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 and 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

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.

Trusted advisors for regulated industries

We understand your challenges and apply our real-world experience to make better decisions with you.

Deliberately responsible

We build in security, compliance, and transparency—and we show up when it counts, owning outcomes 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

RECOGNITION

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
apptitudes scheduled
Mission-critical scheduling that converts intent into booked meetings with the right expert.
500M
Questions answered
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

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.

Dan O'Malley

Chief Executive 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.

Steve Abramson

Chief Financial Officer

Rich leads Engageware’s global sales organization and brings over 20 years of experience building and transforming high growth businesses. Prior to joining Engageware, Rich served as CRO for SundaySky, the leader in the video platform market. Prior to SundaySky, Rich led Acxiom’s Financial Services business as Group Vice President. Previously, Rich served as Vice President, Sales – North America at Experian for their Marketing Platforms business unit. Rich earned a Bachelor of Science degree in Marketing from the University of Rhode Island.

Rich Bossbaly

Chief Revenue 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.

Cindy Crowley

Chief Administrative 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.

Rob Fox

Chief Technology 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.

Matt Wilson

Chief Customer 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.

Christopher Hydak

Head of Hosting Operations and Security Officer

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.

Justin Smith

Senior Director of Product

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