00:00:00 · Reggie Marable, Guillaume Moubeche
[00:00:00] S0: I believe success is a winding road. It's never straight. My whole life is built on relationships, taking calculated risk, failing. When I say, handle the use case on their own, autonomously, with no human intervention. We start off with, like, crazy aspirational goals. And I'll I'll quote Ali, Muhammad Ali, if your dreams don't scare you, they're not big enough. I think failure is a great way to learn more about yourself and to reinvent yourself and and figure out what you can do to become better and stronger. [00:00:28] S1: Today on BILLIONS, I'm sitting down with Reggie Marable, a high performer at every stage of his career. From linebacker in the Canadian Football League to one of the most respected operators in enterprise software. He joined Salesforce as a first line manager, mentored 200 plus people, wrote a book, rose to head of sales for Slack North America, and then walked away from all of it to become employee number 23 at a startup nobody had heard of. That startup is Sierra, founded by Salesforce former co CEO and the creator of Gmail. 100,000,000 in annual recurring revenue in seven quarters, now valued at $10,000,000,000. And at the center of all of it is a bet that should terrify every SaaS company on the planet. Customers only pay if the AI actually solve their problem. Reggie, great to have you here. It's great to [00:01:20] S0: be here. Really excited to be here today, g. Thanks for having me.
00:01:20 · Reggie Marable, Guillaume Moubeche
[00:01:20] S0: be here. Really excited to be here today, g. Thanks for having me. [00:01:23] S1: Yeah. I'm super excited. I know you're, like, a a very energetic sales leader, but you've had, like, a a long career to transform into who you are right now, and you've done various different things among your career. So is this, like, something that's natural, like, for you to kind of, like, change position all along your career, and how exactly did you adapt to the different challenges that you faced?
00:01:49 · Reggie Marable
[00:01:49] S0: No. It's it's... I believe success is a winding road. It's never straight. And my my whole life is built on relationships, taking calculated risk, and failing. So I... When I when I graduated from college, I wanted to play professional football, and I went to a small school. Shout out to Morehouse College, which is one of the greatest schools in the world. And I knew if I didn't try to play professional football, I'd regret it. So I played in the Canadian Football League for a year, quickly realized I was never gonna make it to the NFL, and I was wasting my time. I needed to get a job. Came back to Atlanta and Sprint at the time was hiring college students for entry level customer service roles. So I I started my career in the telecom industry in a call center in customer service. So when you got mad at Sprint, you called in, I was the person that answered the phone. Quickly realized the money in the career progression was in sales. And especially, being a minority, there's no subjectivity in sales. It's either can you produce or can you not? And I love this quote from Jay Z says, men lie, women lie, numbers don't. So I just forged my way through, the telecom industry in sales and when I was a direct direct seller. Then I was a first line, second line, third line leader. Then I ran Sprint's international wholesale business. Then I left there to become a CRO of a mid sized media company. And at the time, gee, I had a big ego, smartest guy in the room, had all the answers, came with my playbook, and it completely failed, got fired after my first year. So I was unemployed for six months. So, and I wanted to get in the technology industry and I've always used the Salesforce product and I had a friend, his name was Ryan Radding. He was a senior leader at Salesforce and he was like, hey man, this is a rocket ship. You should come over here, but no one's going to hire you as a senior leader. You're going have to come in as a first line sales leader if you want to join this company. So I had to swallow my pride and then because I had failed and I had gotten fired, I had to really reinvent myself and think about what real leadership means and it's putting people first, serving leadership. So when I joined Salesforce ten years ago as a first line sales leader, I approached it with humility and my career flourished.
00:03:56 · Reggie Marable, Guillaume Moubeche
So if you would have told me when I graduated from college that I wasn't gonna be a professional football player, and that I'd end up in the technology industry and sales, I wouldn't have believed you. [00:04:08] S1: Nice. I love all these stories. And, you know, when you're at that stage where, you know, like you get fired as a CRO and you have to go back to, you know, like, a frontline sales. Like, goes through your mind at the time? Like, do you feel like it's gonna be a learning experience? Do you feel like it's something brand new? Like, how do you kind of, like, change the mindset?
00:04:08 · Guillaume Moubeche, Reggie Marable
[00:04:08] S1: Nice. I love all these stories. And, you know, when you're at that stage where, you know, like you get fired as a CRO and you have to go back to, you know, like, a frontline sales. Like, goes through your mind at the time? Like, do you feel like it's gonna be a learning experience? Do you feel like it's something brand new? Like, how do you kind of, like, change the mindset? [00:04:30] S0: At the time, it was the worst thing that ever happened to me in my life. Like, I remember sitting in my car crying because I have responsibilities, man. I have a daughter, and I have a son, and my wife doesn't work outside the home. And they look up to me like I'm responsible for them financially. So I was like, man, I got fired. I have no job. Like, I have no, like, belonging. So this quote that I remember from Albert Einstein, like, adversity introduces a man to oneself. So I just figured out what what can I do differently? How do I reinvent myself? How do I position myself so I'm never ever in this situation again? And I started to like deconstruct what I was doing as a leader and why I got failed, like why I got fired. And it was really just my my leadership style, man. You can't be the smartest guy in the room. You don't have all the answers. You have to rely on other people. You gotta put people first. It's not about you. But I will tell you, man, like, it's like the most humbling thing that you'll ever experience when you get fired from a job or you fail at something. So...
00:04:30 · Reggie Marable, Guillaume Moubeche
[00:04:30] S0: At the time, it was the worst thing that ever happened to me in my life. Like, I remember sitting in my car crying because I have responsibilities, man. I have a daughter, and I have a son, and my wife doesn't work outside the home. And they look up to me like I'm responsible for them financially. So I was like, man, I got fired. I have no job. Like, I have no, like, belonging. So this quote that I remember from Albert Einstein, like, adversity introduces a man to oneself. So I just figured out what what can I do differently? How do I reinvent myself? How do I position myself so I'm never ever in this situation again? And I started to like deconstruct what I was doing as a leader and why I got failed, like why I got fired. And it was really just my my leadership style, man. You can't be the smartest guy in the room. You don't have all the answers. You have to rely on other people. You gotta put people first. It's not about you. But I will tell you, man, like, it's like the most humbling thing that you'll ever experience when you get fired from a job or you fail at something. So... [00:05:34] S1: Yeah. I love that. I think this is something European can can learn from because, obviously, like, it's not something we talk too much about, but I think you're a great example of someone, you know, who faced adversity and make, you know, amazing things afterwards. So what what would you say were, like, your main or key learnings at at Salesforce and more specifically at at Slack?