VP, Operations Design & Strategy

Mainstay is the leading market intelligence platform purpose built for buying, managing, and selling homes in the single family rental industry. As an AI native company, we turn complex data into clarity that helps the industry move forward with confidence. Founded within Opendoor, Mainstay launched as an independent company in 2024 and recently raised a Series A round led by Khosla Ventures.

Ready to shape the future of real estate with AI? Join Mainstay and help us redefine what’s possible in the single family rental space. If you thrive on solving complex problems and want to make a tangible impact in a fast-growing industry, we’d love to hear from you - apply now and let’s move the industry forward, together!

The Operations team’s mandate is to imagine, define, and pilot operating systems that allow Mainstay to scale with discipline. It is comprised of two departments Fulfillment and Operations Design and Strategy.

As VP, Operations, you will oversee two of Mainstay’s business lines, HOA and Tax. You will be accountable for operational reliability, execution rigor, strategic project delivery, and prioritization across both departments and business lines. You will work directly with customers to understand their needs, pain points, and expectations. This role sits at the center of the organization, working w/ Product, Engineering, Analytics, and Revenue to translate real customer experience into how the company operates and delivers.

• Own end to end operational outcomes across HOA and Tax, with clear accountability for delivery, prioritization, and process design

• Set and run operating cadences, including metrics, reviews, and accountability rhythms that teams execute against

• Be hands on in execution where needed to maintain continuity of delivery, unblock teams, and model Mainstay’s “way of operating”

• Design, evolve, and enforce processes that improve reliability, quality and scalability

• Make final decisions on issue triage, sequencing of work, and tradeoffs across initiatives

• Translate product strategy into executable operating plans and provide grounded feedback based on delivery realities

• Build, develop and hold accountable a team of leaders, creating clarity around ownership and decision rights

• Identify organizational gaps and make hiring decisions to strengthen execution capacity in partnership with our COO

• Drive cross functional alignment through clear communication, strong judgment, and disciplined prioritization

• Say no to work that distracts from core priorities, even when it’s uncomfortable

• Balance meaningful change with an awareness of team capacity and long term sustainability

• 15+ years of experience in operations, strategy, or execution focused leadership roles

• Experience owning outcomes across multiple businesses, teams, and complex operational surfaces

• Proven ability to step into ambiguity, stabilize execution, and impose structure without over engineering

• Comfortable being deeply involved in the details while building systems that scale beyond the individual

• Track record of leading leaders and making hard calls on priorities, process, and organizational design

• Strong operational judgment and the ability to make decisions without perfect information

• Speaking to operations w/ data is your default more of operating

• High standards for quality and accountability, paired with awareness of how change impacts teams

• Ability to manage friction productively across functions and senior stakeholders

• Willingness to work harder than anyone else on the team, while recognizing and addressing burnout in others

• Clear communicator with the ability to move between operators and executive audiences

• Experience in Real Estate, Fintech, or services heavy business

• Experience stabilizing underperforming operations while continuing to grow

• Startup experience

• You thrive in hands on execution and enjoy bringing structure to complex, messy operational problems

• You can own multiple businesses or workstreams at once and make clear tradeoffs without perfect information

• You set high standards, hold teams accountable, and are comfortable saying no when priorities conflict

• You build credibility by working closely with teams and directly with customers

• You prefer high level strategy with limited involvement in day to day execution

• You need full certainty or deep detail before making decisions

• You struggle to manage multiple product lines without micromanaging

• You avoid conflict or find it difficult to say no to stakeholders or customers

#LI-AW

At Mainstay, trust is at the core of everything we do. We build trust with everyone -- from candidates to employees to partners. We believe in fairness and openness throughout our hiring process, evaluating candidates based on qualifications without regard to race, color, religion, national origin, age, gender, marital status, disability, veteran status, sexual orientation, gender identity, or any other protected status. Our privacy practices describe how we handle applicant information, you can find the policy details for California residents here.

We are committed to providing reasonable accommodations throughout our recruitment processes for candidates with disabilities, pregnancy, religious beliefs, or other reasons protected by applicable laws. If you require assistance or a reasonable accommodation, please contact us at [email protected]