People Systems Manager

Join us in building the future of finance.

Our mission is to democratize finance for all. An estimated $124 trillion of assets will be inherited by younger generations in the next two decades. The largest transfer of wealth in human history. If you’re ready to be at the epicenter of this historic cultural and financial shift, keep reading.

About the team + role

We are building an elite team, applying frontier technologies to the world’s biggest financial problems. We’re looking for bold thinkers. Sharp problem-solvers. Builders who are wired to make an impact. The company isn’t a place for complacency, it’s where ambitious people do the best work of their careers. We’re a high-performing, fast-moving team with ethics at the center of everything we do. Expectations are high, and so are the rewards.

The People Tech & Systems team’s mission is to deliver scalable, intuitive, and secure technology that empowers the company’s people and fuels business growth. Sitting at the intersection of operations, systems, and innovation, the team ensures employees and teams have the tools they need to thrive.

As a People Systems Manager, you will lead the development and operation of the company’s HR and Payroll systems, owning both strategy and execution. You’ll act as a player‑coach—balancing hands‑on systems work with leading and growing a team—while driving impactful, reliable solutions that support the company’s people and processes at scale.

This role is based in our Toronto, Canada office(s), with in‑person attendance expected at least 5 days per week.

At the company, we believe in the power of in‑person work to accelerate progress, spark innovation, and strengthen community. Our office experience is intentional, energizing, and designed to fully support high‑performing teams.

What you’ll do

• Lead and evolve the company’s core People Systems, with a strong focus on Workday across functional and technical domains
• Act as a hands‑on technical leader, driving configuration, integrations, and solution design while guiding execution across your team
• Manage and develop a distributed team of full‑time employees and contractors, fostering ownership, accountability, and growth
• Partner cross‑functionally with HR, Recruiting, Compensation, Finance, and Engineering to deliver scalable and reliable solutions
• Design, build, and maintain integrations within the People tech stack, with deep ownership of EIB‑based integrations and preferred use of Workday Studio
• Drive initiatives such as worker/vendor system implementations, Workday enhancements, and Workday Extend investments
• Support global expansion and M&A through scalable People systems architecture
• Collaborate with AI engineering teams to shape AI‑enabled capabilities across HR platforms
• Lead change management efforts to ensure successful adoption of new tools and processes
• Build and maintain a long‑term roadmap balancing operational excellence and future innovation
• Uphold high standards for data quality, security, privacy, and compliance

What you bring

• 7+ years of progressive People Systems or HRIS experience, including 2+ years in people management
• 4+ years of hands‑on Workday experience, with strong expertise in Core HCM
• Proven experience with Workday integrations, including EIBs (required) and Workday Studio (strongly preferred)
• Familiarity with recruiting tools such as Greenhouse and/or Ashby
• Strong project management and cross‑functional collaboration skills
• Comfort navigating ambiguity in fast‑paced, high‑growth environments
• Curiosity and practical interest in AI, automation, and emerging HR technologies
• Strong analytical and problem‑solving abilities with high attention to detail and a proactive mindset

Leadership expectations

Our ambitious roadmap requires a great culture shaped by exceptional leaders. Here’s what we expect from them:

• Drive high performance by setting clear, focused goals, giving real‑time feedback, stretching top talent, and scaling impact through focus, innovation, and tech.
• Hire and retain top talent by setting a high bar, hiring only those who raise it, investing in onboarding, and addressing talent issues quickly and fairly.
• Create community by connecting work to purpose, removing friction while prioritizing safety, building trust and inclusion, and leading from the front with integrity.

What we offer

• Challenging, high‑impact work to grow your career
• Performance driven compensation with multipliers for outsized impact, bonus programs, and equity ownership
• Top tier benefits to fuel your work, including supplemental health insurance, ancillary insurance, and mental health support programs
• Lifestyle wallet – a highly flexible employer‑paid benefits spending account expenses beyond traditional benefits such as wellness, childcare, learning, and more.
• Time off to recharge including company holidays, paid time off, sick time, paid volunteer time off, parental leave, and more!
• Exceptional office experience with catered meals, events, and comfortable workspaces.
• Monthly commuter stipend to help offset in‑office commuting costs

Vacancy Notice: This job posting represents an existing vacancy that we are actively seeking to fill.

Base pay range (Toronto, ON): $144,500 – $170,000 CAD.

If our mission energizes you and you’re ready to build the future of finance, we look forward to seeing your application.

The company provides equal opportunity for all applicants, offers reasonable accommodations upon request, and complies with applicable equal employment and privacy laws.