VP of Engineering

We are seeking a dynamic and experienced Vice President of Engineering to lead our engineering organization through the next stage of growth. This is a mission-critical role for a seasoned leader passionate about delivering modern, cloud-native software solutions and building high-performing, agile engineering teams. Reporting directly to the CTO, the VP of Engineering will work closely with cross-functional leadership to align engineering efforts with strategic business priorities and drive measurable impact across the product and technology landscape.

The Outcomes You’ll Deliver

• Accelerated Roadmap Execution: Deliver complex, high-impact product features on time and within budget, leveraging modern DevOps, CI/CD, and cloud-native principles
• Engineering Excellence: Elevate code quality, system reliability, and architecture scalability across all engineering pods.
• Talent Development: Build and retain a diverse, empowered team of engineering leaders and contributors with a strong culture of ownership, innovation, and continuous learning
• Operational Efficiency: Optimize engineering processes to ensure predictable delivery, cost control, and high team velocity
• Cross-Functional Alignment: Ensure seamless collaboration with Product, Customer Success, Sales, Marketing, and Finance to translate strategy into actionable technical roadmaps
  
  
  

In This Role, You Can Expect To

• Serve as a core member of the technology leadership team, translating business goals into scalable engineering strategies and architectural plans
• Recruit, mentor, and lead a team of engineering directors and managers, fostering a culture of high performance, accountability, and innovation.
• Define and manage engineering budgets, headcount planning, and vendor strategy aligned with organizational goals
• Own delivery milestones, ensuring high-quality software is released on schedule, with effective scope management and risk mitigation practices
• Implement best practices in agile development, DevOps, observability, and incident response to improve operational health
• Define and monitor KPIs for engineering performance (e.g., delivery predictability, system uptime, deployment frequency), reporting regularly to the CTO and executive team
• Partner with leadership peers across departments to ensure engineering priorities align with customer needs, revenue goals, and market demands.
• Research industry trends to ensure PlayOn stays on top of and leverages emerging new technologies where needed
  
  
  

To Thrive In This Role, You Have

• 12+ years overall software development industry experience
• 5+ years in senior leadership, including managing managers
• Proven track record of delivering complex, scalable, cloud-native applications (AWS experience preferred)
• Deep experience with modern software development methodologies (e.g. agile, scrum, DevOps) and tools (e.g. GitHub, Jira, Terraform, Kubernetes)
• Exceptional leadership and communication skills, with experience working cross-functionally across product, design, sales, and support teams
• Demonstrated ability to manage distributed engineering teams and drive results in a high-growth, fast-paced environment
• Experience with containerization and familiarity with a broad set of technology stacks
• Strong business acumen, with experience defining and managing budgets, staffing models, and engineering metrics
• Education: BS in Computer Science or engineering. MS preferred
  
  
  

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.
  
  
  

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.