Clutch Canada
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 reinvent the rental housing ecosystem for the benefit of all. 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 750+ 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 the Bay Area and New York City. 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. 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 w
Responsibilities
Manage a portfolio of ~40 STR homes in your market, ensuring they are clean, maintained, guest-ready, and performing to standard
Serve as the primary point of contact for assigned owners, answering questions promptly and delivering proactive updates
Visit and inspect each home in your portfolio at least once per month to ensure familiarity and quality oversight
Lead a small in-market team and oversee local vendors
Delegate routine inspections and operational tasks to a team of caretakers, runners, etc
Resolve escalated guest issues with urgency and care
Support onboarding of new homes in collaboration with central and field teams
Help owners understand the expenses on their statements and answer financial questions as they arise
Monitor and manage home-level standards, performance, and guest feedback
Other duties as assigned
Success Measures
High guest satisfaction and consistent 5-star reviews for assigned homes
Average guest review score of 4.8 or higher across assigned homes, with action plans in place for any homes below threshold
Owner satisfaction as measured by Net Promoter Score (NPS) and direct feedback
Owner churn within assigned portfolio kept below 10% annuallyClear, timely communication and issue resolution for owners (SLAs TBD)
Reliable performance and accountability from team members and vendors
Work Environment & Physical Demands
Frequent travel within market required
Availability to frequently work weekends, holidays, early mornings, and evenings (with 2 days off each week)
Qualifications
3+ years in property management, hospitality, or field operations
Exceptional communication skills and a customer-first mindset
Ability to manage local teams and third-party vendors
Working knowledge of STR platforms (Airbnb, VRBO, etc.)
Comfort with expense categories and explaining common STR charges to owners
Strong organizational and time management skills
Comfort with mobile tools and task management systems
Valid driver’s license and reliable transportation required
Bachelor Degree preferred but not required
Compensation Compensation may be adjusted based on experience, skills, and interview performance.
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.
#J-18808-Ljbffr
How it’s going (and growing) With a talented team of 750+ 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 the Bay Area and New York City. 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. 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 w
Responsibilities
Manage a portfolio of ~40 STR homes in your market, ensuring they are clean, maintained, guest-ready, and performing to standard
Serve as the primary point of contact for assigned owners, answering questions promptly and delivering proactive updates
Visit and inspect each home in your portfolio at least once per month to ensure familiarity and quality oversight
Lead a small in-market team and oversee local vendors
Delegate routine inspections and operational tasks to a team of caretakers, runners, etc
Resolve escalated guest issues with urgency and care
Support onboarding of new homes in collaboration with central and field teams
Help owners understand the expenses on their statements and answer financial questions as they arise
Monitor and manage home-level standards, performance, and guest feedback
Other duties as assigned
Success Measures
High guest satisfaction and consistent 5-star reviews for assigned homes
Average guest review score of 4.8 or higher across assigned homes, with action plans in place for any homes below threshold
Owner satisfaction as measured by Net Promoter Score (NPS) and direct feedback
Owner churn within assigned portfolio kept below 10% annuallyClear, timely communication and issue resolution for owners (SLAs TBD)
Reliable performance and accountability from team members and vendors
Work Environment & Physical Demands
Frequent travel within market required
Availability to frequently work weekends, holidays, early mornings, and evenings (with 2 days off each week)
Qualifications
3+ years in property management, hospitality, or field operations
Exceptional communication skills and a customer-first mindset
Ability to manage local teams and third-party vendors
Working knowledge of STR platforms (Airbnb, VRBO, etc.)
Comfort with expense categories and explaining common STR charges to owners
Strong organizational and time management skills
Comfort with mobile tools and task management systems
Valid driver’s license and reliable transportation required
Bachelor Degree preferred but not required
Compensation Compensation may be adjusted based on experience, skills, and interview performance.
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.
#J-18808-Ljbffr