Executive Assistant to the CEO

Proactifi
Chicago, IL

About Bellagent

We are a Chicago based AI startup on a mission to make advanced artificial intelligence truly accessible to everyday business operators especially those without engineering teams or large budgets. After a year of rapid growth we’ve gone heads down in R&D to build a groundbreaking new product now preparing for public launch. Headquartered in the heart of Fulton Market, we’re building a team of exceptional people who want to shape the future of AI from the ground up. We offer competitive compensation equity packages above market for our stage and the opportunity to join a high energy collaborative environment where your work directly impacts the trajectory of the company. If you’re excited about joining a fast moving startup tackling big challenges and creating something transformative we’d love to talk. About the Role

We are looking for an Executive Assistant to the CEO who will serve as a true extension of the founder. This is not a traditional administrative role it is an opportunity to be embedded in the heart of every important decision and to help drive the operational backbone of a high growth startup. You will keep the CEO organized and accountable own task management across productivity platforms and work cross functionally with product sales marketing and investors. The ideal candidate is highly operationally strong, thrives in a fast moving environment and is excited to wear many hats. This role can be structured as either a full-time hire or a three-month contract to hire with a start date as soon as possible. Preference for candidates based in Chicago to join us in our Fulton Market HQ. What You’ll Do

Organization & Productivity • Manage calendars priorities and workflows to maximize CEO effectiveness. • Implement and manage productivity tools such as Jira ClickUp and others to track tasks and projects. • Ensure deadlines and follow ups are clearly owned and executed across teams. Cross Functional Collaboration • Act as a connective tissue between CEO and other departments ensuring clear communication and alignment. • Support preparation for key meetings investor conversations and strategic planning sessions. • Document and track action items ensuring accountability across stakeholders. Operational Support • Help streamline internal processes and identify opportunities to improve efficiency. • Support special projects and company wide initiatives from strategy through execution. • Provide research synthesis and insights to inform CEO decision making. Strategic Exposure • Be behind the scenes of every important conversation and decision. • Gain hands on experience in startup leadership operations and cross functional execution. • Grow alongside the company with opportunities to expand scope and responsibility.

Requirements

Experience

• 2–5 years of professional experience, ideally in a fast-paced environment.

• Background in operations, project management, or executive support is a plus but not required.

Skills

• Highly organized with strong attention to detail.

• Clear and effective communication skills.

• Proven ability to manage multiple priorities simultaneously.

Mindset

• Startup scrappiness with a proactive, “get things done” approach.

• Comfortable wearing many hats and adapting quickly as priorities shift.

Tools

• Familiarity with productivity and project management platforms (e.g., Jira, ClickUp, Notion, or similar).

Bonus Points

• Prior experience in a startup or high-growth company.

• Comfort working closely with executives and leadership teams.

• Strong interest in technology and AI.

Benefits

Why Join Us • Work directly with the CEO on strategy execution and company building. • Competitive compensation with above market equity opportunities. • Flexible arrangement full time hire or three month contract to hire. • Brand new office in Chicago’s Fulton Market collaborative high energy environment. • Accelerate your career with unmatched exposure to the inner workings of a high growth AI startup.

Posted 2025-09-10

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