Kevin O’Brien

Chief Executive Officer InvoiceCloud

Last Reviewed: September 26, 2026

Executive Summary

Kevin O’Brien is Chief Executive Officer of InvoiceCloud, a Boston company whose software lets utilities, government agencies and insurers send bills and collect payments online. It serves more than 3,250 customers. He joined in 2022 as President of InvoiceCloud when it was part of EngageSmart. He was leading it as CEO in August 2024, when it split from EngageSmart and began operating on its own, following Vista Equity Partners’ acquisition of EngageSmart earlier that year. He came from enterprise software rather than payments: before InvoiceCloud he ran PTC’s product lifecycle management business, and before that he spent about ten years at Oracle.

Career Highlights

• Chief Executive Officer of InvoiceCloud, which serves more than 3,250 utility, government and insurance customers.
• Joined EngageSmart as President of InvoiceCloud in 2022.
• Led InvoiceCloud as CEO when it became an independent company in August 2024, and added a new chief financial officer and chief people officer at the same time.
• Divisional Vice President and General Manager of PTC’s Product Lifecycle Management segment, responsible for strategy, product, go-to-market and customer success for offerings including Windchill and ThingWorx Navigate.
• Led the development of PTC’s IoT and Augmented Reality partner ecosystems.
• About a decade at Oracle in global go-to-market leadership roles, building several new growth businesses.

Professional Journey

O’Brien studied government at Colby College and later earned an MBA in General Management at Harvard Business School. He spent about ten years at Oracle in a series of global go-to-market leadership roles, where his work focused on building new growth businesses.

He then joined PTC, where he first led the development of its IoT and Augmented Reality partner ecosystems. He then became Divisional Vice President and General Manager of its Product Lifecycle Management segment, responsible for strategy, product, go-to-market and customer success for PLM offerings including Windchill and ThingWorx Navigate.

In 2022 he joined EngageSmart as President of InvoiceCloud, its business in electronic bill presentment and payment. Vista Equity Partners acquired EngageSmart in January 2024, and InvoiceCloud then separated to run as an independent company. When it announced its independence in August 2024, it named O’Brien as Chief Executive Officer, along with a new chief financial officer, Chris Sands, and a new chief people officer, Jessi Marcoff. O’Brien said the company was “well-positioned to set new industry standards.”

Since then InvoiceCloud has moved its headquarters to Boston’s Seaport and launched the InvoiceCloud Service Module. It has also won Vista Equity Partners’ Global Hackathon and a 2026 Artificial Intelligence Excellence Award. In September 2026 O’Brien said that since InvoiceCloud started using an AI assistant, it had cut its response time by more than 60%.

Outside work he lists skiing, mountain biking, cooking and reading among his interests.

Education

Harvard Business School

MBA, General Management

Colby College

BA, Government