Title: Director of Pay Operations

Location: Remote, Canada

Salary: $110,000 – $155,000 / year CAD

Employment Type: Permanent Full-Time

Overview:

The Director of Pay Operations is the integrator for how pay gets delivered at Raise. Our Payroll and AP teams are a rules, compliance, and data translation engine, and that engine works best when it fits cleanly into the wider back office, including Finance, Systems and Process, Client Services, and Account Management. Team members and leads keep accountability for their work. This role is responsible for the strategic alignment and outcomes of the whole: the handoffs between Payroll and AP, team efficiency and success, and Pay Operations’ readiness for what is ahead, including back office tool revitalization and global expansion.

This role will own the strategy, compliance alignment, development, and operational health of our Canadian and US pay operations functions and overall health. This is not a payroll processing role. It is a Director-level leadership position for someone who has already built and led a payroll function and who brings genuine expertise in payroll operation and taxation, compliance, and governance. This role will lead the Canadian and US Payroll Jurisdictional divisions, own our compliance adherence across both countries, drive automation and process maturity, and build and enhance the capability of a team who handles workloads and responsibilities that process payments for 3,500 workers (T4, W2, and IC) weekly plus Raise’s own internal North American employees.

Pay Operations sits within Raise’s Revenue Operations function and works closely with Finance through a defined partnership. This role sits within Revenue Operations with a Finance dotted line for reconciliations and audits. Tax filings, legislative monitoring, and internal staff payroll all sit within this mandate.

As part of our hiring process, the first step will include an interview conducted by an AI interviewer. This allows us to efficiently and fairly assess all applicants using consistent, unbiased questions.

Please note that this role has been cross-posted as we are considering candidates from either Canada or the USA. There is one role available.

What This Role Is and Is Not:

This role IS

- The internal authority on Canadian and US payroll operational execution, taxation, compliance, and governance
- A leader responsible for developing the team
- An owner of function health including quality, capacity, sustainability, and risk
- A systems and process thinker who drives automation and process maturity
- A strategic partner to Finance, Operations, and Contractor Success

This role is NOT

- A payroll processor. You will not be consumed by transactional work
- A subject matter expert role alone. This role holds both payroll expertise and experienced leadership
- A role for someone growing into leadership for the first time

Key Accountabilities:

Payroll, Accounts Payable and Compliance Expertise

This role is responsible for the strategic alignment and outcomes of the areas below. Day-to-day delivery stays with the leads and team members who do this work today.

- Responsible for the strategic alignment and outcomes related to the accuracy and defensibility of Canadian and US payroll against all applicable federal, provincial, state, and local legislation, delivered day to day by the payroll leads and their teams




- Responsible for the strategic alignment and outcomes related to the accuracy of our Accounts Payable delivery model against contractual commitments and requirements for our business-to-business partnerships with the IC workstream, delivered day to day by the AP team and its lead
- Serve as the final internal escalation point on accounts payable and payroll compliance decisions before external advisors are engaged, in partnership with the jurisdictional leads
- Ensure there is a reliable way to monitor and interpret payroll legislative change across both countries, working with the leads and external advisors, so that what is learned reaches the people who need it
- Assess the operational impact of regulatory change and drive the organizational response ahead of compliance deadlines, with the leads carrying out the changes in their areas
- Responsible for the strategic alignment and outcomes related to payroll tax filing accuracy and timeliness, including T4, RL-1, W2, and 1099 populations, with preparation and filing carried out by the team
- Ensure the department stays audit-ready on a continuous basis, not only when an audit is scheduled

People Leadership and Development

- Directly provide guidance and bring wisdom to the Pay Operations team
- Support and sustain defined mandates and KPIs through regular structured conversations
- Build a deliberate development path for the pay operations team across all levels, from coordinator through jurisdictional lead
- Create a culture where feedback is normal, expected, and given well

Operational Health and Quality

- Responsible for the quality standards for Canadian and US payroll execution
- Implement, monitor, and refine the existing quality control framework
- Establish and monitor pay operations health (Payroll & Accounts Payable) KPIs at the function and support to the lead level
- Ensure the payroll and accounts payable functions operate on documented processes
- Address potential gaps in pre-payroll validation, including duplicate payment and completeness checks

Internal Staff Payroll

- Ensures consistency of delivery for the payroll process for internal employees across Canada and the US
- Document the process, establish controls, and ensure named backup coverage exists (if applicable)
- Treat internal payroll as a protected workstream rather than an activity absorbed into contingent capacity

Automation, Systems, and Scalability

- Identify and collaborate with key stakeholders to drive automation opportunities within the pay operations function
- Partner with the Business and Process Systems function on system improvements and integration work
- Reduce manual process dependencies that create single points of failure
- Build the structure and capability needed for payroll to scale with Raise’s growth without proportional increases in risk

Global EOR Readiness

- Assess payroll compliance requirements for new global markets as Raise pursues EOR / AOR expansion
- Partner on global payroll arrangements including partner-managed models
- Build the compliance infrastructure needed to operate in new jurisdictions

Qualifications:

Required





- 10 or more years of Canadian and US payroll experience with genuine depth across multiple jurisdictions
- Minimum three to five years leading a payroll team or function at a senior or director level with formal leadership responsibility
- Demonstrated expertise in payroll taxation and compliance across both employee and contingent worker populations
- Active practice of monitoring payroll legislative change and assessing organizational impact
- Track record of building structure, process, and accountability in environments that previously operated informally
- Demonstrated experience developing people and building team capability, not just directing work
- Systems and process orientation with the ability to build flexibility into process design
- Comfort leading in a self-managed or distributed authority organization where influence matters more than hierarchy

Preferred

- Skilled payroll certification held and current: PCP, CPM, or CPP
- CPA designation or equivalent accounting qualification
- Experience in an EOR, PEO, staffing, or contingent workforce environment
- Demonstrated experience identifying and implementing payroll automation
- Familiarity with Dayforce, Salesforce, or comparable payroll and workforce platforms
- Experience with staffing industry, global payroll or partner-managed EOR arrangements and/or vendor managed systems related experience

Core competenices:

- Payroll tax and compliance authority: Genuine expertise, not general familiarity. You know what you are looking at when a complex compliance situation arises
- People leadership: You develop people deliberately, give feedback well, and hold accountability with care
- Proactive risk orientation: You monitor for what is coming rather than responding to what has already happened
- Systems and process thinking: You see how the pieces connect and where process design creates or reduces risk
- Calm authority: You hold steady in high-stakes compliance situations and during peak processing pressure
- Cross-functional influence: You build effective partnerships without needing formal authority over other functions
- Change leadership: You have navigated organizational change as the responsible leader and know how to bring people with you

Looking for meaningful work? We can help!

Raise is an established hiring firm with over 65 years of experience. We believe strongly in making the world a better place through work, which is why we’re a certified B Corporation and donate 10% of our profits to charity.

We strive to build teams that reflect the diversity of the communities we work in. We encourage all qualified applicants to apply, including people from traditionally underrepresented groups such as women, visible minorities, Indigenous peoples, people identifying as LGBTQ2SI, veterans, and people with visible/nonvisible disabilities.

We have a dedicated webpage for accommodations where you can learn more about what we offer and request accommodation: https://raise.jobs/accommodations/

In order to submit candidates for roles, our clients will sometimes require personal information to confirm the identity of applicants and their legal status to work. Raise will never ask you for personal or banking information unless you have been selected for a job. If you are ever unsure about the legitimacy of this or another job posting by Raise (or have any other questions), please contact us at +1 (phone hidden) or [email protected]

#CEN24

#LI-VM1

📌 Director of Pay Operations (Canada)
🏢 Raise
📍 Canada