Advertising Sales Specialist- Retention

PlayOn! Sports is looking for actively looking to add an Advertising Sales Specialist- Retention to our growing division. We are focused on our vision of becoming the go-to digital platform for high school sports. Your contributions will be made by fostering trusted relationships with our business sponsors of local high schools across the country.

THE OUTCOMES WE EXPECT:

• Renewing customers at 65% rate.

• Exceptional relationship building skills.

• Maintaining connection and providing proof of performance to align with the sponsor’s goals.

• Steering the full post-sales lifecycle through renewal.

• Providing key feedback in improving operational processes and efficiency to optimize reach outs and overall retention rate

THE TALENTS YOU BRING:

• 3 years of experience working in a sales-specific position (account management, recruiting, sales or (equivalent position or combination of education and experience)

• Ability to communicate effectively over the phone

• Positive attitude and drive to win

• Demonstrated sales ability

• Willingness to fail and motivated to learn from your shortcomings

• Tenacity and ability to overcome objections and rejections

• Highly organized

• Self-starter, with an entrepreneurial spirit

• Salesforce, or similar CRM, experience a plus

• 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.

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 VidSwap—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.