Operations & Systems Coordinator — Property Management / Bookkeeper

JDPM LLC

is a private real estate investment company in Greenville, WI managing a portfolio of residential and commercial rental properties. We're looking for a dependable, detail-oriented person to join us as our Operations & Systems Coordinator. This is a multi-hat role in a small, fast-moving office. You'll handle property management tasks, maintain the books, answer phones, and provide general administrative support — but the bigger job is building the systems that make all of it faster and more efficient. If you already use AI tools daily and get personal satisfaction from finding a better way to do things, keep reading.

SCHEDULE & PAY

Hours:

Monday-Friday, 9 AM-1 PM | 20-30 hrs/week to start, growing to 40+

Pay:

$20-22/hr base Total comp potential: $75,000

• 100,000+ via performance bonuses

Location:

On-site, Greenville, WI (office relocating towards Appleton)

BONUS STRUCTURE

(tied to performance, not accounting profit)

• Quarterly KPI scorecard: $1,500
• 2,500/quarter
• Property acquisition bonus: $200
• 1,500 per property onboarded (7+ acquisitions/year targeted)
• Gross revenue bonus: 1% of gross annual rent collected
• Long-term equity participation after 2+ years

WHAT YOU'LL DO

Property management (Appfolio):

• Review rental applications and screen tenants
• Post rent payments, send late notices, manage tenant ledgers
• Coordinate maintenance work orders with vendors and tenants
• Show vacant units; manage vacancy listings
• Handle move-in/move-out documentation and security deposits
• Issue notices per Wisconsin landlord-tenant law
• Coordinate eviction filings; appear in small claims court as needed
• Manage collections on delinquent accounts Bookkeeping (QuickBooks Online):
• Record and categorize income and expenses across multiple entities
• Post journal entries; reconcile bank and credit card accounts monthly
• Process vendor invoices and coordinate bill payments
• Generate monthly financial reports for ownership review
• Assist with year-end 1099 preparation and CPA coordination Office & admin:
• Answer phones; manage tenant and vendor communications
• Open, sort, scan, and file mail by property and entity
• Assist with paperwork when new businesses or projects launch
• Maintain digital and physical filing systems Systems & process (the most important part of this job):
• Document every recurring task as an SOP from day one
• Identify manual processes and propose automation or elimination
• Use AI tools (Claude, ChatGPT, or similar) actively to improve output
• Participate in weekly operations meetings; set and track monthly/quarterly/annual goals

NON-NEGOTIABLE REQUIREMENTS

• Already using AI (ChatGPT, Claude, etc.) as a regular daily work tool
• Clear, direct communicator — will tell ownership when something isn't working
• Comfortable working independently most of the time
• Willing to appear in court for eviction proceedings
• Trustworthy with confidential financial, legal, and tenant information
• Embraces change — this environment is always evolving

STRONGLY PREFERRED

• QuickBooks Online experience
• Appfolio or other property management software
• Familiarity with Wisconsin landlord-tenant law
• Track record of building SOPs or workflow documentation
• Small business or entrepreneurial environment experience

HOW TO APPLY

Email james@reswis.com with your resume and a short cover letter answering: 1. Which AI tools do you use, and give one concrete example of how you've used AI to do something faster or better at work. 2. Describe a process you found inefficient and what you did about it. 3. Are you comfortable with court appearances for evictions? Any landlord-tenant experience? Applications without answers to these three questions will not be reviewed.

Pay:

$20.00

• $22.

00 per hour

Benefits:

Flexible schedule Application Question(s): Do you have experience with QuickBooks Online or similar bookkeeping software? Briefly describe any experience you have with property management, tenant relations, or working in a real estate office.

Experience:

Bookkeeping:

1 year (Required) Ability to

Relocate:

Greenville, WI 54942: Relocate before starting work (Required)

Work Location:

In person