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Critical Sports and Entertainment

Chief Strategy Officer (CSO)

Critical Sports and Entertainment, New York, New York, us, 10261

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Chief Strategy Officer (CSO) Location: Remote (U.S.-based, preferred)

Compensation Equity-based executive role with salary to follow post-funding (active round)

Industry Sports, Entertainment, Live Events, Media, Creator Economy

About Us Critical Sports & Entertainment (CSE) is a fast-scaling, multi-division company operating across sports, entertainment, media, and live event production. Our platform combines seven management divisions with eight owned live event companies, creating a uniquely integrated ecosystem that spans athlete representation, combat sports, basketball, football, wrestling, NIL and college partnerships, music, creators, and crossover cultural content.

CSE represents more than 70 athletes and works closely with a network of over 18 former professional athletes and industry advisors. Our event portfolio includes a full combat sports promotion, an amateur team-based boxing league, two semi-professional basketball franchises, a national basketball combine, a national wrestling series alongside an in-house wrestling program, and a music and culture-focused college tour launching in 2026. With events currently drawing 800+ attendees and positioned to scale to 3,000+ attendees in 2026, CSE is entering a transformative period of expansion supported by an active raise.

The Role CSE is seeking a Chief Strategy Officer (CSO) to serve as one of the central architects of the company’s next phase of growth. As CSO, you will be responsible for defining the organization’s long‑term strategic direction, aligning the operations of multiple business units, and identifying new opportunities across sports, entertainment, technology, partnerships, and media.

You will work directly with the CEO and collaborate closely with the CMO, CRO, and division Presidents to build an integrated strategy that supports CSE’s multi‑vertical structure. This is an executive role for someone with exceptional strategic thinking, operational literacy, and a deep understanding of how to build scalable systems inside a dynamic, high‑growth environment. This is an equity‑first executive position, with salary following the completion of our funding cycle.

What You’ll Do

Lead the development, refinement, and execution of CSE’s company‑wide strategic roadmap

Integrate operations across all management divisions and live event companies to ensure cohesive growth

Build scalable business frameworks that support expansion, monetization, and long‑term sustainability

Work directly with the CEO and CRO on fundraising strategy and future capital planning

Identify new markets, categories, and acquisition opportunities to support national growth

Establish strategic KPIs and organizational alignment across all divisions

Oversee cross‑division initiatives in partnerships, licensing, and branded content

Provide strategic guidance to division heads in combat sports, basketball, football, NIL, and soccer representation

Translate long‑term vision into actionable, cross‑functional execution plans

Represent CSE in high‑level partner, investor, and institutional conversations

Ideal Background

12–20+ years of experience in corporate strategy, sports/entertainment leadership, media, live events, or high‑growth startups

Proven ability to scale multi‑vertical or multi‑entity organizations

Experience supporting or leading investment rounds (Series A or later)

Strong familiarity with sports leagues, athlete management, live event business models, and media IP

Exceptional communication and leadership presence

Entrepreneurial mindset suited for an equity‑first, high‑upside environment

Ability to build clarity and structure within fast‑moving, complex organizations

Why Join CSE Joining CSE means stepping into an executive leadership role inside one of the most ambitious and culturally attuned sports and entertainment companies in the country. You’ll guide the strategy behind a platform that merges sports, live events, representation, and entertainment into a unified ecosystem, shaping the long‑term growth of several management divisions and event brands. You’ll work alongside a seasoned executive team, nationally recognized advisors, and high‑impact partners while leading the architectural framework for CSE’s expansion into major markets.

If you’re a visionary strategist ready to help define the next era of sports and entertainment, we’d love to connect.

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