Freelance Executive Assistant for Managing Partner & Multi-Venture Founder
Job Description
Hybrid – Chicago Western Suburbs (On-site/Remote Mix)
Supporting: Managing Partner & Multi-Venture Founder
This role offers a monthly compensation range of $2,000–$2,500, depending on experience, skillset, and availability. Additional growth opportunities and performance-based increases are available as the role expands.
We are seeking an exceptionally adaptable, intelligent, and resourceful Executive Operations & Client Experience Manager to support the Managing Partner of Hart David Carson LLP and his portfolio of entrepreneurial ventures. This role is broad, high-impact, and uniquely positioned at the center of multiple fast-moving industries.
This is not a traditional assistant role — it is part executive assistant, part project coordinator, part client intake specialist, and part operational partner. You will work across law, real estate, private equity, AI development, healthcare/wellness, and sports/entertainment ventures, ensuring that communication, follow-up, and operations run smoothly.
The right candidate thrives in dynamic environments, takes initiative without handholding, and enjoys being the connective tissue between high-level strategy and organized execution.
About the Managing Partner You Will Support
The individual you’ll support is involved in several overlapping professional arenas, including:
• Hart David Carson LLP – full-service law firm
• Maven – AI technology & enterprise SaaS development
• Defiant Health – health, wellness, and medical aesthetics
• Land development & large-scale real estate projects
• Private equity & investment strategy
• Sports, entertainment, and event ventures
• Various consulting, e-commerce, and strategic advisory projects
This role touches all of these industries.
Key Responsibilities
Professional & Operational Support
• Manage calendars, travel, scheduling, and prioritization across multiple companies.
• Prepare correspondence, presentations, summaries, and briefing materials.
• Assist in managing workflows and project follow-up across different ventures.
• Coordinate directly with clients, partners, vendors, and internal/external teams.
• Maintain impeccable confidentiality and organizational control.
Sales, Intake & Client Experience
• Handle incoming inquiries, conduct client intake calls, qualify leads, and move conversations toward scheduled consultations.
• Manage and optimize follow-up sequences (email, text, call).
• Represent the Founder with warmth, clarity, and professionalism during client interactions.
• Support sales pipelines by owning follow-up rhythms and closing loops.
Entrepreneurial & Multi-Venture Coordination
• Track deliverables, deadlines, and progress across various businesses.
• Support real estate, AI, wellness, and investment projects through research, organization, and administrative execution.
• Draft communications, updates, and follow-ups as needed.
• Assist in structuring and maintaining order within rapid-growth ventures.
Personal & Lifestyle Support
• Handle occasional personal scheduling, coordination, errands, and logistical items.
• Support professional and personal events as needed (occasional evenings/weekends).
• Seamlessly manage tasks that blend personal and business priorities.
Ideal Candidate Profile
• Highly adaptable: Comfortable switching between legal, business, and personal tasks.
• Operationally sharp: Thinks in systems, organization, and efficiency.
• Professional presence: Polished in communication and client-facing interactions.
• Sales-competent: Confident handling inbound leads and guiding intake conversations.
• Proactive: Anticipates needs and takes ownership without constant oversight.
• Tech-literate: Strong with Microsoft Office, Google Workspace, CRM tools, and workflow systems.
• Trustworthy: Handles confidential matters with absolute discretion.
• Relationship-oriented: Builds rapport easily and represents the Managing Partner well.
Qualifications
• Experience as an Executive Assistant, Operations Coordinator, Client Intake Specialist, Chief of Staff, or similar.
• Strong organizational skills and exceptional attention to detail.
• Excellent verbal and written communication.
• Experience communicating with high-value clients or executives.
• Ability to juggle multiple priorities in a fast-paced environment.
• Bachelor’s degree preferred but not required.
Compensation & Growth
• Competitive salary commensurate with experience.
• Significant opportunity for growth as the Managing Partner’s ventures expand.
• Potential to evolve into operations, business development, client management, or COO-track roles.