Administrative Assistant

• Location: Libertyville, IL
• Type: Direct Hire
• Job #2851

EXECUTIVE ASSISTANT
Libertyville, IL  ·  On-Site  ·  Full-Time  ·  $50,000/year + Full Benefits

We are a growing staffing and recruiting firm with an office in Libertyville, IL, and we are looking for a sharp, self-directed Executive Assistant who doesn't wait to be told what to do, they figure it out.
This is not a task-taker role. The right candidate will observe, learn, and proactively pull work off the owner's plate before being asked. If you need a checklist handed to you every morning, this position isn't a fit. If you thrive on reading a room, connecting dots, and making your executive's day run smoother before problems surface, keep reading.
Ideal candidates will be located in northern Cook County or southern Lake County, IL, and comfortable commuting to our Libertyville office daily.

In this role, success is measured not by completing assigned tasks, but by how rarely the owner has to assign them. The best candidate will:

• Anticipate needs before they're voiced, noticing a meeting needs prep, a deadline is approaching, or a vendor hasn't responded
• Actively pull tasks from the owner's plate by learning their priorities, communication style, and business rhythms
• Serve as a trusted filter — managing what reaches the owner's attention and when
• Run the day-to-day without hand-holding, using good judgment to make decisions independently within agreed boundaries
• Make the owner meaningfully more productive — research shows an effective EA can increase executive output by 8% or more

Calendar & Schedule Management

• Own the owner's calendar end-to-end — scheduling, rescheduling, and proactively flagging conflicts before they become problems
• Prioritize and protect time for high-value activities; push back on requests that don't warrant the owner's personal attention
• Prepare daily briefings so the owner walks into every day fully oriented

Communications & Correspondence

• Monitor and triage email — draft responses, flag urgent items, and handle routine correspondence independently
• Serve as a first point of contact with clients, candidates, vendors, and partners — representing the firm with professionalism and discretion
• Follow up on outstanding items so nothing falls through the cracks

Project & Task Tracking

• Track open projects, pending decisions, and outstanding commitments — keeping the owner updated without being asked
• Research vendors, tools, and solutions and deliver a recommendation, not just raw data
• Coordinate across internal staff and external partners to move initiatives forward

Office & Vendor Management

• Manage relationships with vendors, service providers, and office suppliers — negotiating, ordering, and resolving issues without escalating unnecessarily
• Maintain an organized, efficient office environment
• Handle confidential business information and documents with absolute discretion

Must-Haves

• Proven track record of working proactively — references must be able to speak to your ability to anticipate needs without being told
• Outstanding organizational skills with genuine attention to detail — errors are caught before they leave your desk
• Excellent written and verbal communication; you can draft a professional email and read a room equally well
• High emotional intelligence — you understand the executive's working style, stress signals, and preferences, and you adapt accordingly
• Discretion and trustworthiness — you will have access to sensitive business, financial, and personnel information
• Scrappy resourcefulness — when faced with an ambiguous or tough task, you find a way
• Proficiency with Microsoft Office Suite, Google Workspace, and modern productivity tools
• Located in northern Cook County or southern Lake County, IL; reliable daily commute to Libertyville

Nice-to-Haves

• Prior experience in staffing, recruiting, or professional services
• Familiarity with applicant tracking systems (ATS) or CRM platforms
• Experience supporting a founder or small business owner (vs. a large corporate environment)
• Background in project coordination, office management, or operations

• Base salary: $50,000 per year
• Full benefits package including medical, dental, and vision
• Paid time off and holidays
• On-site position at our Libertyville, IL office

Submit your resume along with a brief note (3–5 sentences) describing a specific time you anticipated a need or solved a problem before being asked to. Applications without this note will not be considered — it's a preview of exactly how this role works.