Owner Success Manager

• Build and maintain strong, trust-based relationships with property owners, serving as their primary point of contact for all STR-related matters.
• Analyze performance data to identify trends and provide actionable recommendations to owners for enhancing occupancy and revenue.
• Provide feedback to technology stakeholders on tools (e.g., Property Management Systems, analytics platforms) to improve owner communication and reporting processes.
• Work closely with revenue management, operations, and listings teams to ensure seamless execution of STR strategies and owner satisfaction.
• Educate owners on STR strategies, portfolio performance, and market trends to align their goals with Roofstock’s operational and revenue objectives.
• Monitor industry trends and competitor strategies to provide owners with insights on maintaining a competitive edge in the STR market.
• Utilize market data, pricing tools, and analytics to underwrite properties, assess their revenue potential, and recommend optimization strategies.
• Stay informed on local, state, and federal regulations impacting short-term rentals, advising owners on compliance requirements (e.g., permits, taxes, safety standards).
• Provide regular updates and reports to owners, highlighting key performance metrics, guest feedback, and opportunities for improvement.
• Coordinate with operations teams to ensure property maintenance and improvements align with owner expectations and STR industry standards.
• Advise owners on prioritizing CapEx opportunities, such as property upgrades or renovations, to increase marketability and rental income.
• Collaborate with revenue management and operations teams to align property performance with portfolio-wide STR goals.

Must be authorized to work in the U.S. is a precondition of employment and we are unable to sponsor H1-B Visas at this time.

Any offer of employment is conditioned upon the successful completion of a background investigation.

Roofstock is hiring an Owner Success Manager to support our expanding short-term rental division. In this role, you will be the primary point of contact for property owners, fostering strong relationships while educating them on short-term rental (STR) strategies, performance metrics, and opportunities for property improvements to maximize revenue. This role requires a blend of analytical expertise, relationship management skills, and a deep understanding of the single-family home vacation rental industry. You will leverage market data and pricing tools to underwrite properties, provide insights on asset management, and guide owners on capital expenditure (CapEx) priorities, maintenance, and regulatory compliance. This is a high-growth, full-time, US-based role with significant opportunities for upward mobility in our dynamic organization, with potential for remote work.

• Proven ability to build and maintain client relationships, with excellent communication and interpersonal skills.
• Familiarity with major OTA platforms (e.g., Airbnb, Vrbo, Booking.com) and their impact on STR performance.
• Experience with data visualization tools (e.g., Tableau, Power BI) for owner reporting.
• Strong analytical skills, with proficiency in underwriting properties using market data, pricing tools, and analytics platforms (e.g., Excel, Google Analytics, or STR-specific software like Guesty).
• Experience in real estate or STR underwriting, with a focus on revenue optimization and market analysis.
• Demonstrate a working knowledge of single-family rental (SFR) asset management, including maintenance best practices, cost management, and tax/regulatory compliance.
• Bachelor’s degree in Business, Real Estate, Hospitality Management, or a related field (or equivalent experience).
• Understanding of STR-specific regulations and compliance across multiple markets.
• Ability to manage multiple owner relationships and properties (e.g., 100+ units) in a fast-paced environment.
• Passion for the short-term rental industry and a proactive mindset for identifying growth opportunities.
• 3+ years of experience in relationship management, property management, or STR operations within the single-family home vacation rental or hospitality industry.
• Working knowledge of SFR asset management, including CapEx prioritization, maintenance processes, and tax/regulatory requirements.
• Knowledge of Property Management Systems (PMS) and channel management tools for streamlined operations.

Our compensation reflects several US geographic markets. The base pay for this position represents the expected salary for this position. Ultimately, in determining your pay it will be based on several factors including location, job-related knowledge, skills, experience and other job related factors. Roofstock is a total compensation company; the base salary is only a part of our total compensation package.

$96,000-$112,700 range on annual base salary. The compensation range may be adjusted based on experience and location.

This position is classified as HYBRID within the Greater Oakland Area, with an expectation to be in-office on Tuesdays, Thursdays. Starting 2026, one additional day of the employee's choosing each week.

Competitive & Unique Benefits Package

Roofstock’s STR team has the opportunity to build and shape an entirely new business unit together, soon taking on over 1200 homes as a franchisee of Casago. The team is obsessed with people – in particular our owners, our guests, and our teammates. We extend our hospitality to everyone around us, there’s no such thing as “not my job,” and we celebrate our wins together. We plan to expand within our current markets as well as to roll out new markets in the years to come. Much like a startup business, things are fast-paced, intense, and exhilarating. And when the team wins, we all win.

• 401k Program
• Volunteer Time Off
• 12 Paid Holidays
• Generous PTO Policy
• Paid Parental Leave
• Robust health, dental, vision insurance, and more
• Wellness and home office/cell phone subsidies