Executive Personal Assistant

About Insights 4 Life:

Insights 4 Life is a premier leadership development and executive coaching firm serving Fortune 500 and Fortune 1000 CEOs and senior leaders. Founded by executive coach, author, and speaker Linal Harris, we help organizations unlock hidden talent and activate instinctive authority through coaching, process consulting, AI Fluency and transformational leadership frameworks. Our work spans corporate training engagements, consulting, keynote speaking, and global leadership experiences including annual leadership expeditions to Uganda.

The Role:

We are looking for a highly organized, proactive, and discreet Executive Personal Assistant to support the Founder & CEO. This is not a traditional 9-to-5 role; it's a dynamic, fast-paced position for someone who thrives behind the scenes, anticipates needs before they arise, and takes pride in making things run smoothly.

You will serve as the right hand to a busy entrepreneur who leads multiple ventures, speaks nationally, coaches C-suite executives, and is constantly generating new ideas. Your job is to protect his time, manage his priorities, and ensure nothing falls through the cracks.

Key Responsibilities:

Administrative Support

• Manage the CEO's calendar, scheduling, and email correspondence
• Provide general administrative support: answering phone service, checking messages, managing email, filing, opening mail and data entry
• Prepare reports and presentations; proofread documents and correspondence
• Set up and attend Zoom meetings, take notes, and assist with technical and administrative needs
• Manage office supplies, maintain an organized workspace, and run errands as needed
• Track deliverables and deadlines across active projects and business ventures

Business Development & CRM

• Assist with CRM tasks: data entry, lead research, and maintaining client relationships
• Support business development by preparing proposals and conducting market research
• Liaise with clients, vendors, partners, and team members on behalf of the CEO

Membership Support

• Handle membership inquiries and communications for the Slay Your Goals coaching community
• Maintain member databases, ensuring information is accurate and up-to-date

Communications & Content Support

• Draft, proofread, and manage professional correspondence
• Support social media scheduling and basic content coordination
• Assist with book-related projects, speaking outreach, and media inquiries

Travel & Event Management

• Organize domestic and international travel for the CEO
• Support logistics for the annual Leadership Expedition to Uganda, including attendee communications and on-site support
• Coordinate workshops, conferences, and events — from logistics to execution

Personal & Administrative Support

• Assist with personal errands, appointments, and household matters
• Manage expenses, invoices, and vendor relationships
• Maintain strict confidentiality and handle all sensitive information with discretion

What We're Looking For:

• 3+ years of experience supporting a C-suite executive, entrepreneur, or high-profile individual
• Exceptional organizational and time management skills — you don't just keep lists, you build systems
• Strong written and verbal communication skills; polished and professional in every interaction
• Proficiency with Microsoft Office and Google Workspace
• Familiarity with CRM systems and business development processes
• Resourceful self-starter who doesn't need to be micromanaged
• High emotional intelligence and discretion — you understand confidentiality at the highest level
• Reliable transportation, valid driver's license, and ability to travel as needed
• Alignment with the mission and values of our organizations
• Bonus: experience in facilitation, coaching, consulting, publishing, or the speaking industry

Mission Alignment:

This role is more than administrative support — it's an opportunity to contribute to a larger mission of helping people grow personally and professionally. We are looking for someone who is not just skilled, but aligned. You will be expected to embrace a growth mindset, seek personal development, and show up as a true partner in advancing the work we do.

What Success Looks Like:

In your first 90 days, you will have mastered the CEO's calendar and communication rhythms, established reliable systems for tracking projects across all businesses, and become someone the CEO trusts completely to represent him and keep things moving.

Compensation & Details:

• Type: Part-time with potential to grow into full-time
• Arrangement: Hybrid (Chicago metro area-based strongly preferred)
• Compensation & Schedule: Discussed during the interview process
• Opportunities for advancement and personal development

Job Type: Contract

Pay: $18.00 - $23.50 per hour

Language:

• English (Required)

License/Certification:

• Driver's License (Required)

Ability to Commute:

• Oak Brook, IL 60523 (Required)

Work Location: Hybrid remote in Oak Brook, IL 60523