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.

We are seeking a highly organized, proactive, and hands-on Executive Assistant to work directly alongside our company’s owner — a driven, entrepreneurial leader with a creative approach to problem-solving and a fast-moving work style. This is a fully in-office position based in Skokie, IL and will play a central role in keeping day-to-day operations flowing smoothly. The ideal candidate is someone who thrives in a dynamic environment, is comfortable wearing multiple hats, and enjoys stepping in wherever needed — whether that means organizing priorities for the day, handling administrative work, or running an important errand to ensure deadlines and commitments are met. This is a role for someone who is sharp, adaptable, and confident enough to speak up when something needs to be clarified, while still being comfortable taking direction and supporting the owner’s vision.

Responsibilities

• 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.

Qualifications

• 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.

Compensation and Benefits

• 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.