Executive Assistant to Founder & CEO

Robinson Hill | Good Trouble Bourbon | Project Sand
Chicago, IL (Hybrid)

About the Role

We are seeking an exceptional Executive Assistant to support entrepreneur and founder Dee M. Robinson across a dynamic portfolio of ventures including Good Trouble Bourbon, Robinson Hill, and Project Sand, a groundbreaking golf and wellness destination built by women with women in mind.

This role goes far beyond traditional administrative support. The Executive Assistant serves as a trusted operational partner to the Founder, helping manage priorities, coordinate strategic initiatives, and ensure flawless execution across a fast-moving entrepreneurial environment.

The ideal candidate is highly organized, proactive, and thrives in high-performance environments where discretion, judgment, and execution matter.

Key Responsibilities

Executive Support

• Manage complex calendar and scheduling across multiple ventures
• Coordinate travel, logistics, and meeting preparation
• Ensure the Founder is prepared for meetings, events, and speaking engagements
• Track priorities, action items, and follow-ups

Project Coordination

Support strategic initiatives across ventures including:

• Good Trouble Bourbon brand growth and partnerships

• Project Sand investor outreach and development

• Robinson Hill business operations

Track project timelines and ensure progress across teams

Communications & Relationship Management

• Manage high-level correspondence with partners, investors, and stakeholders
• Coordinate introductions and relationship follow-ups
• Draft professional communications and briefing materials

Operational Support

• Maintain project dashboards and organizational systems
• Coordinate internal and external meetings
• Ensure smooth execution across initiatives

Qualifications

• 5+ years supporting senior executives or founders
• Exceptional organizational and project management skills
• Strong written and verbal communication abilities
• High discretion and professionalism
• Ability to manage multiple priorities in a fast-paced environment
• Proficiency with Google Workspace and project management tools

Ideal Candidate

You are someone who:

• anticipates needs before they arise
• thrives in entrepreneurial environments
• enjoys solving complex organizational challenges
• communicates clearly and professionally
• takes pride in keeping leaders and organizations running at their best

Location

Chicago, IL (hybrid schedule with in-person coordination required)

Compensation

Competitive salary based on experience.

How to Apply

Submit your resume and a brief note explaining why this role interests you.