Weeby
Tech
Innovator
Ann
Weeby
Tech
Innovator
Ann Gaudard Weeby
Tech Executive
Exploring what’s next
I lead through change, bring clarity to complex problems, and build tools people love to use. Whether rolling out gamified AI learning or aligning a cross-functional project, I move with speed, precision, and care.
about ME:
I build systems that help people learn, grow, and get things done.
At Salesforce, I led Trailhead delivering product education, customer enablement, and AI upskilling at scale. I've launched new initiatives, turned around underperforming operations, and led cross-functional work across product, engineering, marketing, and sales.
I do my best work in high-stakes, high-change environments bringing clarity to complexity and energy to execution. My experience spans enterprise transformation and startup advisory. What ties it together is a focus on building programs that scale, teams that thrive, and outcomes that matter.
I value innovation, equity, and courage and I do my best work with teams that care deeply and move fast.
WORK EXPERIENCE
ADVISOR & CONSULTANT
SAlesforce
AI L&D Startups
Aug 2024- Present
Senior Vice President
Aug 2022- Aug 2024
Vice President
Feb 2021– Aug 2022
Senior Director
Feb 2019– Jan 2021
Director
Aug 2016 – Feb 2019
AI L&D Startups
Aug 2024- Present
Senior Vice President
Aug 2022- Aug 2024
Vice President
Feb 2021– Aug 2022
Senior Director
Feb 2019– Jan 2021
Director
Aug 2016 – Feb 2019
Salesforce Foundation
Senior Manager Feb 2015-Aug 2016
Projects
Career Marketplace
Job seekers can showcase Salesforce-specific credentials — including data, AI, and CRM skills — in a centralized destination, helping employers like Deloitte Digital, Cognizant, and IBM Consulting find the right hire fast.
Hands-On Challenges
Focused the product roadmap on creating learning expereinces for key products: Data Cloud, Mulesoft, Tableau, and generative AI products and use cases
Trailhead to Trials
In partnership with the CMO, helped unlock enablement content to improve company SEO and create the first ever pathways from learning to purchasing
skills & FOcus areas
Organizational Transformation
I’ve led teams through growth, change, and uncertainty, building strong culture while delivering results. I lead with clarity and calm, and people trust me to steady the ship and move it forward.
Platform Strategy and Scale
I’ve led end-to-end strategy for learning platforms that serve global users. At Salesforce, I helped evolve Trailhead into a driver of lead generation, hands-on product learning, and career growth.
Cross-Functional Execution
I’ve delivered complex initiatives by aligning product, engineering, marketing, and sales around shared outcomes. I move from strategy to execution quickly and step into ambiguity when others hesitate.
Learning That Delivers
From customer readiness to AI upskilling, I’ve built learning programs that meet the moment. I focus on making learning useful, trusted, and tied to product adoption and business value.
Operational Clarity at Scale
I make the hard things clearer. I give direction without micromanaging, let good people thrive, and use feedback to keep teams aligned and accelerating.
PRESS
Qualified: Inside the Ohana
In conversation with Dan Darcy, Ann defines her career by service and impact, from her military service to building the veterans program for Salesforce, and shares some of the lessons that have shaped her journey.
Wall Street Journal
Showcased the success of upskilling in the Salesforce ecosystem
America's Best Employer for Veterans
After 10 years of programming, Salesforce was named as the number one employer in America for military veterans.
AI Upskilling
For the thousands of tech workers recently laid off in California and across the country, the future may not be as bleak as it looks right now: Many are likely to retrain fairly quickly for new jobs in the burgeoning field of artificial intelligence.
education & Leadership
Presidential Leadership Scholars
Scholar, Class of 2023
Selected for a cross-sector leadership program led by four U.S. presidential centers, focused on driving national impact through collaboration and civic leadership.
Marines’ Memorial Association
Board of Directors, 2023 to Present
Guiding strategy and modernization for a historic nonprofit supporting veterans, military families, and civic dialogue in the heart of San Francisco.
Technovation
Board Chair Emeritus, 2017 to Present
Led board growth and governance for a global nonprofit that empowers girls to solve real-world problems through technology and entrepreneurship.
Western Michigan University
BA, Marketing and Sociology, 2006
Studied business and human behavior to understand how organizations scale and how people drive meaningful change within them.
Ann Gaudard Weeby
Tech Executive
Exploring what’s next
I lead through change, bring clarity to complex problems, and build tools people love to use. Whether rolling out gamified AI learning or aligning a cross-functional project, I move with speed, precision, and care.
about ME:
I build systems that help people learn, grow, and get things done.
At Salesforce, I led Trailhead delivering product education, customer enablement, and AI upskilling at scale. I've launched new initiatives, turned around underperforming operations, and led cross-functional work across product, engineering, marketing, and sales.
I do my best work in high-stakes, high-change environments bringing clarity to complexity and energy to execution. My experience spans enterprise transformation and startup advisory. What ties it together is a focus on building programs that scale, teams that thrive, and outcomes that matter.
I value innovation, equity, and courage and I do my best work with teams that care deeply and move fast.
WORK EXPERIENCE
ADVISOR & CONSULTANT
SAlesforce
AI L&D Startups
Aug 2024- Present
Senior Vice President
Aug 2022- Aug 2024
Vice President
Feb 2021– Aug 2022
Senior Director
Feb 2019– Jan 2021
Director
Aug 2016 – Feb 2019
AI L&D Startups
Aug 2024- Present
Senior Vice President
Aug 2022- Aug 2024
Vice President
Feb 2021– Aug 2022
Senior Director
Feb 2019– Jan 2021
Director
Aug 2016 – Feb 2019
Salesforce Foundation
Senior Manager Feb 2015-Aug 2016
Projects
Career Marketplace
Job seekers can showcase Salesforce-specific credentials — including data, AI, and CRM skills — in a centralized destination, helping employers like Deloitte Digital, Cognizant, and IBM Consulting find the right hire fast.
Hands-On Challenges
Focused the product roadmap on creating learning expereinces for key products: Data Cloud, Mulesoft, Tableau, and generative AI products and use cases
Trailhead to Trials
In partnership with the CMO, helped unlock enablement content to improve company SEO and create the first ever pathways from learning to purchasing
skills & FOcus areas
Organizational Transformation
I’ve led teams through growth, change, and uncertainty, building strong culture while delivering results. I lead with clarity and calm, and people trust me to steady the ship and move it forward.
Platform Strategy and Scale
I’ve led end-to-end strategy for learning platforms that serve global users. At Salesforce, I helped evolve Trailhead into a driver of lead generation, hands-on product learning, and career growth.
Cross-Functional Execution
I’ve delivered complex initiatives by aligning product, engineering, marketing, and sales around shared outcomes. I move from strategy to execution quickly and step into ambiguity when others hesitate.
Learning That Delivers
From customer readiness to AI upskilling, I’ve built learning programs that meet the moment. I focus on making learning useful, trusted, and tied to product adoption and business value.
Operational Clarity at Scale
I make the hard things clearer. I give direction without micromanaging, let good people thrive, and use feedback to keep teams aligned and accelerating.
PRESS
Qualified: Inside the Ohana
In conversation with Dan Darcy, Ann defines her career by service and impact, from her military service to building the veterans program for Salesforce, and shares some of the lessons that have shaped her journey.
Wall Street Journal
Showcased the success of upskilling in the Salesforce ecosystem
America's Best Employer for Veterans
After 10 years of programming, Salesforce was named as the number one employer in America for military veterans.
AI Upskilling
For the thousands of tech workers recently laid off in California and across the country, the future may not be as bleak as it looks right now: Many are likely to retrain fairly quickly for new jobs in the burgeoning field of artificial intelligence.
education & Leadership
Presidential Leadership Scholars
Scholar, Class of 2023
Selected for a cross-sector leadership program led by four U.S. presidential centers, focused on driving national impact through collaboration and civic leadership.
Marines’ Memorial Association
Board of Directors, 2023 to Present
Guiding strategy and modernization for a historic nonprofit supporting veterans, military families, and civic dialogue in the heart of San Francisco.
Technovation
Board Chair Emeritus, 2017 to Present
Led board growth and governance for a global nonprofit that empowers girls to solve real-world problems through technology and entrepreneurship.
Western Michigan University
BA, Marketing and Sociology, 2006
Studied business and human behavior to understand how organizations scale and how people drive meaningful change within them.
Ann Gaudard Weeby
Tech Executive
Exploring what’s next
I lead through change, bring clarity to complex problems, and build tools people love to use. Whether rolling out gamified AI learning or aligning a cross-functional project, I move with speed, precision, and care.
about ME:
I build systems that help people learn, grow, and get things done.
At Salesforce, I led Trailhead delivering product education, customer enablement, and AI upskilling at scale. I've launched new initiatives, turned around underperforming operations, and led cross-functional work across product, engineering, marketing, and sales.
I do my best work in high-stakes, high-change environments bringing clarity to complexity and energy to execution. My experience spans enterprise transformation and startup advisory. What ties it together is a focus on building programs that scale, teams that thrive, and outcomes that matter.
I value innovation, equity, and courage and I do my best work with teams that care deeply and move fast.
WORK EXPERIENCE
ADVISOR & CONSULTANT
SAlesforce
AI L&D Startups
Aug 2024- Present
Senior Vice President
Aug 2022- Aug 2024
Vice President
Feb 2021– Aug 2022
Senior Director
Feb 2019– Jan 2021
Director
Aug 2016 – Feb 2019
AI L&D Startups
Aug 2024- Present
Senior Vice President
Aug 2022- Aug 2024
Vice President
Feb 2021– Aug 2022
Senior Director
Feb 2019– Jan 2021
Director
Aug 2016 – Feb 2019
Salesforce Foundation
Senior Manager Feb 2015-Aug 2016
Projects
Career Marketplace
Job seekers can showcase Salesforce-specific credentials — including data, AI, and CRM skills — in a centralized destination, helping employers like Deloitte Digital, Cognizant, and IBM Consulting find the right hire fast.
Hands-On Challenges
Focused the product roadmap on creating learning expereinces for key products: Data Cloud, Mulesoft, Tableau, and generative AI products and use cases
Trailhead to Trials
In partnership with the CMO, helped unlock enablement content to improve company SEO and create the first ever pathways from learning to purchasing
skills & FOcus areas
Organizational Transformation
I’ve led teams through growth, change, and uncertainty, building strong culture while delivering results. I lead with clarity and calm, and people trust me to steady the ship and move it forward.
Platform Strategy and Scale
I’ve led end-to-end strategy for learning platforms that serve global users. At Salesforce, I helped evolve Trailhead into a driver of lead generation, hands-on product learning, and career growth.
Cross-Functional Execution
I’ve delivered complex initiatives by aligning product, engineering, marketing, and sales around shared outcomes. I move from strategy to execution quickly and step into ambiguity when others hesitate.
Learning That Delivers
From customer readiness to AI upskilling, I’ve built learning programs that meet the moment. I focus on making learning useful, trusted, and tied to product adoption and business value.
Operational Clarity at Scale
I make the hard things clearer. I give direction without micromanaging, let good people thrive, and use feedback to keep teams aligned and accelerating.
PRESS
Qualified: Inside the Ohana
In conversation with Dan Darcy, Ann defines her career by service and impact, from her military service to building the veterans program for Salesforce, and shares some of the lessons that have shaped her journey.
Wall Street Journal
Showcased the success of upskilling in the Salesforce ecosystem
America's Best Employer for Veterans
After 10 years of programming, Salesforce was named as the number one employer in America for military veterans.
AI Upskilling
For the thousands of tech workers recently laid off in California and across the country, the future may not be as bleak as it looks right now: Many are likely to retrain fairly quickly for new jobs in the burgeoning field of artificial intelligence.
education & Leadership
Presidential Leadership Scholars
Scholar, Class of 2023
Selected for a cross-sector leadership program led by four U.S. presidential centers, focused on driving national impact through collaboration and civic leadership.
Marines’ Memorial Association
Board of Directors, 2023 to Present
Guiding strategy and modernization for a historic nonprofit supporting veterans, military families, and civic dialogue in the heart of San Francisco.
Technovation
Board Chair Emeritus, 2017 to Present
Led board growth and governance for a global nonprofit that empowers girls to solve real-world problems through technology and entrepreneurship.
Western Michigan University
BA, Marketing and Sociology, 2006
Studied business and human behavior to understand how organizations scale and how people drive meaningful change within them.