Executive Assistant

PlayOn is looking for a highly organized, proactive, and trusted Executive Assistant to support several C-Suite executives. This role will steward executives’ time, priorities, and attention by ensuring they are well-prepared, well-positioned, and focused on the work that matters most. Partnering closely with the Executive Assistant to the CEO, this Executive Assistant will manage complex schedules, manage travel, coordinate communications, and anticipate needs, while operating cross-functionally with senior leaders and external stakeholders.

The Outcomes You’ll Deliver

• Executives whose time and attention are aligned to the company’s highest priorities
• Clear, well-managed calendars, meetings, and communications that enable effective decision-making
• Strong preparation and follow-through for internal and external meetings
• Smooth coordination across the C-Suite, senior leaders, and key external partners
• A trusted partnership built on anticipation, discretion, and sound judgment
• A professional brand suited to the executive suite that you’re managing

In this role, you can expect to

• Own and manage complex calendars across multiple time zones
• Protect and promote the executive brand internally and externally
• Act as a steward of executive time and attention
• Proactively prepare leaders for meetings, including agendas, background materials, talking points, and follow-ups
• Coordinate events with internal and external stakeholders
• Coordinate logistics for meetings, offsites, board-related activities, and travel
• Serve as a key point of contact between executives, senior leaders, board members, and external stakeholders
• Track action items, commitments, travel arrangements, and expense reports
• Anticipate challenges, flag risks, and solve problems before they escalate
• Handle sensitive and confidential information with the highest degree of discretion and professionalism
• Support special projects and strategic initiatives as needed

To thrive in this role, you have

• Demonstrated experience displaying exceptional judgment, discretion, and emotional intelligence
• Minimum 5 years’ experience providing Executive Assistant support in a fast-paced, growth-stage organization with direct experience supporting the C-Suite and interacting with other executives
• Strong organizational skills and ability to manage competing priorities
• Proactive approach and ability to anticipate needs
• Comfort working in ambiguous situations
• Excellent strategic communication skills
• Ability to ask clarifying questions and protect executive focus
• Passion for operating in an environment where priorities evolve
• Service-oriented mindset while operating as a true business partner

The Benefits We Offer

• Multiple medical insurance plans to choose from
• Dental, vision, life and disability insurance
• Employee Emergency Fund
• Company equity (stock options)
• Open PTO policy
• 401K plan with company match
• Hybrid/flexible work environment

Note: Must be a full-time employee to participate in the company’s employee health benefit plan. Part-time employees and interns are not eligible to participate.