Executive Assistant

Play On is looking for a highly organized, proactive, and trusted Executive Assistant to support several of our C‑Suite executives. This role will play a critical part in stewarding the 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 ideal candidate brings sound judgment, exceptional discretion, and the ability to navigate a fast‑paced, high‑growth environment with confidence and professionalism.

• 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, ensuring our executives consistently show up informed and impactful
• Smooth coordination across the C‑Suite, senior leaders, and key external partners, and a heightened sense of alignment throughout the organization
• A trusted partnership built on anticipation, discretion, and sound judgment
• A professional brand suited to the executive suite that you’re managing

• Own and manage complex calendars across multiple time zones, balancing strategic priorities, internal leadership needs, and external commitments
• Protect and actively promote the executive brand both inside the organization and with external stakeholders by helping them show up prepared and by communicating reschedules or reprioritizations in a way where the receivers still feel valued and important
• Act as a steward of executive time and attention by evaluating needs and protecting space for strategic work and high priorities
• Proactively prepare leaders for meetings, including agendas, background materials, talking points, and follow‑ups to ensure that meeting time is spent wisely with high impact
• 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, ensuring timely follow‑through and accountability
• Anticipate challenges, flag risks, and solve problems before they escalte
• Handle sensitive and confidential information with the highest degree of discretion and professionalism
• Support special projects and strategic initiatives as needed, adapting quickly to shifting priorities

• 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, with a natural ability to be detail‑oriented and able to manage competing priorities with ease
• Proactive bias toward action and anticipates needs rather than waiting for direction
• Comfortability working in ambiguous situations
• Excellent strategic communication skills with the ability to balance candor with empathy
• High comfort level asking clarifying questions and protecting executive focus
• Passion for operating in an environment where priorities evolve and no two days look the same
• A service‑oriented mindset while operating as a true business partner

• Ownership over Participation- You take responsibility for achieving holistic outcomes, prioritize key objectives, and adapt quickly when situations require a different approach. You follow through even against the toughest challenges.
• Team over Stars- You are a bridge builder, establishing processes and relationships with teams outside your own. You work to rally around common goals, find win‑win solutions, compromise when necessary, and help others succeed.
• Growth over…