Governed AI across agents and workflows
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
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
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
Dave is a senior executive with over 25 years of finance and management experiences at Private Equity-backed technology and software companies, leading organizations in Finance, Sales Operations, and Business Development initiatives. Dave was recently SVP/CFO at PlumChoice (acquired by Allstate), and Head of Finance and Sales Operations at Mformation (acquired by Nokia). Dave has a degree in Accounting from Missouri State University, and Masters degrees from the University of Missouri and Washington University in St. Louis.
Dave Blahnik
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
Bill has led Engageware’s client services organization since 2007, responsible for the company’s customer success, support, and professional services. With more than 25 years of experience in the development and implementation of enterprise software, Bill previously was vice president of client services at EasyAsk, a division of Progress Software Corporation. Earlier, he was vice president of professional services at Oberon, Inc. Prior to Oberon, Bill provided leadership to the Clarify, Inc. professional services organization, and held several roles at Digital Equipment Corporation. He earned a bachelor’s degree in electrical engineering from Rensselaer Polytechnic Institute and an MBA from Clark University.
Bill Bohen
Senior Vice President, Client Services
Cindy is a results-driven financial executive with more than 20 years of experience and success in driving profit improvement, leading business growth and establishing and scaling operations in emerging growth companies. A member of the Engageware team since 2010, Cindy has held senior finance positions with Cloudtree, Venture Enterprise Advisors, Alcatel, Astral Point and Wellfleet Communications. She is a graduate of the Isenberg School of Management at the University of Massachusetts, Amherst.
Cindy Crowley
Vice President, Finance and Administration
Michael leads Engageware’s software engineering organization. Michael joined Engageware in 2019 and has more than 30 years of engineering experience in SaaS and technology companies. Before Engageware, he held senior leadership positions at Imprivata and TruePosition Inc. He earned a bachelor’s degree in Computer Science with a specialty in Mathematics from Fitchburg State University.
Michael Forsyth
Vice President, Engineering
Dan leads Engageware’s global marketing team, bringing over 20 years of experience spanning start-ups, scale-ups, and public companies. He specializes in driving comprehensive go-to-market strategies, fostering cross-functional alignment, and enabling revenue growth. Before joining Engageware, Dan held senior leadership roles at Xtify (acquired by IBM), Zodiac (acquired by Nike), and LiveVox (acquired by NICE). He holds a BA from Cornell University and an MBA from the University of Michigan’s Ross School of Business.
Dan Gesser
Vice President, Marketing
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
John is a cofounder of Engageware. He has 30 years of hands-on experience managing the development of computer hardware and software products. Prior to his role in establishing Engageware, John was vice president of software development for Datawatch Corporation. He earned a bachelor’s degree from the University of Massachusetts, Amherst.
John Loring
Chief Technologist and Co-founder
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