Engageware Appoints Technology Industry Veteran Dan O’Malley as CEO to Drive Expansion of its AI-Driven Customer Engagement Platform

O’Malley’s deep financial services experience strengthens Engageware’s leadership position with enterprise clients

BOSTON, MA – (BUSINESS WIRE)— Engageware, a leading provider of AI-powered customer engagement solutions for the enterprise, today announced the appointment of Dan O’Malley as Chief Executive Officer, effective immediately. Built on three integrated enterprise-grade solution offerings — AI agents, appointment scheduling, and knowledge management — Engageware’s platform, trusted by more than 600 customers, powers enterprises to deliver smarter, more seamless customer experiences. A seasoned leader and proven enterprise software and AI technology executive, O’Malley brings more than 20 years of experience driving digital transformation, practical innovation, and growth across the financial services and technology sectors. Rick Lowrey will continue to serve on the Board of Directors as Executive Chairperson as Engageware accelerates its next phase of expansion. 

O’Malley most recently served as Co-Founder and Chief Executive Officer of Numerated, an AI-driven SaaS platform used by banks and credit unions to originate and manage more than $70 billion in commercial lending. Its technology powered the largest global AI commercial lending deployment at a leading Global Systemically Important Financial Institution (G-SIFI). Within just seven years of launch, Numerated served financial institutions representing nearly $4 trillion in assets. In 2024, it was acquired by Moody’s (NYSE: MCO) and now serves as a core component of Moody’s Lending Suite. Prior to Numerated, O’Malley was Chief Digital Officer of Eastern Bank (NASDAQ: EBC), where he led digital product strategy, the customer contact center, and Eastern Labs, the bank’s innovation arm.   

As Engageware’s CEO, O’Malley will build on the company’s platform, trusted by many of the top 30 U.S. banks and dozens of highly distinguished financial institutions, and be responsible for continued AI innovation, enhancing customer support and services, and expanding opportunities to create added value for customers and the markets they represent. He joins at a time of growth, as enterprises are turning to trusted vendors, such as Engageware, that provide responsible AI to transform how they engage with customers. O’Malley’s leadership will align Engageware’s AI-powered platform–now nearing one billion AI interactions–with evolving enterprise needs and strengthen the company’s position as a trusted partner delivering measurable outcomes. 

“I’m excited to join Engageware at such a pivotal moment for the industry,” said Dan O’Malley, CEO of Engageware. “Enterprises are using real-world interaction and outcome data to rethink how they harness AI to deliver more personalized, flexible, and impactful customer experiences. Engageware’s platform powers streamlined interactions for our customers with their customers, uniquely addressing the requirements of large, sophisticated and regulated enterprises. I look forward to serving our marquee international customer base with trusted solutions and partnership and to building on our company’s collaborative, growth-oriented culture as we unlock even greater market impact and innovation for our customers.”   

“It’s a pleasure to welcome Dan as CEO of Engageware,” said Michelle Noon, Founder and Managing Partner of Clearhaven Partners. “Dan brings a history of leading successful software companies, deep domain expertise in the financial services market and a successful track record of accelerating growth through a customer-centric approach. I look forward to partnering with Dan as he focuses on expanding Engageware’s AI-driven customer engagement platform to deliver superior value to customers.”  

“I’m delighted to support Dan in his role as CEO of Engageware and fortunate to continue to serve Engageware in my capacity as Executive Chairperson,” said Rick Lowrey, Executive Chairperson of Engageware. “Dan is a proven leader with strategic and operational insight and a track record of driving growth. The Board and I are confident in what Dan will drive in this next era of leadership at Engageware.”  

Earlier in his career, O’Malley co-founded PerkStreet Financial, one of the first U.S. neobanks, and held leadership roles at Capital One (NYSE: COF) and Oliver Wyman, advising senior executives on data-driven strategy. O’Malley holds a B.S. in Operations Research and Financial Engineering from Princeton University. 

About Engageware

Engageware is a leading provider of AI-powered customer engagement solutions, helping organizations resolve customer needs on the first interaction and build lasting relationships in critical moments. Anchored by three integrated enterprise-grade solution offerings — appointment scheduling, knowledge management, and AI Agents — Engageware’s platform combines conversational and generative AI to automate routine inquiries, deliver instant knowledge, streamline scheduling, and seamlessly connect customers with the right human resources when needed. In 2023, Engageware acquired Aivo, a conversational AI pioneer, strengthening Engageware’s digital engagement capabilities and expanding Engageware’s global presence. Trusted by more than 600 customers, enterprises across banking, financial services, telecom, retail, healthcare, and education, Engageware orchestrates intelligent customer journeys that reduce friction, improve operational efficiency, and enhance customer satisfaction. Headquartered in Tewksbury, MA, with operations throughout Latin America, Engageware serves customers worldwide. Engageware is a portfolio company of Clearhaven Partners, a Boston-based private equity firm focused exclusively on investments in software and technology businesses. Visit https://engageware.com to learn more. 

About Clearhaven Partners LP

Clearhaven Partners is a Boston-based private equity firm focused exclusively on investments in software and technology businesses. Clearhaven was founded in 2019 by an investor-operator team to partner with differentiated, growing software and technology companies. Clearhaven brings a collective 50+ years of software investing and operating experience to its portfolio companies through its partnership approach to value creation to help companies scale profitably. Clearhaven manages more than $1 billion in AUM as of June 30, 2025. Visit  www.clearhavenpartners.com. 

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