VP, Revenue Strategy

PlayOn is looking for a commercially minded, process-oriented VP of Revenue Strategy to lead development and operationalization of monetization strategy for the company’s National Ad Sales division. With a focus on MaxPreps and the broader PlayOn portfolio, this leader will build the systems, workflows, pricing frameworks, and packaging discipline required to support scalable advertising revenue growth. Reporting to the SVP, National Ad Sales, the ideal candidate combines strong commercial instincts with operational rigor and has a track record of building structure, speed, and accountability across cross-functional teams. The Outcomes You’ll Deliver Monetization Infrastructure – Build the foundational systems, tools, and processes required to support a high-functioning national ad sales organization across pricing, packaging, planning, approvals, execution, and measurement. Cross-Functional Leadership – Cross-Functional Revenue Leadership - Establish strong operating rhythms and clear swim lanes across Sales, Client Strategy, Ad Ops, Research, Product, and Marketing to improve speed, quality, and accountability. Pricing, Inventory, & Planning Rigor – Develop scalable frameworks for inventory forecasting, pricing strategy, rate card governance, and media planning that balance market demand, delivery reality, and business goals. Ad Product Operationalization – Translate existing and emerging ad products across MaxPreps, GoFan, and NFHS Network into sellable, executable offerings with clear positioning, specs, workflows, and ownership. Team Building & Talent Development – Build and mentor a high-performing team responsible for planning, packaging, proposal support, and strategic partnerships.   In this role, you can expect to Own the strategic and operational infrastructure that supports monetization across MaxPreps and the broader PlayOn portfolio. Build and refine ad product packaging, rate cards, planning frameworks, and go-to-market materials that improve seller clarity and market credibility. Create repeatable processes for proposal development, pricing approvals, inventory allocation, and post-sale handoff. Partner with Sales leadership to identify revenue gaps, unlock new packaging opportunities, and improve speed to market. Work cross-functionally with Ad Ops, Client Strategy, Product, Research, and Marketing to ensure products are executable, measurable, and well-positioned. Bring structure and discipline to how the organization evaluates custom opportunities, sponsorships, non-standard programs, and margin tradeoffs. Translate audience insights, content strategy, and advertiser demand into compelling, commercially viable programs. Support the creation and implementation of client and/or company-specific measurement initiatives Develop clear operating models, roles, and responsibilities across pre-sale and post-sale teams, and support measurement strategy that improves proof of performance. Recruit, coach, and develop a high-performing team with strong standards for quality, speed, and collaboration. Evaluate custom programs, sponsorships, and non-standard opportunities through the lens of demand, delivery, and margin. Leverage AI to enhance operational efficiency and eliminate process bottlenecks To thrive in this role, you have Bachelor's Degree and 7+ years of experience in digital media, advertising, revenue strategy, sales planning, monetization, or a related commercial operations function. A demonstrated track record of building scalable pre-sale and post-sale systems in a fast-moving media, ad tech, publisher, platform, or sports media environment. Deep experience with pricing strategy, rate card development, inventory management, packaging, proposal architecture, and commercial decision-making. Proven ability to lead cross-functional initiatives, influence senior stakeholders, and build high-performing teams in evolving environments. Comfort operating in ambiguity and creating structure where none exists, with a bias for action and speed without sacrificing quality. Strong commercial instincts and the ability to balance creativity with operational feasibility and margin discipline. Excellent written and verbal communication skills, especially in translating complexity into clear sales narratives and internal processes. Interest in high school sports, community-based storytelling, and the broader sports marketplace. Strong presentation and storytelling skills, with proficiency in Pitch.com, PowerPoint, Keynote, or similar tools. Deep familiarity with the digital advertising ecosystem, including display, video, social, branded content, sponsorships, audience targeting, and measurement. Strong executive presence and the ability to earn trust with both senior leadership and frontline sellers. 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.