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Executive Assistant, Chicago, IL (Hybrid)

Executive Assistant, Chicago, IL (Hybrid)

We are seeking a highly organized, proactive Executive Assistant to support senior executives in a dynamic, fast-paced environment. This role is ideal for a proactive administrative professional who thrives in an entrepreneurial, hands-on setting, enjoys wearing many hats, and brings strong attention to detail, sound judgment, and a natural sense of ownership.

In addition to providing high-touch executive support, this position offers meaningful exposure to HR-related responsibilities and the opportunity to grow alongside an evolving HR function.

Responsibilities

  • Provide comprehensive administrative support to senior executives, including complex, high-volume calendar management, meeting coordination, and preparation of executive-level materials.
  • Anticipate needs and shifting priorities, proactively identifying and resolving issues before they escalate.
  • Track invoices and expenses, ensuring accuracy, timeliness, and alignment with internal processes.
  • Capture detailed meeting notes, manage follow-up on action items, and help drive initiatives forward.
  • Serve as a trusted partner to executive leadership, supporting organization, focus, and effective decision-making.
  • Assist with benefits administration, including enrollment, premium tracking, and coordination with external carriers.
  • Support year-end HR processes and ongoing people-related administrative needs.
  • Act as a primary point of contact for vendors and service providers, independently resolving routine issues.
  • Provide hands-on operational and administrative support within a lean, collaborative office environment.
  • Serve as an informal leader among the administrative team, helping coordinate meetings and ensure alignment across functions.
  • Partner closely with the administrative manager while taking ownership of day-to-day execution.
  • Contribute to the development of scalable administrative and HR processes as the organization continues to grow.

Ideal Experience

  • Bachelor’s degree required.
  • 3–7 years of relevant experience, ideally in an executive assistant or senior administrative role, supporting leadership.
  • Prior exposure to HR functions (benefits, vendors, onboarding, or related areas) is ideal.
  • Exceptional attention to detail and organizational skills.
  • Confident, inquisitive, and eager to learn; comfortable asking questions and taking initiative.
  • Strong problem-solving skills with the ability to work independently and think ahead.
  • Experience working in a small or lean office environment, balancing multiple responsibilities.
  • Professional presence with excellent written and verbal communication skills.

#117952

Up to $100,000 salary per year (based on experience)

Apply Online.