VP, Cloud Operations

We are seeking a strategic, hands-on VP of Cloud Operations to unify and lead our Cloud Engineering, Site Reliability Engineering (SRE), and DevOps disciplines under a single, cohesive organization. This is a newly consolidated leadership role for an infrastructure executive who cares deeply about building resilient, cost-efficient, cloud-native systems that keep PlayOn’s platforms fast, available, and ready to scale.

Reporting to the CTO, the VP of Cloud Operations will partner closely with Software Engineering, Security, Product, and Data leadership to modernize how PlayOn builds, deploys, and operates its cloud footprint. You’ll play a critical role in supporting a multi-product platform (NFHS Network, GoFan, MaxPreps, PlayOn HQ) that streams over 600K+ live events and processes 700K+ ticketing events annually, all running cloud-native on AWS.

The outcomes you’ll deliver

• Unified Infrastructure Organization - Consolidate Cloud Engineering, SRE, and DevOps into one coherent discipline with clear charters, on-call ownership, and career paths, eliminating duplicated tooling and conflicting standards.

• Platform Reliability at Scale - Own availability and performance for PlayOn’s live-streaming and ticketing platforms, especially during peak concurrent load (Friday night football, championship weekends), with clearly defined SLOs, SLIs, and error budgets.

• Cost-Efficient Cloud Architecture - Build and run a FinOps practice that gives engineering and finance leadership real visibility into AWS spend, with measurable cost-per-stream and cost-per-event efficiency gains.

• Modern Platform Engineering - Deliver a self-service internal developer platform built on Infrastructure as Code (Terraform) and Kubernetes, so product engineering teams can ship and scale without infrastructure as a bottleneck.

• Operational Excellence - Mature incident management, on-call, and postmortem practices to reduce mean time to detect and resolve (MTTD/MTTR) and cut the frequency of customer-impacting incidents.

• Security & Compliance Partnership - Partner with the security organization to harden PlayOn’s cloud posture and keep infrastructure controls aligned with SOC 2 Type II and PCI DSS requirements.

In This Role, You Can Expect To

• Serve as a core member of the technology leadership team, translating business goals into a unified cloud infrastructure and reliability strategy

• Stand up a single Cloud Infrastructure organization out of today’s separate Cloud Engineering, SRE, and DevOps functions, defining team structure, on-call rotations, and escalation paths

• Own cloud architecture strategy across PlayOn’s AWS accounts and regions, ensuring the platform scales cleanly for NFHS Network, GoFan, MaxPreps, and PlayOn HQ

• Define, instrument, and track SLOs, SLIs, and error budgets for critical services, and own the incident command process for major incidents

• Drive adoption of Infrastructure as Code (Terraform) and a self-service internal developer platform that gives product engineering teams golden paths for provisioning and deployment

• Own CI/CD strategy and deployment standards in partnership with Software Engineering leadership, improving deployment frequency and change failure rate

• Lead a FinOps program covering cost visibility, showback/chargeback, reserved capacity planning, and budget forecasting across the AWS footprint

• Own the observability stack (New Relic, CloudWatch, and related tooling), driving a shift from reactive firefighting to proactive monitoring and alerting

• Own capacity planning for major sporting event surges — playoffs, championships, and other high-traffic moments — ensuring zero-downtime scaling

• Recruit, mentor, and lead a team of cloud engineering, SRE, and DevOps managers and senior engineers, building a strong culture of ownership and operational rigor

• Define and monitor KPIs for infrastructure performance (e.g., uptime, deployment frequency, MTTR, cloud cost efficiency), reporting regularly to the CTO and executive team

• Partner with Security, Product, and Data Engineering leadership to balance velocity, reliability, and cost across every major platform decision

To Thrive In This Role, You Have

• 10+ years of infrastructure, platform, or site reliability engineering experience, including 5+ years in senior leadership managing managers

• A proven track record leading the consolidation or scaling of Cloud Engineering, SRE, and DevOps functions into a single, high-performing organization

• Deep, hands-on expertise running production workloads on AWS at scale across multiple accounts and regions

• Strong experience owning SLOs, error budgets, incident management, and on-call programs for high-traffic, real-time systems (live video or streaming infrastructure a strong plus)

• Expertise with Infrastructure as Code (Terraform), containerization and orchestration (Kubernetes, ECS), and modern CI/CD tooling

• Demonstrated success building or running a FinOps practice with measurable cloud cost optimization results

• Experience with observability and monitoring platforms (New Relic, CloudWatch, Datadog, or similar) and modern logging and alerting pipelines

• Solid understanding of cloud security fundamentals, IAM, network segmentation, and compliance frameworks such as SOC 2 and PCI DSS

• Excellent executive communication skills, with experience presenting infrastructure strategy, risk, and investment tradeoffs to the CTO and executive team

• Demonstrated ability to scale infrastructure teams in a high-growth, fast-paced, consumer platform environment

• Strong business acumen, with experience owning budgets, vendor negotiations, and staffing and workforce planning

• Education: BS in Computer Science or a related field. 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.

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