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Chief of Staff to CEO

Synergy Interactive
Synergy Interactive
$150k - $175k
Full-time
Chicago, IL

About the Role:

 We are seeking a highly skilled Chief of Staff to partner directly with our CEO and senior leadership team. This is a critical, high-impact role that blends strategic oversight, operational excellence, and executive support. The ideal candidate will be proactive, sharp, and exceptionally organized, with the ability to drive priorities forward in a fast-paced, entrepreneurial environment. This role requires a strong ownership mindset, dedication to long hours, and full commitment to the demands of a dynamic executive office.

Key Responsibilities:

  • Act as a strategic partner to the CEO, providing leverage across business priorities, special projects, and day-to-day operations.
  • Manage complex scheduling, calendar optimization, and travel arrangements to maximize productivity and focus.
  • Attend executive and board meetings, capture detailed notes, and translate insights into clear, actionable plans for follow-up.
  • Drive cross-functional initiatives, ensuring alignment across teams and timely execution of key deliverables.
  • Prepare reports, presentations, and other high-visibility materials for internal and external stakeholders.
  • Serve as a liaison between the CEO and the broader organization, facilitating communication and decision-making.
  • Proactively identify and resolve operational bottlenecks, anticipating the needs of the CEO and leadership team.
  • Be available on-call, including evenings and weekends, to address critical issues and support time-sensitive priorities.
  • Occasionally assist with personal or administrative tasks when necessary (approximately 10% of the role).

Qualifications:

  • 10+ years of experience in Chief of Staff, senior Executive Assistant, Project Management, or strategic operations roles, preferably in a tech startup or high-growth environment.
  • Proven track record managing complex initiatives and supporting senior executives in high-pressure settings.
  • Exceptional organizational skills, attention to detail, and ability to balance competing priorities.
  • Strong written and verbal communication skills, with experience preparing materials for executive and board-level audiences.
  • Proficiency in Microsoft Office Suite, especially PowerPoint and Excel.
  • Familiarity with technology industry operations and terminology is preferred.
  • Ability to work on-site full-time, five days a week, with flexibility for extended hours and weekends as required.
  • Must have a valid U.S. passport and be open to domestic and international travel.
  • Must own a reliable vehicle for work-related tasks.
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