across provinces, and confidence interpreting requirements that don't have an obvious answer.

• A payroll designation such as PLP, PCP, or equivalent

• Strong operational instincts: you build repeatable processes and quality controls, and you know which steps need a human's judgment.

• Clear communicator who can explain a complex compliance position to a client, an executive, or a new team member and be understood by all three.

• Comfortable partnering across functions, including Client Experience, Product, and Engineering, to improve the service end-to-end.

• A degree in a relevant field, or equivalent experience.

• Bonus: Bilingual proficiency in French and English.

• Bonus: Experience standing up or scaling a managed or outsourced payroll service.

What Rise offers

• Rise is all about creating a positive company culture, both for our clients and our employees. We believe that happiness isn't the cause of employee engagement; it's the result.

• The base salary for this position is $80,000-100,000, depending on experience, plus a bonus and stock options.

• We offer a remote work environment. On occasion, we may meet as a team or one-on-one in person.

• Rise believes that time off is just as important as time spent. We offer 3 weeks of paid vacation, flexible personal wellness days, as well as one day off for your birthday and your work anniversary.

• We support your growth with a personal $1,000 learning and development budget to take courses, attend conferences, webinars, you name it!

• We offer no-wait benefits. This means that starting your first day, you have access to our comprehensive benefits package which includes dental, eye care, and $2,000 in counselling coverage, among many other great health benefits.

At Rise, we care more about where you're headed, not where you've been. We encourage people of all ages, backgrounds, identities, and orientations to apply.