Executive Personal Assistant to Founder; Operations & Compliance

$55,000–$65,000 base + performance incentives

This role exists to remove administrative, operational, and paperwork-related work from the founder entirely, so he can focus on strategic and big-picture decisions.

If done correctly, the founder should no longer:

• Manage email or calendar
• Chase Project Managers, subcontractors, or accountants
• Review routine paperwork
• Follow up on missing documentation

This is a precision, enforcement, and systems role. It is not a creative, social, or client-facing position.

We are a Chicago-based real estate investment, construction, and architecture group focused on residential projects.

Our work includes property acquisition, renovation, construction, and long-term asset management. The organization operates with defined processes, clear accountability, and a strong emphasis on documentation and compliance.

Time & Attention Protection

• Full ownership of the founder’s calendar, including scheduling, rescheduling, and enforcing meeting rules
• Daily inbox triage: filtering, summarizing, and drafting responses
• Only decision-level items reach the founder
• Screen calls and incoming requests

Paperwork, Compliance & Payments

• Manage subcontractor contracts, Certificates of Insurance (COIs), and W-9s
• Track expiration dates and maintain clean, auditable vendor files
• Enforce the rule: no documentation→no payment
• Ensure Project Managers do not submit or approve payments without complete documentation
• Act as the bridge between the accountant, Project Managers, and the founder
• Track expenses and prepare clean monthly handoffs to accounting
• Resolve questions and discrepancies before they reach the founder

Follow-Up & Enforcement

• Proactively chase missing information so the founder never has to
• Close open loops and track outstanding items
• Enforce rules consistently and calmly, even when others push back

Office Operations

• Manage office vendors, supplies, and services
• Coordinate cleaners and maintenance (this role does not perform cleaning)
• Ensure the office environment is professional and fully functional at all times

Systems & SOPs

• Document recurring processes and create checklists
• Improve systems over time to reduce repeat issues
• Identify inefficiencies and propose solutions

This Role Is NOT

• Creative
• Social
• Client-facing
• Sales or marketing
• “Figure it out as you go”

This role values structure, rules, precision, and follow-through.

• Extremely organized and detail-oriented
• Comfortable enforcing rules and saying “no” on behalf of leadership
• Calm under pressure and emotionally steady
• Low ego, high ownership
• You enjoy checklists, systems, and closing loops

• Founder regains 5–10 hours per week
• Inbox and calendar remain clean and controlled
• Founder no longer chases people or paperwork

To apply, email  with:

• Your resume
• Your self-reported DISC profile results (from: )
• A short paragraph answering: “What systems do you rely on to stay organized?”

Subject line: PA – Systems First

Applications that do not follow these instructions will not be reviewed.

This role is highly structured and detail-driven.

It is designed for someone who enjoys clear rules, defined processes, and closing loops.

If you prefer flexibility, ambiguity, or creative freedom, this role may not be a good fit — and that is intentional.