EP 41 - Upstart CMO Chantal Rapport on Leadership, FinTech and C-Suite by Age 30

0:00Today, a very inspiring story. I speak with Chantelle Rapport. She's a marketing executive, actually a public company CMO of a fintech firm called Upstart, which is all about expanding access to affordable credit. She has an amazing story. She got to her current role before age 30, and we talk about Chantelle's journey, what she's passionate about, her leadership style in the financial services space and job.

0:28Welcome to the High EQ Marketer. I'm John Busby. This show is about learning from the best and most interesting marketers in the world, which are, not a coincidence, highly emotionally intelligent. If you'd like inspiration, lessons, war stories from startups or Fortune 500 companies, that's why we're here. So let's go. Hi, Chantal. How are you? Good to see you. I am great. How are you doing? I'm doing really good. Also, it's a gorgeous day down here in L.A. I've got a new backdrop here for the podcast, so I'm feeling really good. And I'm really excited to talk to you today, a marketing executive, CMO of a public company before the age of 30.

1:09I want to talk about that journey, your current company, Upstart, the financial industry, all that stuff. But I've got to ask, you started your career in what seems to be like an auditor at KPMG, kind of the most opposite archetype, I think, of anyway, when I think about someone who's been really successful in sales and marketing. Why that choice out of the gate? Yeah, it's a great question. I would say, you know, you used an interesting word, which is like the marketing archetype. And I guess I will start this conversation by saying, I am definitely not and still not the marketing archetype. So I never envisioned myself to be what I thought was marketing or a marketer by any definition that I had known in school and in business school.

2:00I was very and am very left-brained, very analytical, very structured, very pragmatic. While I have creative outlets, it was never thinking about brand and thinking about some of these things that really captivated my attention. I liked numbers. I liked ops. I like execution. And so when I was thinking about what I want to do and started a career in auditing, you know, really checked the numbers box for me, of course, working in accounting, it felt very logical. The parents were proud, you know, big four. But I very quickly learned it was not going to scratch the itch for problem solving that I wanted.

2:41So I switched into management consulting really quickly. And I loved working in management consulting and worked in a boutique firm, got a ton of exposure, worked across many, many companies and really focused on go-to-market strategies. So less like marketing and acquisition, but how do we enter a market? How do we think about what products we should be bringing to market? How should we think about our consumers and how to serve them? So related to the marketing functions and got a lot of exposure to various functions in that time. But most importantly, just got to love solving hard problems and got to do that at a very, very early age where I was able to see a lot quickly, worked in a lot of financial services.

3:29So that helped kind of with this tie later in life, working in a fintech. A lot of financial services, a lot of telco, and then also a lot of private equity diligence, which just meant how do you evaluate companies and do so with the executives of those companies. So I always found that consulting was just kind of this like amazing boot camp. You hate it while you're in it and you love it once you're out of seeing a lot quickly. And, you know, you work a bajillion hours, but I would not trade that time for kind of anything in my career. And I think that really started the itch for problem solving, which is kind of how I think about my career, less how do I become a marketer?

4:08How did I become a marketer? But how did I take the skill set that I had learned in being analytical and being a good executor by nature, having an action for bias, and applying that to the largest problem set I could find, which kind of over time brought me to this position of leading growth where, you know, what's a meatier problem and how to grow a business and how to bring and retain customers. This was kind of the most interesting problem I could find. I love that answer so much. A couple of things that jump out to me there. One is working a bajillion hours. If you're passionate about learning that stuff, and even though it's bootcampy and all that, there's like no better advice that I would give to someone.

4:59and find something that you are really passionate about and enjoy doing and work a ton early in your career, pays off dividends so much. And it obviously happened in your case. And the other thing that jumped out at me is your response to how I phrased the question about a marketing archetype. Because it's right. You're right. Like you see Mad Men or you're exposed to brand advertising on TV. And maybe that's what a lot of people think the marketing discipline is about. And you certainly need, as a CMO, you need creative people on your team or creative outlet or creative teammates. But maybe the most important relationship a marketer can have in many companies is with their sales function and relating to their sales function and being able to put together plans, execute and meet your numbers.

5:54Is that some of the secret of your success? I'm trying to read between the lines here. Yeah, I think that's right. I mean, I think when any business function ultimately is boiled down, and I think I've certainly found this, and I think some of the people that I look up to in their success have done this as well. Most great business women or businessmen are just very good problem solvers who make sound decisions in short periods of time with the best available data. And that is 90 % plus of any business function is being able and confident in making decisions to move the business forward. They're not always going to be the right decisions, but being able to make the best decision you can with the best data that you have available, I think is really the crux.

6:44And marketing in that way and growth is no different than operations or finance for that matter. And they're all very, very similar. And it is all at the end of the day about growing the business, hitting those numbers, monitoring your margins and your acquisition costs, and ultimately building a roadmap and executing against it on time and really ensuring that the world knows you have whatever product you are trying to sell. Because if you have the world's best product and no one knows about it, does it really matter? And so it's an incredibly important function and is so much more than what I had also traditionally thought of like a marketing org.

7:27And I think right now, especially in tech, you see marketing being redefined as growth. So at Upstart, the marketing team was always called growth. And now we have growth marketing, We have growth product and we have all of these different subsets of our growth team. But there is still this like element of like, well, growth is different than marketing. And I think more and more marketing teams and growth teams are one in the same. We're all still using data and analytics to make decisions. But I think people are using the term growth more often to try to paint that picture of, hey, this is broader than just let me do top of funnel, lead gen, create campaigns.

8:06And there are teams that do brand marketing, and that's all they do. But that's just one part of the marketing funnel. And different companies will put emphasis on brand marketing versus performance versus, you know, the lead gen and B2B marketing in different ways. But ultimately, they all do fit under the marketing umbrella. You mentioned earlier bias for action and, you know, a big percentage of someone's success is making a quick decision and executing it. So that makes me think that in your prior jobs, that it was safe. It was like a safe place to make mistakes, if you will. And, you know, unless you were just, you know, you're just 100 % right on everything.

8:52Gosh, I wish I could turn back time and be that way. But but is that like here at my company, we have the concept of getting up to the bat and swinging. You know, we have a baseball team going on. And so like like to try to encourage people to make quick decisions and learn from them, whether it was positive or negative. So I suspect that was somehow that was injected into earlier in your career. Is that am I right about that? Absolutely. I mean, I think it's a bit of a cliche, but failing fast is just one of the most important things you can do. And that is true in, I think, tactical performance marketing success, which is take many, many swings, big and small, and fail as fast as you can, learn and move on, right?

9:42That's how you have to execute good experiment velocity and how you get fruit from experiments. You have to be willing to fail. but it's also true in your career. And I think being comfortable, which is something that I have luckily never struggled with, but know that some people do, is comfortable with that failure and saying, I don't know how to solve this problem. Did I know how to do marketing when I came here? Absolutely not. When I was hired at Upstart, I was hired to do partnerships. And we can talk a little bit about why I came here. There was lots of reasons, but part of it It was like, they want me to do a job that I have literally zero experience in, but I know I am smart and I have this bias for action.

10:27I will figure it out because at the end of the day, it's data, it's decisions, and it's people management. And how different could it be than what I was doing at my prior company? And the reality is like the output is very, very, very different, but the inputs are the same. And I think having that confidence to go in and be like, I might shoot from the hip and be wrong and that's okay. That's how you learn and move forward. And especially in the earlier of your career, being comfortable taking those big swings and saying like, I'm going to take this job and if I fail at it, I fail at it. Then where am I really compared to where am I now?

11:03If you're too scared to move forward, I think that's how you make very, very small iterative changes and don't really get where you want to be or don't learn about yourself fast enough of like, what do I really love to do? What do I really hate doing? And so you can pass what makes you happy, not necessarily what title you want or what team you want to work on, but what is going to fulfill kind of your brain itch and what will make you happy in your career, I think is really important. So finding those elements to fail, and I failed many, many, many times in my career, and especially at Upstart, some of the most valuable learnings that I have and can guide my team on now, especially with disciplines like product management or other things that are traditionally very outside like the CMO growth org.

11:54But I was there. We didn't have a product manager. So I said, fine, I'll PM this back in the day when we were a very small company. Did I have any idea what I was doing? Absolutely not. And if I were to go look back at that requirements doc I built, it was atrocious, but I learned a ton. I understood finally where the pitfalls were, how easy or hard things were to do, how engineering actually worked and getting exposure to those things really quickly has enabled me to be a much better leader. Now, if I was kind of just too scared of like, I'm not a technical person. This is like, let's hire someone else to do it.

12:29I never would have been where I am today. Yeah, it's interesting and so important. I mean, there are many paths to becoming a CMO. One is the Procter & Gamble brand marketing path. It's a great, it's a great path. Many people have been successful with it. My own journey is like yours in that I was in a bunch of different roles. I was in product, I was in analytics. And the benefit of that was learning how all different types of the businesses that I worked in operated, which was hugely, hugely helpful to me in marketing. It sounds like that was to you. So I do want to know what attracted you to Upstart.

13:11It sounds like in management consulting, you got to understand a little bit about the industry. Am I getting that wrong? But why make the move and then the pivot into marketing? Yeah, I think in consulting, by working with some really big Fortune 500 financial service companies, just learn how slowly they move and how easily they can be disrupted. and really that speed was what drew me into tech and started at MuleSoft, which was later bought by Salesforce, which is an enterprise SaaS company that also served a lot of financial services and make it faster, make your data stack stronger. I really understood the value of being in a smaller, disruptive company that was fintech.

13:56Ultimately, when I was deciding to come to Upstart, there are kind of three things that I was really looking for in my next career move. One was a great product. So I wanted real product differentiation. And this is kind of like the nerd in me needed it to be really interesting. And for me to say like, this is cool and different. It's not just a better wrapper, which there are brilliant businesses out there that are amazing brands around the same product. And some of those are great. So no disrespect to any of those businesses. But for me, I really wanted a product I could hold and feel and understand that it was truly a unique product.

14:35So having a great product was number one. And number two was great people, which is important. I think finding your cultural fit is really, really important. If you're going to be somewhere for a long time, I mean, I've been at Upstart for five and a half years now, Like, you know, you see those people more than you see your friends and family and do a lot of things. So it is important that they are similar and finding, you know, a mix of great experience, but also humbleness and just working the ability to kind of roll up your sleeves and just solve a problem together was very important to me.

15:11Very lack of silos within people. And that certainly was here at Upstart at the time and still is. And it's something that I really love about this company. And then the last thing, the third prong that I was looking for and attracted me to Upstart was big problems to solve, which I think I keep repeating, but it is such an important part of my journey and story and what I hope people take away from this conversation is great company. And, you know, you're often there's a saying of if you're offered a seat on a rocket ship, you don't ask which one. I full heartedly am behind that. I think I've done that twice and had great experiences in both.

15:53But also ensuring that there's ability to make impact. So what I loved about Upstart was really great product. I could see the market fit. I understood what they were doing and what they were doing differently in the runway. But I also knew that there were some meaty decisions to be made and some pivots that may or may not be required. Not big ones, but really understanding how we're going to go to market. Everything wasn't figured out yet. And that was exciting to me because that to me was like, I can come into this business and I can help decide and really build a company. And we still have those decisions to make even now as a much bigger public company.

16:28And that's what I always am really trying to push on the right candidate of like, this is the place for you if you want to own a large problem. It's not easy. You have to have the initiative to go do that. But the opportunity to really make impact is there. And so those three things kind of check the box for me here. And I get bored very, very easily. And they're just like a new challenge, new opportunity every day. And that's what keeps me growing. And ultimately, I think what's most important and not just in your career, but in life is just like that constant curiosity and growth. Chantel, what's your leadership style?

17:07As you tell your story, you're clearly were an amazing, superb, and are still individual contributor, rolling up your sleeves, doing anything that's asked, whatever seat on the rocket ship you'll take. And as you've extended your influence, you've had to become a leader and a manager. You've done it for many years now. But what's your style? It's like the most rewarding and most challenging part of what I do. I'm curious your perspective on that topic. Yeah, I mean, I think that is a great summary. It is definitely the most rewarding and the most challenging part of, I think, any management role.

17:53And I had a unique experience where my team went from a couple of people, you know, to 20 to 40 to overseeing a larger vertical of almost 100 people very quickly. And so that was a really interesting learning curve for myself of having the confidence that I could do that and really spending the time investing in people to ensure that they have an even more successful career path than I have. And I think that really taking time to understand how your team members like to be managed was an interesting learning for me. So I am very energetic. I'm very direct. I like to get things done. Right. I think we've covered that and established it.

18:45That's not how everybody operates. And while it may be the best, you know, course of action to be very direct with some and really push them to their potential over time, as my team has gotten bigger and bigger and bigger, I've really had to learn how different teams, different functions and different individuals. need to be motivated to get the best out of themselves. And really expanding that trust too, as you manage more and more people, there's a little bit of lack of one-on-one mentorship that you have when you have a smaller team. And I do really miss that. So a lot of it is like, how do I move things out of your way so you can just run as fast as possible?

19:29And I'm really just here to support you. My goal is to always hire people that are smarter than me and better than me and continue to move out of the way to do those things and run as fast as they can, which is ultimately going to help me in my goal of making the company succeed. I love that answer, Chantel. And it is interesting how you talked about when you're managing a small team, it's one on one mentorship. And then when you're managing leaders of leaders, it's enabling them to be the best that they can be. and adapting to different ways that people get things done. I was also tough for me at first.

20:10I have a certain style. And I found when I built teams where everyone was the exact style as me, we had a bunch of strengths, but we all had the same weakness. And like folks that get things done in different ways was super important. You know, you're probably asked this question because you were on the Forbes 30 under 30 list. Do people ask you, how do I get on that list? And how do you answer that question? People ask me that all the time. And it is a little bit of a frustrating question to get, I will be honest. I think that, you know, I am very grateful that I was on that list. Everyone loves an accolade.

20:57I will take it. It was an amazing moment. but it really was a moment. It was so awesome to wake up and be on that list. I was at a work offsite and so got to celebrate with my peers and my boss. And that was really cool. I called my husband. And it was an amazing day to say, I've worked really, really hard to be where I am. And And to be recognized for that is great. But it was a moment. The day went by and I was back in work mode, back like, what am I doing? Why am I solving these problems? And how am I going to continue to build my own career to be challenged? And the struggle that I have with people sometimes who reach out and say like, hey, can I grab five minutes of your time?

21:44And I got a lot of LinkedIn messages on this. Can I grab five minutes of your time? So amazing that you were on the Forbes list. I want to know how I get myself on the Forbes list. And my feedback often to them is like, if you get five minutes with any of these people that you are messaging, please do not make your question, how do I get on the list? Because it's just the wrong question to be asking if you truly want the accolades to come at some point in time. Because life is just so much more than trying to like solve for a title or a very specific scope or a team size, which happens a lot, or a spot on a list in a moment in time.

22:21time. And what I would encourage people to ask instead is like, tell me what excites you about your job. What do you do? What challenges get you up at night and every day being excited to go to work? How did you, you know, the questions that you're asking on, how did you fill that gap between like, this is a really exciting problem, but these are the skills I have, like, how do I get there? And how do I either have the confidence to just take the leap of faith that I can do it? Or if it's a hard skill, figure out how to go fill those hard skills or learn from people who have done skill building, which can get you there faster.

22:54Maybe they've taken a longer route and they can provide you some shortcuts. I think those are really important things to ask so that people can understand how to just build themselves, solve the bigger and bigger and bigger and bigger problems that they want to solve and that ultimately excite them. And the rest, the rest will come. Like I think the accolades and all those things, like they will come or they won't, but what you'll be remembered by and satisfied by at the end of your career is going to be like what you've really built versus a list that comes out every year and has hundreds of people on it for some of these.

23:29So yeah, I hope that some of those who get that response do really think about that feedback. And I'm sure half of them at least don't just go to the next person who's willing to help them figure out the thing to get on a list. But this is a challenge in a lot of just like high performing people who we want that next step. We want to get into the best college. So what are the things I need to like checkbox to make sure I get there? And I think it can be really dangerous. It can be this like trap of not really being introspective. Like what do I really want? But just here's the checkbox, the school I want to go to, the business school I want to go to, like the next thing that I want to have.

24:11And I'm not, I'm definitely not an expert and I still have a lot of life to live, but I'm not sure that that's ultimately what brings happiness in a long-term life. I think how I'm distilling it is a focus on the process and doing the best thing you can in your job, whatever endeavor you're going through. That's the reward ultimately. Yep. Let's zoom out and talk about the economy. You're in the fintech space. Upstart's about expanding access to affordable credit. What's your core focus right now? I mean, we're not, these aren't necessarily boom times, at least for many companies. Yes, definitely not boom times for sure in financial services and fintech.

24:58It's a challenging macro environment. And we certainly have felt that. I mean, anyone who's been following the Upstart story has seen that. And it's a very public story to see. But ultimately, our mission is still the same, which is enabling access, more fair access, better access, easier access to personal credit. And that is today, personal loans, auto loans, and soon to be home loans. And in times where things are tough, we still have the same mission. We still have borrowers coming to us and lending partners that want to lend. And our job is to make sure that we're matching them as effectively and efficiently as possible.

25:43It allows us, I think, some breathing space to really think about our consumer and what they need in this moment. There's certainly a lot of fear, I think, in the American economy right now. And those feelings are totally valid. And a lot of them are really that, like they're feeling. Someone really knows what's going to happen. And I think that's an important thing for us to understand and take a moment to just rally around our consumer. Like what do they need in this moment? What does our business need in the moment? And resharpen our pencils and get to work just like we would any other quarter.

26:20So it really hasn't changed our operating sense. I would say it allows us maybe to think a little bit more long term than the like constant day to day in a short term environment where things are just going crazy for the better. But it doesn't change our mission and overall what the team is working on. Well, tough times can help you focus, too. I mean, if you have a great business model, a great brand, a great company, and you invest during tough economic times and you really, really focus, you come out ahead. I was years into my career in the 08 housing crisis where that was a very, very scary time.

27:04And companies that invested, doubled down on their mission came out ahead. I mean, I think the performance marketing space that I'm in, I mean, Google absolutely crushed it during that time and coming out of it. And not that they weren't a leader by that point anyway, but they really, really differentiated themselves. There are a bunch of other examples of that. Yeah, I always like to say, my saying is always, when the tide goes out, you see the trash in the sand. Oh, yeah, I like that. It is a great time to see that and pick it up, right? Like you uncover many problems that were always there, but now they're just more visible.

27:50and it's a great opportunity to get excited by those problems and say, great, we're going to fix it. And that way, when the tide comes back in, you're just that much stronger of a business. So I think these are really important opportunities to take advantage of. How do you win the hearts and minds of colleagues or managed lead, whatever term you want, when they might not be so sure? Like the economic times are tough or the financial services industry is tough or there are changes that happen internally to a company. How do you, how do you, what's your technique to getting folks to believe, buy in, et cetera?