Cheri Holmes

CEO

San Francisco, California, United States16 yrs 4 mos experience
Highly StableAI Enabled

Key Highlights

  • Led GitLab's IPO and strategic initiatives.
  • Expert in cross-functional team leadership.
  • Passionate about improving healthcare outcomes.
Stackforce AI infers this person is a strategic leader in the SaaS and healthcare industries.

Contact

Skills

Core Skills

Strategic PlanningArtificial Intelligence (ai)Operational ExcellenceProgram ManagementStrategic InitiativesExecutive-level CommunicationBusiness ManagementStrategic Thinking

Other Skills

Objectives and Key Results (OKRs)Strategic CommunicationsCross-functional Team LeadershipProduct LaunchTeam DevelopmentExecutive LeadershipOperations ManagementCritical ThinkingCorporate CommunicationsStart-upsDriving ResultsBudget ManagementAnalytical SkillsCommunicationStreamlining

About

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.

Experience

16 yrs 4 mos
Total Experience
2 yrs 2 mos
Average Tenure
1 yr
Current Experience

Clover health

Chief of Staff

May 2025Present · 1 yr · San Francisco Bay Area · Remote

  • Leading strategic planning, operations, external communications, cross-company initiatives and executive alignment at the intersection of healthcare and technology.
  • I work directly with Clover Health's executive leadership team at the intersection of healthcare and technology, where I drive strategic initiatives that define how we scale and compete in one of the most complex industries in America.
  • My job is ensuring our executive team operates with clarity, alignment, and speed so we can focus on what matters: transforming healthcare outcomes. I set and drive priorities across our leadership team, ensuring our efforts are aligned, measurable, and connected to our mission of improving health outcomes for America's most vulnerable populations.
  • Focus areas:
  • Corporate Strategy & Long-range Planning
  • AI Strategy & Transformation in Finance
  • External & Internal Communications
  • OKR Framework & Performance Management
  • Board Preparation & Investor Relations Strategy
  • Monthly Financial Close & Quarterly Business Reviews
  • Talent Strategy, Organizational Design & Future-state Planning
  • Executive and Org-wide Offsites & Strategic Retreats
  • Cross-functional Strategic Initiatives
Strategic PlanningObjectives and Key Results (OKRs)Artificial Intelligence (AI)Strategic Communications

Github

2 roles

Director, Strategic Planning and Operations (Product)

Oct 2023Jan 2025 · 1 yr 3 mos · Remote

  • As the Director of Strategic Planning and Operations within Product at GitHub, I steer the strategic direction and operational excellence for a $1 billion+ product portfolio. My role is central to evolving GitHub’s product operating model and implementing continuous planning processes that adapt swiftly to changing market demands. I take pride in owning and refining our strategic planning processes and initiatives, ensuring they are seamlessly aligned with Microsoft's broader planning cycles and GitHub's long-term objectives
  • Key Responsibilities:
  • Lead the strategic planning and execution for GitHub’s extensive product portfolio, driving initiatives that significantly enhance operational efficiency and foster product innovation.
  • Establish and evolve the product operating model to maximize efficiency and effectiveness across the entire PDLC, adapting to new challenges and opportunities in the tech landscape.
  • Implement and refine continuous planning processes, ensuring GitHub remains agile and responsive to both market trends, tech innovations, and customer & community needs
  • Develop and evolve Semester Planning for Product in collaboration with Engineering and Design teams to ensure execution of GitHub’s product strategy
  • Develop and refine the Rhythm of Business for Product organization identifying key forums, milestones, and operational processes
  • Lead the development of OKRs working in conjunction with executive leadership to ensure alignment from top to bottom and across teams
  • Lead analysis of OKRs, metrics, and data to track product performance and identify areas for improvement to enable data-driven decisions
  • Work cross-functionally with engineering, marketing, revenue, customer support, and other teams to ensure alignment and effective execution of product plans
  • Contribute to the development of best practices in project management, resource allocation, budget management, etc.
Strategic PlanningOperational ExcellenceCross-functional Team LeadershipProduct LaunchStrategic Communications

Chief of Staff

May 2023Jun 2024 · 1 yr 1 mo · Remote

  • Leading EPD (Engineering, Product & Design) Strategic Planning at GitHub, I specialize in driving operational excellence within the Product organization. My role involves closely aligning with Microsoft's semester planning, ensuring effective collaboration across Product, Engineering, and Revenue teams. I focus on implementing strategies that enhance operational efficiency and foster product innovation.
  • Key Responsibilities:
  • Drive execution of strategic programs and initiatives to drive operational efficiency and process improvements across the Product org
  • Develop and evolve Semester Planning for Product in collaboration with Engineering and Design teams to ensure execution of GitHub’s product strategy
  • Develop and refine the Rhythm of Business for Product organization identifying key forums, milestones, and operational processes
  • Lead the development of OKRs working in conjunction with executive leadership to ensure alignment from top to bottom and across teams
  • Lead analysis of OKRs, metrics, and data to track product performance and identify areas for improvement to enable data-driven decisions
  • Work cross-functionally with engineering, marketing, revenue, customer support, and other teams to ensure alignment and effective execution of product plans
  • Contribute to the development of best practices in project management, resource allocation, budget management, etc.
Team DevelopmentProgram ManagementExecutive LeadershipStrategic PlanningOperations Management

Gitlab

2 roles

Chief of Staff to the CRO

Promoted

Oct 2021Oct 2022 · 1 yr

  • https://about.gitlab.com/job-families/sales/chief-of-staff-cro/
  • Promoted from Staff EBA to CEO to CoS to CRO. The CoS role is a key leadership position on the Chief Revenue Officer’s team. Act as a trusted partner to the Chief Revenue Officer (CRO) to drive operational excellence and deliver repeatable business results. Serving as a partner to the CRO as a strategic advisor and executing cross-functional and cross-organization initiatives and activities supporting the CRO's strategy and vision in alignment with company values
  • Focus on CRO's Success
  • Priority Setting - ensuring the CRO is as efficient as possible and focused on the long & short-term goals and objectives of the company and CRO organization. Includes time management in partnership with CRO’s Sr. EA
  • Advise CRO and CRO LT on priorities to ensure CRO’s time is leveraged effectively
  • Act as a representative of CRO in various forums. Stepping in for CRO as needed (delegating tasks, meetings, projects, etc)
  • Own and/or follow up on projects directly commissioned by the CRO, including driving due dates, next steps, and deliverables. Including organizational design & planning,
  • Support the needs of the CRO Leadership team by surfacing and prioritizing critical issues for the CRO
  • Partner with internal and external Communications to ensure content is in the CRO’s voice, maps back to the strategy, goal, and priorities of the business
  • Prepare the CRO for critical meetings, including external and internal (curating material, providing context to the CRO in advance of meetings, etc)
  • Connector; prioritize communications with the leadership team, E-Group, and overall company
  • Advisor and confidant to the CRO. While considering the needs of the entire CRO organization without turf considerations
  • Efficiency; CoS saves the CRO time, through delegation, prioritization, and giving the CRO time back to focus on the broader picture.
Strategic InitiativesCritical ThinkingCorporate CommunicationsBusiness ManagementStart-upsStrategic Thinking+25

Staff, Executive Business Partner to the CEO

Oct 2018Oct 2021 · 3 yrs

  • Manager of GitLab's EBA team and sole EA to GitLab's Co-Founder & CEO, CRO, and CFO
  • Hire, develop and retain the function's EBA team by setting the strategy and prioritizing GitLab’s Objectives and Key Results (OKRs)
  • Own and proactively manage a complex, changing, high-volume calendar across multiple time zones. Ensure CEO and CRO are prepped for every meeting
  • Run cadence of weekly staff meetings and other important meetings, including planning agenda, organization, and follow-up on action items, while infusing our company values throughout
  • Responsible for coordinating cadence of Board of Directors meetings
  • Plan events such as team off-sites, team building activities, and company kick-offs as needed
  • Draft internal and external communications on behalf of the CEO & CRO
  • Seamlessly coordinate extensive domestic and international travel, including air and ground transportation, hotel reservations, security, visas, and other travel documentation. Accompanying the Executive when necessary
  • Assist the full life cycle of recruiting including booking interviews, liaising between the hiring team and the candidate, and coordinating onboarding of new hires
  • Manage Executive's email inbox, including drafting internal and external communications on behalf of Executive
  • Run and lead special cross-functional projects upon request
Strategic InitiativesTeam DevelopmentCritical ThinkingBusiness ManagementStart-upsStrategic Thinking+24

Five9

Senior Executive Assistant (C-Level)

Sep 2017Oct 2018 · 1 yr 1 mo · San Ramon, CA

  • Senior Executive Assistant to the EVP, Cloud Operations
  • Driving Operational Excellence, Strategic Alignment & Executive Enablement
  • Optimized executive efficiency by managing a high-volume, multi-time-zone calendar, ensuring the EVP was fully prepared for every meeting.
  • Led executive meeting cadence, structuring agendas, driving key outcomes, and ensuring follow-through on action items.
  • Orchestrated quarterly leadership meetings and key department events, enhancing alignment and engagement.
  • Spearheaded internal and external communications, drafting strategic messaging on behalf of the EVP.
  • Oversaw high-priority cross-functional projects, stepping in as a strategic partner beyond traditional EA responsibilities.
Strategic InitiativesCritical ThinkingBusiness ManagementStart-upsStrategic ThinkingExecutive-level Communication+23

Synergy global housing

Executive Assistant To Chief Executive Officer

May 2015Sep 2017 · 2 yrs 4 mos · San Ramon

  • EA to Co-CEO's and President & Office Manager of NorCal HQ
Strategic InitiativesCritical ThinkingBusiness ManagementStrategic ThinkingExecutive-level CommunicationDriving Results+16

Prysm

Executive Assistant

Feb 2014May 2015 · 1 yr 3 mos

  • Executive Assistant to the CFO, VP of Solutions, VP of HR, VP of Marketing
Strategic InitiativesCritical ThinkingBusiness ManagementStrategic ThinkingDriving ResultsBudget Management+11

Direct line communication

Executive Assistant to Controller

Jun 2012Jul 2013 · 1 yr 1 mo

Strategic InitiativesCritical ThinkingBusiness ManagementStrategic ThinkingDriving ResultsBudget Management+11

Pros install inc.

Owner

Jul 2008Jul 2012 · 4 yrs

Critical ThinkingBusiness ManagementStrategic ThinkingDriving ResultsBudget ManagementAnalytical Skills+9

Education

Mission College

Accounting and Finance

Jan 2007Jan 2010

Fremont High School

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