Payroll Systems & Automation Specialist

Open Door Inc.; Toronto; On-site; CAD 90,000 - 130,000; Full time

Job summary

Opendoor seeks an AI and automation-forward analyst to streamline Payroll and Equity Operations. You will design AI agents, reusable skills, and automated workflows that save time and improve accuracy, partnering with Payroll, Equity, Accounting, and People teams.

Reporting to the Payroll Manager, you will identify bottlenecks, test outputs, document solutions, and train teammates while measuring time savings and reliability improvements across systems like Rippling and E*trade.

Qualifications

• 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.

Responsibilities

• 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.

Skills

AI agent development

Automation

APIs

Scripting

Data analysis

Problem solving

Cross-functional collaboration

Confidential information handling

Training teammates

Tools

Rippling

E*trade

Spreadsheets

NetSuite

Job description

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.