Stephen Drew in

Stephen Drew

Critic · DISC type C
Chief Executive Officer at Speechicon
📍 Greater Chicago Area, United States

Stephen Drew is the CEO of Speechicon, leveraging extensive experience in AI and operations to modernize enterprise contact centers. His career includes serving as COO and Chief AI Officer at Ruffalo Noel Levitz and holding leadership roles at Five9 and Uniphore. He holds a Doctorate in Business Administration focused on applied AI from DePaul University.

Stephen demonstrates a keen interest in the practical application of technology across various sectors, including higher education and healthcare. He actively participates in industry-specific events, such as the ViVE health tech conference, to connect with leaders and explore new innovations. He also maintains an interest in the DePaul University community.

He has deep expertise in migrating large-scale legacy systems to modern cloud-based AI platforms.

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Experience
25 Years
Current Role
Chief Executive Officer
Job Level
Leadership
Location
Greater Chicago Area, United States
Personality Overview

How Stephen shows up

Information Seeker
Precise
Objective Thinker

They enjoy working alone and do not rely on others very often. They don’t appreciate bells and whistles unless backed by data. They are quite likely to negotiate on pricing or other key terms.

Priorities

Topics Stephen cares about

Conversational AI
His career is centered on leading teams that design and implement conversational AI technologies to modernize customer and student engagement across multiple industries.
AI in Higher Education
As the former Chief AI Officer at RNL, he focused on using AI to enhance student enrollment, engagement, and fundraising for university partners.
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Career

Work history

1-2026
Chief Executive Officer
Speechicon
8-2024 - 10-2025
Chief Operating Officer & Chief AI Officer
Ruffalo Noel Levitz
10-2023 - 8-2024
Chief AI Officer & Head of Product Management
Ruffalo Noel Levitz
8-2022 - 10-2023
VP, AI and Automation Solutions
Five9
3-2021 - 8-2022
Vice President Of Professional Services
Uniphore
In the press

Media appearances

No media yetWe could not find public media appearances for this person.
Education
Master of Science
University of Notre Dame - Mendoza College of Business
Doctor of Business Administration
DePaul Driehaus College of Business
Social presence
in
Behavioral profile

DISC profile (public)

C

Calculativeness (C)

Calculativeness (C) reflects the degree to which a person is likely to be cautious, systematic and analytical. Those scoring high tend to emphasise quality and accuracy.

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