Cavaliers Holdings LLC is obsessed with delivering epic experiences for our team members, our fans, our community and the world. Fueled by an unapologetically bold, inclusive and high-impact culture, we strive to recruit individuals who are enthusiastic and purposeful in carrying out our vision as transformative leaders in sports and entertainment. If you are ready to bring your best to the dynamic, high‑performance environment of the Cavs, Cleveland WNBA, Monsters, Charge, RESN and Rocket Arena - where we come together to create moments that move, inspire, and uplift - then we want to hear from you.

JOB SUMMARY:

Rock Entertainment Group is looking for a Director of Digital Experience to lead the intersection of marketing strategy and technical execution across our portfolio of properties — including the Cleveland Cavaliers, Cleveland Monsters, Cleveland Charge, WNBA Cleveland, Rock Entertainment Sports Network, and Rocket Arena.

This role sits at the seam between marketing and technology, where the right person brings enough marketing fluency to collaborate effectively across marketing, retail, ticket sales, partnerships, and events, and enough technical depth to earn the respect of development and data teams. This leader translates marketing campaigns into digital execution with a strong user experience focus on conversion and lead capture, connecting that execution back to business outcomes.

This role reports to the SVP of Digital Experience, directly oversees a manager and two coordinators, and has ownership of web, mobile, e-commerce, and digital experience across the REG portfolio.

ESSENTIAL DUTIES & RESPONSIBILITIES:

Fan Experience & Ticketing - 

• Own the digital experience roadmap across REG properties — from first fan touchpoint through post-event engagement — with a mobile-first approach across web and app.
• Partner with Ticket Operations, Ticket Sales, and Marketing to support and execute ticketing strategies through REG websites and mobile applications, ensuring purchase flows, promotional placements, and inventory surfaces reflect business priorities.
• Drive conversion and lead capture optimization across ticket funnels, membership acquisition, and ancillary revenue channels through structured A/B testing and UX improvements.
• Define personalization strategy in partnership with Consumer Marketing and Growth Marketing, connecting digital touchpoints to a unified fan profile.
• Collaborate with the retail team on digital merchandising touchpoints to ensure a cohesive fan commerce experience across channels.

Digital Partnerships & Revenue - 

• Work closely with the Partnership Team to identify, develop, and execute new sellable digital assets and platforms dedicated to digital revenue.
• Serve as the product and execution lead for partner-facing digital integrations and co-branded digital experiences — ensuring partner commitments are fulfilled accurately and on time.
• Identify new digital inventory opportunities across web, mobile, and emerging platforms that can be brought to market through the partnerships team.
• Translate business goals from Sales, Marketing, and Partnership teams into digital initiatives with clear outcomes and measurable KPIs.

Platform, Technology & AI - 

• Serve as the business-side owner of REG's core digital platforms — web, mobile app, personalization engine, and analytics infrastructure — partnering with Development and Data teams to scope and deliver.
• Bring technical literacy sufficient to contribute to architecture discussions — APIs, headless CMS, data pipelines, web performance, and mobile platform dynamics — without needing to write the code.
• Partner with REG’s dedicated AI team to identify how AI capabilities can enhance web and mobile fan experiences and stay current on how emerging areas like answer engine optimization (AEO) and generative search are reshaping digital discoverability.
• Own digital tagging and instrumentation strategy with Data & Analytics and manage platform vendor relationships including contract performance and roadmap alignment.
• Ensure all digital properties meet standards for web performance, accessibility (WCAG 2.1 AA), security, and uptime across the REG portfolio.

REQUIRED QUALIFICATIONS:

• Bachelor’s degree in a related field, or equivalent experience.
• 5-8 years of experience in digital, with at least 3–4 years in a leadership role owning digital products, commerce, or experience strategy.
• Strong command of user experience and digital marketing principles — funnel optimization, conversion rate strategy, lifecycle marketing, and digital merchandising.
• Technical fluency to partner effectively with development and data teams: APIs, headless CMS architecture, data pipelines, web performance, and mobile platform dynamics.
• Experience with digital analytics platforms (GA4, Amplitude, Adobe Analytics, or equivalent) and the ability to connect instrumentation to business reporting.
• Familiarity with how AI is reshaping digital discovery — including AEO, generative search, and conversational interfaces.
• Experience with enterprise CRM and marketing automation platforms (Salesforce or equivalent).
• People leadership experience managing direct reports and cross-functional teams.
• Comfort in a fast-paced, event-driven environment where game-day urgency is real and deadlines are non-negotiable.
• Must be able to work flexible hours including weekends, evenings and game nights as assigned.

We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, national origin, sex, sexual orientation, age, disability, gender identity, marital or veteran status, or any other protected class.

Actual compensation will depend on your experience, education/credentials, skills, and how they fit our organizational needs. Rock Entertainment Group offers a robust perks package with healthcare, dental, vision, retirement, and more!