Executive Assistant

PlayOn 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.

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, 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

In this role, you can expect to

• 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 escalate

• 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

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, 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

**How You Play **

• 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 Comfort- You are driven by a desire to grow and actively seek opportunities to expand your comfort zone, skills, and confidence. You embrace new challenges with curiosity, accepting discomfort and failure as opportunities to learn.

• Fairness over Popularity- You approach decisions with a scientist’s mindset, challenging your assumptions and remaining objective. You consider long-term impact rather than relying on short-term gains, proactively seek others’ perspectives, and manage emotions in decision-making.

PlayOn is where high school sports come to life. Through GoFan, NFHS Network, and MaxPreps, we give every fan a front-row seat to the moments that matter most: the buzzer-beaters, the comeback wins, the senior nights, the rivalries that define a town.

We built our technology for the people who live and breathe high school athletics — the parents who never miss a game, the alumni still cheering from across the country, the communities that show up week after week. From buying tickets to watching a live stream to reliving the highlights, we make it simple to stay close to the sports and the athletes you love most.

Backed by KKR, we build the technology that powers high school athletics from the inside out: Schools trust us to handle ticketing, streaming, fundraising, concessions, merchandise, and more so the people running programs can stay focused on the athletes and fans we all serve together.

We're a growth-stage company on a mission to make high school sports more accessible, more memorable, and more connected than ever before.

When being there means everything, we make sure you never miss a moment.

Why You'll Love Working at PlayOn

Product, potential, and people. We’re a leader in the high school event space, constantly evolving our product to meet the needs of administrators. We focus on solving real challenges, learning quickly, and creating impactful solutions.

This is a growth-stage company, meaning your contributions have real impact. You’ll have opportunities to grow your skills, tackle meaningful problems, and make a difference in the lives of schools and the students and fans they serve.

Our culture is built on accountability, collaboration, growth, and fairness. We don’t just show up—we show up for each other. Everyone wears the same jersey, and we play hard, make the extra pass, and cheer one another on. Losses teach us, challenges motivate us, and persistence drives us forward. We value integrity over shortcuts, choosing to do what’s right even when it’s hard. Together, we strive to be better every day—because we know that’s how we win as a team.

**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. _