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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this powerful episode, Amy Weaver shares her unconventional journey from lawyer to CFO at Salesforce to CEO of Direct Relief, one of the world's largest humanitarian organizations. (05:30) Amy discusses how she navigated career transitions, including the unprecedented move from Chief Legal Officer to CFO at Salesforce. (20:10) The conversation explores her current role leading Direct Relief, which provided nearly $2 billion in medical aid across 92 countries in the past year. (27:21) Amy reveals how she's applying scale lessons from Salesforce to amplify humanitarian impact globally.
Amy Weaver is the CEO of Direct Relief, a global humanitarian organization that distributes billions of dollars in medical aid annually. She previously served as Chief Financial Officer and Chief Legal Officer at Salesforce, where she was part of groundbreaking initiatives including gender pay equity efforts. Amy comes from a family of lawyers with over 15 members in the legal profession, including her grandfather who served on the Washington State Supreme Court.
Jeff Berman is the host of Masters of Scale and has had a nonlinear career himself, having worked as a public defender before moving to companies like Myspace and the NFL. He brings a unique perspective to interviewing leaders who have taken unconventional paths to success.
Amy's transition from Chief Legal Officer to CFO at Salesforce was absolutely unprecedented in Fortune 500 companies. (20:15) Despite feeling unqualified and recognizing the public scrutiny she'd face, she chose to embrace the challenge. Her friend Brett Taylor's advice was transformative: "You're not qualified to be the traditional CPA CFO, but that's not what I'm looking for. I want you to take the job and make it yours." This reframed her thinking from comparison to creation, allowing her to leverage her unique skills rather than trying to fit a traditional mold.
When Amy joined Direct Relief as CEO, she followed a leader who had been there for 24 years. (33:38) Rather than immediately implementing changes, she spent extensive time listening - meeting with every employee individually, each board member separately, and traveling to field locations in Uganda and Ghana. She recognized that people join humanitarian organizations because they deeply care about the mission, and any perceived threat to that mission creates fear. This listening approach built the trust and credibility necessary for meaningful change.
Salesforce's 1-1-1 program demonstrates the power of starting small with scalable impact. (11:21) When Mark Benioff and Parker Harris adopted this model, the equity was worthless, they had four employees, and no product. Twenty-six years later, it has generated hundreds of millions of dollars in donations, millions of employee volunteer hours, and serves 70,000 nonprofits. Amy emphasizes that you start small but keep at it consistently - that's how you scale good works over time.
At Salesforce, Amy learned that expecting women to ask for equal pay puts pressure on the person with the least information. (17:19) The company that has all the salary data should be using that information to identify and fix disparities. This principle extends beyond gender pay to workplace equity broadly - leaders should use their data and authority to create fairness rather than placing the burden on those who lack information and power.
Amy's key insight from Salesforce is that "it's very hard to scale if you have a rickety platform." (32:27) You must invest in the right systems and processes first. At Direct Relief, she's focusing on technology, data capabilities, and end-to-end process optimization - from the first pharmaceutical company call to medicine arriving in Uganda. Strong platforms and optimizing for speed are two of the most important areas for scaling impact effectively.