Stephen Drew

Critic
DISC Type : C

Chief Executive Officer at Speechicon

Greater Chicago Area, United States

Overview

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.

Personality Overview

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.

Topics They Care 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.
Contact Center Modernization
His current role as CEO of Speechicon focuses on helping enterprises migrate from legacy infrastructure to modern, cloud-based, AI-driven platforms.

Media Appearances

Stephen has no verified media appearances

Work History

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

Education

Master of Science from University of Notre Dame - Mendoza College of Business
Doctor of Business Administration from DePaul Driehaus College of Business

More Information

Social Presence :

Prographics :

Exp : 25 Location : Greater Chicago Area, United States Job Level : Leadership Designation : Chief Executive Officer at Speechicon
URL has been copied!

Insights For Selling To Stephen

During A Call Or A Meeting

DO's

  • Don’t forget to mention how you compare to competition on both features and pricing
  • Use phrases like ‘expect X% improvement’, ‘data clearly shows’ etc.
  • Be formal and objective, they will appreciate it more

DONT's

  • Don’t rush them till they have clearly gotten all the necessary information
  • Don’t try to give too many examples of other users, they like to make their own decisions
  • Do not use very emotional or colorful language

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Stephen is

  • Strong evidence of ROI, effective pricing, and proven data points matter the most to them.
  • Will you ever get a clear answer from Stephen

  • It is not very hard for them to say no if they are not convinced about the decision.

Insights For Deal Planning

    How fast (or slow) will Stephen move?

  • They are neither the fastest nor the slowest decision makers, they are somewhere in the middle.
  • Can Stephen take some risk or not?

  • They can bear some risk if their analysis backs the decision.

You And Stephen

Personality Compatibility


More Profiles

Discover additional public profiles from our index.

Search more profiles

Looking for someone else? Search here for anyone.

Or visit Humantic AI to know more.