Location

This is an in-person role in the Toronto, Ontario office. Candidates must be based within a 50-mile commuting distance of the office (240 Richmond St W, Toronto, ON) and able to be physically present in the office 4 days a week.

About the Team

The Executive Operations team supports Opendoor’s leadership. We operate as a direct expression of Opendoor’s values: Founder Mentality, Mission Over Ego, Default to AI, and Default to Open.

Our job is simple to say and hard to do well: we clear the path so our leaders move fast. We protect time, surface the right information, anticipate friction, and solve problems before they land on a leader’s desk.

About the Role

We’re hiring an Executive Operations Partner to support a senior leader out of our Toronto office, while also serving as the local point of contact for the Toronto workplace (~80% executive support, ~20% light office support).

The leader you’ll support is collaborative, fast-moving, and values directness. This role is built around a real partnership, someone who’ll push back when something doesn’t make sense and isn’t afraid to get into the details. There’s no formal playbook. You’ll build your own systems and approach from day one.

The long-term vision for this role is to use AI to automate the core operational work, which frees up your time to expand into more strategic, partnership-level responsibilities. The more you automate the basics, the more your role evolves. This isn’t a role where the work stays static.

What You’ll Do

The Operational Backbone:

• Own complex calendar management: protect focus time, flag conflicts proactively, and keep meeting cadence aligned with business priorities.
• Run end-to-end travel planning and logistics: flights, hotels, ground, itineraries, and real-time adjustments.
• Coordinate meeting logistics: agendas, pre-reads, notes, action items, and follow-ups.
• Draft emails, Slacks, and internal comms in your leader’s voice, at their standard.
• Manage expenses and Ramp submissions accurately and on time.
• Plan team events, offsites, and All-Hands from kickoff through run-of-show.

The Strategic Partnership:

• Prepare briefing docs ahead of key meetings so your leader walks in ready.
• Know your leader’s priorities well enough to say no on their behalf and reroute low-value asks.
• Anticipate what’s coming two weeks out and stage the work so your leader isn’t scrambling.
• Come with a solution, not just a problem. When you escalate, bring options and a recommendation.
• Drive cross-functional follow-through across teams, even ones you don’t own.
• Over-communicate. Your leader is never left wondering where something stands.

Toronto Office Support (~20%):

• Serve as the local point of contact for the Toronto office.
• Coordinate with building management and vendors for basic office needs.
• Support local events, team gatherings, and engagement activities.

AI and Automation:

"Default to AI" is a core value at Opendoor, and the Executive Operations team lives it. You don't need to be a developer, but you should already be an active user of tools like ChatGPT, Claude, or Gemini. We're looking for someone who is genuinely curious about new technology and is already experimenting with ways to use AI to work smarter. Over time, you'll partner with the team to automate routine tasks and expand into more strategic, high-impact work.

What You’ll Bring

• 2+ years in any role where you were the person making things run smoothly, whether that was operations, a startup, running your own business, or supporting a team.
• A partnership mindset. You view your leader as a primary stakeholder and take pride in driving their effectiveness and the broader team's impact.
• Experience in a fast-paced environment where you’re comfortable with ambiguity and shifting priorities.
• Strong execution. You can manage multiple priorities, stay organized, and care about getting the details right.
• Clear written and verbal communication. You can draft in someone else’s voice and know when to be brief vs. thorough.
• Proactive ownership. You don’t wait to be asked. You see the gap and close it.
• You’ve built or improved a system, process, or workflow because you saw something that needed fixing.
• Experience supporting a senior leader and understanding what it means to be a true partner.
• Familiarity with AI tools and a genuine curiosity about using them to work smarter.
• Judgment and discretion with sensitive information.
• Fluency with Google Workspace and modern collaboration tools (Slack, Notion, Ramp, or similar).

Why You’ll Love Working at Opendoor

• Work side-by-side with senior leaders and get real exposure to the business.
• Be on a team that treats Exec Ops as a strategic function, not back-office admin.
• Use and learn AI every day.
• Help shape the in-office experience for the growing Toronto team.
• Room to grow: as you automate the basics, your role expands into more complex leader coverage, team leadership, or adjacent operations roles.

Equal Opportunity

Opendoor is an Equal Opportunity Employer. We are committed to building a diverse and inclusive workplace and encourage all qualified candidates to apply.

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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.