Executive Assistant

Location:

Worcester, MA (In-Person)

Cunningham & Associates (C&A) is seeking a high-performing Executive Assistant to directly support the senior leadership team.

This is a strategic support role for an experienced professional who anticipates needs, manages competing priorities, and serves as a trusted partner to firm leadership.

The Executive Assistant will play a critical role in managing executive workflow, client communications, scheduling, and confidential matters -- enabling leadership to focus on growth, strategy, and client relationships.

We are seeking a proactive problem-solver who thrives on ownership and accountability.

• Executive Support
  • Manage complex calendar scheduling and prioritization
  • Coordinate meetings, client appointments, and internal leadership sessions
  • Prepare meeting materials, agendas, and follow-up documentation
  • Draft professional correspondence on behalf of leadership
  • Serve as gatekeeper and liaison between leadership and clients/staff
  • Anticipate scheduling conflicts and proactively resolve them
• Client & Relationship Coordination
  • Support high-level client communication and follow-ups
  • Track key client deadlines and documentation requests
  • Ensure executive-level responsiveness and professionalism
  • Assist in preparing presentations and reports for clients
• Operational & Strategic Support
  • Assist with workflow tracking and project coordination
  • Support internal reporting and performance dashboards
  • Coordinate special projects across departments
  • Help streamline executive processes and systems
• Confidential & Administrative Support
  • Handle sensitive financial and personnel information discreetly
  • Assist with invoicing and administrative accounting oversight as needed
  • Coordinate travel, events, and professional engagements
  • Support recruiting coordination and onboarding logistics

• 5+ years supporting senior executives or firm leadership
• Exceptional organizational and time-management skills
• Strong written communication and document drafting ability
• Experience managing confidential information
• High level of discretion and professionalism
• Advanced proficiency in Microsoft Office (Excel, Outlook, Word required)
• Ability to anticipate needs and operate independently
• Experience in professional services, accounting, legal, or consulting preferred

• Competitive salary (based on experience)
• 401(k) with company match
• Health, dental, and vision insurance
• Health & flexible spending accounts
• Paid time off
• Direct partnership with firm leadership
• Opportunity to contribute to strategic firm growth