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In this episode of Medley Moments, Edith Cooper speaks with Robin Washington, President and Chief Operating and Financial Officer at Salesforce, about leadership development, navigating organizational change, and building resilience through discomfort. Drawing on nearly 40 years of experience across finance and technology, Robin shares actionable insights for senior leaders on staying grounded in fast-moving environments.
From making bold career pivots to leading Salesforce through one of the most disruptive technological shifts of our time, she shares the leadership mindsets that have shaped her path including operational clarity, continuous learning, and people-first leadership. Robin also shares how Salesforce is applying these principles at scale: the company’s new Agentic AI platform recently surpassed 1 million conversations and now autonomously resolves 85% of customer service queries, signaling a powerful shift in how AI and human teams can work together.
This Q&A is a curated summary of their full conversation.
Q: Robin, what are the key moments or experiences that have shaped your leadership journey?
A: As I think about this, I’m starting to feel a bit dated because I added up the years and I’m approaching about 40 years of being on this journey.
If I zoom out, I’d say what’s been core for me is having a natural curiosity to learn and understand. I’m a continuous learner—I can learn from everyone and everything around me. I’ve thrived in organizations where the pace of change is fast and you’re forced to reinvent yourself.
One thing I’ve learned is how to push myself outside of my comfort zone. I’ve commonly used the phrase:
“Get comfortable being uncomfortable.”
Those moments—where the outcome isn’t clear—have consistently been where I’ve grown the most.
Q: You’ve taken unconventional career paths—tech to biotech, finance to operations. Were there ever moments you doubted yourself?
A: Definitely. That voice in your head? It’s real. My biggest critic is me. But when I go back to my fundamentals, even as a child, I had parents who really instilled in me that I could do anything if I was willing to work hard enough. And sometimes working hard is also working smart: asking questions, surrounding yourself with people who can help, and being a student of the world.
It’s also about remembering how you’re going to feel on the other side of it. You stretch yourself, you grow—and when you see that cycle repeat enough times, you trust it.
“Can do, will try.” That’s been my philosophy.
Q: Salesforce is in the front row of the AI revolution. What’s most exciting for you about the future of how we work, connect, and thrive?
A: This is one of the most transformative moments in the history of technology. The AI revolution is a digital labor revolution. Our team says this all the time—we're probably the last generation to work with all human workforces. Every job, team, and company is going to employ AI agents working alongside us.
At Salesforce, we’ve added our Agentic AI platform to our help site, and we just hit 1 million agent conversations. Right now, agents are autonomously resolving 85% of all customer queries. That’s huge.
But it’s more than a technology shift—it’s cultural, operational, and organizational. AI can’t just come out of the office of the CIO. It requires cross-functional buy-in, the right tone at the top, and a commitment to upskilling your people. Even I was training on Sunday, earning Trailblazer badges!
Q: How should people—especially those early or mid-career—think about differentiating themselves in this new era of work?
A: I think the most important thing you can do is figure out how you learn. Make sure you're in environments that allow for continuous learning. If you’re picking a first job, look for roles that let you rotate, try different things.
Honestly, in the first 10 years of your career, you're going to learn more about what you don’t want to do than what you want to do. So being open and receptive to different experiences is key.
Also, be balanced. I’m a finance person—but I love art, I love fashion. Be a student of the world. That curiosity and openness are what’s going to set you apart.
Q: We have a lot in common but we also have a lot of things that are different—this is the power of diverse perspectives. Why do you think this is important as a leader?
A: I call it constructive friction. It’s okay to debate. At some point we’re going to make a decision—but that decision needs to be our decision. That doesn’t mean we’re 100% aligned, but effective leaders have explained the why.
“Technology is never going to take that away… learning how to articulate your viewpoint, sometimes without emotion, sometimes with—it’s all a core skill.”
I think about my learning experience as I went through my executive MBA. They purposely put us in groups with people from very different backgrounds because learning how to work together, learning how to articulate your viewpoint—those are core skills. I love what Medley does from that perspective.
Q: What role have sponsorship and community played in your journey—and how are you building that for others through initiatives like Black Women on Boards?
A: I talk about having a personal board of directors. One of mine is a friend I’ve known since sixth grade. We’re on different paths, but she’s someone I trust deeply. Sponsorship isn’t always visible—but I know there were leaders who took the time to see me, support me, and remind me I mattered.
Sometimes it’s as simple as spending time with someone, like Virginia Walker did for me early in my career. She was CFO of a biotech company. She invited me into her office and spent two hours with me. That changed everything.
In 2020, I co-founded Black Women on Boards. It started as a Zoom call and turned into a real community. We help coach women through the board journey, from bios to interviews. But more than that, we help women build their own personal boards—with others who look like them because sometimes candidly it can still be very lonely.
“Lifting others up is not a choice—it’s a responsibility.” That’s how I see it.
Q: Any final thoughts on reflections?
A: When you step out of your own aura, you see the world more clearly. I've always been a person to ask: how can I help make the world a better place? It’s important to me as a daughter, as a mother, as a partner to my husband, as a friend. I think shaping the future is everyone’s responsibility. I want to give my time and perspective back in the same way people did for me along the way.
Missed the live conversation? You can watch the full episode here. And if you’re not already following along, we share upcoming Medley Moments each month on our LinkedIn page here.
