Senior Manager, Global Payroll Systems – Equity Operations

This is a fully remote position, open to applicants in Canada.

📋 Description

• Oversee the comprehensive global payroll operating model encompassing employees, contractors, EORs, PEOs, and local service providers.

• Lead and cultivate a team of 2–3 direct reports while ensuring execution discipline and maintaining high operational standards.

• Direct the operational administration of employee equity within Shareworks, including grant processing, data updates, and reconciliation across multiple departments.

• Recognize and implement automation workflows to reduce manual data transfers, recurring exceptions, and data friction.

• Collaborate with HR Technology, IT, and Finance to drive the consolidation of payroll platforms and enhance system reliability.

• Strengthen compliance protocols, payroll controls, and documentation to safeguard the business from financial risks and ensure audit preparedness.

• Create clear processing calendars, accountability metrics, and data scorecards to evaluate function accuracy and capacity improvements.

• Tackle complex payroll challenges related to tax, equity, and specific markets to facilitate rapid cross-functional resolutions.

⛳️ Requirements

• Global Payroll Leadership: Demonstrated experience in managing multi-country payroll operations, particularly in navigating EOR, PEO, and local provider frameworks.

• Equity Administration Expertise: Direct experience with equity platforms such as Shareworks, including managing grant lifecycles and coordinating complex equity tax matters.

• Systems & Automation Focus: Proven track record of designing HRIS integrations, optimizing workflows, and deliberately reducing manual interactions in financial operations.

• Controls & Compliance Rigor: Extensive knowledge of payroll controls, financial audit readiness, and tax implications within a high-growth technology or fintech corporate environment.

• Player-Coach Capability: Proven ability to manage and enhance the skills of a remote operational team while also serving as a hands-on technical expert.

• Commercial & Analytical Mindset: Proficient in transforming complex operational patterns into clear, data-driven decisions that enhance efficiency across the company.

🏝️ Benefits

• Well-funded and established startup with significant aspirations, offering a competitive salary along with the advantages of pre-IPO equity packages.

• Hopper pays 100% of the premiums for the group insurance plan.

• Hopper provides life insurance, as well as short-term and long-term disability coverage.

• Health Savings Account (HSA) that covers eligible medical and dental expenses.

• All employees and their dependents have access to Dialogue’s telemedicine services, anytime and anywhere.

• All employees have access to an RRSP plan with automatic pre-tax deductions from each paycheck.

• Inquire about our exceptionally generous parental leave policy, which exceeds industry standards!

• Unlimited Paid Time Off (PTO).

• Carrot Cash travel stipend.

• Access to co-working spaces on demand through FlexDesk and a work-from-home stipend.

• An entrepreneurial culture that encourages pushing boundaries and taking risks as part of daily operations.

• Open lines of communication with management and company leadership.

• Small, agile teams that create a significant impact.