Engageware, a leading provider of AI-powered customer engagement solutions, announced the appointment of Dan O’Malley as Chief Executive Officer, effective immediately, on September 3, 2025. O’Malley’s extensive experience in financial services and AI technology positions him to lead Engageware’s expansion, enhancing its platform trusted by over 600 enterprise customers, including many of the top 30 U.S. banks.
Dan O’Malley named CEO of Engageware, succeeding Nina Vellayan.
Brings 20+ years of experience in financial services and AI-driven technology.
Platform supports AI Agents, appointment scheduling, and knowledge management.
Trusted by 600+ customers, nearing 1 billion AI interactions.
O’Malley previously led Numerated, acquired by Moody’s in 2024.
Engageware is backed by Clearhaven Partners, managing $1B+ in AUM.
O’Malley succeeds Nina Vellayan, who served as CEO since December 2022, driving record revenue and profitability. Rick Lowrey remains Executive Chairperson, supporting O’Malley as the company accelerates its growth phase. This transition aligns with Engageware’s focus on scaling its AI-driven platform to meet evolving enterprise needs.
With over 20 years of experience, O’Malley has driven digital transformation and innovation in financial services:
Co-Founder and CEO of Numerated: Led an AI-driven SaaS platform managing $70 billion in commercial lending, acquired by Moody’s in 2024.
Chief Digital Officer at Eastern Bank: Oversaw digital product strategy and innovation.
Co-Founder of PerkStreet Financial: Pioneered one of the first U.S. neobanks.
Held leadership roles at Capital One and Oliver Wyman; holds a B.S. from Princeton University.
O’Malley will focus on advancing Engageware’s platform, which integrates AI Agents, appointment scheduling, and knowledge management to deliver seamless customer experiences. With nearly 1 billion AI interactions, the platform automates routine inquiries, streamlines scheduling, and connects customers with human resources when needed. His leadership aims to enhance customer support, drive AI innovation, and expand market reach.
Engageware’s platform, strengthened by the 2023 acquisition of Aivo, supports industries like banking, telecom, retail, healthcare, and education. O’Malley’s expertise in financial services and AI positions Engageware to capitalize on the growing demand for responsible AI solutions, delivering measurable outcomes like improved customer satisfaction and operational efficiency.
“I’m excited to join Engageware at such a pivotal moment,” said O’Malley. “Enterprises are using real-world data to harness AI for personalized, impactful customer experiences.” Michelle Noon, Founder at Clearhaven Partners, stated, “Dan brings a history of leading successful software companies and deep financial services expertise.” Rick Lowrey, Executive Chairperson, added, “Dan is a proven leader with a track record of driving growth.”
For more details, visit www.engageware.com.
Engageware is a leading provider of AI-powered customer engagement solutions, helping organizations resolve customer needs on the first interaction. Its platform, combining conversational and generative AI, automates inquiries, delivers instant knowledge, and streamlines scheduling. Trusted by over 600 customers, Engageware serves industries like banking, telecom, retail, healthcare, and education. Headquartered in Tewksbury, MA, with operations in Latin America, Engageware is a portfolio company of Clearhaven Partners.
Clearhaven Partners, founded in 2019, is a Boston-based private equity firm focused on software and technology investments. With over $1 billion in assets under management as of June 30, 2025, Clearhaven partners with growing companies to drive profitable scaling through 50+ years of collective experience.
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