Compass Staff |
Every organization is facing the same tension right now: How to move faster with AI without leaving its people behind. Salesforce has found a way to do both. The cloud provider has achieved ~50% internal role-fill rates by embracing the ethos of upskilling, reskilling, and otherwise training current employees for new, in-demand roles — positions that might not exist yet, but will be vital to helping businesses remain resilient in the face of rapid change.
“We are in control of how we use this technology,” Jenny Simmons, the company’s VP of Enterprise Learning, said in keynote remarks at Guild Opportunity Summit 2025 Tuesday. “It's important to remember that and to be really thoughtful about how you’re bringing that to your employees.”
A big part of Salesforce’s recent mobility success, Simmons stressed, is having a point of view on how AI should be used — and being explicit about the skills employees need to use it that way. New research by Guild underscores why this matters. According to the “The Talent Resilience Index,” upskilling and reskilling can drive $8.5 trillion in extra revenue by 2030, whereas defaulting to external hires carries an average 28% salary premium and leaves value on the table.
“We know we can only move with this massive change that's happening if we help our people move with that change, too,” Simmons said. “We needed a way to think about it, to be able to speak about it as well, to help change that culture, because we know that's a huge part of what we do.”
How exactly did Salesforce do it? The company drove success through two linked moves: its Workforce Innovation Playbook and Career Connect, the company’s internal, AI-powered talent marketplace that helps employees find new career opportunities and growth within the company.
1. The Workforce Innovation Playbook
The 4Rs for a human + agent workforce
As part of Saleforce’s strategy, the company introduced its Workforce Innovation Playbook, a framework built on “4Rs” (redesign, reskill, redeploy, and rebalance) to guide leaders in building a human + agent workforce that’s agile, adaptable, and prepared for the future.
Redesign: Salesforce re-architected roles and workflows to integrate AI where it augments human work, shifted routine tasks to agents and elevated judgment-, relationship-, and creativity-heavy tasks to people.
Reskill: The company then equipped employees with the skills needed to guide, lead, and scale with agents. Salesforce identified the top 10 enterprise skills that workers need to be successful in a future with AI agents. These fall into three categories: human skills, agent skills, and business skills.
Redeploy: The organization then increased internal mobility by moving employees into high growth areas of the business like professional services, sales, and other roles within customer success. Salesforce reskilled and redeployed a team of support engineers through a six-week bootcamp and transitioned them into high-demand, forward-deployed engineer roles.
Rebalance: Finally, Salesforce orchestrated the right partnership between agents and humans to ensure each does what they do best; set quality, risk, and ethics guardrails; and tracked outcomes to refine partnership over time.
2. Career Connect
An internal marketplace that makes career growth visible and actionable.
The second prong of the strategy is a platform called Career Connect, which treats career growth as “more than finding the next job,” as Simmons put it. The platform brings learning, mentorship, stretch assignments and gigs, and internal roles into one place so employees can see — and act on — their options. Adoption has been strong, and the impact is measurable:
Career Connect, a fully opt-in tool, has achieved an 80% employee adoption rate;
Internal fill rates hit ~50%;
Career growth scores improved 8 points;
Employee confidence in their ability to grow a career at Salesforce jumped 20 points in the company’s internal survey after launch; and
Critical talent was successfully redeployed while maintaining workforce stability.
“We built it by listening to the barriers employees faced and investing in what they said they needed — skills, coaching, and visibility into the ‘jobs of the future’ — so the platform doesn’t just train people; it helps them use those skills to move,” Simmons said.
Closing thoughts
When asked to give advice to other learning-leader peers in the room, Simmons emphasized the importance of being “thoughtful” and “having a point of view.”
“Certainly that's been a big part of our success,” she said. “We really thought about [it] and are continuing to think about [it] and evolve.”
