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Engageware Builds Out C-Suite with Three Proven AI Operators


Engageware Builds Out C-Suite with Three Proven AI Operators
  • by: Business Wire
  • |
  • September 3, 2026


Engageware, the most used AI-powered customer engagement platform for regulated industries, has expanded its executive leadership team with the appointments of Steve Abramson as Chief Financial Officer, Rob Fox as Chief Technology Officer and Matt Wilson as Chief Customer Officer - three leaders who have each built, deployed and scaled AI inside regulated enterprises.

Quick Intel

  • Engageware builds out C-Suite with three proven AI operators sharpening edge in regulated industries.
  • Steve Abramson appointed CFO, Rob Fox as CTO and Matt Wilson as CCO – leaders who built and scaled AI in real world.
  • Appointments come as Engageware moves to lead AI adoption where hardest to deploy – banking, financial services, wealth management and telecom.
  • Platform has powered more than 1 billion AI interactions and scheduled 1.5 billion appointments worldwide.
  • Abramson to oversee global finance, legal and admin; Fox to lead engineering and product advancing governed AI; Wilson to oversee customer success and enablement.
  • Trusted by more than 600 global enterprises including 25% of top 50 banks in Americas and 20% of top telecom providers.

Leading AI Adoption Where It's Hardest to Get Right

The appointments come as Engageware moves to lead AI adoption in the sectors where it's hardest to deploy. Banking, financial services, wealth management and telecom demand accuracy, governance and trust with no room for error, and they depend on Engageware, whose platform has already powered more than 1 billion AI interactions and scheduled 1.5 billion appointments for clients and their customers worldwide.

Abramson will oversee global finance, legal and administrative functions. Fox will lead global engineering and product teams, accelerating platform innovation and advancing governed AI across the company. Wilson will oversee customer success, support, enablement and customer operations, helping clients maximize the value of Engageware's platform while scaling customer experience initiatives globally.

"There is a lot of talk about AI transformation, but very few executives have actually led it," said Dan O'Malley, CEO of Engageware. "Steve, Rob and Matt are the rare exceptions. Each has built, deployed and scaled AI inside real businesses in regulated markets. Together they strengthen every critical area of our company, from product innovation and operational scale to customer success and growth. With this team in place, Engageware isn't just participating in the AI revolution in regulated industries, we're positioned to lead it."

Three Leaders Who Built, Deployed and Scaled AI

Chief Financial Officer Steve Abramson: Abramson brings 20 years of finance leadership across technology and high-growth organizations. He most recently served as CFO at Numerated, where he led global finance and administration, legal and investor relations through the company's acquisition by Moody's. Previously, Abramson was CFO at JUNO, scaling the finance function to support rapid growth and its acquisition by GrowthZone.

Chief Technology Officer Rob Fox: Fox is a veteran technology leader with deep expertise guiding product innovation and engineering execution within PE-backed software companies. Most recently at Supplier.io, he led its company-wide AI and product transformation. Previously at HG Insights, he built the Innovation Team and helped enable a successful $250 million exit to Riverwood Capital.

Chief Customer Officer Matt Wilson: Wilson is a customer-focused leader and proven technology executive with extensive experience driving customer success, enablement and digital transformation in and around the financial services industry. Previously, Wilson led AI at Alkami Technology, where he drove the company's internal AI transformation. Having joined Alkami ahead of its IPO, he helped guide the digital banking platform to the public markets while advancing AI initiatives across a diverse portfolio of financial institutions.

 

About Engageware

Engageware is the most used AI-powered customer engagement platform for regulated industries. Trusted by more than 600 global enterprises - including 25% of the top 50 banks in the Americas and 20% of the top telecom providers - Engageware helps organizations modernize service and sales with governed conversational and generative AI. Headquartered in the technology district outside of Boston, Massachusetts with operations throughout Latin America, Engageware is a portfolio company of Clearhaven Partners.

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