Part-Time Real Estate Operations Assistant

JOB DESCRIPTION

Part-Time Real Estate Operations Assistant

Location: Milwaukee, WI | Type: Part-Time (20–30 hrs/week) | Compensation: $3,000–$3,500/month + commission

ABOUT THE ROLE

The XL companies are a Milwaukee-based portfolio of real estate businesses operating across four divisions: residential construction (XL Property & Contracting), property management (XL Management Group), sales and listings (XL Property Group), and investment acquisitions (XL Property Buyers). We are a lean operation moving fast, and we need someone who can keep pace.

This is not a sit-at-a-desk-and-wait role. We need a sharp, self-directed assistant who can own a wide range of tasks — from pulling comps and filing insurance claims to conducting property inspections and coordinating vendors — and do it without needing their hand held. If you are licensed, organized, have real estate instincts, and genuinely enjoy staying on top of things so your principal does not have to, this role was built for you.

COMPENSATION AT A GLANCE

$3,000 – $3,500 / month base (part-time, 20–30 hrs/week)
60% of tenant placement fees for leasing cycles managed end-to-end
Real estate license preferred — unlicensed candidates with strong RE experience considered
WHAT YOU WILL DO

Responsibilities span three of the four XL entities. You will rotate tasks based on operational need, always working from a clear assignment list.

XL Property Group & XL Property Buyers — Real Estate Support

Pull comparable sales for active listings, buyer/seller consultations, and investment deal analysis
Research after-repair values (ARV) to support acquisition underwriting
Assist with MLS data entry — verify listing accuracy before properties go live
Coordinate listing photography: schedule photographers, organize and review deliverables
Host open houses and coordinate property showings
Manage staging logistics and listing preparation for active inventory
Track and collect transaction documents across active deals to keep files complete
Log addresses, property conditions, and notes from driving-for-dollars scouting runs
XL Property & Contracting — Construction Support

Note: This role supports construction operations in a coordination and documentation capacity. Material procurement, inventory management, and finish quality judgment are not day-one expectations and will be transitioned into the role over time as familiarity with our projects and vendors develops.

Serve as a communication point with vendors and suppliers on delivery schedules, updates, and issue escalation
Prepare and submit documentation for storm and damage-related insurance claims
Capture organized, timestamped job site progress photos for project records and insurance support
Assist with punch list tracking — logging open items and following up on completion status
XL Management Group — Property Management Support

Conduct routine property inspections and turnover walkthroughs
Complete photo checklists and condition reports at tenant move-in and move-out
Log and route incoming maintenance requests; follow up to confirm completion
Track punch-out items across vacant units to ensure readiness for re-leasing
Serve as on-site point of contact for assigned renovation or improvement projects
WHAT WE ARE LOOKING FOR

Real Estate License: Active Wisconsin real estate license strongly preferred. Will consider candidates with substantial hands-on RE experience in lieu of licensure.
Attention to Detail: You catch things others miss. Whether it is a missing doc in a transaction file or an unresolved maintenance ticket, you are thorough.
Task Execution: You work well from a list. You complete assignments independently, follow through without reminders, and flag issues early.
Memory & Proactivity: Part of your value is remembering what the principal does not. You track open items, follow up proactively, and keep things from falling through the cracks.
Fast Learner: No construction background required — but you need to be the type of person who picks up new processes quickly, asks smart questions, and gets up to speed without hand-holding.
Cross-Functional Flexibility: You are comfortable shifting from a property inspection in the morning to pulling comps in the afternoon. No two days look the same.
Communication: Clear, timely, and professional — by text, email, and phone. You do not go silent.
Milwaukee Market Knowledge: Familiarity with Milwaukee neighborhoods, values, and vendors is a meaningful advantage.
NICE TO HAVE

Experience in property management or residential real estate transactions
Familiarity with MLS platforms, Buildertrend, or property management software
Prior experience with insurance claim documentation or restoration projects
Background as an executive assistant, operations coordinator, or transaction coordinator
SCHEDULE & STRUCTURE

This is a part-time role averaging 20–30 hours per week. Hours will vary based on active projects and operational needs — some weeks lean field-heavy, others are more desk-based. You will report directly to the principal and receive task assignments via a shared system. Scheduling of your own work hours is flexible within reason, but responsiveness during business hours is expected.

Pay: $25.30 - $30.47 per hour

Benefits:

Flexible schedule
Application Question(s):

Have you ever assisted with a real estate transaction from contract to close? What did your role look like?
This role spans real estate, property management, and construction support. Which area is furthest outside your experience, and how would you approach getting up to speed?
Experience:

Real Estate: 2 years (Required)
License/Certification:

Real Estate License (Preferred)
Ability to Commute:

Milwaukee, WI 53208 (Required)
Work Location: In person