Senior Manager, Global Payroll Systems & Equity Operations

Hopper
CA$150,000 - CA$180,000Remote

About The Position

As the Senior Manager of Global Payroll Systems & Equity Operations at HTS, you will serve as a player-coach reporting to the Head of People Operations & Workforce Technology to modernize and scale our workforce compensation infrastructure. Sitting on the leadership team, your mandate is to transition the function away from manual, multi-vendor handoffs into an automated, highly scalable operating model that maximizes systemic efficiency without proportional headcount growth. This high-visibility role uniquely blends global cross-functional system design with hands-on execution to directly mitigate operational and financial risk.

Requirements

  • Global Payroll Leadership: Proven experience managing multi-country payroll operations, specifically navigating EOR, PEO, and local provider frameworks.
  • Equity Administration Expertise: Direct familiarity handling equity platforms like Shareworks, including managing grant lifecycles and complex equity tax coordination.
  • Systems & Automation Focus: A strong track record of designing HRIS integrations, optimizing workflows, and intentionally removing manual touchpoints from financial operations.
  • Controls & Compliance Rigor: Deep knowledge of payroll controls, financial audit readiness, and tax implications within a high-growth technology or fintech corporate structure.
  • Player-Coach Capability: The demonstrated capability to manage and upskill a remote operational team while simultaneously acting as a hands-on technical expert.
  • Commercial & Analytical Mindset: The ability to convert complex operational patterns into clear, data-driven decisions that improve company-wide scaling efficiency

Responsibilities

  • Own the end-to-end global payroll operating model across employees, contractors, EORs, PEOs, and local providers.
  • Manage and develop a team of 2–3 direct reports while maintaining execution discipline and high operational standards.
  • Lead the operational administration of employee equity in Shareworks, covering grant processing, data updates, and multi-department reconciliation.
  • Identify and implement automation workflows to minimize manual data transfers, recurring exceptions, and data friction.
  • Partner with HR Technology, IT, and Finance to drive payroll platform consolidations and maximize system reliability.
  • Strengthen compliance protocols, payroll controls, and documentation to protect the business from financial exposure and ensure audit readiness.
  • Establish clear processing calendars, accountability metrics, and data scorecards to measure function accuracy and capacity gains.
  • Step into complex tax, equity, and market-specific payroll challenges to drive swift cross-functional resolution.

Benefits

  • Competitive salary and upsides of pre-IPO equity packages.
  • Hopper covers 100% of the premiums for group insurance plan.
  • Life, short term and long term disability coverage.
  • HSA that covers eligible medical and dental expenses.
  • Access to Dialogue’s telemedicine services, anytime, anywhere.
  • Access to an RRSP plan with automatic pre-tax withdrawals per pay.
  • Generous parental leave, much above industry standards!
  • Unlimited PTO.
  • Carrot Cash travel stipend.
  • Access to co-working space on demand through FlexDesk.
  • Work-from-home stipend.
  • Entrepreneurial culture where pushing limits and taking risks is everyday business.
  • Open communication with management and company leadership.
  • Small, dynamic teams = massive impact.
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