Director of Operations & Strategy

Who we are

AvantStay delivers world class, authentic, tech-enabled short-term rental (“STR”) group experiences targeted at the millennial generation. We are venture funded and growing rapidly in the explosive $100+ billion dollar STR industry. We deliver a customized end-to-end experience that is tailored just for groups and powered with technology at every layer.

What we are looking for

We are seeking a strategic and hands-on Director of Market Operations & Strategy to oversee multiple markets and drive operational excellence. This role blends market leadership with central operational strategy: you’ll lead high-performing local teams, launch new markets, integrate acquisitions, and scale systems that improve both guest satisfaction and owner outcomes. The ideal candidate combines quantitative rigor with operational savvy, thrives in ambiguity, and knows how to balance strategic leadership with a roll-up-your-sleeves mindset.

What you'll do

• Lead multi-market operations. Oversee Regional Area Managers, Area Managers, and General Managers across multiple geographies; manage teams of 50+ with a culture of accountability, innovation, and continuous improvement.
• Coach layered management. Provide guidance and development across multiple levels of management, ensuring leaders at each layer are empowered, aligned, and equipped to succeed in a matrixed organizational structure.
• Launch & scale new markets. Build operational playbooks to enter new geographies, ensuring successful stand-ups across staffing, vendor networks, owner onboarding, and guest experience.
• Integrate local acquisitions. Lead operational integration of newly acquired property management businesses (including small/mid-size operators), aligning them to AvantStay’s systems, standards, and culture.
• Operational excellence. Ensure markets meet or exceed KPIs including guest satisfaction (CSAT, NPS), owner retention, quality standards, and financial performance. Drive efficiency in cleaning, maintenance, and vendor management.
• Owner relations. Build strong, trust-based relationships with property owners. Serve as a strategic partner by understanding their goals, aligning them with operational objectives, and providing transparency through effective communication and reporting.
• Financial & strategic management. Own budgets across markets; track and improve unit economics, overhead costs, and portfolio profitability.
• Data-driven leadership. Use spreadsheets, dashboards, and reporting tools to guide decision making and improve operations. Partner with Data, Product, and Engineering to leverage technology that scales quality and efficiency.
• Cross-functional collaboration. Serve as the voice of the field for central functions including Product, Engineering, Finance, and CX. Ensure alignment on strategy and execution.

What you'll bring

• Proven success as an operational leader managing 50+ people across multiple markets.
• Experience launching new markets or business lines, building scalable processes, and delivering strong unit economics.
• Demonstrated ability to integrate acquisitions, including cultural alignment, systems migration, and operational uplift.
• Comfort working with data and spreadsheets (Excel/Google Sheets) to analyze performance, track KPIs, and inform strategy.
• Strong leadership and communication skills, able to inspire and develop teams while influencing executives and cross-functional partners.
• Willingness to travel up to 50% time to oversee market performance and team development.

• Salary range of $120,000-130,000 per year, dependent on skills and experience

• Annual bonus based on performance
• Equity
• Generous company-sponsored insurance (medical, dental, vision, life, etc.)
• Flexible paid time off
• Complimentary and discounted stays at AvantStay properties
• Pre-tax retirement savings plans offered via Betterment
• Paid parental leave
• Fitness reimbursement
• Cell phone reimbursement

When you join AvantStay

You’ll be doing work that matters alongside an experienced and dynamic team, transforming the way people travel and vacation. Your place within the colossal travel and real estate industries will leave you with a wealth of opportunities to feel both challenged to innovate and rewarded for your efforts. Of course, we will offer you pay and benefits, but we’re about more than that. AvantStay is a place where you can craft your own path to greatness. Whether you think in code, words, pictures or numbers, find your future at AvantStay.

Equal Employment Always

We're proud to be an equal opportunity employer and we celebrate our employees' differences, including race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, and Veteran status. Different makes us better.

No soliciting from staffing agencies. Thank you!