Greg Caplan in

Greg Caplan

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Co-founder and CEO at Upcraft
📍 Greater Chicago Area, United States

Greg Caplan is the Co-founder and CEO of Upcraft. ai, an AI sales agent platform. A serial entrepreneur, he previously founded Remote Year, a program for professionals to work while traveling globally, and oBaz. com, which was acquired by Groupon. He holds a BBA from the University of Michigan.

Outside of his tech ventures, Greg has a clear passion for travel and building communities. His background includes leadership in environmental initiatives during college, where he co-chaired the Michigan Student Assembly Environmental Issues Commission and Michigan Earth Week. He is an alumnus of the Alpha Epsilon Pi fraternity.

Unique fact: He successfully signed a new client for Upcraft. ai just 20 minutes after they had demoed Salesforces competing AI product.

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Experience
16 Years
Current Role
Co-founder and CEO
Job Level
Leadership
Location
Greater Chicago Area, United States
Personality Overview

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Communication Style
Decision Approach
Work Preference

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Priorities

Topics Greg cares about

AI Sales Agents
His current company, Upcraft. ai, focuses on building AI agents that significantly increase sales conversion rates for inbound leads, a topic he frequently posts about.
Startup Founding
As a multi-time founder of companies like Upcraft. ai, Remote Year, and oBaz. com (which was acquired), he is deeply experienced in building ventures from the ground up.
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Career

Work history

1-2021
Co-founder and CEO
Upcraft
5-2020 - 1-2021
Interim CMO
Cameo
6-2015 - 4-2020
Founder / CEO
Remote Year
7-2013 - 9-2014
Category Manager - Things to Do
Groupon
6-2011 - 7-2013
Co-founder and COO
oBaz.com (aquired by Groupon)
In the press

Media appearances

No media yetWe could not find public media appearances for this person.
Education
2007 - 2011
bba
University of Michigan
2008 - 2010
BBA
University of Michigan - Stephen M. Ross School of Business
2002 - 2007
Education details unavailable
Highland Park High School
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

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