Head of Corporate Development

About the role

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.

Key facts

What you'll do

Drive the end-to-end M&A pipeline by sourcing, screening, and prioritizing acquisition targets that align with PlayOn's strategic objectives and growth ambitions.

Lead the development of investment theses and due diligence frameworks, translating business strategy into clear valuation assumptions, synergies, and risk assessments for leadership review.

Own the evaluation of strategic and financial fit, working cross-functionally to assess market positioning, product complementarity, technology capabilities, and operational integration complexity.

Negotiate key transaction terms and commercial structures, collaborating with legal counsel and external advisors to draft and refine deal documentation, agreements, and closing conditions.

Partner with the Finance and Strategy teams to model transaction economics, test acquisition scenarios, and evaluate affordability, tradeoffs, and capital allocation implications.

Coordinate cross-functional diligence, aligning product, legal, finance, and operations stakeholders to validate assumptions and uncover execution risks before decision points.

Represent PlayOn in discussions with founders, advisors, investors, and boards, maintaining professionalism and credibility throughout the negotiation and closing process.

Develop and maintain relationships with external advisors, including investment banks, law firms, and consultants, to access high-quality deal flow and market intelligence.

Champion integration planning early in the evaluation process, identifying key milestones, resource requirements, and value realization pathways for completed transactions.

Provide executive-level reporting and recommendations, synthesizing complex analyses into concise insights that support timely, high-quality decision-making by the leadership team.

Champion a data-driven, hypothesis-driven approach to opportunity assessment, using quantitative models and qualitative judgment to refine deal criteria over time.

Lead the preparation of internal and external materials, including confidential memoranda, term sheets, and regulatory filings, ensuring clarity, accuracy, and alignment with governance standards.

Promote a disciplined, repeatable corporate development methodology across the deal lifecycle, from initial screening through post-close value capture and portfolio oversight.

Act as a thought partner to the executive team on broader market trends, competitive threats, and strategic inflection points that could reshape the industry landscape.

Requirements

Demonstrate a proven track record of successfully executing M&A transactions in the sports, media, technology, or adjacent sectors, with a strong grasp of valuation, due diligence, and negotiation.

Bring deep expertise in corporate finance, financial modeling, and valuation methodologies, with the ability to build and stress-test complex financial models used in acquisition decision-making.

Showcase outstanding written and verbal communication skills, with the ability to synthesize complex analyses into clear, compelling narratives for executive audiences and stakeholders.

Exhibit strong judgment and the capacity to operate independently while managing ambiguity, balancing competing priorities, and making high-impact decisions in fast-paced environments.

Possess exceptional interpersonal skills, with a track record of building trusted relationships with founders, operators, investors, board members, and external advisors in high-stakes settings.

Have a history of collaborating effectively with cross-functional leaders, including Finance, Strategy, Legal, and Operations, to align on objectives, manage risk, and drive execution.

Demonstrate a rigorous, detail-oriented approach to analysis and documentation, ensuring accuracy, transparency, and consistency across all stages of the transaction lifecycle.

Nice to have

Experience advising or working with Board-level committees on M&A matters, including interactions with Compensation, Nominating, and Audit committees.

Familiarity with governance processes and disclosure considerations relevant to public or regulated companies, even if the target operates in private markets.

Practical notes

This is a full-time position based in the United States with remote flexibility; candidates must be able to work U.S. hours and support global time zone collaboration.

No relocation assistance or visa sponsorship is provided for this role.

The engagement is full-time, and the start date is aligned with the needs of the business and the successful candidate's availability.