Craig J. Lewis

Inquirer
DISC Type : dc

Co-Founder & CEO at Ogentic AI

United States

Overview

Craig J. Lewis is a serial entrepreneur focused on transforming enterprise productivity as the Co-Founder and CEO of Ogentic AI. He previously founded the fintech company Gig Wage, raising over $25M to innovate workforce payments. He holds a BA from Morehead State University and authored "The Sport of Sales. "

Outside of his ventures, Craig is a dedicated supporter of the startup ecosystem, serving as an angel investor, a Limited Partner at Outside VC, and a Global Governing Board Director at MassChallenge. He is a former professional basketball player who played in Europe and is a husband and father to four daughters.

Interesting fact: Prior to his career in tech and finance, Craig played professional basketball in Germany and Portugal.

Personality Overview

Judgemental

Demanding

ROI Conscious

They can be nudged to make faster decisions by offering what they value.  They focus on objectivity in a pitch and pay little attention to bells and whistles. They respond well to confident salespeople.

Topics They Care About

Enterprise AI
Currently building Ogentic AI to solve enterprise productivity and automation challenges, believing that AI's value is in reimagining business operations, not just generative tricks.
Future of Work
His career has evolved from traditional payroll at ADP, to the gig economy with Gig Wage, and now to AI's impact on the workforce with Ogentic AI.
Fintech & Payments
Founded Gig Wage, a venture-backed company that built modern payroll, payments, and banking tools for independent contractors, moving nearly $1B in volume.

Media Appearances

Craig has no verified media appearances

Work History

6-2025
Co-Founder & CEO at Ogentic AI
5-2024
Global Governing Board Director at MassChallenge
5-2024
Angel Investor at Fondo
3-2025
Angel Investor at Quiltt
1-2023
Limited Partner at Outside VC

Education

2002 - 2004
BA from Morehead State University
2001 - 2002
Associates from Connor State College

More Information

Social Presence :

Prographics :

Exp : 2 Location : United States Job Level : Leadership Designation : Co-Founder & CEO at Ogentic AI
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Insights For Selling To Craig J.

During A Call Or A Meeting

DO's

  • Get to the point quickly instead of spending too much time on pleasantries
  • Highlight the competitive differentiation of your product
  • Be crisp while making the pitch

DONT's

  • Don’t expect them to change their mind quickly if they say no once
  • Don’t try to be an alpha salesperson, give them equal space
  • Avoid repeating yourself or making generalizations

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Craig J. is

  • Conviction in the product matters to them, followed by proof points and strong testimonials.
  • Will you ever get a clear answer from Craig J.

  • They may not be very forthcoming, but they will say no if needed.

Insights For Deal Planning

    How fast (or slow) will Craig J. move?

  • They are neither the fastest decision makers nor the slowest.
  • Can Craig J. take some risk or not?

  • They can take risks but after weighing up the pros and cons.

You And Craig J.

Personality Compatibility


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