# Charles Sword

> Charles Sword is a New York-based revenue and go-to-market executive who has spent two decades building sales organizations for enterprise and B2B SaaS companies. He has served as Chief Revenue Officer at UpMetrics, Blueprint Software Systems, and Payfone (now Prove), founded Masthead Consulting and Ready Set Track, and held VP roles at CAST and iRise. He is now associated with Mobot, the NYC robotic mobile-testing startup, and writes regularly on how mission-driven organizations can use data and AI to measure impact.

- **Role:** Revenue and go-to-market executive associated with Mobot
- **Organizations:** Mobot, UpMetrics, Blueprint Software Systems, Ready Set Track, Payfone (Prove), CAST, iRise, Masthead Consulting
- **Nationality:** American
- **Education:** B.A. in Economics, University of Pennsylvania
- **Known for:** Held the Chief Revenue Officer title at multiple B2B software companies, including UpMetrics, Blueprint Software Systems, and Payfone/Prove, Founded and led two companies, Masthead Consulting and Ready Set Track, Built and scaled go-to-market teams across identity, enterprise software, and impact-measurement markets

## Career timeline

- **2003-2011** — Founder and CEO of Masthead Consulting
- **2010s** — Vice President roles at iRise and CAST, focused on sales and operations
- **2018-2019** — Chief Revenue Officer at Payfone (now Prove)
- **2019-2020** — Founder and CEO of Ready Set Track
- **2020-2022** — Chief Revenue Officer at Blueprint Software Systems
- **2022** — Named Chief Revenue Officer at UpMetrics
- **2023** — Publishes essays on AI and data for mission-driven organizations
- **2020s** — Associated with Mobot, the NYC robotic mobile-testing company

## Achievements

- Held the Chief Revenue Officer title at multiple B2B software companies, including UpMetrics, Blueprint Software Systems, and Payfone/Prove
- Founded and led two companies, Masthead Consulting and Ready Set Track
- Built and scaled go-to-market teams across identity, enterprise software, and impact-measurement markets
- Published bylined articles for technology and nonprofit publications on data, AI, and impact measurement

## Latest updates

- **2023-09** — Published 'Mission-Driven Organizations Realize the Power of AI' on Techstrong.ai
- **2022-10** — Joined UpMetrics as Chief Revenue Officer

## Links

- Website: https://www.mobot.io/
- LinkedIn: https://www.linkedin.com/in/chsword/

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Profile page: https://yespress.io/charles-sword
Published by YesPress — https://yespress.io
Last updated: 2026-07-22