Synergy Interactive is hiring: Executive Assistant in Chicago

Role Overview

We are seeking a highly reliable, discreet, and polished Executive Assistant to support the Director of Strategy & Investments. This role is critical to the smooth execution of investor-related operations and day-to-day strategic support.

You will act as a trusted extension of the Director—handling scheduling, coordination, and follow-through for high-value investor interactions while serving as on-the-ground support in the Chicago office when leadership is remote.

This is an execution-focused role with exposure to senior leaders and investors. While prior investor relations experience is not required, professionalism, judgment, and confidentiality are essential.

Key Responsibilities

• Provide direct day-to-day support to the Director of Strategy & Investments
• Manage calendars and scheduling, including coordination for 1–2 external investors who may require assistance
• Coordinate investor meetings and calls, including agendas, materials, and follow-ups
• Serve as a professional point of contact for external stakeholders, maintaining discretion at all times
• Triage communications, assess priority, and ensure timely responses and follow-through
• Prepare and organize materials for meetings (presentations, briefs, reference documents)
• Track action items, requests, and next steps tied to investor conversations
• Maintain organized records of meetings, communications, and documentation
• Anticipate scheduling or logistical issues and proactively resolve them
• Act as the “eyes and support” in the Chicago office while the executive is based in Los Angeles

Experience & Qualifications

• Approximately 4–6 years of experience in an executive assistant, operations, or administrative support role
• Comfortable supporting senior leaders and interacting with external, client-facing stakeholders
• Strong organizational and time-management skills
• Excellent written and verbal communication
• High level of discretion and trustworthiness with sensitive information
• Proficiency with standard business tools (calendar systems, email, Microsoft Office / Google Workspace)
• Willingness to learn and grow into the role; learning on the job is expected

Nice-to-Have (Not Required)

• Exposure to investor relations, finance, or venture-backed environments
• Notary certification
• Valid passport