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Masters of Scale

The Salesforce CFO who left to save lives

18 Dec 2025

Transcription

Chapter 1: What is the main topic discussed in this episode?

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Does it ever feel like you're paying for 20 platforms to do the job of what really should be just one? That's not software as a service or SaaS. It's SAD, software as a disservice. Replacing your stitched together tech stack with one platform for all your departments? Well, that's rippling.

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Rippling eliminates the bottlenecks and busy work of legacy tools and point solutions by uniting your global HR, IT, and spend teams on just one platform. And right now, you can get six months of Rippling free when you sign up at rippling.com slash scale. That's R-I-P-P-L-I-N-G dot com slash scale. Don't get sad, get Rippling. Terms and conditions apply.

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Got to the end of the call, and I agreed I would at least think about it. So the next week I'm thinking about it, and I came to the same conclusion. This is ridiculous. I am not going to do it. Because you're not— Crazy. Right. Yes, exactly. It was absolutely unprecedented. Amy Weaver had just been offered a new job, Chief Financial Officer of Salesforce.

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It took her totally by surprise, but the opportunity was too intriguing to pass up. Amy had already spent enough time at the iconic software company to know it'd be hard work, but hard work worth doing. How do we make it faster? How do we make it more efficient? How do we get rid of any of the bottlenecks? It's very hard to scale if you have a rickety platform.

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You really have to invest in having the right systems, the right processes in place. If you've got those, you can scale very, very quickly. You got to have incredible talent at every position. There are fires burning when you're going home. Can you believe it? Such an idiot. And then you go back to, this is totally going to be amazing. There are so many easy ways. I have no idea what to do.

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Sorry, we made a mistake. But you have to time it right. Oops. Working as a three-bedroom apartment. Stuff that just seems absolutely nut balls. Ten years later, we're like, well, that's just how you do it. We haven't made it just how you do it. This is Masters of Scale. I'm Jeff Berman, your host. This week on the show, we're talking with Amy Weaver.

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As someone who's had a pretty non-linear career myself, after all, it is not every former public defender who goes on to work at places like MySpace and the NFL and lead companies and host a podcast like Masters of Scale. I'm always drawn to others who've charted unconventional paths, and Amy's story is truly an extraordinary one.

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We reveal how Amy, a lawyer by training, zigzagged her way into the job of chief financial officer at Salesforce. We also dig into the latest challenge she's taken on. As I dove in and started learning more and more about direct relief, I realized that it's probably the largest, most efficient, most effective, and most impactful global humanitarian group that you may never have heard of.

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Amy is now the CEO of Direct Relief. You may not have heard of it, but you need to know what it is. It is an incredible humanitarian organization that distributes billions of dollars worth of medicine and supplies to people in need every single year. We'll talk more about that later in our conversation. Amy, welcome to Masters of Scale. Thank you, Jeff. I'm really excited to be here.

Chapter 2: What motivated Amy Weaver to leave Salesforce?

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And I was so earnest as a 12-year-old that I remember I actually sat down and made a list of who my cabinet would be. And I remember very distinctly that one of my best friends at that time, I decided she just wasn't there for vice president. And I gave her secretary of interior. I broke the news to her and she went skipping off.

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And when she went skipping off, I thought, I knew she wasn't vice presidential material. Yeah. What I didn't anticipate is that my career would take me to Salesforce, to being a CFO, and then now to being CEO of Director Life. Amy's first step away from the traditional law career she'd always imagined happened because of her love of travel.

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I got a call from Expedia, and they were looking for a securities lawyer. Expedia operated all over the world. It was a product that is simply my favorite thing in the world, which is travel. So I jumped over. It was a wonderful jump, but it was very hard. I remember I told my father on Father's Day, and...

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The entire day, he kind of looked like all he wanted for Father's Day was for me to say I was joking about going in-house. Why? I mean, it's not like you are leaving the law to go do, you know, some... Be a CFO or a... Or frankly, to go do some, you know, 12-person bootstrap startup where you're just like, I'm throwing away one career and I'm going to take a big shot.

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What was it where your dad wasn't like, this is awesome, good for you? You know, I think what was hard is we have so many lawyers in my family and they're all doing different things, but they're all very strictly within the law. Mm-hmm. And I remember my father kept asking me, but will you still be a lawyer? They really view law in the most lofty terms.

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There's something beautiful about it and about the profession. And I think he wanted to make sure he was still going to be part of that. And I'll tell you, many years later, I still feel like I'm part of that. I don't think I'll ever not identify as a lawyer. Yeah, I very much understand that feeling. So you were Expedia for how long? Five and a half years.

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Worked for a terrific general counsel, but I recognized I'd gotten very comfortable in that second seat. And I really realized I need to push myself and find that number one chair and see if I could do that. Where did you find that number one chair? It was a company called Univar. It was a 100-year-old Northwest company, and I was very committed to being in Washington State.

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So jumped and went over, loved being in the number one seat. But within one year, CEO who had recruited me left. Mm-hmm. And the new CEO decided to move the company to Illinois. Wow. It was one of those times in my life I remember waking up at 2 a.m. quite a bit and just feeling like I'd really done the research. I thought about this. I thought I was doing... everything right.

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And suddenly I felt like my career was just skidding and did not know what to do. Can we just pause for a second? Because I think this is an experience that so many of us feel. We have these moments where we just, we're waking up at two in the morning and going, I made a wrong turn. I just know it. I feel it in my body on a personal level. How did you deal with that?

Chapter 3: How did Amy transition from CFO to CEO of Direct Relief?

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We don't pay women less. Three weeks later, Mark went on an interview live and said, we would be investigating whether we had a gender pay discrepancy. We would publish anything we found and we would fix it. Wow. And I'll tell you, at that point, I was general counsel. And half of me as a woman was so excited about what we were doing.

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As general counsel, I remember thinking, I'm not so sure this is a good idea.

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Chapter 4: What is Direct Relief and what impact does it have?

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We had no idea what we were going to find and no idea what the scale was going to be in terms of trying to fix it. We're trained as lawyers not to ask a question we don't already know the answer to. Exactly, exactly. It was like, how about like a little digging in behind the scenes before we jump in? But it showed a few things. First, huge credit to Cindy and Layla for raising this.

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But Mark really makes decisions on where to go on that. And once he makes a decision, we are lined up and we're going to make it happen. Yeah. So we did dive in, we did a very deep study and we found out, no surprise really at the end, that there was a discrepancy and we fixed it. But one of the things we learned in that is that you can't do that once.

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So we ran the study again the next year and sure enough, we also found a gap. So we had to look at what was causing that, how is this repeating? And they've continued to do it every year. But I also think this really goes to something about gender pay and your expectations at the workforce.

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When people first started talking about the differences in gender pay, what I heard a lot was, look, it's because women don't ask for more pay. I mean, Bobby's in my office every week demanding more. And I always hated that argument. First, as a manager, the last thing I wanted were more Bobbies coming in my office and demanding more pay. Right.

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But second, you're putting the pressure on the person who has the least amount of information. So if Julie on your team thinks she might be underpaid, she doesn't know anyone else is being paid, and it's her job to fix it, is just the wrong approach. What you need is that the company... That has the information, needs to be using their data.

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They need to see what's going on and they need to fix it. And I think you can use that analogy for so much about what is going on in the workplace. Yeah. And that is both leading nationally, globally as a company that has innovation as one of its core values. Right. showing away, it's also doing what's right for your team, right?

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And frankly, to your point, for your leadership, for your managers who don't want people in their office every week, you're incentivizing wrong behavior. So let's go back to your Salesforce journey, because you're now the top lawyer at one of the top companies in America. You could have a wonderful and linear... path from there. Definitely not done the linear path. No.

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And it's one thing for general counsel or chief legal officer to jump to an operating role. It's another thing to become CFO. Yes. How does that happen? Very unusually. So at Salesforce, I had been there about seven years. And by this point, I was the chief legal officer. And it was 2020. And

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And we realized that our current CFO, Mark Hawkins, who's just a wonderful person, had indicated that he was thinking about retiring. So behind the scenes, I was working on a global search for a new CFO with Mark Benioff, our CEO and our audit chair. And one day, I remember Mark FaceTimed me out of the blue. I remember it very clearly because he was in Hawaii. It was his birthday.

Chapter 5: How does Amy's background influence her leadership style?

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And I remember thinking it was almost midnight on the East Coast, but I did it anyhow. And what she wanted to tell me about was how she moved from general counsel to North American CEO. And she said at Accenture, they knew she was hardworking. They knew she was bright. They knew that she knew Accenture inside out. But she said at Accenture, what gets you the credibility is can you sell?

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So she said she took the first six months and focused on showing everyone she could sell. Mm-hmm. And her advice to me was, find what is gonna give you the most credibility on the job and focus on that. So for me, I decided it was Wall Street. It was the relationships with the shareholders and our analyst community. So immediately started listening to her with our shareholders.

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We were still kind of coming out of the pandemic, so I was able to do this very quickly on Zoom. But I also started making sure I could speak the language of Wall Street. And I remember our investor relations team and our PR team really putting me through the paces, just throwing question after question.

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These days were just brutal as I was trying to memorize a million numbers, trying to learn the approach on this. I remember one day, Evan Goldstein, who was then leading in IR for us, throwing out a question. It was a pretty technical question financially. Mm-hmm. And I answered it and I knew it. And I was so proud of myself. I looked at Evan and he said, and I said, Evan, I got it right.

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And he said, yes, you got it right technically, but you didn't sound like a CFO. You didn't use the words a CFO would use. You didn't organize it. Do it again. And we would do it over and over until I had that comfort level and I knew I could go head to head with our analyst community.

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And not only was Julie's advice just game changing for me in terms of credibility, but investor relations and working with the analysts and working with our shareholders actually turned out to be one of my favorite things about the job. It's a great reminder that getting the substance right is only part of it. Yes.

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And having truth tellers on your team who, because I'm guessing Evan was reporting into you. He was, and he did not shy away from giving me that feedback. Which is a big deal because you could imagine a lot of people would be like, new boss, not sure I want to say this. So remarkable.

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Okay, Amy, you've got this stunning run at Salesforce, one of America's best-run companies, certainly shortlist for any number of extraordinary roles. You made another leap in this next phase of your career. So tell us about going to Direct Relief. I had an incredible experience at Salesforce and never really considered going to another company.

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It would be very hard to beat the experiences I had there, just the faith that Mark put into me and the opportunities he put in front of me. But particularly when I took the CFO role, I knew it was going to be an opportunity to learn, an opportunity to see more about how to run a company. But I really wanted to take those experiences and use them in a different way.

Chapter 6: What challenges did Amy face when moving to Direct Relief?

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Because I'm working with a group of people who are there every day because they care so much about the mission. And doing anything that might change that mission or change the focus on the people we serve is really scary. So I came in determined to listen.

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And that meeting with almost every single employee at the organization, meeting with our board of directors, each one individually, and then getting out into the field to meet our partners. So traveling down to the Santa Barbara Neighborhood Clinic to see what the needs were locally, traveling to Uganda and Ghana

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and being on the ground, all of that has been incredibly important in terms of gaining, I think, the trust and the credibility with the team. But the other part goes back to values. So I pulled together the top 12 executives at Direct Relief. We went offsite for a day. And I said, I wanna talk about where we're going. What is the next version of Direct Relief? What's the evolution?

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But before we do any of that, I wanna talk about what our values are. And we were off site for five hours and we spent the majority of that just trying to hammer out what do we believe our core values are. And I think if you tell people that you're starting with your values, any change that comes from that, they can trust that you're doing it for the right reasons going forward.

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I mean, I have to ask. I understand you don't rely on government dollars. You have never taken a dime of government funding. But we're in a moment where health care is politicized. Science is under attack, not just in the U.S., but this is happening globally. As you focus relentlessly on this profound mission and you are serving people all over the world and all over the U.S.,

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How are you navigating this? And I ask that question both as a leader of an organization with this profound mission, but also as a leader of humans who wake up and seemingly almost daily, there is something else to read about kind of the attack on the values of the work that they're doing at Direct Relief. And I'm not asking to be political here.

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I'm just I'm trying to understand as a leader how you manage through this. So the week I received my offer from Direct Relief was the week that USAID was defunded. And in a time period from that moment to the time I started the job, we watched budget cuts coming up at that point still being discussed to Medicaid. We saw PEPFAR cuts.

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And there were definitely times when I asked myself, and certainly a lot of other people asking me, why would you move into humanitarian aid at this time? This is going to be the most difficult time. And really thought about that. I also think this is the most important time to be doing it and the opportunity to have the most impact. Direct Relief is incredibly well positioned.

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We don't take any government funding. So we're very, very solid. We have wonderful relationships with both the biotech and pharmaceutical companies, as well as organizations on the ground throughout the world. That gives us the opportunity to step up. And I think right now it's all about meeting the moment. You know, I talk to people every day who just don't know what to do.

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