Executive Assistant to the CEO

Location: Initially 100% remote, but will become hybrid. Candidates should live in the Chicago metro area.

Position: Full time.

Department: Operations

Salary: $75,000 to $100,000 per year, depending on experience


Authentic’s team is growing! We’re looking for kind, smart, and creative individuals to join our diverse, progressive media agency.

At Authentic, we run ethical digital marketing programs for Democratic campaigns and non-profit advocacy organizations. We’re a values-driven company dedicated to building a safe and collaborative working environment for our employees.

As Executive Assistant to the CEO, you’ll report directly to the CEO and Founder of Authentic – helping to manage his schedule and correspondence as well as handling special projects and administrative responsibilities as part of the Operations team. The ideal candidate has impeccable written and oral communication skills, strong time management and organizational experience, and can adapt well to changing priorities.


  • Calendar Management – Manage the CEO’s calendar, schedule meetings, handle appointments, plan travel and lodging, and ensure the CEO’s time is managed effectively and is in alignment with company-wide priorities as directed.
  • Daily Briefings – Provide regular updates on completed tasks, deadlines, key priorities, and changes to the schedule.
  • Correspondence Support – Serve as the primary point of contact for internal and external constituencies. Shadow the CEO on calls to take comprehensive meeting notes and capture and disseminate action items. Provide support for screening/responding to calls, emails, and Slack messages as needed. Develop a system to help the CEO maintain relationships and deliver correspondence regularly for connections that have birthdays, anniversaries, big life moments, and more.
  • Partnership Management – Maintain relationships with agency clients, stakeholders, and sales targets. Help manage the company’s sales pipeline including the development of proposals and other marketing materials, including social media postings. Handle research ahead of pitch meetings. Coordinate attending events to help the CEO strengthen existing relationships or develop new ones in order to expand our business and partnership opportunities.
  • General Administration – Assist with organizing OneDrive and Google Drive files and other project management needs, manage personal contacts, light cleaning (should we reopen a Chicago office), send documents, handle receipts, and other administrative or operational tasks as needed.
  • Special Projects – Take on additional special projects on behalf of the firm as needed by working with the leadership and operations teams.
  • Personal Support – Provide assistance to the CEO for personal matters from time to time, so he can focus on leading and growing the company.


  • Three years of relevant work experience providing C-Suite executive support;
  • Strong project management skills with a demonstrated ability to manage multiple projects and prioritizing tasks;
  • Exceptional time management, planning and organization skills;
  • Experience working in fast paced, ambiguous environments;
  • Excellent interpersonal and communication skills;
  • Proficient in Zoom, Slack, Asana, Google Suite, Word, Excel and social media applications such as Twitter and LinkedIn;
  • Able to perform duties with a high level of confidentiality and discretion while exhibiting integrity and trustworthiness with sensitive information;
  • Ability to anticipate needs, identify issues impeding success, and propose creative, viable solutions;
  • Experience working in a small or startup company environment
  • Agency experience highly preferred


  • 100% employer-paid health care, vision, and dental
  • 100% employer-paid life and disability insurance and
  • 401(k) with up to 5% employer contribution, fully vested on day one
  • Flexible vacation and sick leave
  • Flexible telecommute and remote work policies
  • Monthly phone reimbursement
  • Wellness benefits
  • Mental health benefits
  • Commuter benefits
  • Home office stipend or local hot desk
  • Up to $5,000/year for gender-affirming surgeries and related treatment

Additional Information:

  • Work environment: This role routinely uses standard office equipment such as computers and phones,.
  • Physical Demands: This is a largely sedentary role. The ability to look at screens for extended periods of time is required.