Senior Manager, Global Payroll Systems and Equity Operations

About the Position

As the Senior Manager of Global Payroll Systems and Equity Operations at HTS, you will act as a leader-coach reporting to the Director of People Operations and Workforce Technology to modernize and scale our global compensation infrastructure. Seated within the executive team, your mandate will be to evolve the function from a manual transfer and multi-vendor model to an automated, highly scalable operational model that maximizes systemic efficiency without proportional headcount growth. This high-visibility role uniquely combines global, cross-functional system design with hands-on execution to directly mitigate operational and financial risks.

What Your Day Will Look Like

• Take ownership of the end-to-end global payroll operational model for employees, contractors, EORs, PEOs, and local payroll providers.
• Lead and refine a team of 2 to 3 direct reports while maintaining high execution rigor and operational standards.
• Drive the operational administration of employee equity in Shareworks, including grant processing, data updates, and inter-departmental reconciliation.
• Identify and implement automation flows to minimize manual data transfers, recurring exceptions, and data friction.
• Collaborate with HR Tech, IT, and Finance teams to achieve payroll platform consolidation and maximize system reliability.
• Strengthen compliance protocols, payroll controls, and documentation retention to protect the company against financial exposure and ensure audit readiness.
• Establish clear processing schedules, accountability metrics, and data dashboards to measure function accuracy and capacity gains.
• Intervene directly in complex tax, equity, and payroll cases specific to each market to guide rapid cross-functional resolution.
• The Ideal Candidate Possesses
• Global Payroll Leadership: Proven experience in managing multi-country payroll operations, particularly within EOR, PEO, and local provider structures.
• Equity Administration Expertise: Direct knowledge of equity platforms like Shareworks, including grant lifecycle management and complex tax coordination.
• Systems and Automation Orientation: Strong background in HRIS integrations, workflow optimization, and voluntary elimination of manual interventions in financial operations.
• Rigor in Controls and Compliance: Deep understanding of payroll controls, financial audit preparation, and tax implications within a rapidly growing tech or fintech company structure.
• Leader-Coach Capability: Demonstrated ability to manage and develop a remote operational team while simultaneously acting as a hands-on technical expert.
• Commercial and Analytical Mindset: Ability to translate complex operational frameworks into clear, data-driven decisions that enhance enterprise-wide scalability efficiency.

Benefits

• A well-funded and proven startup: Ambitious goals, competitive salary, and all the benefits of pre-IPO equity blocks.
• Group insurance: Hopper covers 100% of group insurance premiums.
• Income protection: Hopper offers life insurance and short- and long-term disability insurance.
• Health spending account (HSA): Covers eligible medical and dental expenses.
• Telemedicine: All employees and dependents have access to Dialogue's telemedicine services anytime, anywhere.
• Retirement savings: All employees have access to a RRSP with automated pre-tax deductions at every payroll.
• Parental leave: Don't hesitate to ask about our very generous parental leave, which far exceeds industry standards!
• Unlimited paid time off (PTO): A flexible vacation policy to help you recharge.
• Travel allowance: "Carrot Cash" travel credit for your own trips.
• Flexible work arrangement: On-demand access to coworking spaces via FlexDesk AND a home office allowance.
• Entrepreneurial culture: A dynamic environment where pushing boundaries and taking risks are part of the daily routine.
• Transparent communication: Open exchanges with managers and the company's executive team.
• Maximum impact: Small, dynamic teams for concrete and direct impact.
• Learn More About Hopper

At Hopper, our mission is to become the world's leading travel platform – by powering the Hopper mobile app, our website, and our B2B division, HTS (Hopper Technology Solutions). By leveraging massive volumes of data and advanced machine learning algorithms, Hopper combines its world-class travel agency offerings with exclusive fintech products to bring transparency, flexibility, and savings to travelers worldwide. We have developed several unique fintech solutions that address all travel challenges, from price volatility to travel disruptions, helping people travel better and save more.

The Hopper platform serves hundreds of millions of travelers and continues to gain market share worldwide. The Hopper app has been downloaded over 120 million times and has become particularly popular among young travelers – 70% of its users are from Generation Z and Millennials.

While we are recognized as the go-to travel app for Generation Z and Millennials, Hopper has greatly evolved. Over the past few years, we have become a travel fintech provider, an e-commerce platform, and a global travel agency that powers some of the world's largest brands.

Through HTS, our B2B division, the company powers its partners' direct channels by integrating our fintech products into their websites or powering their end-to-end travel portals. Today, our partners include leading travel brands such as Capital One, Nubank, Air Canada, and many others.

Here are some statistics that highlight our recent growth:

• Billions of dollars in travel and travel fintech products are sold annually through Hopper and HTS channels.
• Our fintech products – including Cancel for Any Reason and Flight Disruption Assistance – have exceptionally high customer satisfaction scores (CSAT), as terms are always clear and customers receive instant resolutions, no questions asked.
• Nearly 30% of our app users purchase at least one fintech product during their booking; and consumers are 1.6 times more likely to book again if they add a fintech option, compared to a travel-only purchase.
• Fueled by the success of its fintech products, Hopper launched the B2B HTS (Hopper Technology Solutions) initiative, which now represents over 75% of the company's activities.
• Through HTS, any travel provider (airlines, hotels, banks, travel agencies, etc.) can integrate and distribute Hopper's travel fintech or inventory transparently on their own direct channels. As part of its first HTS partnership, the company partnered with Capital One to co-develop Capital One Travel, a new travel portal specifically designed for its cardholders. Other HTS partners include Air Canada, Uber, CommBank, Nubank, Flair Airlines, and several others.
• Hopper was named the number 1 most innovative company in the travel industry by Fast Company. The Hopper app has surpassed 120 million downloads and continues to record millions of new installs each month. Hopper is now ranked as the 3rd largest travel agency in the world.