Todd Gagne

So can you guys like, how do we do this where I can actually, just see Raj and not all the rest of you guys? Like, yeah.

Mike Vetter

It doesn't matter,

Todd Gagne

I guess.

Mike Vetter

That is a question beyond my skill level. I think Okay.

Todd Gagne

We'll figure it out.

Mike Vetter

I think he I need a good spotlight. So

Todd Gagne

Okay.

Mike Vetter

Alright, everyone. Well, welcome today. It's a privilege to be here today and we're excited to talk a little bit more about, how to scale a $1,000,000,000 startup. And so, I'm gonna be your podcast host and your webinar host, and I just wanna tell you a couple of things before we get into today's session. So, today's guest is Raj Singh.

He's gonna talk about how he took 2 startups from, 0 to a very large company that's not publicly traded. And then Todd is gonna be your, your interviewer today. But before I turn things over to Todd, I wanna a couple, cover a couple, webinar housekeeping items. 1st, you'll be on mute during the presentation, but you can ask questions about our speakers, in chat, and I'll be responding to those at the end. Also, this event is hosted by Wildfire Labs.

Wildfire is an accelerator that helps founders take an idea and turn it into a software product with revenue in 6 months. If you're on the webinar today and you have an idea that you wanna turn into a business, you can get in touch with us directly, and I'm actually gonna be posting our, application link into chat. So before we cover any more other things, let's turn it over to you, Todd, and you can get started. So go ahead, Todd.

Todd Gagne

Okay. Well, thanks, Mike. I appreciate it. Raj, I appreciate you coming. Let me just do a quick background, on kind of, your, you know, your history a little bit.

Raj is the CEO and chairman of the board of Accolade, a publicly traded company. Raj joined as CEO in 2015 and then took the public, the company public in 2020 and has integrated over 4 companies with over $1,000,000,000 in acquisitions. Prior to that, Raj and I worked together at Concur. He was the co founder of, Concur with his brother Steve and Mike Hilton. And it's a travel and expense management company.

In 2 in 1998, Concur went public, and, had over $800,000,000, 4,000, employees and 20,000 customers. And it was acquired, in 2014 for $8,300,000,000 by SAP. Raj was the president, COO, and, member of the board of directors. So welcome, Raj. It's, good to see you, and I appreciate you taking the time.

Raj Singh

It's always good to see you, Todd. It's been too long, man. It's been too long.

Todd Gagne

It has been a long time. So why don't we dive in here a little bit? To me, it's interesting. You've had this joke with me before where you said for a guy who's had 3 jobs, things have worked out pretty well for you. So you had a job right out of college, then you basically started Concur and took it to 8,300,000,000, then you became the CEO of another company, take that public.

So maybe your resume is thin, but you've done pretty well. Congratulations.

Raj Singh

It's thin. It it's thin for sure, Todd. And, and I think the people at Ford Motor Company, back then it was just called Ford Motor Company, would tell you, it was probably a good idea that I leave there. So of the 2, one, actually, I I worked with you at Concur and, obviously, that's worked well. And, and, Accolade, we're in the journey, man.

We're in the journey. We took the company public back in 2020, and we're bouncing around in the public markets. It's a tough time to be in the public markets, but we're battling and we're trying to do, really great things for human beings, in the universe of healthcare in the United States, which is a tough place to work, but, we're gonna keep battling until we build something great.

Todd Gagne

Well, that's good. That's great. So maybe talk a little bit about, like, did you kind of envision this is what you were going to be doing? I mean, from an entrepreneurship standpoint, right? You went to school to be an engineer.

Like you said, you were at Ford. But like, how did you end up going from, you know, the story about you taking the summer off, you were looking at being a lawyer. But like, was entrepreneurship, either something that was modeled to you kind of early on? Or was this something that basically you just kind of grew into?

Raj Singh

I think of it as anti modeling, Todd, in some way, shape, or form. And I say that in, like, the the most complimentary possible way. My dad is an Indian immigrant, who came to the United States. He had 3 kids. He brought over his 2 brothers, so he had like it's like he had 5 kids that he had to support, and, he didn't have the luxury of entrepreneurship.

He could take no risk. He worked at one place. He worked at Eaton Corporation for 30 years, and you could see him chafe at being told what to do when he I think tangibly, I think Steve would attest my brother Steve, for those of you who don't know what I'm talking about with Todd, my brother Steve would attest my dad is far smarter than any of his kids, far more ambitious than any of his kids, and far more capable than any of his kids. But he had a battle of his own. He had to take care of a family.

He didn't have a rut he didn't have the opportunity. And so we watched that, all of us watched it, and all of us turned out to be entrepreneurs in some way, shape, or form. And I think in some ways, it's, it's a tribute to my mom and dad.

Todd Gagne

That's cool. That's a cool story. And I think, you know, the anti modeling is is a good one. I think my dad has some of that too. I mean, I think, they had a young family, and didn't have a lot of education, had to provide.

And I think if you asked him what to do over with, he'd have some very concrete ideas of what he'd like to do differently. Yeah. And so I think that is good. So maybe just like talking about, maybe talk a little bit about your jump from Ford to Concur, right? You were in your 20s, and you basically had an opportunity to you were thinking about going to law school, and then you kind of basically did a little bit of work for your brother on this kind of expense management space, and then you took a chance.

And so what about that opportunity and the risk taking? Maybe your dad had given you some of that idea, but that was the first time you really got to test it in a professional environment.

Raj Singh

Yeah. Probably the first modeling of risk taking was my brother, Steve. He went off and started his own company, right, you know, he dropped out of college to go do it, which really pissed my parents off. And, and then and then I got the job at Ford. This is later, my brother's 7 years older than me, and my dad was, like, kinda happy.

He's, like, you got a job. You went to engineering school so you could get a job. And I within 9 months, I quit that job. I actually didn't call my dad and tell him for 2 weeks. I was scared to tell my dad that I quit.

I was really scared, probably more scared of my mom.

Todd Gagne

So I

Raj Singh

didn't, but I knew that wasn't for me. I knew I couldn't do that, and I got lucky that Steven Mike called and said, we're gonna go start this company, Concur at the time, just called something different. And you're unemployed. You're not going to law school for 6 months. Why don't you make yourself useful?

Like, you know, build a prototype, do something useful. And you know what I found, Taba? I found, when I moved out to the West Coast, and this is, in no way, shape, or form. I think the world has changed pretty dramatically. But back then, the the technology infrastructure and the technology mindset that existed on the West Coast didn't exist in Michigan.

Now I just think that that's totally different in 2024 than it was in 1993.

Todd Gagne

Yep.

Raj Singh

Look much like it's different in South Dakota than it was in 1993. And so our view, is is very much that, like, when I got out there, I met a bunch of people who were like, I'm gonna change the world. And I was like, wow. I'd I'd you're 23 like me, and you think you're gonna change the world. Maybe I could do that.

And, and that led to sticking with it. I never went to law school. I stuck it out with Mike and Steve, and we did it together for 21 years. That that was by happenstance at some level, but I think the world was kinda pushing me in that direction. When I quit at Ford, I knew I was never going back to a company with a 100,000 plus employees.

I was a number and I wasn't a very good number. Yep. You know?

Todd Gagne

Well, that's good. Maybe talk to me a little bit about like just that inflection point where it's like, it's one thing to take a take a risk and basically do kind of the summer job and see it coming together, with, you know, like Hilton. That's another thing to realize that like, this is, you're onto something big, right? And so was there a moment, kind of in that journey where you kind of saw, hey, man, this is not just like, hey, I'm getting a job and I'm getting a paycheck, but this is something that, like, is really has the potential to scale and have a material impact to the business world.

Raj Singh

Yeah. It took me a minute for that one, Todd. Probably the first, like, year the 1st year, I was I was just in love with, making decisions that were gonna impact a product that people were gonna use. You know? Like and so it sounds really dumb now, but, I would sit there.

I was in a room with Mike Hilton. I was in our my apartment with Mike, and we would work there all day, and we'd play video games all night. And the the you know, there would be moments where I'd be like, hey. You know? I think the interface should look like this, and I think it this is the way an expense report process should flow.

And I'd look at Mike, ex you know, expecting somebody to give me input. He'd be like, I I guess you're right. Like, do it. And I realized like, oh, shit. I get to make these decisions.

I get to decide. And then we shipped a product a year later, and people used it and liked it, and, man, I was I was hooked. I was just hooked on the idea. Like, I built this shit, and it's and it's good, and it could be better. And, I fell in love with that.

Before I realized that this could scale, I never for a minute, for a long time. It took me a long time before I believed, oh, this is an $8,300,000,000 company, whatever. I just love the idea of building stuff. And, and I think anytime I get away from that in my career, Todd, anytime I get away from building stuff and the the love of the building process, I get in trouble.

Todd Gagne

And so but it kind of wrapped up in that, I guess what I heard you say was some ownership, right? Some autonomy, to basically test out some theories and basically, you know, go do what you said you're gonna do. So I get to build products, but I think either as my entrepreneur and working for you at concur, having that ownership component to take a risk and see how it works out, I think was a big part of that.

Raj Singh

Amen. Amen. I mean, isn't it it's it's incredibly empowering to know that you own a decision that could tangibly move a business. I think when people think about why they love their job, I don't care whether they're starting a company or not starting a company, they talk about their boss, they talk about impact. You know, am I actually moving the needle on something?

Oftentimes, compensation is not even, like, the top 3, 4. Totally agree. It's way more about the people they work with and can they have an impact on something that's important. And I think that was, that's addictive. It's addictive.

And I think if you create a culture where people feel like they have that in their work, they get addicted as well.

Todd Gagne

Yeah. Okay. Let's, so the theme of this is really thinking about like, is there some patterns in the way that you thought about scaling Concur and Accolade that we can kind of leverage from a startup perspective? And so I took a swag at some of the things that I think we were good at at Concur. And I think these are elements that you can basically scale all the way down to a 2, 3, 5 person company, all the way up to having multiple thousands of people.

The scale of each one of them probably changes a little bit, but I do think these are elements that make sense. And so the 4 that we came up with were vision, culture, execution, and people development. So I'd like to spend a little bit of time in each one of these, but I really think that these are some of the core elements that I think I felt like really were solid at Concur. And I think that even as I'm working with entrepreneurs, I kind of talk about these things in just a smaller scale. And so, any comments on that?

Do you think those are core elements that you think that you've leveraged kind of consistently?

Raj Singh

Yeah. I think those 4 are yeah. Those are the right 4, Todd. I think, the ex exploding each of those, I think, vision and culture are required for execution. Execution is a son of a gun.

Even when you have vision and culture, like, execution turns out to be really, really hard, and and, and people develop the same story. So, like, I think 2 of them are, like, sort of foundational building blocks. You gotta have them. And then once you have them, that's like a ticket to the game, and the game turns out to be really tough. There's a lot of major league baseball players out there throwing throwing hard fastballs at you every day.

And so, but, yes, I agree with the 4, bud.

Todd Gagne

Okay. Sounds good. So let's go let's start with the vision piece of it. I think that every entrepreneur that starts is basically saying, I wanna change somebody's behavior. I wanna change the world.

Right? And so, even from the very smallest start, I think they're thinking about thought leadership. They're thinking about, like, the process works like this today. I'd like to change it for like this tomorrow. And I think over the history of concur, you guys did this very, very consistently, right?

Whether it was going from a shrink rep product to an on premise to, SaaS, you know, environment to integrated travel and expense to a platform play to, the perfect trip. Right? Like, there were a bunch of pivots where I think, in general, what you were trying to do was say, where should this industry really be? Not where we're at today and where we're competing, but where do we think it's supposed to go? And then how do we lead an industry to get there?

And what I thought was really interesting and and I maybe at the time I didn't always appreciate it was basically, lots of people were trying to play catch up. Right? And the number of bets that were right over that 21 period 21 years that you get did that was actually pretty remarkable. And so let me just stop there and see if that resonates with you. Do you agree with that?

I think it was something that basically, was a differentiator and became a moat for us over time.

Raj Singh

I think you're right, Todd. I think, I think there's a there is a there's an innate sort of human instinct in there that you that you can have or you maybe you don't have, which is growth. Like, I gotta grow. We gotta keep growing. And you could put that in the context of commerce and public markets.

Your growth rate better keep stay high. Therefore, you better find new problems to solve no matter what you do. You could put it in the context of human behavior. Like, if we can do that, why can't we do this next thing? Why can't we do the next thing?

And I think, I I'd like to think we were pretty good at it. We certainly made some bad bets over the over time, and those bad bets, knocked us in the head a couple a few more than a few times. But I think where we when we got really good at it, Todd, is, like, you're supposed to grow because you have a vision for the problem you're trying to solve. And, and when you're really good at it, you're really close to your customer, you understand your customer's needs really well, and you can anticipate the next need. Right?

If you just do what your customer tells you, you usually don't solve the problem. But if you understand your customer really well and you can you keep anticipating what their next need is, you might you have a chance to build something pretty remarkable. But you better be talking to customers a hell of a lot if you're gonna paint a vision that's gonna keep growing every day.

Todd Gagne

So a couple of things in that that I think are good. One of them is, I think maybe just to use different nomenclature, you're expanding your TAM, right? You started off with kind of like a focused area and then basically this total addressable market over time just continue to get bigger and bigger. And so the market opportunity for your product and your services just got bigger and bigger. So I think that's one where I think that's really important.

And I think, especially for young entrepreneurs, you start off with a beachhead, you start off with something that's super specific that you're trying to solve the customer problem, and then you're trying to expand to take on more and more opportunity. And so that's good. The second piece to it, which I think really resonates, is focus on the customer, man. The the more you do that, the closer you get to, like, the problem. How much of the time though, do you think that the customer understood where to go?

Right? Like a lot of times they're talking about the problems, and the change management to get them to do something totally new and innovative sometimes is a challenge. And like, you've got behavior that they're kind of, this is the way I've always done it. And so if you just made it incrementally a little bit better versus shifting entirely to a new paradigm. So how do you lead a customer through that process with a vision like that?

Raj Singh

Yeah. There's times where a customer's gonna tell you the wrong data. When, Todd, you'll go back I don't know. It must be 15 years ago now. We were leading the expense reporting category.

We decided we were gonna add travel and that online travel booking. Logically, every online travel booking ends up on an expense report, therefore, the 2 pro the 2 processes should be tied together. Every one of our customers said, well, yeah. No. That's the travel agency's job.

They have a travel booking tool. We're never gonna use yours. You're not the travel agency. If we if you had surveyed a 100 customers about, putting those two things together, you would have got 95 of them saying, no. No.

No. We're never gonna buy that from you. And we just knew that was intuitively. That didn't make any sense. And so, like, you can hear it, and then you can look at the business problem and you can look at the universe the way it's supposed to be and say, like, okay.

We don't agree with you. We're gonna buy it, by the way. We'll come up with a unique pricing model that makes it really enticing for you to wanna buy it from us. By the way, we're gonna make it a really cool tech stack, and we're gonna be able to partner with all of those, travel agencies that you're worried about. So we solved the problems that the customer perceived, but we didn't let the customer talk us out of something that mattered.

But you had to you did have to go back to, like, the things that they said, I need my travel agency partnered with you. I need it to work in the following 5 ways to deal with, you know, policy issues and duty of care responsibilities. And And those were things we didn't know. So, like, we got a lot out of those customer conversations, but we ignored the big point, which is you shouldn't do this at all.

Todd Gagne

Yeah. So I think that's pretty cool. I mean, it's, it's there's some nuance to it. Right? You listen to your customer, and then you gotta basically, you know, ferret through the forest to figure out how to get there.

Right? And and bring them along for the journey. Right? Because otherwise They'll come they

Raj Singh

that's right. That's right. They'll come along, Todd. They'll come along. Right?

Like, they like, you we you and I witnessed it together. As long as you say, like, hey, I disagreed with you on this. This is why we did it. But here's the 5 things we agreed on and I did those things. People wanna be heard, man.

And by the way, building innovation and technology is really hard, and most customers know that. And so if they feel like they've got the ear of somebody who can keep moving them forward in the technology game, they know that's worth money and that's worth value.

Todd Gagne

Good. Well, that's good. So let's talk about culture next. I do think this was a key foundational issue at Concur, and it's like I got hired, I think in 97. And, you know, I probably went through, I don't know, 7

Raj Singh

Those were lean years. That's what those were lean years. That's why we had to that's we had to get Gagne. We thought, oh, man. We've gotta get this kid from South Dakota.

Todd Gagne

Do you remember, like, you had a guy named Lanny who did, like, the industrial, like, interview at the end? And so

Raj Singh

Oh my god. Those are the worst. Those are the worst. I remember that. It was

Todd Gagne

interesting though, Raj. The part that was cool to me that I keep focusing on was you basically built a profile on you and a handful of other people have said, this is the type of culture we want. Or these are the type of people that we want with certain characteristics. And then you hired like an industrial psychologist, essentially, to basically, at the end of all of these meetings, like all these interviews to say, does this individual actually meet to like the criteria that we had? And so I know that's not the start.

I mean, that's a start of, like, understanding culture and starting to say there are attributes that we value in this. And this is a method to do it. Maybe it wasn't the long term method for us. It didn't scale. But it was just interesting to say you were pretty, pretty prescriptive on what you thought were aspects of the culture and the types of individuals that you needed to have.

And then you blew it out into a culture that we could hire against in a set of core values that we rewarded that I think helped scale and bring on people in a unified way.

Raj Singh

Yeah. Yeah. That I think, I think writing good to great changed our lives at concur. Yep.

Todd Gagne

That that

Raj Singh

that book fundamentally changed our lives. And, and I I I never hesitate to say that. I think Jim Collins wrote down a bunch of things that we knew intuitively would be true, but then he gave us a lexicon and a framework that we can hand out to every employee in the company and say, like, hey. We believe that. And so if you ever question, like, what it is we're thinking about, go read that book again.

And, a part of that was writing down core values. We've done the same thing at Accolade, and it's it's just a constant framework. I open every one of my exec staff meetings. One of my exec team members will pull one of our 6 core values at Accolade and say, like, this week, here's my theme. Here's why, you know, whether it's be fearless or relentless execution or, embrace reality.

Whatever those those those are, they become a part of the vernacular of the business. They become a framework of a reference point to say, well, this is one of those moments we gotta embrace reality. And what that does is it just sort of weaves together when you're interviewing people, when you're firing people, unfortunately, you're referring to that framework and saying, do these people fit? You know, there was a there was a moment at Concur, and I'm I'm still working towards it in many respects at Accolade. And so if anybody from Accolade listens to this, that's not a criticism.

That's that's an aspiration, where people would interview at Concur, they might interview 7 different people, and they'd be like, man, you guys sound a lot alike. And it wasn't because we are from the same place and because we have the same vision or the same view of, like, a particular challenge. It was we talked about the problems we were trying to solve and the way we wanted to go solve them in very, very similar ways. Aspirationally, when your company gets to scale, you should feel that way. There shouldn't be much there shouldn't be much, dissonance in the way we the way you talk about what you're trying to solve.

And that to me, culture is, is the only way to build something great. Last point, Todd, because I know I'm rambling on. The culture doesn't have to be like, Amazon's culture is fundamentally different than the culture we had at Concur or fundamentally different than the culture we had at Accolade. It's fundamentally different than the culture that that yeah. You have at Microsoft.

The there is no such thing as good or bad per se. You you just gotta choose it and be consistent, and you're gonna get what you choose.

Todd Gagne

So, you know, I've kinda gone through this with a couple of startups over time, doing it. And what what's interesting to me is they go through the exercise, but they don't operationalize it nearly as well as maybe we did or, like, or it's a challenge, right? It's a set of things that you put up on the wall, but it's not like, how do you take it from an exercise of documenting it to an exercise of we live it every single day, right? And so there's there's things about rewarding the behavior, calling out bad behavior. But I think, you know, as startups go from this where it's like, it's really founder led.

Right? A lot of the culture is defined by the first founders. Yeah. And then basically they publish some things and say, this is how we're gonna hire because they're not involved in every hiring decision. But then sometimes there's an atrophy or like we just don't live it as consistently because it doesn't get enforced.

Do you have any ideas like how how do you make that transition from a body of exercise that you do to publishing some things to then living it?

Raj Singh

Yeah. First thing is don't bullshit yourself about what you really believe. Like, some people will write down their core values, and it's not really their core values. It's just what they think, like, treat people with respect. It's absolutely Correct.

So I say write down what you really believe. Even your imperfections, like, the company is as a founder, the company is gonna build around the way you behave. And if there's dissonance between what you write down about what you believe and the way you actually behave, it will work against you in the worst possible way. It'll be insidious because people will realize, oh, this guy writes down shit that he doesn't really believe, but I can watch it in action. And therefore, there's a gap between the truth and and and behavior that would that, that is probably admissible or permissible from the rest of the business as well.

That's a bad thing. So that's first. 2nd, it has to be in the hiring process. And the hiring process, even later at scale has to be pretty, significant. It's true at Accolade for me right now, and it was true certainly I concur.

People used to complain. Of, like, god, I had to talk to a lot of people before I got that job. And it was one of the big complaints we had at Concur is, like, your hiring process is a huge pain in the ass, and I almost gave up on it because I did talk to another 3 people. I think that's okay. Like, go slow, but insist on a, a cross functional team interviewing important particularly important roles, knowing that the that culture is gonna come out in every one of those areas.

The I think the the second part of that story beyond hiring is promotions. You know as well as I do is but the time you get to a 100 employees, people who manage 10 people, 15 people, 20 people, are massive culture carriers for your business. And so you promote you promote somebody who's gonna manage 10 or 15 people and they're countercultural in any way, shape, or form, they are gonna kill you. They are gonna kill your business. They can make their numbers, but they are just gonna they're gonna be there's gonna be cutting underneath what you believe in every single day and you won't even know what's happening.

But the 10 or 15 people below are gonna blame you for the fact that you have promoted that person. And so making making director, even senior manager promotions, cross functional in nature, it says you can't just promote that person. You gotta go get 3 cross functional peers in a room, to agree that this is the this is a person to get promoted. Like, those things protect your culture. Those are just a couple examples in my mind.

Todd Gagne

That's good, Raj. That that's important. You gotta live you gotta live it, and you gotta basically, embrace the culture. And I think all of your managers need to promote good behavior and then stamp out bad behavior. It's part of your job.

And I think that's what helped us. So maybe the next one I have is really talking about execution. Again, I think we did a relatively good job of executing at Concur. And I think it boiled down to a couple of different things for me. One of them was the priorities of the exec staff were relatively clean.

So you knew kind of what we're going to do. And we could basically bring down to the next level of people, that were trying to execute a list of deliverables that needed to happen. And there was ownership. There was somebody that owned a problem. And, basically, they were their responsibility.

And and then there was kind of a trickle down of of that. And so as the business got more complex, that became harder to do because there was conflict. But I think early on, especially with startups, the more you can execute well, there's so many things and there's so much noise and there's so many distractions. But good startups, and I think in a lot of cases, we did this well kind of post 2000, we stayed focused. We understood what we were trying to go do.

And we, and we put priority we put priorities on, like, what was important to us. And then we had teams and people that basically were rewarded for execution. And so I don't know if you agree with all that, Raj, but, like, man, I think me and growing up in that culture, I I felt like at the end of the day, I was paid to execute. Right? That was that was that was how I made my paycheck.

Right? If I delivered on what you asked me to go do, that was the most important thing.

Raj Singh

Yeah. And I agree with that, Todd. I think I you're a good example in my mind of, your career just kept growing because we we did think about things in the context of what problem are we trying to solve. And then you would find your biggest problems and and, you know, I've said this a couple of times at Accolade actually, Todd. Like, we should get gag me to do this, and people would remind me that you don't actually work for us.

And so that always doesn't work out well for me. We never really get that problem solved. But the, but we would we would find the biggest problems and we'd like, hey, let's get Trevor. Let's get Trevor Davenport. Let's get Tidegag.

Let's go get them, and let's move them out of what they're doing. Let's hand them the responsibilities to make decisions. Let's get out of their way. Let's check-in on them every 30 days, but let's go. And the priorities were very clear.

I everything you said, I I I think makes a ton of sense. The one thing I would add to it, Todd, is is we were we were flat from the beginning to the end. Meaning, at 850,000,000 in revenues, before we sold to SAP, I had 12 or 13 direct reports. And almost every, like, organizational person who would come in and review that when they'd meet with us, when we're doing hiring, we bring in exec recruiters. They'd be like, when are you gonna fix that?

And I'm like, I don't think that's a bug. I think that's a feature. Like, I think that's what, that's the way it's supposed to work. And we were lucky, in in many respects in that, you know, we had Steve who was sort of on the outside, looking outside, and I was on the inside looking inside. But, but the the flatness of staying close to the business, not having too many layers between you and a customer, not having too many layers between, you and the biggest problems and therefore not having as many layers between you and your superstars.

Not every superstar is gonna report to the president or CEO of the company, but you better damn well on who they are because when you got a hard problem, you got you got to find that person and say, Dude, here's the problem. Here's the context of the business and why I need you to go do it. And when you have a deep enough bench to go do that work, man, you can do some damage.

Todd Gagne

Yeah. I think it's all good. I I think that makes sense. How do you preserve kind of that founder mentality? Like, I felt like I was an owner in the business.

And I felt like every time I had a problem, it was my problem to go solve. Right? And so there was a high degree of ownership in that. And it's like, how do you go from, you know, like, your small startup and you continue to scale that and it's not about a job, right? Like, I think as soon as, like, you're kind of punching the clock, you kind of lose some of that.

You don't take it personally anymore. And so what is it that, like, you preserved through that process that you're trying to recreate that starts out really small where you basically all kind of had that mentality and you're trying to scale it?

Raj Singh

Yeah. That's probably the hardest question of all right there. Like, how do you maintain a hunger and a thirst, that's not entirely compensation driven. You know, Todd, when you joined in 97, we went public in 90 8, the stock went to hell in 2,000, 2,001, and the stock was in hell for 4 or 5 years, 3 or 4 years at least. If you were working at Concur during that time period to make $1,000,000, you were probably delusional.

Right? Like, it was there was no there was no concept of, like, don't worry. This $2 stock is gonna be a $129 stock one day.

Todd Gagne

Oh, it's under the work.

Raj Singh

Correct. Correct. And so you did the work because you were passionate about the work. You were passionate about the company. You were passionate about your peers.

You were passionate about your customers. And, I I think this particular problem is harder in 2024 than it was in 2000. The universe moves faster, data flows faster, people change jobs more often. There was a time, Todd, in 2,005, 2006, if if I looked at your resume and you had 3 jobs in the last 4 years, I just wouldn't interview you.

Todd Gagne

Yeah.

Raj Singh

And that's that's that's a lot harder to do today because the majority of candidates you're talking to have spanned a number of jobs over the course of the last 4 or 5 years. And so, how do you maintain it? I think you reward performance, you reward culture, you, you get very, very, very focused on, on the people who are consistently making the best cultural decisions about the problems they're seeking to solve and solving. And that's really hard to do, man. That's really, really hard to do.

And so I think the best piece of advice I can give you as a founder is, before you start creating layers in your business, you better know that the people below you have the same core values, behave the same way as owners, and and have the capacity with their span of control to actually pass on those values. And so, if they don't, you will slowly but surely kill your business. And and that's there's a reason why most companies don't get to that scale is because that that's the insidious thing from within that kills you.

Todd Gagne

Okay. That makes sense. I I guess this kinda goes to the next one, which is really people development. Right? It's one thing to have those kinda cultural values, that kinda ownership mentality.

But, you know, going from, you know, I don't know what it was, like when I started, it was relatively small and we went all the way to 5,000 people or whatever. The job was different every year for me, right? I mean, and I think what I was kind of always joke on was 50% of it's going to be different. I just don't know which 50%. Right?

And so, you know, you kind of had to evolve. And so this idea of people development, once you have kind of the cultural alignment, once you have a strong degree of ownership, how do you take somebody and scale them from, you know, like a small startup and how far they can go? Right? And that starts with like the CEOs. Right?

Like I work with a lot of small startups and like the guy that basically is doing everything at the very beginning to the guy that's now leading a $10,000,000 company that's trying to take it to $20,000,000 that's a very different CEO. And that trickles down to every single person in the organization that wants to scale. And so to me, this is really a fundamental problem. If you can basically help your high performance talent continue to scale up, then, basically, your ability to execute and and win in that space, I think, becomes a lot higher percentage of opportunity for you. But it's hard.

Right? It's super hard. And so maybe just talk a little bit about that. And and do you kinda agree? Like like, what what are the characteristics for you personally going from, you know, where you started to your job at the end?

Like, you are totally different manager over that period of time.

Raj Singh

Mhmm. A 100%. I I believe, and I, I'd be curious about your perspective on this as well, is that, there's a growth mindset, learning mindset that exists in great leadership where you're constantly looking around the corner, not just about like what's the next trend in your industry. Like to put that one to the side is like, what are the next set of skills I need to grow in order to continue to advance who I am as a human? Not to get the next promotion, but to just advance, like as a leader, as a manager, as a father, you know, as a husband, whatever it might be.

And that growth mindset in part translates to the people who you're working with every day. Because as you as you expand your desire to go try new things and to go learn new things. For me, in 1993, when I joined Concur or when we started Concur, if you'd asked me to read a balance sheet and a p and l, I'd have been like, well, I can't do that. I just couldn't do that. And, you know, I'd taken one accounting class in in engineering school and maybe a couple business classes.

If you ask me in 2015 when I started as the CEO at Accolade, to map out the healthcare supply chain and explain to you where every dollar was spent, why it was spent that way in the Persian Bazaar manner, which it's managed across the universe, I wouldn't have been able to do it for you. But, the the mentality of it's learnable, I'm growable, I'm gonna learn it, and I'm gonna study like a son of a bitch until I understand it, And then I'm gonna pass that understanding on every single person. Like, as a leader, you recognize that once you know it, all you all that really happened is now you know something. When everybody knows it and everybody understands your perspective and everybody understands the problem you're trying to solve based on that perspective, you're cooking with gas. Getting everybody to that page, and and by the way, in 2024 harder because not everyone's in the office sitting right next to you, is the mission.

And whether that's, what you learned about the industry, what you learned about management, about leadership, what you learned about culture and values, as a leader, passing that on to everybody underneath you and and building some common rapport or framework or vernacular or structure associated with that, I think is mission critical to growing the people underneath you and them doing the same below you. I I think last point on that, Todd, in my mind is is that, that translates in both good and bad. You know, one of the things I say, all the time at Accolade and at Concur was, like, the the bad news should travel fast. And so if I got bad news, like, the first people I was gonna I was not there was no way not not a day I was gonna hide that data. I was gonna go talk to the people above me and the people below me.

Everyone was gonna know, because I needed their brilliance to solve the problem. And, so good news, bad news, and growth has to travel fast, which is like a constant communication and learning vehicle. But if your leader doesn't have it, if your CEO doesn't have it, if your if if your leadership doesn't have it, your company's slowly dying.

Todd Gagne

Yeah. I I think it's good. I think one of the things that maybe you didn't mention that I would challenge a little bit is, is just a culture of of a failure. Right? Like, it's okay to fail if you're trying to do what's right from a cultural value standpoint and you learn from it.

Right? Like, we had this kind of thing where it was like, I think there was a risk tolerance in our business where you could take some chances if it aligned with what was good for the customer, what was good for our business. And, you know, sometimes you're not going to nail it. Right? But if we allowed you to do that and create that, like, ownership mentality, I agree with you.

This, like, intellectual curiosity of continuing to learn, continue to grow, continue to find new things. But there was, like, an element of, it's okay to take risk in this business because you're gonna be rewarded if it works out. And basically, you're going to learn something if you don't. And I do think that that's part of a uniqueness that we had that really did allow people to grow because we're moving fast and you're not micromanaging any of these people. You're giving them autonomy to continue to figure things out.

Do you agree with that or, like, would you spit it out differently?

Raj Singh

I do. No. I think it's right, Todd. I think that your degrees of freedom grow as the business grows. Right?

And so you can take more risk and you can grow. I remember, a moment with in your career where, you were managing clients and you flipped and we we said, like, hey. Like, Todd's gonna be one of the people to run this company one day. We need to grow him in sales and marketing. Let's make him the head of marketing.

And there was probably, like, a whole bunch of salespeople who were like, what in the hell are you doing? Like, that guy's never run marketing before in his life. And then he went and crushed it. And, like, was the risk did the risk exist that, you were gonna go fall flat on your face? Yeah.

And, honestly, the conversations that we were having about you in that moment, Todd, were, if he falls flat on his face, will he get so discouraged that he leaves? Because that would be devastating to the company, or will he be the kind of guy who's like, thank you for the opportunity. Now what it what what do I do next? And we were pretty confident. Like, we wouldn't have made that we wouldn't have done it if we thought you would have punted if if things got tough.

But that was a a great example where, like, boy, if you couldn't do that job, it turns out you could, you you were gonna impact the number of the company, like, the revenue line of the company of a public company, that year. Like you were gonna have that was gonna have an impact. And, and that was risk we took because we were thinking about growing people, about people development, and about this idea of, the more breadth of skills that people had who really understood our business problem, the more we could achieve.

Todd Gagne

So, and I'm super thankful of that. I mean, I think literally you just said, don't screw up this one. You would and I'll give you the next one. Right? You do you knock it out of the park.

Raj Singh

I think I might use I think I might have used different words than don't screw up, but yes.

Todd Gagne

Yes, you did. Yep, you did. But I guess one of the things that's interesting to me, and I think we ended up having this at Concur, and I've seen it in other companies, is how long can generalists survive leading new things, right, before the company decides, hey, look, I need a marketing guy who's basically gonna that's got 20 years of doing this. And I'm gonna put that guy in there and I'm gonna bring him from the outside. And so each startup, I think, has this thing where it's like saying, how do I grow them from inside?

And how do what is what is the benefits to doing that versus the downside? And then there's some inflection point where I think a lot of companies say, I I don't do that anymore. And I think by the time I left, there were a lot of frustrated, talented people in Concur that basically were not moving their careers forward. And they didn't they the the paths that I had from a generalist standpoint just weren't nearly as available as they used to be.

Raj Singh

I think that's true, Todd. I think I think it does happen. I think the critical element of that is in many ways, how close is the management team to the top talented people in the business? And as as you get to that kind of scale, you've gotta have things like talent reviews. You have to have an understanding of, like, who are you investing in and making sure you create growth for them, and that gets harder and harder to do.

But I think you also do have, there are different elements. Like you begin to grow into different spaces, you know, if you if you were to think about, marketing as a challenge, when you're trying to grow 25% off of a 100,000,000, you gotta generate $25,000,000 worth of new business every single year, presuming you retain a 100% of your customers. When you're trying to grow a 100% off a 25% off of a 1,000,000,000, you gotta find $250,000,000 worth of new opportunity across the universe in multiple markets. And some of that shit, you just need somebody who's seen it before. And

Todd Gagne

Yep.

Raj Singh

And figuring out when you max out, and you're like, we have tried everything, and we don't know how to solve this problem, is with with the with the brainpower we have internally is a trick. It can't be all of the jobs. And especially it can't be in my mind, it can't be engineering and product. Like engineering and product, you gotta grow inside. You gotta find really talented people to add to the mix.

But the vision of the product and the vision of the infrastructure and the vision of the tech, the the tech stack, you damn well better own that forever. The the rest of it though, you gotta find scale in in a number of different spots.

Todd Gagne

Okay. I mean, that that's that's a good one. I just see I think some people do it too early where they start pulling in and saying, you know, I I'm growing, you know, maybe I'm not even to $10,000,000 and I need to go find the expert that's going to go do this. And I think

Raj Singh

what I wouldn't do that. I wouldn't do that.

Todd Gagne

Yeah, I wouldn't either. And I think like, I think they'd look at it and saying, I just don't understand this. And so it's a black box to them. Right? And so I think they don't understand their business well enough.

And so they're outsourcing the solution to somebody who looks like on paper they've had it. And I think what you're really trying to say is, no, you got to, A, understand this problem inside and out. And then you need to put talented people that can help you grow to it. And I think doing this internally for as long as you can is a good strategy.

Raj Singh

Oh, I couldn't agree more, Tom. A 100% agree. Like, if you're an engineer and you don't understand lead generation and pipeline development and deal closure and forecasting, well, then you better fucking figure it out. Like, you're not gonna build anything if half of the business you decide, like, I don't care about that. I'm just gonna build stuff.

Although, you know, there are there are product led growth strategies that say you can just build product and not worry about it, but you gotta choose a strategy that allows you there is every part of revenue generation is a part of your job if you're building a company. Every part of it, which is customer retention, customer acquisition, all of it. If you don't understand those metrics cold, up until hell, 150,000,000 to 250,000,000 of revs, if you don't know those those to a tee, you're not gonna build anything you, particularly good.

Todd Gagne

Yeah. That's good. Okay. We're gonna go to like the rapid fire round. So I just got a couple of quick questions for you.

I'm curious on some of your feedback. So, I know you're, intellectually curious. You read, is there a good, couple of books that you recommend to founders or people that are, kind of going through that entrepreneurial journey?

Raj Singh

Well, I've mentioned it'd be great. That's I think that's awesome. I I love, Andreessen Horowitz is an investor in Accolade. Ben's books are I think awesome. I'm a big biography, autobiography guy, Todd.

Like, I just love reading people's stories. I just finished probably 3 months ago, I finished the Musk biography from Walter Isaacson. Isaacson's any of his biographies, I think, are spectacular. His his books on on, the world's innovators, like, how yeah. I think Steven Johnson wrote a book on how we got to now.

Those are all amazing. One of the things I ask every candidate I interview is what are you reading right now, or what are you listening to right now? And if people stumble on that answer, I think, you're probably not curious enough for me. But those are the ones, to me, like, just constantly reading about the struggle of others and the challenges they went through. Like, we finished that must book at some point, and it's like, there was a day where Tesla was about to go out of business and SpaceX was go about to go out of business within, like, 48 hours.

Todd Gagne

Yep.

Raj Singh

And I I think of the pressure I face sometimes, as I walk into my earnings calls and I think, yeah, it's not as bad as he had that day. So I'll be fine.

Todd Gagne

So maybe, unpeel that a little bit. Do you look at it from a pattern matching standpoint? Do you look at, like, experiences, like, ways that they dealt with it, you know, parallels from different industries and how that can apply to you? Like, reading biographies is great, but I always think it's not always a one to one match because it's a point in time that they're actually in. And so abstracting that to your current problems, you have to be kind of careful to kind of basically apply it.

But it does kind of make you think differently because most of the problems and most of the things that people have gone through, they already happened. Right? And so you're not really going through anything unique. And so is it is it really the pattern matching, or is it something else you're drawing from those bios?

Raj Singh

I think it's I think at some level, it's pattern matching, Todd. I do think most often when, at least in my history and my experience, when companies I've been responsible for owning or running are hitting bumps in the road, I can always trace back to have we lost sight of the customer and have we lost sight of the product and the technology that we're building. And, and if that's true for whatever reason, because, you know, I've been doing Accolade for 9 years now and 21 years that concur, I can always trace it back to some bad decision I made that I gotta go back and go untangle and understand and figure out where the challenge is. And so, I think you find that in a lot of different stories. Like, it's always about going back to your roots.

And the question is sort of, like, how do you identify that problem faster? How do you see it faster? And how do you get there faster? And I just learned I I learned by we get so wrapped up in our shit, Todd. Like, there are times you know, I've been doing this for 30 plus years now, and I still get wrapped up in my own stuff.

And reading about somebody else's problems or listening to, like, the acquired podcast, and listening to the to 10 the 30 year story of Bernard Arnault and LVMH. I listen and I think, damn it. I know I I know I just screwed something up that I shouldn't have screwed up. And so you you never stop making mistakes, unfortunately. And so the other people's stories just help me see my mistakes.

Todd Gagne

Yeah. Well, that's good. I love reading. I love learning. So that I just wanted to double click on that one.

Maybe talk to me a little bit about, what do you think, like, maybe list out a handful of, like, key skills as a founder. So you've gone through this, you and and now, like, in hindsight, what would you say, like, are some of the key attributes that you would look for in in a startup or, like, a startup founder, as they're kind of going on their journey and starting at the beginning?

Raj Singh

Culture building first, clear understanding of the of the customer's business problem. Like, vision is a tough one, Todd. Like, so I would say, like, a clear understanding of the customer's business problem. That's where you start. Like, the vision of, like, how this thing is gonna be a giant business one day, that'll come over time.

But if you know the core problem you're trying to solve and you know your customer exceptionally well, I'm really interested in the problem you're trying to solve, especially if it's a big problem. And so culture building, can this person convey a sense of how we wanna go about doing things and that's the right thing? 2nd, do they understand the customer and the customer problem? 3rd, are they a good human being? Are they somebody that I would wanna hang around with and spend time with?

You know, there's there's plenty of people who are really compelling founders who can paint a vision and can, and can, can outline a culture. But if they're not really good human beings, they won't build a great business, I think, over time, by and large. There's gonna be some exceptions to that rule. And I think the the last one for me is, is someone who, has a has a genuine, a genuine empathy for, the others around them, like a responsibility set. Founders should own the responsibility, should own the failures and the successes of their business, and, and should have an empathy for the people that they're built that are coming around them.

Like, the the the interesting first 10, 20 employees of a company, they're not founders, but they're as close as you can get. And you're gonna be demanding of them things that are unnatural, and, and you better be compelling as a human being to to to inspire them to wanna do that work.

Todd Gagne

Yeah. Those are really good. It's hard to get that stuff right out of the gate. Right? You gotta spend some time with the individual to kind of figure out how much of that have.

We see a ton of, entrepreneurs coming through our program and stuff, and candidates. And so we're always trying to sharpen, like, what is it that we're really looking for and how do you identify it as quickly as possible? Is there any kind of overrated go ahead. Sorry.

Raj Singh

Don't you one of the things that I always I I I would love, and I'm sure you guys do it, but to be out of the startup ecosystem is this bullshit about I'm crushing it. We're killing it. It's amazing. You know, when I talk to founders who are early in their journey and they tell me how awesome things are and how incredible they are, I know they're lying. Yeah.

They have to be. And they have to be. And and so, like, retiring that narrative, like, I gotta fake it till I make it, instead of, like, I'm just grinding through and I'm crushing problems and I'm doing it as fast as I can and I know, this is hard. Like, it is really hard, especially when you're talking to other founders. Just be honest.

Tell the truth, and obviously you don't wanna get in front of your customers and say, I'm dying. Like, I'm I'm I'm struggling every day. But, acknowledging that this is a hard journey and, that there's honor in the honesty of acknowledging that difficulty and then calling on, people like you guys at Wildfire to help them with that, that would be really valuable to the whole ecosystem.

Todd Gagne

Yeah. I agree. I think it's it's totally true. And I guess we try to do that in some sort of well way because we we see them, like, multiple times. And so, essentially, when they come to us, we try to give them some more work to go do.

And, basically, there's different touch points in saying, how well did you actually do that? And like, and do you take coaching well? You know, how well did you execute on that? And so you try to get a snapshot of how well are they kind of going through this process with you even before they come into the program. And so you try to get people that are pretty humble and can be honest about where they're at because it's a difficult road.

It really is. Is there any overrated, like, sort of advice? You talked about kind of the narrative that we have today, and I completely agree with you. Is there any other stuff that you think is kind of, overrated from an advice standpoint that is a narrative in the startup community that basically we need to unravel?

Raj Singh

I don't think you need to know what your company is gonna be 10 years from now on day 1. And, you can paint a picture, you're probably gonna be wrong. Feel comfortable painting the picture that's gonna be wrong, but don't expect that you're gonna know that and don't pretend like you do know it, when you're talking to smart investors. That's 1. 2, I think people have a a false perception that, that to be a great founder, you have to have this enormous charisma and everybody wants to hang around and be around you.

That's all bullshit. Leadership comes in, like, a 1,000 different forms. Whatever you are as a leader, that's what you need to be. You need to embrace that authentically and be that human being. You'll find the right people to surround you if you've got a big enough problem, and you've got a good answer for that problem.

But, the, the sort of hard charging charismatic CEO who knows everything, that person doesn't exist. Don't try to be that person. Those would be the 2.

Todd Gagne

Okay. That's good. Maybe the last question I got for you, Raj, is if you had to go back and and talk to you or give advice to your younger self, let's say that you're, you know, starting out and doing concur in your twenties, what you've learned today, what would you impart back to that individual, you know, back then?

Raj Singh

I would tell myself to slow down. I still have a hard time slowing down. And so, sometimes and this is maybe unique advice to me, but I don't know. I don't know. I I'll give you my introspective view.

I'm in such a rush once I see a problem to solve a problem that, that sometimes I I run right past an easy answer because I'm just like, we gotta go. I gotta get on to the next one. So slowdown would be 1. 2, if you don't know the answer, it's in the product somewhere. It's in the customer problem somewhere.

Stop looking at other places and go go solve the core the root problem. Those 2, those are 2 mistakes I've made a lot over the course of the last 25 to 30 years.

Todd Gagne

1. Well, that's good. Raj, I I appreciate you taking the time, brother. This is, this has been great. As you can tell, I have a lot of affinity to my time at Concur and working with you.

It really shaped me professionally. It really shaped me professionally, and and you gave me an opportunity to do some pretty incredible things, jobs that I had no responsibility or no, credence in doing that you gave me an opportunity. And so it's been fun. And it's cool to rehash these. Right?

And I do think there is some framework and some principles that we that you really drove at Concur that you can apply to these startups as they scale. And I think a lot of the work that I do with the teams is direct result of the experiences I had with you and the rest of the team at Concur. So thank you. I

Raj Singh

love the fact that you're doing this work, brother. I love the fact that you're doing this work and, always good to see your face, man. Hope the fam's good.

Todd Gagne

Yeah. You too. Well, thanks a lot, Raj. I appreciate you taking the time. And, and, Mike, is there any do is there any questions?

We got a couple of minutes left.

Mike Vetter

We we got probably time for 1 or 2, at most. So, the first one is, how do you walk alongside top performers when they're just struggling hard?

Raj Singh

Mhmm. I think if you tell them the truth, I think the best leaders tell the truth, and the struggling hard part of that story is, in in part, like, you have to understand why they're struggling. And so the only way you can understand why they're struggling is is not trying to pretend like they're gonna be fine. It's gonna be okay. A lot of founders are really shitty at providing rapid feedback that says people are failing.

Start there, and you'll figure out what's breaking.

Mike Vetter

Great. And then what is one painful leadership lesson that you had to learn early on? We'll we'll close with that one. Because I think, back to your point about being authentic and not painting this picture, it's painful being a founder and it's painful to scale when you're growing.

Raj Singh

Yeah. If you don't invest in actually, like, you we did a lot of just throwing people into the deep end and we did a lot with Todd and he's he's he swam, he swam to shore every time, but, I think over time what I learned is just constantly just throwing people into the deep end of the pool. Like, you're gonna drown some people and, and investing a little bit and helping them understand how to grow, especially as you scale. As a founder, you've jumped into the deep end and you expect everyone to just be able to figure it out the same way. That's a that's a flawed assumption.

Mike Vetter

Alright. Well, that's our time today. Raj, thank you so much. It was fun. I learned it was it's fun to hear about your journey.

And for those of you who are founders on here today, there's some really great leadership lessons that'll help you to grow. So thanks again for joining, this morning. I put a link in the chat. If there's something that resonated with you and you're interested in scaling your startup, consider applying. And, Todd and Raj, thanks for your time today.

Have a great day, everyone. Bye.

Raj Singh

Yeah. Thanks, guys.

Todd Gagne

Sounds good. Take care. Thank you. Bye bye.