rosssherman.com Let’s Connect

Hi, I’m Ross

I’m an entrepreneur at heart—building and scaling teams, products, and platforms at the intersection of customer experience, operations, and data.

Product Leadership Design & CX Enterprise Platforms Data Strategy AI Enablement Identity Security Agentic AI Digital Commerce Org Scaling Operating Models Global Delivery Shared Services
Ross Sherman headshot
Product & Technology Leader
Work Experience
SailPoint (NASDAQ: SAIL)
2026 – Present
Sr. Director, Global Agentic AI
Leading a specialized global team of architects and engineers driving SailPoint’s Agentic AI go-to-market motion and helping translate complex identity and AI capabilities into scalable field execution.
Lithia & Driveway (NYSE: LAD)
2018 – 2026
VP, Product, Engineering & Design
Executive team member and co-founder of Driveway.com; led product/data/platform strategy and a global org of ~400 across product, design, engineering, and data.
SmarTek21 (Private)
2016 – 2018
Managing Director
Owned client outcomes, employee engagement, and P&L; shifted the business from staff augmentation to solutions-led consulting and scaled global delivery.
Viad Corp, now Pursuit (NYSE: PRSU)
2011 – 2016
Director, Global Technology Operations & Strategy
Led global IT operations and strategy; built shared services, service desk/NOC, and governance across North America and Europe.
Education
Stanford University Graduate School of Business
2014 – 2015
Executive Education
Executive program; d.school design thinking bootcamp.
Arizona State University
2006 – 2010
B.S., Business & Communication
Foundation in business strategy, operations, and stakeholder communication.
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