Regional General Manager – Midwest
Hospitality / Short-Term Rental Operations
Remote (Midwest-Based) | Approximately 50% Travel
A rapidly growing hospitality platform is hiring a Regional General Manager to oversee multi-market operations across a large Midwest portfolio.
This leadership role is ideal for someone with deep short-term rental (STR) or extended-stay operational experience who thrives in fast-paced, high-growth environments. You’ll own operational performance across multiple markets, manage key vendor and property relationships, and help scale operational excellence across a distributed portfolio.
What You’ll Be Responsible For
- Overseeing operations across multiple Midwest markets and hundreds of units
- Driving operational consistency, guest satisfaction, and portfolio performance
- Managing regional P&L and controlling operational costs
- Leading relationships with:
- Property owners and building partners
- Housekeeping providers
- Maintenance vendors
- Coordinating with centralized support and guest services teams
- Conducting regular market visits and operational reviews
- Identifying process improvements and helping scale systems as the portfolio grows
- Acting as the escalation point for operational and service-related issues
What We’re Looking For
Required Background
- MUST have short-term rental (STR) operations experience
- 8+ years of hospitality or operational leadership experience
- Experience overseeing multi-property and/or multi-market operations
- Strong vendor management and relationship management skills
- Experience leading through influence rather than direct authority
- Comfortable operating in fast-changing, entrepreneurial environments
- Strong operational problem-solving ability
- Tech-savvy and comfortable using multiple operational systems and apps
Strongly Preferred
- Multi-market STR platform experience
- Experience in extended-stay hospitality environments
- Background managing distributed teams or third-party service providers
Not a Fit
- Traditional hotel-only backgrounds
- Pure property management backgrounds without STR operations exposure
Location
This is a fully remote position, but candidates should be based near one of the following markets:
- Indianapolis
- Cincinnati
- Louisville
- Denver
Compensation
- Base salary target: approximately $100K–$120K
- Bonus opportunity included
- PTO and benefits package
If you’ve successfully managed distributed hospitality operations at scale and enjoy building structure inside a high-growth environment, we’d love to connect.
Who is Rainier Recruiting?
Rainier Recruiting is a boutique, award winning national staffing agency and executive search firm. Using an approach that “treats every candidate like an executive search”, we offer positions in contract-to-hire, Full-Time, and executive search. Named the #1 Best Workplace in Washington State in 2022, recognized as a ClearlyRated Best of Staffing firm, and identified as a top recruitment firm by multiple business journals, Rainier Recruiting is fast becoming a respected company. We are no longer the “best recruiters you have never heard of”. Rainier Recruiting is also proud to share our clients have a 93% repeat business rate. Rainier Recruiting is an equal opportunity employer and service provider and does not discriminate on the basis of race, religion, gender, gender identity, national origin, citizenship status, sexual orientation, disability, political affiliation or belief, or any other protected class. We are committed to the principles of Equal Opportunity Employment and are dedicated to making employment decisions based on merit and value, for ourselves, our client companies, and for the candidates we represent. We engage in socially conscious business practices and believe that diverse, equitable, inclusive, and non-biased talent and recruitment processes are foundational to the success of every organization that we partner with.