Field Operations Associate — Portfolio Manager Track
Hospitality / Short-Term Rentals
Who We Are
Your Key Rental Management runs a portfolio of short-term rentals with a guest-first approach without sacrificing profitability or owner trust. We operate with discipline, hold a high standard, and scale through systems and accountability.
The Role
This is a field-based career track with a clear destination: Portfolio Manager. You'll start in the field learning every aspect of how our operation actually runs, graduate into a Project Manager role with broader ownership, and grow into a Portfolio Manager owning day-to-day performance for a book of properties. For the right person — a self-starter who moves with urgency and leads with action — this path can be completed in about a year.
This is not an office job. The work happens at the properties, in the field, on your feet. One morning you might be inspecting a property before a guest arrives. That afternoon, you might be coordinating cleaners, responding to a guest message, swapping out a smoke detector battery, or supporting the onboarding of a new property. The next day might be entirely different. You'll learn our operation by doing the work across Guest Readiness, STR Associate tasks, Portfolio Management support, and Business Development — earning real exposure to each function as the business demands it.
Short-term rentals don't pause for nights and weekends — and neither does this role. Weekend availability is required, along with some evenings; the more availability you bring, the faster you advance. When a new property comes online, that takes priority. When a guest issue blows up, we move resources to fix it. The people who succeed here are the ones who lean in to whatever the day demands and solve problems before they're told to.
Reports to: COO
The Career Path
We've designed this role as a deliberate progression, not an open-ended job. A motivated self-starter can move through all three stages in roughly a year.
Stage 1 — Field Operations (start here)
Learn the entire field operation by doing the work. You'll rotate through every operational function based on what the business needs, building hands-on mastery of how properties get turned, how guests get served, and how standards get held.
Stage 2 — Project Manager
Take on broader ownership across operational areas — coordinating projects end to end, holding vendors and timelines accountable, and driving outcomes with less supervision. You prove you can own results, not just tasks.
Stage 3 — Portfolio Manager
Own day-to-day performance for a book of properties with flawless documentation and financial accuracy. Manage owner relationships, prevent problems before they happen, and partner with field leadership to develop standards and people.
What You'll Actually Do (Stage 1)
You'll move between the following areas of work based on what the business needs that day or week — all of it in the field, none of it from a desk:
Guest Readiness work
- Pre-arrival inspections to verify cleaning quality, staging, and presentation
- Walk-throughs against our QA checklist: linens, towels, supplies, lighting, décor placement
- Restocking consumables and welcome amenities
- On-the-spot fixes for anything that would create a negative guest experience
- Coordination with cleaners on re-cleans and touch-ups
- Documentation of property condition before check-in and after checkout
STR Associate work
- Guest communication across our PMS and OTA platforms (Airbnb, VRBO, Booking.com, direct)
- In-stay troubleshooting: Wi-Fi, appliances, lockouts, neighborhood questions
- Processing reservation changes, cancellations, and refund requests per policy
- Coordinating daily scheduling between cleaners, inspectors, and maintenance
- Handling damage claims through OTA resolution centers
- Maintaining accurate listings across platforms
Portfolio Management support
- Supporting Portfolio Managers on owner communication and reporting
- Assisting with monthly performance reviews and owner deliverables
- Capturing and documenting all billable maintenance and services accurately
- Coordinating with vendors and contractors and holding them to standards
Business Development support
- Supporting property onboardings: contracts, photography coordination, listing setup• Assisting with property assessments for prospective owners• Helping prepare owner-facing proposals and materials
Minor maintenance — a real part of this job
We need to be direct: this role requires you to handle light handyman tasks yourself. We don't dispatch a service truck for a loose toilet seat or a paint scuff.
- Paint touch-ups (we keep matched paint at each property)
- Replacing light bulbs, smoke detector batteries, and air filters
- Resetting tripped breakers, GFCI outlets, and Wi-Fi routers
- Tightening loose hardware (door handles, toilet seats, cabinet pulls, towel bars)
- Unclogging slow drains with basic tools
- Replacing remote batteries and pairing simple smart-home devices
- Re-hanging fallen wall art, adjusting blinds, swapping out worn small items
- Knowing when something is beyond light maintenance and needs a licensed pro
You'll be issued a basic tool kit and a stocked supply bin. Recognizing the line between what you handle and what gets escalated — and not letting small problems become big ones — is part of the job.
What It Takes to Advance to Portfolio Manager
By the time you reach the Portfolio Manager stage, you'll be expected to operate at this standard:
- Own portfolio operations, owner communication, and follow-through
- Ensure all maintenance and billable services are captured, documented, and billed correctly — with no preventable billing mistakes
- Escalate risks early and appropriately
- Support property onboarding/offboarding readiness and standards
- Serve as a partner resource to field leadership for team development and standards adherence
- Deliver clear documentation and clean handoffs, with stable portfolio performance and proactive issue prevention
Required Experience & Qualifications
- Self-starter who leads with action and takes initiative without being asked — you move on problems rather than putting them off
- Strong problem-solver who can work through ambiguous situations and make sound decisions, including under pressure• Highly organized; able to juggle many moving pieces — properties, vendors, guests, owners — without dropping handoffs
- Excellent written and verbal communication; able to de-escalate frustrated guests and have professional conversations with owners
- Comfortable learning new software platforms quickly (PMS, OTA dashboards, dynamic pricing tools, owner portals)
- Comfortable with physical work: in and out of properties, on your feet, lifting up to 40 lbs, ladders, occasional tight spaces
- Weekend availability required, plus some evenings — broader availability accelerates your advancement
- Reliable transportation, valid driver's license, clean driving record
- Willingness to adjust priorities as business demand shifts
Preferred
- Prior experience in hospitality, property management, real estate, or customer service• STR familiarity — guest messaging, maintenance coordination, billing awareness — as a host, guest, or operator
- Basic handyman or DIY experience
- Bachelor's degree or equivalent work experience
Not a Fit If
- You're looking for an office job — this role lives in the field
- You can't work weekends and the occasional evening
- You need a fixed, predictable list of daily tasks to function
- You avoid physical work or minor maintenance
- You struggle with follow-through, documentation, or accuracy
- You wait to be told what to do, or you put off problems rather than acting on them
- You're not interested in growing into greater responsibility over time
Job Type: Full-time
Pay: $40,000.00-$50,000.00 per year
Application question(s):
- Why are you interested in the Portfolio Manager role at Your Key?
What stood out to you about this role or how we operate?
- Describe a role where accuracy and follow-through were critical.
What systems or habits did you use to avoid mistakes?
- Tell us about a time you caught a financial or documentation issue before it became a bigger problem.
What did you do, and what was the outcome?
- This role requires knowing when to escalate rather than “handle it quietly.”
Describe a situation where escalation was the right call.
- How do you manage multiple stakeholders (owners, internal teams, vendors) while keeping work organized and documented?
- What does “portfolio health” mean to you in a hospitality or STR context?
- Where do you see yourself professionally in the next 1–3 years?
What skills or experience are you hoping to build?
- The compensation range for this role is $50,000 - 69,000.
Does this align with your expectations at this stage of your career?
☐ Yes ☐ Open to discussion ☐ No
Experience:
- Hospitality/STR/ Property Operations : 2 years (required)
Language:
Work Location: On the road
