Episode 5 - Steven Broudy
Key Learnings From An Army Special Ops Sniper Turned Tech Sales Exec
4 Key Learnings – Steven Broudy
About this Episode
From the battlefield to the boardroom, Steven Broudy has been there done that. Steven served as an Army Special Ops Sniper for 6 years before building the Inside Sales team at Mulesoft through IPO and eventual sale to Salesforce for $6.5 billion dollars. Regarded as one of the top up and coming sales leaders in the industry by Sales Hacker and other notable sales resources, Steven has put his learnings from the Army to the test. His story is as inspiring as it is action-packed, full of transferable knowledge.
“I think the first thing it instilled in me is the value of failure and when you move into any sort of sales role inevitably, you’re not going to win them all. It’s what you do when you’re faced with failure and how you view that failure either as something that was out of your control or as something that’s well within your control and you could have done something differently and, more than anything, viewing it as a growth opportunity is just an incredible mindset to adopt.”
More on – Steven
Steven Broudy (LinkedIn, Twitter) has an extensive track record in performance leadership. He spent over five years in Army Special Operations, serving in 2nd Ranger Battalion as a Special Operations Sniper Team Leader. Following his military service, Broudy ran the Business Development team for an HR analytics startup, Evolv, Inc. (now a part of Cornerstone OnDemand) before joining MuleSoft, a company that helps organizations change and innovate faster by making it easy to connect their applications, data, and devices. Broudy spoke with us about hiring and onboarding sales teams, how to manage and develop performance, using data to drive coaching, setting audacious goals, prioritizing ruthlessly, and more.
Connect with Steven
- Leading Change by John Kotter
Welcome to another episode of The Career Hacking Podcast. On today’s show, we have Steven Broudy, special ops sniper turned inside sales leader at a company that just sold to Salesforce for 6.5 billion dollars.
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Super exciting show for me today because we have my good friend Steven Broudy on. I had the pleasure of getting to know Steven as a friend and colleague over the past few years and he’s one of the most interesting stories out there. He went from living in San Francisco to somehow becoming an army special ops sniper for six years. After that, he landed as a sales executive and inside sales leader at a company called MuleSoft, that just sold to Salesforce for 6.5 billion dollars. Steven is one of the most self-aware, self-reflective people I ever met so on top of having a great story, he’s also somebody who can impart a lot of wisdom for us today. Welcome to the show, Steven. Thanks for coming on. Welcome and thanks for joining us, Steven.
Thank you. Hey, I’m super excited to be a part of this. Thanks for having me.
Yeah. You had an incredible story going from sniper to sales, 65 people under you, doubling your headcount this year, recently IPO-ed, pretty incredible journey. Why don’t you tell us how the hell did you get started as a special ops sniper and how did that turn into a head of sales at a pre-IPO [inaudible 00:02:28] currently post-IPO?
Yeah. I think that’s what we term in tech a pivot, right? The long story I’m happy to share, the short story is I ended up where I’m at today and, frankly, in army special operations absolutely by accident.
The story goes that I was at UC Santa Barbara and for those of you who don’t know UC Santa Barbara, it’s not what one would typically associate with a school that generates a large volume of army special operations snipers, it’s more of a school that generates a lot of people who are really good at surfing and, frankly, sales, actually. Anyhow, my sophomore year at college, I thought I was taking a 6:00 a.m. workout class at UC Santa Barbara and I probably should have known that there is no 6:00 a.m. workout classes at UC Santa Barbara, it was actually an Army ROTC class. Now, for those of you who are familiar with Army ROTC, the way army ROTC typically works, at least this is my experience at UC Santa Barbara, was 50% of the people there were probably a little bit meh, 25% of the people were pretty good people and 25% of the people were also really incredible people. This was right early on, when we had just kicked off a couple of wars in Iraq and Afghanistan.
Frankly, what was interesting to me was that at 19 years old, a lot of these kids like me knew exactly what they’re going to be doing for the next four years, five years, six years, whatever the case was. The other thing that was really appealing about army ROTC apart from the fact that they were willing to pay for my college was the fact that these kids in this program knew that they were going to be doing the most difficult thing they could possibly do. I sort of hung around, did the workout classes with them, took some military history classes and, frankly, I realize like, hey, if I really want to do the most difficult thing possible, this is the best path for me. On top of that, frankly, I was just genuinely curious what it will be like to go to war. I know that sounds like a strange, almost morbid curiosity but one of my favorite books growing up had been Black Hawk Down and here I was working with one of the cadre who had literally been on one of the chalks in Mogadishu that has gone on that fated day.
I ended up getting the commission I wanted. The way ROTC works is if you’re in the top X percent of your class, you get the branch of choice you want. In the army, there’s army aviation where you go and fly helicopters, there’s the field artillery corner where you go and shoot really big cannons at stuff that you can’t see and then there’s the army infantry which is considered the most prestigious assignment you can get as an officer because it gives you the highest likelihood of actually seeing combat. Now, knowing what I know now, most infantry officers and, frankly, most infantry units don’t end up really truly seeing combat. They might go out on patrol to go and shake hands with some shake in some small town in Afghanistan and someone takes potshots at them or they might be out in a convoy to go and visit the local Iraqi police chief and they get blown up but they’re not going out and doing direct action raids like a special operations unit will be.
Anyhow, I was still excited that I had landed a commission as an infantry officer. The way ROTC works is you got all these colleges graduating at different times and UC Santa Barbara, I believe, was maybe not the last but certainly one of the last schools to graduate. After getting word that I had gotten the branch that I wanted, I immediately got notified that the army had over-slotted all of the infantry officer slots and that instead of being an infantry officer, I was going to be a supply officer.
Now, no offense to anyone who is a supply officer, I think it’s a very prestigious career but I did not feel like being 22 years old in the midst of two wars pushing a desk. I was a little bit disheartened but I decided that I was going to fight it so I wrote an appeal to Army Cadet Command and they not only, actually, approved my appeal, they actually circulated it as an example of how to write a really good appeal. I ended up getting excited again because I thought I was getting the branch of my choice and they came back six weeks later and said, “You know what, sorry, you’re still going to be a supply officer. By the way, your first duty assignment is in Alaska.”
At that point, I decided to go and seek advice from my trusted set of advisers and I had been lucky, like I said, to work with some of the cadre in the program who were non-commissioned officers who had both been in the 75th Ranger Regiment, one had been in 3rd Ranger Battalion in Mogadishu and Panama and one had been in 2nd Ranger Battalion and coincidentally, actually, ended his career in 2nd Ranger Battalion as the sniper section leader so things really came full circle for me. Both of them said, “Look, if you honestly want to go to war and do what you think you do when you go to war, then being an officer is probably not the right approach. Frankly, ranger regiment does what you think you want to do and if you’re an officer, you have to wait four years to try out for ranger regiment. What you can do is decline your commission as an officer and enlist with a contract to go and assess for ranger regiment.” Much to the chagrin of the head of our ROTC program, I notified him that that’s what I wanted to do.
Now, I thought it’ll be easy but it actually ended up taking something like six months for the appeal of my decision to actually get approved. It was the best decision I ever made. I can honestly say that the safe bet would have been to take my commission as an officer, it’s an incredibly prestigious career, maybe I would have gotten to see a little bit of action, maybe not, I certainly would have grown as a leader but, frankly, I knew that I wouldn’t be pushed and I knew that I really wouldn’t be forced to be the best version of myself just to be amongst my set of respective peers.
You did the hardest thing you could do early in your career, then you stood up and appealed a decision to your superiors while you were still pretty junior, then you sought advice from your advisers and then you made the hard decision which was the best decision but it was not an easy decision, you could have gone the easy path. I picked up on at least four things here throughout this part of the story and I’m going to let you keep going but I just wanted to point that out.
Yeah. Here’s another one, it’s one thing to appeal your decision to go and do something difficult but the reality was getting into ranger regiment is one of the most excruciatingly grueling and brutal selection processes probably on the planet.
A lot of people know about the Navy SEALs and how you go through BUD/S and then they have this sort of hell week thing where they just destroy you for a week. I’ve never been to BUD/S and I have the utmost respect for anyone in the SEAL teams but the thing about BUD/S is you learn stuff like you learn how to dive, you learn how to do combat maneuvers. In our selection which at the time was called the Ranger Indoctrination Program and … Jesus Christ, we got to edit that part. Our selection process was called the Ranger Indoctrination Program and the acronym was actually RIP which was very fitting because you might start with 360 people in the pipeline and 60 make it all the way through to the end. What that naturally dictates is only the best of the best make it out and that everyone who makes it into the unit genuinely wants to be there.
It was absolutely brutal, it was essentially just a process solely designed to make people quit. There was no focus on, actually, really teaching you anything. Truth be told, at the time, I thought it was the stupidest thing possible and if I would have done anything in my power to just fast-forward through to the end but the amount of mental fortitude and grit and tenacity that that breeds in you if you make it through that selection program is second to none. What’s interesting is I honestly can remember just trudging up the mountains in Afghanistan in the middle of the night or literally running up and down a hill as we’re engaged with the enemy like time and time again just absolutely gutted and thinking to myself, “Well, hey, at least this isn’t as hard as RIP.”
How did that you get you into the immediately next phase of your career which was becoming a sniper?
Yeah. The way it works in ranger regiment is, first of all, you go through the selection process and, like I said, they don’t teach you anything, they expect that they’ll be capable of training you on everything you need to do in the six months prior to each deployment that you go on. Because at the time we’re on the six-month deployment cycle where you’d go back to the rear for six, seven months in training, then you’d go and deploy for a period of time and that was just a constant cycle. I got back to ranger regiment and the way it works is when you’re a new guy, there’s absolutely nothing worse than that. It’s actually, frankly, a little bit worse than being in RIP but the volume of information that you learn and the rate and pace at which you’re learning that is incredible and that’s really a function of the incredible leadership that that unit breeds.
Anyhow, everyone has to do time “on the line”, right? To give a little more context, in the global war on terror, the ranger regiment which is considered the army’s premier special operations direct action raid unit, our job was essentially to “kill or capture”, really, bad dudes wherever they were, wherever they happen to be which is typically at home. Everyone goes through a period of time where they’re on the line and being on the line means you’re kicking their door down in the middle of the night and get them out of bed. You’re constantly going through this process of doing psychological evaluations and reevaluations to make sure your head is in the right place. At a certain point, I took a psych battery and I got called in by the battalion psychologist and he said, “Hey, just a heads up, you’re going to sniper section.” I sort of looked at him and I was like, “What? What are you talking about?” I think it was my third deployment. He said, “Yeah. Here’s, basically, your answers and here’s the answer sheet for what the profile of a sniper should look like and I think you’re perfect.”
The funny thing is there’s a lot of guys who are really eager to go and join sniper section in ranger regiment, it’s largely because you tend to be the first person to climb the roof of the objective, you get to weed out on all of the infiltrations, it’s a really really phenomenal place to be and there’s a ton of autonomy in that role. I actually really was adamant that I didn’t want to go, I wanted to stay with the team that I had on the line. Again, this was absolutely not a choice I had but it ended up being the best decision possible because when you take a kid who grew up in San Francisco and had never fired a sniper rifle, let alone any rifle until I joined the military and say, “Hey, you need to learn tomorrow how to shoot this thing,” it really forces you to adopt a growth mindset and really adopt that beginner’s mind.
What’s incredible is when you go to sniper school in the army, what you realize is the only thing you’re doing different than the guys who are on the line when it comes to shooting a sniper rifle, apart from reading wind and adjusting your sight, all you’re really doing is focusing more on fundamentals and executing better on those core fundamentals. It’s pretty incredible how that’s just been so incredibly applicable to just other parts of my life. There’s this Bill Walsh quote and I’m going to butcher it but, essentially, the gist of what he said is if you focus on the fundamentals, the score takes care of itself and I genuinely believe that has been a lesson that stuck with me throughout my career.
You went from sniper to director of inside sales. MuleSoft, how many were they when you join the company?
300, something like that.
What are they now?
Yeah. You’re hiring in San Francisco, Chicago, Atlanta, New York City so you’ve grown out of the original headquarters. You’ve been there for four years, obviously stacked up quite a team, so what are some of the things you learned from and maybe even stories from the front end of your career, you know, being a sniper, being in the army that you’re applying in your current role?
Yeah. I talked a lot about this idea of the growth mindset. I certainly had to adopt that moving into sniper section. Earlier in my career, when I [inaudible 00:19:03], I was the honor graduate. I don’t know how, it was probably because so many people graduated that there was a limited pool to select from. When we got to 2nd Ranger Battalion, we basically had all these squad leaders line us up. I was 6’3″, 235 pounds and the honor graduate and my squad leader is like, “I want that guy because I need a guy who can carry the SAW.” We have this weapon Mark 46 but it’s essentially a special operators variant of the Mark 249 which is a belt-fed machine gun. One man carries it and you end up typically carrying seven to 1,000 rounds and it’s really heavy and it’s also really awesome, quite possibly the coolest weapon ever made.
He handed it to me and I was like, “What the fuck is this thing?” Pardon my French. He’s like, “Hey, learn how to use it.” What I didn’t know at the time was he had handed me a broken weapon, frankly, he didn’t know it at the time. I soon found out because the first day of training, basically, every five rounds, and by the way, five rounds might sound like a lot but not when you’re feeding off a 50 to 200 round belt, every five rounds my weapon would jam. There’s a procedure for clearing it and I still remember it to this day like the back of my hand. I had to because the feeder pawl, I came to find out later, was actually broken. What that forced me to do was become incredibly adept at clearing jams with my weapon to the point where I could do it blindfolded in the dark faster than anyone in 2nd Ranger Battalion could do with their eyes open.
I remember, literally, the week before we deployed, my squad leader who, now, by this time … because he’d absolutely just decimated me for constantly having a weapon that went down, by this time I hated the guy, I couldn’t stand him. I had the utmost respect for him but he was like the daddy you can never please, he was just a horrible horrible person to spend a ton of time around but just an amazing leader unto his own right. Anyway, he pulled my weapon and he flipped it open and he’s like, “Oh, hey, your feeder pawl is broken,” and he went to the armor and they fixed it and lo and behold the thing worked perfectly. What’s funny is I was, at that time, essentially the best Mark 46 gunner in all of 2nd Ranger Battalion because I had been handed and dealt such a terrible hand.
I had an option at that point, I could have, basically, been really resentful and externalize blame or I could have seen it as a massive growth opportunity. Frankly, I think at first I was just pretty pissed but I immediately realize the value that having been handed such a terrible hand had done for me. It’d actually been a massive opportunity for me to grow and to learn how to be as effective as humanly possible and as [inaudible 00:22:37] humanly possible with this weapon and I really ended up reaping the rewards of that.
I think the first thing it instilled in me is the value of failure and when you move into any sort of sales role inevitably, you’re not going to win them all. It’s what you do when you’re faced with failure and how you view that failure either as something that was out of your control or as something that’s well within your control and you could have done something differently and, more than anything, viewing it as a growth opportunity is just an incredible mindset to adopt. There’s a great book Mindset: The New Psychology of Success, I believe that’s the full title, it’s incredible. I actually send it to every new hire that we make.
If you want to see what exemplifies the difference between you and others and your mindset coming from this background of discipline, just take a look at Steven’s LinkedIn profile, you know, where most people will list their own attributes or numbers or other things, basically, the job description for people he’s hiring. It’s a very team-oriented approach. Even the wording you use on this, committed to excellence, believes that good enough is not good enough, strives to embody excellence in each and every engagement with prospects and customers, driven to win, gravitates towards work where there is an opportunity to compete and achieve, rises to the challenge, gritty, coachable, growth-oriented, I won’t go into all that but you can tell how much your previous experience in a discipline, competitive, growth-oriented environment has shaped and molded your career from that point on even in a completely different environment of an inside sales software company in Silicon Valley compared to where you were before, in the desert somewhere in the Middle East.
It’s pretty incredible how you’re able to take a lot of the learnings from the front end of your career which is completely different in the second act, let’s say, in your career which is completely different but has a lot of the same core themes. What about from a management standpoint, are there any stories that you have or key lessons that you’ve learned in terms of managing a team whether it was managing up or managing down in your organization as a sniper or in the army compared to now?
Yeah. I think two key lessons still stand out to me. One, it’s so critically important to focus as a leader on making yourself obsolete. I say that because in ranger regiment, we could be doing a [inaudible 00:25:51] and we’re moving to an objective and we could be trudging through the hill and suddenly someone steps on an IED and you lost half the unit and you’re now in charge of the entire platoon. Now, the way we operated in ranger regiment was the expectation is you’re capable of doing the job two levels above yours. What’s amazing in hypergrowth company is how many opportunities there are for growth and because of that, you might have your leader go and move elsewhere in the organization and suddenly you’re in charge. It’s happened to multiple people on the team.
I’m actually moving into this global business operations role and the transition has actually been really easy for the leaders that are stepping into my role because, frankly, I’ve been so focused on making myself obsolete that they’re absolutely unequivocally ready and they’re probably going to be a hell of a lot better than I am, frankly. I think that absolutely stuck out for me as an operating mantra as the leader that I’ve still carried through. I know I had another one and I’m totally spacing. The other piece, let’s see, give me a second here.
Well, I just want to go into that for a second. Delegating is one of the most important things you can learn in your career, the earlier the better because it’s something that’s so hard to do. I see this with the people I manage all the time that have trouble delegating and they’re worried about giving up that control. It’s something you learn with experience, it’s not something that you know how to do, it’s something you learn with experience, that there are plenty of times in your career where you’ll get overwhelmed and you’ll realize, wow, I should have outsourced this, I should have delegated this, this should be somebody else’s responsibility, why am I still doing this, not only can I find somebody better at this individual test that can do it but it’s not core to what I’m doing right now, I need to be able to do a better job of moving this off my plate and trusting somebody else to manage it.
Those things come with experience, we’ve all been on a team project and I don’t know who you were in the group and I’m not going to say who I was in the group. When you’ve done the team projects in high school and there’s a five-person group and maybe three people are doing the heavy lifting and the other two are just coasting by but once you get into the workforce, the cream rises to the top and there’s no room for coasting by. I think if you’re in a work environment and, hopefully, you’re at a company where you can trust the other people around you, you have to delegate. If you’re running your own business, the only people you should be hiring are the people you can trust to pick up the slack or to do those things better than you do and that’s exactly when you know time to start hiring out when it’s like, “Oh, why am I doing this? One, I’m not that great at it. Two, if not core to what I’m doing, I could easily hire somebody for less than my time’s worth to do it for me.”
I use Fiverr, Upwork, we use virtual assistance in the Philippines and then we try and hire really competent people who can self-start. They don’t even need me to say at some point, “Hey, I need you to take this off my plate,” they can see it with experience once they’ve been working with us for a little while and then, “Oh, hey, I’m really good at that,” they raise their hand. Those are the type of people you want to hire. Have you thought of the second thing yet?
Yeah. I did. I think you absolutely hit the nail on the head there on a lot of fronts. I think the second thing that I realize and it’s so absolutely relevant whether you’re in an army special operations unit or at a hypergrowth company like MuleSoft, in many ways, our biggest challenge is just identifying enough A players in a very noisy market to be able keep up with the demands in the market. I think the lesson that is applicable across both of those domains is that if you do one thing well in order to essentially guarantee your success, you need to ensure that assessing and selecting the best people possible is your number one priority as a leader. I say that because when you only bring aboard the best of the best, you can actually trust that they’re capable of executing.
Stanley McChrystal who was the commander of 2nd Ranger Battalion and then he was the commander of JSOC and then he commanded, I believe, the wars in Iraq and Afghanistan, he wrote this incredible book Team of Teams that really synthesized how the special operations community delegates and empowers its leaders to lead. Essentially, what he said is if you share the maximum amount of information, what he called a shared consciousness, and he did this, by the way, by having a daily video conference with every interoperating agency that we were working with and you might have 1,200 people on a call but he was sharing the maximum amount of information possible. When you do that and you very clearly articulate your intent, you can actually empower people to go and execute at a level at or above what one could possibly be expected to deliver.
You would have these ranger commanders who were running whole feeders within Afghanistan as the taskforce commander and because they had been given the maximum amount of information possible and empowered to go and execute, the fact was while one might expect that when you do something like that, you’re going to get 70% of what you expect or would get if you did something yourself back, you end up typically getting 120% of what you could have possibly expected delivered. I think that mindset is really really incredible.
I think the other thing that I learned is the value of really just creating an environment where radical candor can thrive. Radical candor, you know, there’s a great book by Kim Scott if you ever want to read it called Radical Candor. Essentially, the premise is that as long as you have built up a level of trust and you demonstrate that you care about someone, you can be as direct as possible with them and that direct feedback is incredibly valuable. Direct and frequent feedback is really an essential ingredient for ensuring that someone has the opportunity to grow.
Now, it’s difficult to create in an environment where … In army special operations, it’s like the trust is taken for granted. I live with these guys, I literally go into some of the most dangerous places on the planet pursuing some of the most dangerous people on the planet and we’re literally going to their houses in the middle of the night and if I go into a room and I go left and they don’t go right and there’s a guy on the right side of the room with an AK-47, then we literally both die so the trust is taken for granted and you can actually be a lot more direct with people. If I’m in a shoot house and we’re training for a deployment and someone goes left when I go left, I can tell him in a very unkind way that they need to get their stuff together.
Now, I think that doesn’t necessarily translate in the private sector. In the private sector, you need to develop that trust over time and you need to demonstrate it in how you communicate and that’s really challenging, to be totally frank. That was a really difficult skill for me to grow and develop, it’s that demonstration of care and how I communicate, I think it’s still something I’m working on. Just making my team aware of the fact that that’s something that I want to be better at and asking them to hold me accountable and constantly, actually, asking them for feedback before really giving any of myself creates that kind of trusting environment. That’s been a couple of really really valuable lessons as I’ve transitioned into the private sector.
Awesome. Well, that was a pretty incredible conversation. Obviously, I let you do a lot of the talking because you got an amazing story here but I want to get into the lightning round while we still have some time. I’m going to throw a quick curve ball at you though because I didn’t give you this question beforehand. I want to know as part of your lightning around, what’s your why? At this point in your career, what makes you feel the most accomplish? Why do you get out of bed and do this every day?
I get out of bed every day and this has really been the case since committing to go into ranger regiment, I get out of bed to be the best version of myself. I know that sounds trite and contrived but it’s true, I really like taking the lens of, hey, everything I’m doing at work, in my personal life is an opportunity for me to grow and just be better.
Now, that’s part of my why, my other why currently is that when I was 12 years old, I went to this really … I grew up in San Francisco and I’m a poor kid, a product of a single mom with a lot of brothers and sisters and I got this full ride to this really good private school and I was, essentially, a charity case. Anyhow, my best friend in sixth grade, his family was real old money. When I say old money, I mean they have their name on a lecture hall at Cal. Every day after school, I used to literally go to his mansion in Sea Cliff, in this really nice posh neighborhood in San Francisco and then at 8:00 p.m., his nanny would give me a ride to the bus stop where I would get unto minibuses and go home. I remember thinking at 12 years old, I said to myself, I was like, “Fuck this, I’m not dying poor.”
Honestly, that’s the reason I’m not still in army special operations, it’s that commitment to myself that I made because the reality is I needed something that would … I don’t know how to put this but that’s a really powerful motivating driver for me. I don’t need to be stupidly rich but I do want to some day own a house in San Francisco and you need to be not stupidly rich but at least very affluent to be able to do that so that’s driving me too.
Yeah. I mean, that’s pretty powerful. Into the next one, what’s the one thing you wish you knew at 22?