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Owner Success Manager

Dallas, Texas, United States

What we do and why we do it

As the leading end-to-end investment platform for single-family rental homes (SFR), our mission is to make real estate investing radically accessible, cost effective, and simple. We successfully merge our passion for helping investors build wealth through real estate with cutting edge technology that transforms the way they do it.

How it’s going (and growing)

With a talented team of 600+ Roofsters, our collaborative, can-do culture is what fuels our growth. In 2022, we closed on our Series E, raising $240 million, and have offices in California, Texas, and New York as well as many remote opportunities. Our growth includes recent acquisitions of Stessa (financial and asset management software), RentPrep (tenant screening and placement service for landlords), and Mynd (property management platform for both Retail and Institutional investors). In 2025, Roofstock took an ownership stake in Casago (short-term rental management services), expanding our platform to support both long-term and short-term rental investment services.

Roofstock’s Values → Short-Term Rental (STR) Org Reflection

  • We are entrepreneurs → Launch a startup within a startup
  • We are better together → Work across functions & business units to do it fast and well
  • We focus on impact → Build a profitable business unit with satisfied owners, teammates, and guests
  • We think like investors → Enhance owners’ and Roofstock’s ROI

About the Team

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.

About the Role

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.

Responsibilities

Owner Relationship Management

  • Build and maintain strong, trust-based relationships with property owners, serving as their primary point of contact for all STR-related matters.
  • Educate owners on STR strategies, portfolio performance, and market trends to align their goals with Roofstock’s operational and revenue objectives.
  • Provide regular updates and reports to owners, highlighting key performance metrics, guest feedback, and opportunities for improvement.

Property Performance and Strategy

  • Utilize market data, pricing tools, and analytics to underwrite properties, assess their revenue potential, and recommend optimization strategies.
  • Collaborate with revenue management and operations teams to align property performance with portfolio-wide STR goals.
  • Analyze performance data to identify trends and provide actionable recommendations to owners for enhancing occupancy and revenue.

Asset Management and Improvement

  • Advise owners on prioritizing CapEx opportunities, such as property upgrades or renovations, to increase marketability and rental income.
  • Demonstrate a working knowledge of single-family rental (SFR) asset management, including maintenance best practices, cost management, and tax/regulatory compliance.
  • Coordinate with operations teams to ensure property maintenance and improvements align with owner expectations and STR industry standards.

Regulatory and Industry Expertise

  • Stay informed on local, state, and federal regulations impacting short-term rentals, advising owners on compliance requirements (e.g., permits, taxes, safety standards).
  • Monitor industry trends and competitor strategies to provide owners with insights on maintaining a competitive edge in the STR market.

Cross-Functional Collaboration

  • Work closely with revenue management, operations, and listings teams to ensure seamless execution of STR strategies and owner satisfaction.
  • Provide feedback to technology stakeholders on tools (e.g., Property Management Systems, analytics platforms) to improve owner communication and reporting processes.

Qualifications

  • Bachelor’s degree in Business, Real Estate, Hospitality Management, or a related field (or equivalent experience).
  • 3+ years of experience in relationship management, property management, or STR operations within the single-family home vacation rental or hospitality industry.
  • 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).
  • Proven ability to build and maintain client relationships, with excellent communication and interpersonal skills.
  • Working knowledge of SFR asset management, including CapEx prioritization, maintenance processes, and tax/regulatory requirements.
  • Familiarity with major OTA platforms (e.g., Airbnb, Vrbo, Booking.com) and their impact on STR performance.
  • Ability to manage multiple owner relationships and properties (e.g., 100+ units) in a fast-paced environment.

Preferred Skills

  • Experience in real estate or STR underwriting, with a focus on revenue optimization and market analysis.
  • Knowledge of Property Management Systems (PMS) and channel management tools for streamlined operations.
  • Understanding of STR-specific regulations and compliance across multiple markets.
  • Passion for the short-term rental industry and a proactive mindset for identifying growth opportunities.
  • Experience with data visualization tools (e.g., Tableau, Power BI) for owner reporting.

Location:

Dallas, TX

Compensation

$83,500-$98,000 range on annual base salary. The compensation range may be adjusted based on experience and location.

Pay Transparency

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.

Competitive & Unique Benefits Package

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

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.  

Commitment to Equal Employment Opportunity 

The company provides equal opportunity in all of our employment practices to all qualified employees and applicants without regard to race, color, religion, sex, gender, gender expression, gender identity, national origin, ancestry, citizenship, age, physical or mental disability, marital status, sexual orientation, military or veteran status, genetic information or any other category protected by federal, state and local laws. This policy applies to all aspects of the employment relationship, including recruitment, hiring, compensation, promotion, transfer, disciplinary action, layoff, return from layoff, training and social, and recreational programs. All such employment decisions will be made without unlawfully discriminating on any prohibited basis.

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