Operations Manager
Trove is the leading short-term rental management company in Chicago. We operate a portfolio of high-end properties across the city and are known for delivering top-tier guest experiences, unmatched operational quality, and strong financial results for our real estate partners.
We’re growing, and we’re hiring an Operations Manager to lead day-to-day operations in our flagship market. This is a hands-on, leadership-level role with real responsibility. You’ll be directly accountable for the performance of a current 75 unit top-tier STR portfolio expected to grow to over 200 in the next year, managing teams, maintaining standards, and making sure every process runs smoothly, every day.
About the RoleYou’ll oversee all field operations in Chicago, which includes housekeeping, maintenance, guest services, and new property launches. You’ll lead a dependable team, ensure each property meets Trove’s brand standards, and help build the systems that keep quality consistent as we scale.
This is a role for someone who likes structure, handles complexity with focus, and takes ownership of outcomes. When things go well, it’s because you’ve put the right systems in place. When things go wrong, you step in calmly and fix them.
What You’ll Do- Oversee daily operations across housekeeping, maintenance, and virtual guest support
- Lead new property launches, ensuring spaces are set up correctly both physically and digitally
- Monitor performance, quality scores, task completion, response times, and guest reviews
- Ensure consistency across all units through systems, standards, and regular follow-up
- Support client relationships by keeping operations on track and communicating proactively
- Resolve issues quickly, then implement long-term improvements to avoid repeat problems
Tools & Systems We Use- PMS (like Guesty and Breezeway), Google Workspace, Notion, WhatsApp, Miro
- Internal SOPs, quality-control checklists, inspection templates (you’ll help shape and manage these)
- Regular reporting and KPI dashboards
What We’re Looking For- 5+ years of experience in operations, property management, hospitality, or logistics
- Strong leadership skills. You've run teams and earned their respect
- Highly organized, detail-focused, and reliable
- Tech-comfortable and able to learn and optimize digital systems
- Calm under pressure, steady in a crisis, and clear in your communication
- You care about doing things right, not just getting them done
- Team player - works well with others, is able to accept and provide feedback
- Must be bilingual in English and Spanish
What You Can Expect- Direct responsibility for the daily performance of Chicago’s best STR portfolio
- A supportive leadership team and clearly defined expectations
- A company that respects systems, processes, and people who take ownership
- A clear growth path into a senior operations leadership role
- Competitive salary and performance-based compensation
Who This Role Is ForYou take pride in being reliable. You notice what others miss, and you follow through without being asked twice. You believe good systems prevent problems. And when issues do come up, you resolve them quickly and completely.
You value clarity, consistency, and a job done well. You hold yourself to a high standard and expect the same from your team. You don't need constant direction, just a clear mission and the tools to execute.
This role carries real responsibility. If you're someone who leads with quiet confidence and finds satisfaction in making complex operations work seamlessly, we’d like to hear from you.
