Executive Assistant – Commercial Insurance

Our organization is a dynamic, client-focused insurance agency specializing in commercial property and casualty insurance solutions. Since 2005, we have been dedicated to crafting customized insurance portfolios that protect businesses across a wide range of industries nationwide. With a team of 40 professionals operating between our Skokie and Lakewood offices, we maintain a collaborative, high‑energy culture built on transparency, accountability, and a commitment to delivering exceptional service.

• Provide high‑level administrative support to the owner by managing calendars, scheduling meetings, organizing priorities, and ensuring that each day runs efficiently.
• Serve as a key point of communication for both internal team members and external contacts, handling emails, phone calls, and correspondence with discretion, judgment, and a professional tone.
• Monitor workflow, deadlines, and ongoing projects, helping the owner stay organized while ensuring follow‑up and completion of tasks and commitments.
• Prepare and refine reports, presentations, internal documents, and other materials for meetings, client interactions, and various business initiatives.
• Coordinate and support meetings from start to finish, including planning agendas, capturing detailed notes, and following up to ensure that action items are completed.
• Assist with day‑to‑day operational support, which may include running errands, coordinating appointments, supporting personal scheduling needs, and stepping in to resolve logistical challenges as they arise.
• Work closely with the broader Skokie office team to help streamline processes, support collaborative workflows, and enhance organizational efficiency.
• Take ownership of special assignments and research tasks, applying creativity, resourcefulness, and independent problem‑solving to deliver strong outcomes.
• Maintain strict confidentiality and handle sensitive information with professionalism and maturity.

• Bachelor’s degree or equivalent experience in business administration, office management, or a related field.
• 3–5 years of experience as an executive assistant or in a similar role supporting a senior leader, preferably in a fast‑paced or entrepreneurial environment.
• Exceptional organizational and time‑management skills, with the ability to manage shifting priorities and multiple demands simultaneously.
• Strong communication skills—both written and verbal—with the confidence to ask questions, clarify expectations, and provide thoughtful input when needed.
• A hands‑on, solutions‑oriented mindset, with a willingness to handle tasks ranging from strategic preparation to everyday logistical support.
• Ability to stay grounded, composed, and focused even when the workload or pace intensifies.
• Proficiency with Microsoft Office Suite and Google Workspace, and comfort learning new tools as needed.
• Experience in commercial insurance is helpful, though not required.
• A positive approach to work, a strong sense of ownership, and a genuine desire to contribute to a close‑knit, high‑performance team.

• Salary: $80,000–$90,000 annually, based on experience.
• Benefits:
  Full package including health, dental, and vision insurance, plus 401(k).
• Perks:
  Access to an on‑site gym and fully stocked kitchens.
• Work Environment: A supportive, tight‑knit culture where initiative is recognized and contributions make a visible impact.

Wealthy Group of Companies LLC