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Red Mug Construction · 4 days ago

Executive Personal Assistant to Founder (Operations & Compliance)

Chicago, IL

Full-time

Onsite

Mid Level

$55K/yr - $65K/yr

Red Mug Construction is a Chicago-based real estate investment, construction, and architecture group focused on residential projects. They are seeking an Executive Personal Assistant to support the founder by managing administrative tasks, compliance, and operational coordination to allow the founder to focus on strategic decisions.

Construction

Hiring Manager

Jorge Catrain Ostáriz

Responsibilities

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

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

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

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

Document recurring processes and create checklists

Improve systems over time to reduce repeat issues

Identify inefficiencies and propose solutions

Qualification

Compliance managementOrganizational skillsAttention to detailProcess documentationSystems improvementEmotional stabilityRule enforcementCommunication skills