About the Role
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..
What would your day-to-day look like
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.
An ideal candidate has
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
Benefits
Well-funded and proven startup with large ambitions, competitive salary and upsides of pre-IPO equity packages.
Hopper covers 100% of the premiums for group insurance plan.
Hopper offers life, short term and long term disability coverage.
HSA that covers eligible medical and dental expenses.
All employees and dependents have access to Dialogue’s telemedicine services, anytime, anywhere.
All employees have access to an RRSP plan with automatic pre-tax withdrawals per pay.
Please ask us about our very generous parental leave, much above industry standards!.
Unlimited PTO.
Carrot Cash travel stipend.
Access to co-working space on demand through FlexDesk AND 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.
More about Hopper
At Hopper, we are on a mission to become the leading travel platform globally – powering Hopper’s mobile app, website and our B2B business, HTS (Hopper Technology Solutions). By leveraging massive amounts of data and advanced machine learning algorithms, Hopper combines its world-class travel agency offering with proprietary fintech products to bring transparency, flexibility and savings to travelers globally. We have developed several unique fintech solutions that address everything from pricing volatility to trip disruptions – helping people travel better and save more on their trips.
The Hopper platform serves hundreds of millions of travelers globally and continues to capture market share around the world. he Hopper app has been downloaded over 120 million times and has become largely popular among younger travelers – with 70% of its users being Gen Z and millennials.
While everyone knows us as the Gen Z and Millennial travel app, Hopper has evolved to become much more than that. In recent years, we’ve grown into a travel fintech provider, commerce platform, and global travel agency that powers some of the world’s largest brands.
Through HTS, our B2B division, the company supercharges its partners’ direct channels by integrating our fintech products on their sites or powering end-to-end travel portals. Today, our partners include leading travel brands like Capital One, Nubank, Air Canada, and many more.
Here are just a few stats that demonstrate the company’s recent growth:
Billions of dollars worth of travel and travel fintech are sold through Hopper and HTS’ channels every year.
Our fintech products – including Cancel for Any Reason and Flight Disruption Assistance – have exceptionally strong CSAT because the terms are always clear, and customers receive instant, no-questions-asked resolutions.
Almost 30% of our app customers purchase at least one fintech product when making a booking; and consumers are 1.6x more likely to repurchase if they add fintech to their booking vs if they booked just travel.
Given the success of its fintech products, Hopper launched a B2B initiative, HTS (Hopper Technology Solutions), which represents more than 75% of the business.
Through HTS, any travel provider (airlines, hotels, banks, travel agencies, etc.) can integrate and seamlessly distribute Hopper’s fintech or travel inventory on their direct channels. As its first HTS partnership, the company partnered with Capital One to co-develop Capital One Travel, a new travel portal designed specifically for cardholders. Other HTS partners include Air Canada, Uber, CommBank, Nubank, Flair Airlines and many more.
Hopper has been named the #1 most innovative company in travel by Fast Company Hopper has been downloaded over 120 million times and continues to have millions of new installs each month. Hopper is now the #3 largest online travel agencies in North America and 70% of our app customers are Gen-Z and millennials travelers.
Hopper has raised over $750 million USD of private capital and is backed by some of the largest institutional investors and banks in the world. HTS is primed to continue its growth as the leading travel ecommerce provider in a $1 trillion online shopping category. The Hopper app and website will also continue to be the preferred travel provider for Gen Z and Millennials.
Come take off with us!
#LI-REMOTE
Compensation Range: CA$150K - CA$180K