Payroll Manager

About the Role

Location: Toronto, ON or Phoenix, AZ (Hybrid, 4 days onsite, Wednesdays remote)

Opendoor employs a talented workforce throughout the US and Canada and across multiple legal entities. We're looking for a hands-on, detail-driven, fast-moving payroll professional to own the process end to end, be the person people come to with questions, and to streamline and refine our systems and controls.

We are a product company. AI and automation is at the heart of what we do. We expect this person to bring a technology-forward operating style: using automation to reduce manual work, and stay ahead of the volume spikes and edge cases that come with running payroll for a growing company.

This role reports to the Assistant Controller and works closely with Accounting, People, and Tax.  It also partners closely with our Equity & Payroll Manager, who owns equity administration, and the two of you share a Payroll and Equity Analyst. You'll work together on anything that touches both: RSU vestings, option exercises, and ESPP purchases all flow through payroll, so the two of you will coordinate closely on timing, withholding, and reconciliation. You'll also serve as a backup and partner to each other: you will support certain equity items, just as the Equity & Payroll Manager will support certain payroll items.

Your responsibilities will include:

• Own multi-entity, multi-country payroll. Process US and Canadian payroll on semi-monthly cycles across multiple legal entities.
• Own payroll tax compliance across federal, state/provincial, and local jurisdictions. Research and register in new states and provinces as we expand and ensure all records are kept current.
• Lead quarter end and year end processes including audit wages, verify W-2 / T4 box configurations, and deliver clean, on-time filings.
• Partner with the Equity & Payroll Manager on equity payroll events. Incorporate RSU vestings, option exercises, and ESPP purchases into payroll runs with correct supplemental withholding, and reconcile payroll records against our equity administration system (E*Trade).
• Handle the complexity that comes with operating across states and provinces: state-specific final pay deadlines, state paid leave programs, imputed income items like group term life, and cross-border sourcing for employees who work in more than one state (or country).
• Use AI and automation to reduce manual reconciliation, data flows and reporting work, and keep improving the workflow instead of accepting it as-is.
• Prepare and/or review payroll and related journal entries and balance sheet reconciliations, ensuring they're accurate and completed on time each cycle.
• Be the point person for employees. Give fast, accurate answers on payroll questions, and handle sensitive, confidential situations with discretion. Use AI to automate answers where you can, and keep payroll information readily available and self-serve on Glean.
• Partner with Accounting, People, and Equity on system enhancements, testing, and process design.
• Co-manage and develop the Payroll and Equity Analyst alongside our Equity & Payroll Manager, reviewing their work and building their skills.

We're looking for teammates who have:

• 10+ years of payroll experience, including running payroll for a distributed, multi-entity organization
• Hands-on US and Canada payroll experience, including multi-state / multi-province tax compliance, SUI, and local withholding
• Experience with the edge cases that come with multi-state or multi-country payroll: final pay deadline compliance, state paid leave programs, imputed income, or cross-border sourcing
• Multi-entity payroll experience across hourly and salaried populations
• A technology-forward operating style: hands-on use of AI tools (Claude, ChatGPT, Copilot) to automate your own work
• Comfort owning outcomes in a fast-changing, high-growth environment while driving clarity and predictability in processes and outcomes
• Exceptional accuracy, organization, and discretion with highly sensitive, confidential data
• Strong communication skills, and credibility with employees and cross-functional partners
• Proficiency with Google Workspace and comfort operating across multiple systems

Bonus Points:

• Rippling payroll experience
• Equity / RSU compensation experience: RSU vesting, ESPP, option exercises, and E*TRADE Stock Administration
• Payroll and equity journal entry and balance sheet reconciliation experience
• Payroll certification (CPP / FPC)
• NetSuite experience
• Prior experience at a high-growth, public, or proptech company