Playeasy

Playeasy is a Boston-based digital platform for the sporting event and sports tourism industry. It brings event organizers, destination marketing organizations and sports commissions, athletic facilities, hotels, local businesses and visitors onto a single network, and supports steps across the event lifecycle: discovering and comparing host destinations, issuing and responding to event RFPs, marketing events, registration and ticketing links, hotel and attraction information, and economic impact reporting. The company describes itself as a social network tailored to the sporting event and tourism industry, and distributes a mobile app through the Google Play Store and Apple App Store.

The platform is organized around distinct audiences. For event organizers, a single RFP is matched with destinations and venues competing to host; organizers also get event marketing exposure and engagement/impact reporting. For destinations, the product provides lead generation and RFP alerts, destination and facility marketplace profiles, event microsites with hotel and attraction content, community partner activation, and analytics on leads, bookings and referrals. For DMOs, the Compass suite comprises Compass Tour Guide (a branded AI visitor concierge built on the destination's own content), Compass Elements (embeddable modules for hotel booking, deals and listings), Compass Insights (attribution and engagement measurement) and Compass Advisor (an internal AI layer for reporting, content drafting and data queries). The company positions Compass against a stated 30–50% decline in DMO website traffic as AI answers replace search clicks.

In October 2025 Playeasy restructured into two business lines sharing one technology foundation: Playeasy Network, focused on connecting destinations with event organizers, and Playeasy Experiences, focused on visitor engagement products for destinations, both powered by the Playeasy Platform.

Founding story

Co-founder Sean Flaherty, a former Boston College football long snapper, was unable to find a field for a youth training camp after graduation and held it in a parking lot instead, prompting the idea of an online booking layer for athletic space comparable to Airbnb or OpenTable. Fellow Boston College student-athletes Kerri Shields (basketball) and Ryan Quigley (football) had met similar obstacles organizing shooting camps and clinics. The three began exchanging ideas in 2015 and launched the platform three years later.

Business model

Playeasy operates a two-sided platform: destinations, sports commissions, DMOs and facilities subscribe to marketing, lead generation, microsite, AI visitor experience and analytics products (including tiered Gold and Silver destination profiles and advertising), while event organizers use the network to submit RFPs, market events and access reporting. Products are grouped under Playeasy Network and Playeasy Experiences, both built on the shared Playeasy Platform.

Revenue is associated with destination- and facility-side platform products — profile tiers (Gold and Silver), advertising, event microsites, lead generation and the Compass visitor experience suite — sold to destinations, sports commissions and DMOs. In its earliest form the platform also enabled organizers to book and pay for facilities online.

Traction

Within a year of its 2018 launch the platform listed more than 500 sports facilities and supported bookings for organizations such as Global Premier Soccer and Zero Gravity Basketball. Current site figures cite 300+ destinations, 20,000+ venues and facilities, 10,000+ marketed events, 900+ event organizers (1,000+ on the go.playeasy.com site), 2,000+ event RFPs, 100,000+ hotels and attractions, and 4 million+ visitor interactions. Named destination partners include Discover Central Massachusetts, Lansing Sports Commission, Sports Salt Lake, Ann Arbor Sports Commission, Myrtle Beach Regional Sports Alliance and Lackawanna County Visitors Bureau.

Latest developments

On October 28, 2025 Playeasy announced a restructuring into two business lines, Playeasy Network and Playeasy Experiences, both running on the Playeasy Platform, with Kerri Shields promoted to CEO of Playeasy Network and Sean Flaherty remaining Chairman and CEO of Playeasy Inc. while functionally leading Playeasy Experiences. The company said existing partner products would be unaffected and held a webinar on October 29, 2025 to unveil a new Playeasy Experiences product. Current product marketing centers on the Compass AI visitor experience suite for DMOs.