Payroll Systems & Automation Specialist

Posted Yesterday
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Toronto, ON, CAN
Hybrid
Entry level
eCommerce • Fintech • Real Estate • Software • PropTech
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The Role

About Opendoor

At Opendoor our mission is to tilt the world in favor of homeowners and those who aim to become one. Homeownership matters. It's how people build wealth, stability, and community. It's how families put down roots, how neighborhoods strengthen, how the future gets built. We're building the modern system of homeownership giving people the freedom to buy and sell on their own terms. We’ve built an end-to-end online experience that has already helped thousands of people and we’re just getting started.

About the Role

Opendoor is looking for an AI and automation-forward analyst to help simplify and streamline our Payroll and Equity Operations. You’ll work directly with the team to identify opportunities and build AI agents, reusable skills, and automated workflows that save time and improve accuracy. This role requires solid, hands-on AI experience. Payroll or equity experience is a plus, but it is not required. Reporting to the Payroll Manager, you’ll partner with Payroll, Equity, Accounting, and the People team to turn operational challenges into practical, reliable solutions.

Your responsibilities will include:
  • Identify manual steps, bottlenecks, and duplicate work in payroll workflows.
  • Build and maintain AI agents and reusable skills that help the team complete recurring tasks consistently.
  • Create automations for payroll preparation, data validation, exception identification, reconciliation, and reporting.
  • Improve data flows between Rippling, E*trade, spreadsheets, and related systems using integrations, APIs, scripts, or automation tools.
  • Partner with the payroll and equity managers to simplify workflows supporting equity events and payroll processing.
  • Test solutions, evaluate AI outputs, and build clear exception handling and human review into sensitive workflows.
  • Document solutions and train teammates to use and maintain them.
  • Measure improvements through time saved, fewer manual steps, and increased accuracy and reliability.
We're looking for teammates who have:
  • Experience creating AI agents and reusable skills, including instruction design, tool use, workflow orchestration, and evaluation, with examples of agents or automations you have delivered.
  • Ability to connect systems and work with structured data using APIs, scripting, or automation platforms.
  • Strong problem-solving skills and the ability to take an operational improvement from discovery through implementation.
  • Experience testing AI outputs, troubleshooting failures, and incorporating appropriate human review.
  • Attention to detail and sound judgment when handling confidential information.
  • Clear communication and effective cross functional collaboration.
  • Willingness to learn payroll and equity processes. Prior payroll experience is not required.
Bonus Points:
  • Payroll experience, particularly US or Canadian payroll.
  • Experience with Rippling or automating HR, payroll, or finance workflows.
  • Familiarity with equity administration, including RSU vestings, option exercises, or ESPP purchases.
  • Experience with reconciliations, accounting workflows, Google Workspace, or NetSuite.

Location
We're looking for team members who are enthusiastic about an in-office culture — people who want to build alongside others and not from a distance. This role is based in one of our talent hubs where we welcome everyone 5 days a week with the requirement of Mo, Tu, Th, Fri.
#LI-RS1

Skills Required

  • Experience creating AI agents and reusable skills, including instruction design, tool use, workflow orchestration, and evaluation, with examples of delivered agents or automations.
  • Ability to connect systems and work with structured data using APIs, scripting, or automation platforms.
  • Strong problem-solving skills and ability to take an operational improvement from discovery through implementation.
  • Experience testing AI outputs, troubleshooting failures, and incorporating appropriate human review.
  • Attention to detail and sound judgment when handling confidential information.
  • Clear communication and effective cross-functional collaboration.
  • Willingness to learn payroll and equity processes.
  • Payroll experience, particularly US or Canadian payroll.
  • Experience with Rippling or automating HR, payroll, or finance workflows.
  • Familiarity with equity administration, including RSU vestings, option exercises, or ESPP purchases.
  • Experience with reconciliations, accounting workflows, Google Workspace, or NetSuite.

Opendoor Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Opendoor and has not been reviewed or approved by Opendoor.

  • Healthcare Strength — Health coverage is broad, including medical, dental, vision, life/AD&D, short- and long-term disability, HSAs/FSAs, and mental-health/EAP resources. Company materials and current job listings consistently describe these as core offerings for U.S. full-time employees.
  • Leave & Time Off Breadth — Time off is presented as generous, with PTO, sick leave, volunteer time, and in some roles 12 paid holidays. Several postings and profiles also reference open/unlimited PTO in certain job families.
  • Equity Value & Accessibility — Equity grants and an Employee Stock Purchase Plan are commonly included alongside base pay and incentives. Public filings and employer profiles indicate these ownership programs are broadly accessible across many roles.

Opendoor Insights

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The Company
HQ: San Francisco, CA
1,600 Employees
Year Founded: 2014

What We Do

Founded in 2014, Opendoor’s mission is to empower everyone with the freedom to move. We believe the traditional real estate process is broken and confusing. It often comes with unexpected costs, the added burden of coordinating multiple third parties and the uncertainty of a transaction falling through. Our goal is simple: build a digital, end-to-end customer experience that makes buying and selling a home simple, certain and fast. We have assembled a dedicated team with diverse backgrounds and talents across engineering, operations, design, operations, mortgage, finance, legal, and more to deliver strong results. More than 85,000 customers have selected us as a trusted partner in handling one of their largest financial transactions.

Why Work With Us

We’re on a mission to power life’s progress one move at a time

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