PlayOn Sports is seeking an experienced Head of Corporate Development to lead the company's inorganic growth strategy and execute high-impact strategic transactions. Reporting to the CFO, this is a senior individual contributor role that owns PlayOn's corporate development function and partners closely with the CEO, President of Strategic Growth, and executive leadership team to identify, evaluate, negotiate, and execute acquisitions that accelerate the company's long-term growth strategy.

The Head of Corporate Development will serve as the company's M&A leader, helping shape acquisition strategy while leading every stage of the transaction lifecycle—from developing investment theses and evaluating strategic and financial fit to negotiating transaction terms, managing cross-functional diligence, partnering with legal counsel and external advisors, and driving transactions through successful closing. This role will also provide thoughtful guidance on capital allocation, valuation, deal structure, affordability, and the financial and strategic tradeoffs associated with potential acquisitions.

The ideal candidate is an exceptional M&A practitioner with deep expertise in corporate finance, valuation, transaction execution, and strategic analysis. They possess outstanding business judgment, the ability to synthesize complex opportunities into clear recommendations for executive leadership, and the credibility to engage effectively with founders, advisors, investors, shareholders, and members of the Board. This is a highly visible role with significant executive exposure, requiring a collaborative leader who can influence decisions across the organization while independently driving complex, cross-functional initiatives.

In this Role, You Can Expect to Drive:

Corporate Development and Strategy

Partner with the CEO, CFO, and President of Growth Strategy to develop and execute PlayOn's inorganic growth strategy.
Build and maintain a pipeline of acquisition opportunities aligned with the company's strategic priorities.
Develop investment theses and strategic rationales for acquisitions, partnerships, and other strategic opportunities.
Evaluate market trends, competitive dynamics, and emerging technologies to identify opportunities that strengthen PlayOn's market position.
Advise executive leadership on capital allocation decisions and the role of M&A in creating long-term shareholder value.

M&A Execution

Lead end-to-end execution of acquisitions from initial evaluation through signing and closing.
Develop valuation analyses, financial models, synergy assessments, and investment recommendations.
Structure and negotiate letters of intent, term sheets, purchase agreements, and other transaction documents.
Lead cross-functional due diligence across finance, legal, product, technology, commercial, HR, tax, accounting, and operations.
Manage outside legal counsel, financial advisors, accounting firms, and other transaction partners.
Drive transaction timelines, coordinate internal stakeholders, and ensure successful execution through closing.

Financial Analysis and Decision Support

Evaluate target company business models, financial performance, growth drivers, unit economics, and key risks.
Build sophisticated financial analyses, including valuation, scenario modeling, accretion/dilution, and return analyses.
Assess strategic and financial synergies, integration considerations, and long-term value creation opportunities.
Prepare investment recommendations and executive materials for the CEO, Board of Directors, and shareholders.

Executive Partnership

Serve as a trusted advisor to the CEO, CFO, and executive leadership team on acquisition strategy and strategic investments.
Build trusted relationships with founders and executive teams of acquisition targets.
Support communications with the Board, investors, lenders, and shareholders regarding strategic transactions.
Partner closely with Finance, Legal, Product, Strategy, and Business leaders throughout the transaction lifecycle.

To thrive in this role, you have:

Required Experience

8–10+ years of experience in corporate development, mergers and acquisitions, investment banking, private equity, or a combination thereof, with substantial experience leading complex M&A transactions.
Corporate development experience in the consumer technology sector with a successful acquisition track record strongly preferred.
Demonstrated experience independently leading acquisitions from strategy and valuation through negotiation, diligence, signing, and closing.
Deep understanding of transaction structuring, valuation methodologies, deal mechanics, accounting considerations, and corporate finance.
Experience managing outside legal counsel, financial advisors, and cross-functional diligence teams.
Experience preparing and presenting recommendations to executive leadership, Boards of Directors, investors, and shareholders.

Skills and Capabilities

Exceptional financial modeling, valuation, and analytical skills.
Strong strategic thinking with the ability to connect acquisitions to long-term business objectives.
Outstanding negotiation and influencing skills, with the judgment to balance strategic opportunity, financial discipline, and execution risk.
Excellent executive communication and presentation skills.
Ability to lead complex cross-functional initiatives while influencing without direct authority.
High degree of ownership, intellectual curiosity, sound judgment, and attention to detail.

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

PlayOn! Sports

Head of Corporate Development

About the Job

Requirements

Responsibilities

Desired Qualifications