Senior Manager, Global Payroll Systems & Equity Operations

Hopper Inc.

Job Overview

Location

Ontario - Remote

Job Type

Full-time

Full Job Description

📋 Description

• Own the end-to-end global payroll operating model across employees, contractors, EORs, PEOs, and local providers, ensuring seamless execution across multiple jurisdictions.
• Manage and develop a team of 2–3 direct reports while maintaining high operational standards and execution discipline in a remote environment.
• Lead the operational administration of employee equity through Shareworks, including grant processing, data updates, and multi-department reconciliation to ensure accuracy and compliance.
• Identify, design, and implement automation workflows to eliminate manual data transfers, reduce recurring exceptions, and minimize data friction across payroll and equity systems.
• Partner with HR Technology, IT, and Finance teams to drive consolidation of payroll platforms and enhance system reliability and integration.
• Strengthen payroll controls, compliance protocols, and documentation to mitigate financial exposure and ensure audit readiness across global operations.
• Establish clear processing calendars, accountability metrics, and data scorecards to measure function accuracy, efficiency gains, and capacity improvements.
• Step into complex, jurisdiction-specific payroll challenges involving tax regulations, equity coordination, and local legal requirements to drive swift cross-functional resolutions.
• Translate complex operational patterns into data-driven decisions that improve scaling efficiency and reduce proportional headcount growth.
• Serve as a player-coach by balancing leadership responsibilities with hands-on technical execution in payroll systems, equity administration, and workflow automation.
• Maintain alignment with global labor laws, tax frameworks, and financial reporting standards to safeguard the company from regulatory and financial risk.
• Collaborate cross-functionally to ensure payroll and equity data integrity across HRIS, finance systems, and external vendor platforms.
• Drive continuous improvement in payroll and equity operations by leveraging technology to scale without linear increases in team size.
• Act as a key liaison between People Operations, Finance, and Legal to align compensation infrastructure with corporate strategy and growth objectives.
• Ensure all payroll and equity processes are documented, repeatable, and scalable to support Hopper’s rapid international expansion and HTS B2B growth.

🎯 Requirements

• Proven experience managing multi-country payroll operations using EOR, PEO, and local provider frameworks
• Direct hands-on expertise with equity administration platforms such as Shareworks, including grant lifecycle management and multi-jurisdictional tax coordination
• Demonstrated track record in designing HRIS integrations and automating financial operations to remove manual touchpoints
• Deep knowledge of payroll controls, financial audit readiness, and tax implications within high-growth technology or fintech environments
• Ability to lead and upskill a remote operational team while maintaining hands-on technical execution as a player-coach
• Commercial and analytical mindset to convert operational data into scalable efficiency improvements

🏖️ Benefits

• Competitive salary and pre-IPO equity packages
• 100% coverage of group insurance premiums by Hopper
• Life, short-term, and long-term disability coverage
• HSA for eligible medical and dental expenses
• Access to Dialogue’s telemedicine services for employees and dependents
• RRSP plan with automatic pre-tax payroll deductions
• Unlimited PTO
• Carrot Cash travel stipend
• Access to co-working spaces via FlexDesk and work-from-home stipend
• Generous parental leave policy above industry standards
• Entrepreneurial culture with open communication and high-impact teams

Skills & Technologies

Swift

Design

Senior

Remote

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Hopper Inc.

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About Hopper Inc.

Hopper is a travel technology company that uses predictive analytics and machine learning to forecast flight and hotel prices, allowing consumers to book travel at optimal times. Founded in 2007 and headquartered in Montréal, Canada, it operates mobile-first booking platforms and provides fintech products like price freeze, cancel-for-any-reason, and rebooking guarantees to reduce travel risk.

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