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
Skills Required
- Minimum 5 years' experience providing Executive Assistant support in a fast-paced, growth-stage organization supporting C-Suite
- Demonstrated exceptional judgment, discretion, and emotional intelligence
- Strong organizational skills with attention to detail and ability to manage competing priorities
- Proactive anticipation of executive needs and bias toward action
- Comfort working in ambiguous situations and adapting to shifting priorities
- Excellent strategic communication skills, balancing candor with empathy
- High comfort level asking clarifying questions and protecting executive focus
- Ability to handle sensitive and confidential information with discretion
- Experience coordinating complex calendars, travel, offsites, board activities, and events
- Service-oriented mindset and ability to operate as a business partner
PlayOn Sports Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about PlayOn Sports and has not been reviewed or approved by PlayOn Sports.
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Leave & Time Off Breadth — Open/unlimited PTO, paid holidays, and sick time are prominently offered. Feedback suggests the PTO experience and time-away flexibility are strong.
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Retirement Support — A 401(k) with company match is a standard part of the package. Feedback suggests the retirement program is viewed positively.
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Healthcare Strength — Multiple medical plan options plus dental, vision, life, disability, and mental health support are included. Feedback suggests core health coverage is solid for full‑time employees.
PlayOn Sports Insights
What We Do
PlayOn is the all-in-one fan engagement platform for schools. Backed by KKR, our family of brands—including GoFan, NFHS Network, and MaxPreps—empowers schools with innovative solutions and exceptional service. We save administrators time so they can focus on what truly matters: supporting the students, staff, and fans who bring their programs to life. Trusted by thousands of schools across the country, we're here to help create more instant replays, hold-your-breath moments, last-minute comebacks, and games you want to watch over and over again.
Why Work With Us
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.
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