Kevin O’Brien

Chief Executive Officer

Kevin leads the strategic direction for InvoiceCloud, focused on delivering innovation and high-quality service to our customers. Prior to joining EngageSmart and InvoiceCloud in 2022, Kevin was the Divisional Vice President and General Manager of the Product Lifecycle Management (PLM) segment at PTC. In this role, Kevin is responsible for PTC’s strategy, product, go-to-market, and customer success for PLM offerings including Windchill and ThingWorx Navigate. Previously at PTC, Kevin led the build out of PTC’s award- winning Internet of Things and Augmented Reality partner ecosystems. Kevin also spent a decade at Oracle in a series of global go-to-market leadership roles building several new growth businesses.

Kevin holds an MBA in General Management from Harvard Business School and a B.A. in Government from Colby College. He loves spending time with his wife and four kids and enjoys skiing, mountain biking, cooking, and reading.

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