Advertising Sales Specialist

PlayOn is looking for an Advertising Sales Specialist to connect local businesses to our schools through sponsorship opportunities on our digital tickets and school athletic websites. As an Advertising Sales Specialist you will be responsible for owning the entire sales process for your territory from prospecting to close.   

In this role, you will bring your sales experience to find and connect small businesses within communities across the country with their local high schools. 

The Outcomes You’ll Deliver 

Source multiple opportunities per week in efforts to sign new business quarterly. 

• Strategically Prospect: Actively source and identify high-potential leads within your assigned territory through multiple channels, including UpLead, Google, LinkedIn, Facebook, and industry-specific directories. 

• Drive Daily Activity: Making outbound cold calls each day to new prospects while also maintaining ongoing engagement with warm leads and existing accounts. 

• Own the Full Sales Cycle: Manage the entire sales process from initial outreach, discovery, product demonstration, proposal, negotiation, and closing. You’ll be accountable for hitting your monthly and quarterly targets. 

• Maintain Accurate Records: Keep CRM data up to date, document all interactions, and maintain pipeline hygiene to support accurate forecasting and reporting. 

• Collaborate and Share Insights: Provide feedback to internal teams on what's resonating in the market, challenges you're encountering, and opportunities to improve product positioning and sales enablement. 

• Sales Experience: 2+ years of experience in a sales-focused role such as account management, recruiting, or business development—or an equivalent combination of education and professional experience. 

• Strong Communication Skills: You can clearly articulate value propositions, tailor messaging to specific personas, and confidently handle objections during calls and presentations. 

• Creative Prospecting Ability: You’re resourceful and proactive in finding new ways to identify and engage with potential customers—whether through unconventional outreach or tools like email automation and social selling. 

• Self-Starter Mindset: You take ownership of your pipeline and performance, show initiative in tackling challenges, and thrive in a fast-paced, results-driven environment. 

• Coachability & Growth Orientation: You welcome feedback, continuously seek improvement, and are excited to grow your skills and career within the company. 

Company Overview 

PlayOn is a dynamic growth-stage company dedicated to championing the spirit of play in the high school space. Backed by KKR, our family of brands—including GoFan, NFHS Network, and MaxPreps—empowers schools with innovative solutions and exceptional service. Our fan engagement platform is the only one that offers event ticketing, streaming, fundraising, concessions, merchandise sales, and website management in one place. 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. 

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.