Charles Sword

Chief Executive Officer at Mobot

Overview

Charles Sword serves as Chief Executive Officer at Mobot [1][3]. Sword is the Founder and Senior Advisor at Work Different, a GTM advisory services company focused on helping early stage B2B technology companies scale their teams and revenue, and brings over 20 years experience as a GTM leader including multiple successful exits [2]. Sword's prior roles include Chief Revenue Officer positions at UpMetrics [5], Blueprint Software Systems [6][8], and Prove [7], as well as Vice President of North America Sales and Operations at CAST [9] and Vice President of Strategic Industries at iRise [10]. Sword holds a Bachelor of Arts in Economics from the University of Pennsylvania [11].

Profile introduction
Source excerptLinkedIn [2]

Charles Sword is the Founder and Senior Advisor at Work Different, a GTM advisory services company focused on helping early stage B2B technology companies scale their teams and revenue. He brings over 20 years experience as a GTM leader including multiple successful exits.

Career history

  1. Chief Executive OfficerJun 2026 to presentMobot
  2. GTM AdvisorJul 2025 to Jun 2026Work Different
  3. Chief Revenue OfficerOct 2022 to Aug 2025UpMetrics
  4. Chief Revenue Officer2020 to 2022Blueprint Software Systems
  5. Chief Revenue Officer2018 to 2020Prove
  6. Chief Revenue Officer2014 to 2018Blueprint Software Systems
  7. Vice President, North America Sales and Operations2013 to 2014CAST
  8. Vice President, Strategic Industries2011 to 2013iRise

Education

  1. Bachelor of Arts, EconomicsUniversity of Pennsylvania

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