Job Description

Executive Personal & Professional Assistant

Location: [Chicago, IL] -- Hybrid (Remote + In-Person)

Schedule: Full-Time (30 hours/week)

Compensation: $20/hour- $30/hour + performance-based growth opportunities

Our firm is seeking a highly capable, solutions-driven Executive Personal & Professional Assistant to support a senior leader within our insurance and financial services practice. This role will serve as a critical extension of leadership, providing high-level operational, administrative, and personal support to ensure both the practice and the executive's personal life operate with efficiency, structure, and excellence.

This is a dynamic, hybrid position that blends executive support, practice operations, and personal life management. The ideal candidate is proactive, detail-oriented, naturally organized, and comfortable handling sensitive information with complete discretion.

Key Responsibilities

1. Financial Services Operations

Manage the full lifecycle of insurance applications and underwriting processes Communicate with carriers, underwriters, and clients to gather requirements, submit updates, and follow through on outstanding items Oversee contracting, licensing, renewals, and compliance-related documentation Prepare, organize, and monitor investment paperwork, transfer forms, and regulated client materials Ensure accuracy, completeness, and compliance across all documentation and submissions Maintain up-to-date CRM records, notes, and service tasks Track pending business, deadlines, and operational workflows to ensure timely completion
2. Executive & Practice Leadership Support

Manage the executive's schedule, projects, priorities, and weekly structure Support internal communication with team members, prospects, and clients Prepare agendas, summaries, project lists, and follow-up items for leadership meetings Help maintain operational accountability rhythms and performance tracking Support recruiting initiatives, onboarding processes, and team development Assist with event coordination, workshop logistics, and practice-wide systems Ensure the practice runs smoothly, professionally, and efficiently
3. Personal Life & Lifestyle Management

Coordinate the executive's personal calendar, appointments, and commitments Organize travel details, itineraries, reservations, and logistics Handle personal errands and organizational tasks as needed Maintain systems, reminders, and structure to support consistency in personal life Anticipate needs and provide proactive support across personal and professional responsibilities
Ideal Candidate Profile:

We are seeking an individual who is:

Highly organized, structured, and detail-focused A strong communicator with professional written and verbal skills Comfortable with detailed, regulated paperwork within insurance/financial environments Capable of strategic thinking, proactive planning, and anticipating needs Experienced in providing high-level support to business owners, executives, or entrepreneurs Able to handle sensitive information with absolute confidentiality Tech-savvy (Google Workspace, CRM systems, digital productivity tools) Reliable, positive, self-directed, and committed to excellence
Preferred backgrounds:

Executive assistant, operations coordinator, office manager, or similar Experience in insurance, financial services, real estate, law, or compliance-heavy fields Familiarity with CRM systems and client service workflows
Requirements:

Proven experience in executive support, operations, or administrative management Strong writing, communication, and organizational abilities Ability to work independently and take initiative without constant supervision Reliable transportation for occasional personal or professional errands High level of trustworthiness and professional discretion Ability to navigate both business responsibilities and personal support seamlessly
What We Offer:

A long-term role with stability and growth Opportunity to support a senior leader in a growing financial planning practice Flexible schedule within a consistent weekly structure Growth potential into an Operations Manager or Chief of Staff position Engaging, positive, and forward-thinking work environment
How to Apply:

Please submit your resume along with a brief statement describing:

Why this role aligns with your strengths Relevant experience supporting executives or managing operations in financial or regulated environments What you are seeking in your next long-term role
Job Types: Full-time, Part-time

Pay: $20.00 - $30.00 per hour

Expected hours: 20 - 40 per week

Benefits:

Professional development assistance Referral program
Application Question(s):

Do you have access to a personal vehicle if needed to travel for a specific event?
Ability to Commute:

Chicago, IL 60606 (Preferred)
Work Location: In person