about
The most used AI-powered customer engagement platform for regulated industries
about us
Engageware’s AI-powered platform provides the orchestration, governance, and proven workflows to build seamless customer journeys that are compliant, contextual, and human even at massive scale.
Welcome to Engageware.
Flexible & scalable
Built for regulation
Designed from the start for industries where security, compliance, and auditability aren’t optional
Proven at scale
Powering 3 billion customer interactions across 600+ organizations in 20+ countries
Outcome-driven
Measurable results matter more than promises. We deliver ROI you can prove
Our North Star:
Built for high-trust moments
OUR MISSION
Our mission is simple: co-create the most effective AI-powered customer engagement solutions for regulated companies.
WE LIVE IT THROUGH HOW WE SHOW UP
- Outcome-driven: We focus on measurable business value—everything we do (even AI) only matters if it delivers meaningful results for you.
- Deliberately responsible: We build in security, compliance, and transparency—and we show up when it counts, owning outcomes with you.
- Trusted advisors for regulated industries: We understand your challenges and apply our real-world experience to make better decisions with you.
- Hands-on partners: We design, implement, and iterate with your team so that it works in your world.
Trusted by industry leaders
25%
of the top 50 banks in the Americas
20%
of the top 20 telecom providers
600+
Enterprise clients globally
We won an award!
Honored with a 2025 Silver Stevie® Award for Sales & Service for accelerating real-world adoption of responsible, AI-driven customer engagement.
1B
AI interactions orchestrated
Enterprise-grade agentic AI that helps customers reach the right outcome faster.
1.5B
Appointments scheduled
Mission-critical scheduling that converts intent into booked meetings with the right expert.
500M
AI interactions orchestrated
The compliance-ready accuracy layer that helps frontline teams deliver answers faster.
Careers
Shape the future of AI engagement in regulated industries
We’re growing our team of trusted advisors, hands-on operators, and outcome-focused builders who believe regulated industries deserve trusted engagement that works safely at scale.
Our leadership team
Dan O’Malley
Chief Executive Officer
A seasoned leader and proven enterprise software and AI technology executive, Dan brings more than 20 years of experience driving digital transformation, practical innovation, and growth across the financial services and technology sectors. Dan is responsible for continued AI innovation, enhancing customer support and services, and expanding opportunities to create added value for customers and the markets they represent. Among his previous roles, Dan served as Co-Founder and Chief Executive Officer of Numerated (acquired by Moody’s) and as Chief Digital Officer of Eastern Bank.
Steve Abramson
Chief Financial Officer
Steve Abramson is a senior finance executive with 20 years of experience across technology, start-up, and high-growth companies. He recently served as CFO at Numerated, leading global finance and administration, legal, and investor relations ahead of the company’s acquisition by Moody’s. Previously, he was CFO at JUNO, scaling the finance function to support rapid growth and acquisition by GrowthZone. Steve holds an MBA from the University of Massachusetts Amherst and a BS in Finance and Accounting from Syracuse University.
Cindy Crawley
Chief Administrative Officer
Cindy is a results-driven executive with more than 20 years of experience and success in driving financial improvements, leading business growth, building high-performing teams, and establishing and scaling operations in high-growth technology companies. Cindy oversees the company’s financial management functions, including accounting and controls. She leads Human Resources, Revenue Operations and the company’s internal operations and administrative functions. She is a graduate of the Isenberg School of Management at the University of Massachusetts, Amherst.
Rob Fox
Chief Technology Officer
Rob leads technology, data, and product engineering with over 30 years of expertise driving product innovation at scale. Most recently as CTO at HG Insights and Supplier.io, he built AI-powered B2B intelligence platforms serving enterprise customers. Rob is inventor on six filed patents in AI and data technologies and earned his Computer Science degree from UC Santa Barbara.
Matt Wilson
Chief Customer Officer
A customer-focused leader and proven technology executive, Matt brings extensive experience driving customer success, enablement, and digital transformation in and around the financial services industry. At Engageware, Matt is responsible for delivering exceptional customer outcomes, scaling support and enablement programs, and ensuring clients realize the full value of the platform. Among his previous roles, Matt led customer success and technical operations teams at Alkami Technology, supporting digital banking and AI initiatives across a diverse portfolio of financial institutions.
Christopher Hydak
Head of Hosting Operations and Security Officer
Christopher leads the Hosting Operations team and is the Security Officer for the organization. He has been a technical leader for multiple startups and has over 23 years of industry experience in Cybersecurity, IT, Software Engineering and SaaS Operations. Christopher was most recently at Labelbox, where he provided leadership for the DevOps and Security Roles. Earlier, he was a founding member of Identropy where he served various critical roles such as VP of Product and VP ISO. Christopher has a degree in Computer Engineering from Texas A&M University.
Justin Smith
Senior Director of Product
Justin Smith leads product strategy with over 20 years of expertise driving software development for customer and healthcare engagement platforms. As Senior Director of Product Management at Engageware, he guides teams to deliver market-ready solutions that create measurable business value. He earned his degree from the University of Florida and lives in Michigan with his wife, two sons, and two granddaughters.
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