Riley brings a background in enterprise sales leadership and business-building discipline to his role at Point B, with a focus on thoughtful process, exceptional client service, and the operational rigor required to build and scale a successful book of business.
His connection to Martha’s Vineyard began with childhood summers on the island—starting with a lemonade stand and developing into a lifelong pull back to the Vineyard. He later returned to work on the island during his college years. Riley studied at Johnson & Wales University at both its Providence and Charlotte campuses and spent two years living in Manly, Australia, before beginning a successful career in enterprise technology sales.
Most recently, Riley served as a Senior Business Development Director at Gartner, where he led complex, high-value sales initiatives across the banking, financial services, and insurance industries and consistently ranked among the firm’s top performers.
At Point B, Riley brings that same high standard to every owner and guest relationship. He approaches each property as an important business asset and each stay as an opportunity to deliver the level of service, attention, and follow-through that defines the Point B experience.
Outside of work, Riley lives in Edgartown and can often be found exploring the island’s back roads and coastline with his dog, Roy Kent. He also has a longstanding interest in antiques, watches, and the distinctive culture of coastal New England.