Cheri Holmes — CEO
I’m a purpose-driven Chief of Staff who loves bringing people together to turn ambitious ideas into reality. I’ve had the privilege of working with incredible leaders at GitHub and GitLab—leading everything from AI-driven product strategies to major milestones like GitLab’s IPO. I thrive on solving complex challenges, building cross-functional partnerships, and helping teams achieve meaningful outcomes—while keeping things fun along the way. At my core, I believe that people come first. I’m passionate about creating environments where everyone feels valued and collaboration fuels success. Whether it’s driving strategic initiatives or ensuring daily operations run smoothly, I’m all in and love what I do. Outside of work, I’m a #SportsMom, acting as a chauffeur & cheerleader to my aspiring soccer and football stars. When I get some downtime, I enjoy exploring new places with my family, diving into a great book, or swimming. And of course, I’m always on the hunt for the perfect plate of nachos—because life’s too short for anything less than cheesy, crunchy perfection.
Stackforce AI infers this person is a strategic leader in the SaaS and healthcare industries.
Location: San Francisco, California, United States
Experience: 16 yrs 4 mos
Skills
- Strategic Planning
- Artificial Intelligence (ai)
- Operational Excellence
- Program Management
- Strategic Initiatives
- Executive-level Communication
- Business Management
- Strategic Thinking
Career Highlights
- Led GitLab's IPO and strategic initiatives.
- Expert in cross-functional team leadership.
- Passionate about improving healthcare outcomes.
Work Experience
Clover Health
Chief of Staff (1 yr)
GitHub
Director, Strategic Planning and Operations (Product) (1 yr 3 mos)
Chief of Staff (1 yr 1 mo)
GitLab
Chief of Staff to the CRO (1 yr)
Staff, Executive Business Partner to the CEO (3 yrs)
Five9
Senior Executive Assistant (C-Level) (1 yr 1 mo)
Synergy Global Housing
Executive Assistant To Chief Executive Officer (2 yrs 4 mos)
Prysm
Executive Assistant (1 yr 3 mos)
Direct Line Communication
Executive Assistant to Controller (1 yr 1 mo)
PROS Install Inc.
Owner (4 yrs)
Education
Accounting and Finance at Mission College
at Fremont High School