Bridging The Gap Between Sales and Marketing: ‘How I Work’ EP17 with Chris Bixby (Sezzle)

Chris Bixby is the VP of Growth at Sezzle, a purpose-driven digital payments company with a point of sale financing option for consumers that other traditional forms of credit have typically left behind. Chris is the jack of all trades with entrepreneurial experience, years of marketing expertise, and a recent transition into the sales side of things.

How I Work, Episode 17 with Chris Bixby (Sezzle)

Chris joins Josh Becerra in episode 17 of How I Work to share how organizational alignment, call integration, and feedback loops help bridge the gap between sales and marketing – and the importance of developing customer personas to aid in that organizational alignment. Plus:

  • Why the ‘Buy Now Pay Later’ space is experiencing rocket ship growth
  • The fundamental differences of SMB vs. Enterprise
  • 3 avenues to sales credibility: Individual Personalization, Camaraderie, and Humility

Learn more about Chris Bixby and Sezzle:

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Transcription: How I Work, Episode 17 (Chris Bixby, Sezzle)

Josh: Hi everybody. This is Josh Becerra from Augurian. I’m here with Chris Bixby, the VP of growth from Sezzle. Thanks for being here. 

Chris: Yeah. Great to be here. It’s fun to get out of the house and into Northeast to me. I love this building and it’s got beautiful offices. 

Josh: Yeah. Yeah. We love it too. Although nobody’s here right now because we’re in the mix of a pandemic. So hopefully in a couple of weeks, we’ll be able to bring the team back. I’m excited about that. So, like I said, thanks for being here. One of the things that I think is really cool about your experience and what I want to talk to you about a little bit is how you’ve kind of been on the marketing side and now have moved to the sales side of things, enterprise sales. So you’ve kind of seen both sides of the equation. And we’ll get into that a little bit more. So why don’t you just tell us a little bit about your background, your experience at Sezzle and how that transition to experience has gone for you? 

Chris: Yeah, that sounds great. Maybe I’ll give a quick, “what is Sezzle?” and then jump into a little bit of how I got there. Sezzle is a purpose-driven digital payments company that offers a point of sale financing option for consumers that have typically been left behind by other traditional forms of credit. So today we’re in what we would call the “buy now pay later space.” So someone comes on to an e-commerce platform like a Northern brewer or a Target.

They, for a whole host of reasons, need different reasons to make that purchase. They may not have a credit card. They may not have availability on their credit card, or they just want a more easy, seamless way to pay and they select Sezzle at checkout, and then they pay in four payments over six weeks with no interest ever.

So I joined the company about three years ago, the company is Minneapolis based. We’ve been around for about five or six years. It was founded by some Carlson guys and alums and it’s been a terrific ride. And so the company itself started as really SMB focused. So where we got our initial traction as a business and a payment solution was really in the SMB world.

Josh: So small businesses like mom and pop shops, or a little bit bigger than that? But not the big Targets of the world.

Chris: Yeah, a lot of mom and pops, a lot of small businesses, you know, boutiques that are going online, CPGs, beauty brands, you know, fashion brands and apparel. That was really the start of kind of where buy now pay later. And Sezzle started, a lot of those are Shopify merchants, you know, WooCommerce, Magento, and other platforms.

And what they saw immediately was just unbelievable results with this new payment option. So they saw larger basket sizes, they saw more frequency, and it just took off, right? Like as an industry and a category, it took off. And so we, as a business, were just so focused on integrations, partnerships and really that SMB world. And so I joined about three years ago.

I led our rebranding initiative and a big part of that rebranding initiative was to capture the consumer, understand kind of who that consumer was and bring forward really our purpose and our mission. But then also doing a better job of connecting what our brand matters to that merchant, right. Primarily that SMB merchant.

Josh: Well, and there’s some synergy there, right? I feel like the person who may need that little assistance on their credit side of things, the SMB kind of gets that person. Like they’re kind of in the fight too, as a, as a small business, trying to make it a go. There’s some good value driven alignment. And I think that’s part of what I think is super cool about. 

Chris: So, and having been an entrepreneur myself in a tough, challenging business environment, yeah, absolutely. It’s something that’s always centered. I mean, cashflow is on your mind, growth on your mind, how you get by, as you know, when, when, when are the receivables coming in?

I think that’s something that, you know, a lot of also boutiques and people that build these brands. Or also it resonates with them because the customer is them in a lot of ways, especially as you think about that kind of smaller, you know, smaller middle-market business that was created by a founder who had a problem that they wanted to solve.

And then, so that audience is them. And so I think you’re right. I think it just resonated, it worked and the growth was terrific. And I think, you know, I came in with, was on the marketing side. We are going through very much that, you know, you asked about the marketing and sales transition. We are really focused on that area. But what we started to recognize was like either competitors or other businesses are starting to get into the space and they were kind of taking a top-down approach in terms of, you know, big businesses, big retailers, like, you know, the Macy’s of the world. And we started looking at our product and we’re like, well, look, our products are just as good.

Right. We’ve got great approval rates. We’ve got XYZ, we’ve got yadada. Why are we not resonating? Or why is it not working with that enterprise kind of customer? At the time we brought some external people in, we started growing super rapidly and then I transitioned actually over into the enterprise sales side.

And that was a really cool transition to understand, but we were also going through that transition into “how do we be an SMB focused” it’s got a terrific product lead. But then enterprise is really how we’re going to start bridging that gap. And that was definitely an opportunity and a challenge for us organizationally.

Josh: So let’s kind of lean into that a little bit. So you’ve kind of, we’ve talked around it a little bit, but like what have you learned about the messaging or like the approach to enterprise versus SMB now that you’re kind of seeing both of these worlds. How does it differ? 

Chris: I think the first thing for me, the fundamental difference for me is the needs are just completely different internally and how to navigate, sell into, and then ultimately, service an enterprise level customer.

And so we always think of our products as super scalable. You know, it works for any customer consumer, whether you’re, you know, small business or a Target, the product works the same. And so I think from a marketing, from a business standpoint, we always just thought, well, the sales story is the same, right?

Like the things that businesses care about, it’s going to naturally, you know, resonate with enterprises. I think what we started realizing is that the decision-makers are completely different. And so at a smaller business, again, it’s usually a founder, you know, a CEO, president, head of e-commerce, someone in marketing. At a big company you start to involve, you know, finance, multiple decision makers, you know, people that also have very different priorities.

Josh: IT is like, wait, what?

Chris: Exactly. What the integration looked like, we had to actually come out with different integration solutions. We weren’t going through platforms anymore. So that was a piece on the backend that we came out with different solutions that were fitting per enterprise level.

To your point around, you know, just like finance, getting involved, other groups, getting involved, you know, procurement, getting involved, analytics like the analytics and kind of the, the rigor that they want to see in terms of the reporting and ongoing basis of updates is very different. And so I think we started to realize that like, look, the product is great, it works for the consumer, resonates with, with what we’re doing, but it’s all these different functions actually internally to match the external kind of, you know, enterprise that we had to build out. And that, that was a journey for us. And we did it really quickly. And the team, the team activates that stuff very, very fast.

And we did a really great job at it. But it’s, it’s a, it’s a learning curve and you, you learn a lot in terms of that difference in your sales materials change, and your approach to marketing changes. So it was, it was a journey. 

Josh: Well, from what I understand it’s working amazing. You guys are totally like rocking it, rocket ship growth. So that’s awesome. And I do think that like getting into enterprise, just like it’s, it’s like jet fuel, right? You can grow an SMB, but like one big enterprise client can mean a huge amount. So we’ve talked a little bit about you being on the marketing and sales side and this transition. I’d be curious, you know, one of the things that I have had a lot of conversations about is like the, a little bit of the friction that exists between sales and marketing. And so you’re kind of uniquely qualified because you’ve been on both sides. We just published our 2022 SsaS marketers confidence report. And one of the key findings is that the kind of friction between sales and marketing still hasn’t been resolved very well by marketers. Those are the people that we ask when we do our survey that they’re still feeling misaligned in a lot of ways with the sales side. So I’m curious from your perspective, having been on both sides, What would you tell either sales or marketing leaders or their organizations? Like what are some of the things that you think could help improve that? Or like eliminate some of that misalignment? 

Chris: It’s really challenging. I don’t think anyone’s going to ever eliminate it. There’s different roles, responsibilities, and kind of focus points of the two teams. I think where we saw it, and I saw it when I was on the marketing side. I saw sales and now I’m on sales, I have plenty of feedback on the other side. I think the biggest thing for me is alignment organizationally, you know, and we talked about SMB focus, you know, mid-market focus enterprise focus. You know, building out personas, building out kind of who we’re targeting and how we’re targeting them.

And we’re talking about that offline just a little bit ago. 

Josh: Right.

Chris: The more alignment that can be driven there, you know, is just massively important. And so really understanding again where dollars are being spent and why. So one of the things we were doing on the marketing side and, you know, it was challenging.

I don’t know if I ever did it to the extent that, you know, we really wanted to, or really got all the sales on board. Was that we really broke down kind of what brand we are building and what it meant, you know, what content was and what it meant, and then what activation, or, you know, spend in marketing ads and where we were spending that, how we’re spending it.

So I think the level of transparency is really important from the marketing team. And then I think the flip side is like, I really think the sales team can and should be doing a better job of including and bringing marketing into the process. And I think we have a lot of, you know, there’s different personalities of, of salespeople, you know, if it’s the lone Wolf, for sure, you know, the running gun.

And I think sometimes that team leaves behind marketing rather than bringing them along in the process. And I think that’s a big part of it that we’ve seen is that the more times we can involve marketing sooner in our sales process, in our conversations, in our actual presentations and meetings with merchants, actually the more empathy that’s built on both sides and that team brings back.

There’s always, you know, I think a natural, unfortunately, friction shouldn’t be the right word, but it is. But I think the more just collaboration, you know, working from home is really tough. Bringing the teams onto a call, I think is immensely important. And we also did feedback loops. So we typically would do a monthly feedback loop where on the marketing side, we’d share out kind of what we were doing, what was working and why we were doing it.

And then we opened up the forum for our sales team to kind of get feedback. It’s risky, I guess, in some cases, but it was, it was what I think was pretty good. And what I’ve appreciated now, being on the sales side, I’ve really appreciated seeing what the marketing team is doing, because then I can say like, you know, Hey, one or two things are working.

Here’s my perspective, based on this merchant I’ve talked to. And I think that the ongoing feedback loop is just, it’s really important. And I think, you know, for all organizations to think about.

Josh: For sure. I just feel like you’re talking about the lone wolves or like certain types of salespeople. I mean, they are out there belly to belly with the customer, right.

And there’s a lot of marketing kind of ideas that could get unlocked. And so like the fact that you’re bringing along some marketing team members too, like sales presentations and things like that, I just, I think that that is the level of collaboration, and you used the word empathy. I think that’s where it really has to get to in order for like those teams to start becoming way more aligned and like eliminate some of that friction, which might be a bad word.

Chris: And I would just say like, you know, one of the, one of the companies I’ve always been impressed with in terms of how they treat internally, but then also externally their customers is LeadPages. I think LeadPages has always talked about how their customer is a person, right? Like they were one of the earliest that really adopted this idea. That it’s not about the functional product. It’s not about, you know, benefits, not even about value add, it’s about treating the person you’re selling to like an individual, like a person. And, and I think, you know, when I was on the marketing side, that was really important, right.

I actually started to see like, you know, LinkedIn ads, they’re going, looking more and pulling in TikTok ads, right? They’re becoming more raw, more open, more transparent, all the things that you’re seeing on the consumer side. 

Josh: Right. 

Chris: They’re bringing in, you know, a lot of elements that I think have worked in consumer marketing. And I think LeadPages has always done that really well. And I think we’re, you know, we’ve done it or at Sezzle or others is like, it’s still a personal sale. Right. You can still give them, you know, the benefits of everything you’re doing. And I think when marketing starts to see and realize that they also recognize like, oh, this is a really important way and maybe I can spin it my value prop a little bit differently. Maybe I can treat that person a little bit more, you know, as a person versus a, you know, a product decision maker.

Josh: A prospect.

Chris: A prospect. Yeah. And I think that’s been an important part of that personalization of it, in terms of, you know, bringing people into calls and together and, you know, et cetera.

Josh: Yeah. I love that. I feel like the more that we can see… As marketers, like the sales team as people and like our collective prospects as people, and even like, I’ve had conversations on a different, one of these, ‘How I Work’ videos, talking about leaders, the people that we as marketers have to go to and ask for budget, etc. They are also people and everybody just wants to kind of understand what other people are trying to accomplish and what their motivations are. And the closer that we can get to just treating each other, like people, I think the more success we have. So I think LeadPages is a great example of that.

Chris: From a personal standpoint, it’s been something that, you know, my wife and former intern used to tell me to smile more, and it’s like one of those things that even, even when you’re in a sales meeting, you’ve got to remember that you’re still just talking to someone.

And I think for me, and just like new into the sales world, kind of being in it for about two years now, I think that was something that took me a little bit, you know, it’s kind of coming into the room and you’re buttoned up and you know, it’s four walls, right. And I think there’s an element and it’s different than I think the traditional, like, let me get to know your family and you know, like there’s an element of obviously relationship building, but that’s not, what’s going to, you know, lock the deal.

And I think it’s just this element of like comradery banter back and forth that ultimately builds stronger bonds. And also allows you to push back. And I think that’s the other thing from the sales side that I’ve recognized is the more, you know, not in a bad way, but the more you push back, the more you have that engaging conversation, the more you’re kind of being equals in, in the room or in the call or on the call, I think that goes a long ways in terms of credibility, understanding, listening, uh, et cetera. And, I also would say humility in the sense that when you don’t know what’s going on or they’re bringing up really good ideas, that’s frankly, another reason why I love to have marketing and product on our calls was I hear great ideas and I’ll ask, you know, our prospects, these ideas, and they’re immediate feedback loops for our marketing team and I’d say, and our product team. The more, the more honestly success we see is getting our product team involved also, actually in the selling process. Because that’s another part for them that they’re building, they’re learning, especially with enterprise, because there are customizations, there’s unique value props that they need.

And so in addition to marketing, I think product has been an unbelievable partner to understand and recognize those kinds of things. 

Josh: That’s awesome. Well, cool. So I have two more questions. We’ll make them quick. Uh, but you know, we just started 2022. So I’m just curious, what are you kind of excited about for this year?

Chris: Other than travel and the big things. I mean, it’s weird to say “excited,” I don’t know if it is the right word. But I’m really keen to see what happens with the economy. I mean, just straight up, I think, you know, inflation, pressures, interest rates kind of, you know, whether we’re in a bubble or we’re not in a bubble and I’m not going to pine on it from a personal standpoint, but like, there’s just a lot of still insecurity out there where we’re at.

So I think I’m excited for not the insecurity, but the, you know, hopefully by the end of the year, having a little bit more of a foundation in those things, there’s just a lot, you know, just a lot of questions. So I’m excited for stability, I guess, in those areas and to see also where they play out, you know, whether it’s a real estate market, even e-commerce and retail, et cetera. So I’m excited to see where it all plays out. 

Josh: Okay, cool. So we’ll see. So yeah, I mean who knows, that’s a whole nother video. Right. But, I would be curious too, to see how that in the end might impact Sezzle, right? Because your business model is kind of about credit and helping people, you know, to be able to purchase things that maybe they wouldn’t be able to otherwise.

So how those factors may impact your business will be interesting to see. 

Chris: Yeah, there’s a lot going on. I mean, regulatory, I think the way the consumers are being treated and the way, you know, CFPB and you know, governments getting involved and looking at things that I think they hadn’t been looking at in previous, I think a lot of that’s coming in because of low interest rates and how they’re thinking about if there’s going to be other things out there. So it’s an interesting point where we’re at and we’re hopefully coming out of something, but there’s a lot on the horizon. I mean, even, even geopolitically, there’s a lot going on right now. 

Josh: Yeah, for sure. Cool. So the last question is, I always ask this, who are you paying attention to? What are you reading or listening to on a podcast like who’s out there that has some cool ideas that you’re latched on to right now?

Chris: So the two things I’ll just say, so one is “HBS After Hours.” I love their podcasts. They’re three professors, business school professors that will just talk about current events.

And current business issues, climate issues, everything. They do a weekly, I think it’s phenomenal. They just bring the latest and greatest and they do it in a way that ‘s very conversational, super smart, with different ideas, different opinions. I listen to them every week and love it. And then I’d say on the business and kind of going back to our original side on sales.

I’m new to the sales world. And so I happened to be reading sales books and self-help sales books. And I think, you know, it’s been really interesting to me to seeing the different types of selling the different types of characteristics. So I think “Challenger Sales” has been a really good one. There’s been some HBR articles that have come out around, you know, they call like, you know, sense building.

And so there’s, I think there’s a lot of evaluation of we’ve we’ve gone through different evolutions. The sales cycle and what works, you know, the strategic sale was really, really big challenger sales are, you know, more, more nuanced and more recent kind of an idea. But I think we’re starting to say like the sales models continue to change and evolve and like I’ve been kind of taking a step back and looking at it over time.

And I think that’s an interesting area that, you know, relevance wise that I’ve been spending some time with. 

Josh: I definitely love sales. And I honestly think that people, sometimes when they think about sales, they don’t think about the level of thought and sophistication that goes into it. But like, there are some really amazing thought leaders that are out there talking about different models for sales and approaches. And so it’s cool that you’re reading that. I enjoy that stuff too. So 

Chris: Yeah, the psychology is a pretty interesting side of it. 

Josh: Yeah. Yeah, for sure. Well, Chris, thank you. 

Chris: Yeah. 

Josh: Appreciate you being here. And that’s going to be it for today. 

Chris: Thanks so much. This is great. Thank you. 

Josh: Thanks.

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