Matt DiBari === Matt Arbesfeld: [00:00:00] Everyone, super excited to be chatting with Matt today. Who's the CPO at Spot Hero. Welcome to the podcast, Matt. Matt DiBari: Thanks for having me. Also, Matt. Matt Arbesfeld: Great name. Awesome. We'd love to just learn a bit more of your journey into product management and how you find yourself as chief product officer today. Matt DiBari: Yeah, I've spent 15 odd plus years in product management. uh, Started out, in the early days of product management. Digital product management where, we were still trying to find our way, When you'd go to a conference or a meetup, the first question you'd ask is who do you report into? Cause it was always, are you part of sales? Are you part of marketing? Are you part of engineering? And now it's cool that we've become our own leg of the company and, there's titles like CPO available. So I started in a big B2B company and worked my way through there. And at a certain point, I wanted to learn the B2C side. Jump ship to cars. com where I learned How to deal with 30 million unique users a day and, or a month. And what does it mean we have a million uniques a day and how can you use those audiences and how do you do things for, at that point app and, mobile web and all of that, and then fell into a groove where I moved into [00:01:00] marketplaces where you get to do both that hard sassy B2B, Kind of solutioning, and then also the quick nimble B2C side and then move over to spot hero and, Haven't looked back and really love kind of building these big marketplaces. Matt Arbesfeld: Awesome. Yep. Marketplaces are super interesting. So we'd love to learn just how you think about the B2B side versus the B2C. Do you staff those teams differently and just in general, how you think about investing across such disparate types of products Matt DiBari: Yeah. It's one of the most important decisions I think I make on an annual basis with my peer, the CTO, is how do we decide how much money to spend on each area, right? Because as a marketplace, you need that B2B side to have inventory, to have things to sell, to have, in our case, have parking spots to sell, and how do we make sure that we're growing that side of the business to then have. An awesome web experience for the B2C to then take advantage of. And if we don't have good inventory with good photos and good descriptions and good pricing and all of those things, take Airbnb or any [00:02:00] other popular marketplace you can really struggle even if you have the best web commerce experience. So annually we do a really tough evaluation on where do we want to put our people and our money, right? Where do we want to focus and how do we build that virtuous cycle where we're getting a good amount of. Operator buy in and giving them the tools they need to succeed to then give us great products to then sell on the other side to the users, but also knowing that constantly there's, e commerce only companies that are raising the bar and the expectations on that side. So you can't throw all your eggs in one basket, right? You've got to Constantly be reevaluating and balancing those two. And on a quarterly basis, we do some tweaks, but really the big tweaks happen on as part of the annual planning process where, we really decided we need to fund an extra team. Do we need to, get a bunch of skill sets in a new area or what have you to really take advantage of an opportunity or sometimes play catch up to where the rest of the, like I said, the e commerce world is doing. Matt Arbesfeld: in your experience has the B2C side been more demanding in terms of headcount or B2B [00:03:00] where, what has that shifted over the years? Matt DiBari: Yeah. One of our big, Like the number one kind of value we hold here at spot hero is gives drivers the right away. So B2C does come first. So if I was to look at our spend or our focus, it's probably 50%, 60 percent on the driver's side on those parkers. And then the other 40, 50 percent is evenly divided between teams that are helping run the business, right? Teams that are working on internal tools and internal solutions and teams that are working on kind of the B2B side. Matt Arbesfeld: And then within each area, you've talked about this layered portfolio idea, maybe just walk us through that and how that applies to each Matt DiBari: Yeah it starts like I said that portfolio view at the top of how much Resource money people spend do we want to do on? Internals, standard kind of internal. I treat my internal teams like B to B teams. Like we, they're similar road mapping, similar skills. And then how much do we invest in the B to B side? And then even amongst that then there's a second layer of kind of how do we want to spend? Because. , as a product led growth [00:04:00] kind of company, we have to spend a lot on just acquiring new users. We're constantly breaking into new markets. We're still introducing the idea of digitally parking to people. So there's a certain amount that I have to set aside on the consumer side to just introduce us to people to go find new users all the time. There's an acquisition budget, if you will, there's a retention budget. Okay, great. You parked with us once. Yeah, you used us for that Cubs game or , that important lunch meeting downtown with a new client. How do I use you a second, third, fourth time? What are your other use cases? So I take a second cut and Go, okay, this is our consumer spend inside of that. How much do I need to be spending next year? What are our financial goals on growing new usership versus repeat? How much of that is built into the plan? And I work with marketing and finance and what that plan looks like. And then again, in the annual cycle, I'll move around, dollars and people into the right buckets. It based on that on the B2B side, it's similar, right? How much do we need to spend to help our business run faster? How much money do I need to spend to grow new [00:05:00] operators? Get new locations, right? Like I said, we're constantly adding new cities and new arenas. Versus how much of that is, okay, you're on the platform. How do we make you more successful? How do we make you more money? And what kind of tooling do we need to make the B2B operators more successful? So that's definitely a second layer of view that we have to put on top is what are our goals, right? Like how many for sales, how many locations are we going next year versus how much same store growth do we have next year? If those numbers are wildly different in the plan, I should probably spend in a line accordingly But I also look at the three year plan because product isn't as much we love being agile and trying to be quarter to quarter There is a bit of especially on the b2b side I may have to build something or my teams have to build something today That is for 2025, right? We've got to get ahead of some of those cycles. consumer is a lot more quarter to quarter And, year to year than the B2B side for sure. Matt Arbesfeld: On the consumer side, do you have any kind of high risk, high reward type projects, or how do you select what to work on in that B2C Matt DiBari: Yeah. The nice part is because we are still in a high growth stage we're [00:06:00] still introducing people to parking. We do get to take a lot of high risk projects, right? Like we can do things where we're, recommending locations or highlighting different needs or introducing new segments of parking, right? Yeah, I may use digital parking for going to a sporting event because I don't go to the stadium often. I don't know what parking looks like around there. But when I go to work, I know what to expect. So in different arenas by arenas, not actually sporting arenas, but different areas of the customer journeys, right? We can take a lot more risk because you may use this for the airport. And you're not going to use this again for three to six to nine to 12 months. Or families don't take big family trips that often. So we can take a risk with those users and if they fall out and don't repeat, they weren't really planned to repeat anyway, which, we'd love every user to use this all the time, but there's just logistically of you're not that high of a repeat user. If you're someone way out in the exurbs or in the rural areas, that's coming to the airport. Are you going to have a big use case to come downtown every day? Probably not. We look at different areas of the business of where we can take on risk and definitely B2C just lends [00:07:00] itself to that anyway, because we're constantly finding new users. Matt Arbesfeld: Are you able to see what type of user I am? Am I the commuter or the sport goer and the traveler and kind of tailor the experience, each of those, or yeah. Matt DiBari: Yeah. So we do know where you came from or what your first experience is or what your first search is for or anything like that. We do some tailoring today. There's a lot more of that coming. Because we are finding that while we can cross sell you across, like the person that goes to a sporting event on a weekend. tends to also come into the city for a fancy restaurant or a new dining experience or a, musical, a play or what have you more often than not. We're historically, we've thought of those as two very different users and we're finding out that they're a lot the same. Similarly, our airport users look a lot like people that do staycations and just come to the city to enjoy a couple of museums for the weekend and stay overnight because they don't drive all the way back and forth. So we are starting to really dive into that and find those synergies and now starting to tailor those experiences. For those different users. And then the commuter user, they do [00:08:00] everything, right? Like they start commuter, they fall in love with the product. And as we introduce them to more usage, typically if you're driving downtown every day, or maybe in a post COVID world, three days, two days a week, you're probably also occasionally going to a sporting event or out to dinner with friends or what have you. Matt Arbesfeld: That's really cool. And one thing I'm a believer in is that. Right now, consumer experiences are almost all the same. When you visit a site to buy something or order food, it's a bit personalized, but will there be a future where it knows what I'm looking for? And so we'd love to just understand how you identify those cohorts and how you tackling that problem logistically, internally. Matt DiBari: Yeah. There's a lot of it is historical behavior analysis, right? We luckily have 13 years of parking data and behavior data. And. The interesting layer on top of the fact that we know what you started with, right? What your first search was, what your first purchase was is. We also see what that looks like over time because we have all that time horizon for people, you know Our average user is over three and a half years old [00:09:00] because well in established markets Right so you sticker if you've used us in chicago, that's where we started. You know We know how you started. We know what you've done over time. We also learned, because markets are very different, what a Chicago user does is very different than a New York user. So there is, we have to take location into account. New York is largely valet only. In Chicago, you've got all three. You've got open lots, you've got garages, You've got valets. And as we start diving into the data, we learn really quickly. Some people will only park at valets because they don't want to deal with, probably the complexities and tricks of getting in and out of garages and all that. and you've got other people that will never use a Validate in their life. We just ask you that. Like it's not, sometimes it's okay to just ask the customer, what's your preference? We can give, but the flip side of that is if you're going to ask the customer that, you better do something with it. Like I, there's nothing I love more than as a user. If they ask me like my preference or you want to save your filters or what have you like, great. Yes, use that. If you're going to ask me that and then not do anything with it, I'm going to get pretty [00:10:00] turned off pretty quickly. So is that the balancing act of what can we infer on you? And then what can you just tell us? And it's okay to ask the question as long as you do something. Matt Arbesfeld: Yeah. It's like being asked if you have an allergy at a restaurant and they serve you like the peanut butter or the shellfish right away. Matt DiBari: Yeah. Amazon's finally like I'm a, like everyone uses Amazon. I do the same three steps on my filter every time I log in and it's yeah. They've started saving some of them though. I'm so happy. They're finally doing something with that. But yeah, that's the stuff where you know Amazon gets where they're because they're so big but a lot of other sites wouldn't right if every time I tell you i'm on four stars and up like at some point you need to respect that So Matt Arbesfeld: in a personalization project like that, is the shape, how's that sort of from beginning to end shape? Does someone have the hypothesis and then ask the question and then just, is there a data team just walk, maybe you can walk us through Matt DiBari: yes we start a lot of that with the Our product design team, all of our designers are full stack. So they go from research through X all the way through visual, visual design. And and, we find [00:11:00] a lot of value in that, right? There's not a bunch of handoffs. It's one person who intensely thinks about your. Search experience and they will kick off and anywhere is a good source of a question, right? So somebody will say hey, how can we don't do this and they think about it and then they go kick off some research And along that way right product engineering get involved and look at is it valuable, right? So if we do this customization Hey, you've heard from users that they're excited about it. If we do it as their value there that will actually change a behavior And how much of a behavior does it have to change to make it worthwhile? Because engineering saying, Hey, that's expensive or cheap, or we don't have that data to your question. We do some quick rough research on just, is it a real problem? Once we established that it's a real problem, then we do deeper research into how big of a problem is it? Along with. Is it possible to solve and how expensive and then is it actually value creation? So we really quickly moved to all three people swarming on that. But it does start with our product design team before it moves over. Matt Arbesfeld: and then , are projects usually tested or do you [00:12:00] find that doing all that work when you do launch, you have enough conviction that you can go fully Matt DiBari: Yeah, and this is where again the big difference in b2c and b2b come in on b2c we can do a five percent ten percent audience test. We get enough users on a daily basis We can get the stats statistical significance pretty quickly But it's also not something that we always have to consider because we get a new audience the next day, right? Or we can try something in just a hundred percent in a single market. So we've got some flexibility there and how we want to test things. But we do a lot of testing. Like we do definitely, we do, we very rarely go from, Hey, this is an idea to launch it in front of, millions of people. Without some level of validation throughout the way. B2B is a very different animal, right? So B2C, you get the flexibility. Hey, new audience tomorrow. If we lose some customers, yeah, it hurts, but it's not as high risk of, Hey, if you're on the B2B side and I've been at companies where you've had as few as 12 customers, 12 massive customers to like here, 10, 000 customers You can take some risk there. You can't take as many risks if you have a million [00:13:00] customers. So on the B2B side, it's a lot less live testing and a lot more, Wireframes and, testing with a select group of operators or things like that. So again, when you talk about like hiring, recruiting, building out these teams the skill sets are very different on both sides. It's one of your questions, but they're being about the portfolios. the makeup of who's on those teams, the PM, the PD, even to some degree, the engineering side you do have a different style because there's a, lot more thoroughness that kind of has to go in the B to B side from just a, It's agile, but it's not as agile, right? It's not a, we had an idea on a Tuesday. We threw it in. We did some quick sketches, messed around with some basic AB testing and got it up the next week. You can't really do that when you've got five or 10, 000 customers and a lot of risk involved. Matt Arbesfeld: for sure. you need to have convict a good amount conviction to build or else you're doing, building a lot of technical debt with the CS team and the engineering architecture and the customers. Matt DiBari: Or you're burning your sales reps. And at a certain point, you can't wreck their relationships. [00:14:00] I Matt Arbesfeld: Yeah. If you're pushing bad product or bad bad things to them. I'm, yeah, I'm curious on the on the, consumer side. One thing I've heard from folks who are doing a lot of personalization and AB tests is you have so many variations running for all your customers. It's hard to really find problems and see what's going wrong and track is this thing working as you keep expanding the feature set. Is that something you've run into or? Do you find the tech, it's been pretty stable and Matt DiBari: We do try to limit ourselves to what actually gets tested on in production with real live users to like an ABC, we don't go much deeper than that, the bigger challenges, because like I said, we've got a lot of our investment on that customer side. Is when multiple tests are running at the same time, and you don't know if there's a compounding effect, so you could say, hey, this one caused a gain in conversion, and this one caused a decrease in bounce rate and more time on screen. So when you combine those, you don't necessarily get a multiplying effect, right? you may get [00:15:00] just the effect of one of those. you may get the effect of one of those tweaked up a little bit. Usually you don't see it go down. Usually when you combine two things that don't go backwards, but you just don't get the same magnitude. So you may come out of a test or multiple tests going, man, we feel really good about all these things. This next release, especially like when you get to app releases that are a little more time bound. We think there's gonna be a lot of great stuff in there. And then it's. Oh, it's. only okay. Because you didn't get that compounding of that caused more time on screen and that caused more conversion and that caused better retention. It's no, those were all getting the same audience doing the same action. So you've got to discount those when you put them together. And that's okay. You just have to know that going into it, that these results are not necessarily going to bear all The way out. Matt Arbesfeld: yeah, that makes sense knowing when you combine everything, they actually are competing a bit for the user's attention. And Or one thing already accomplished what you're looking for. So the other one doesn't double the effects of that change. Matt DiBari: Or you're both solving the same problem differently, right? Which is sometimes you don't think about that when you're writing the hypothesis. Oh, we're actually both trying to solve the same thing because we wrote it up a little [00:16:00] differently, our problem statements a little different. But our solutions all aim at the same thing. Matt Arbesfeld: As you add more capabilities and more segments. The app grows in complexity. Does that introduce other problems that you now have instead of one user, probably when you first started, it was one user flow, book your spot. And now you have 500 user flows. Is that a source of complexity and, or have you been able to manage that and not have it introduced problems? Matt DiBari: Yeah, I think the bigger thing is just the cost of change. So now to your point, the question earlier about, do you have a different experience based on the use case we do, but that also means if we want to do something. Completely standard Hey, we want to add a new payment type, right? We want to add Venmo, right? Whatever it is. Now we're going to do that five times. So it's not that the complexity is raised from a product problem solutioning. It's more, Oh, we want to update style [00:17:00] guides. We want to update, some core things, or we want to swap out a provider for a software that's underneath, that's doing, tracking or what have you. That becomes five times the effort. Cause we've got five different workflows, or five different, user journeys. That's where that, that rears its ugly head. Sadly. It's more of the, tech debt or, lights on type activities than it is anything else. Do sometimes random bugs pop up? Yes, but actually I think having things bifurcated it eliminates or it limits the amount of spread that they have. Because and it also makes finding and fixing faster because it's, Oh, it's specific to this one use case over in this one area. There's some gains there that maybe offset some of those other costs I'd ever, I've never done the, math on it, but my guess is there's probably some, Cost benefit analysis we could do that says, eh, this actually, net is a little better. Matt Arbesfeld: That makes sense. Cause you have so many paths that a code change likely only affects. A fraction of users. And yeah, I remember when we first started and you'd have an idea for a feature and in a day it would be out and now you look, you got to add something and I've talked to this team and there's this [00:18:00] edge case. So just the cost of a complexity, I guess. maybe shifting gears a bit. Like you've accomplished a ton in your career going B to B to C. Marketplaces, And would just would love to hear any advice you have for maybe PMs who have their first job or looking to break in. Any suggestions you have for how to think about product and break into the space. Matt DiBari: Yeah, I think, It's I'll answer the second part first, which is the trying to break in. It's a hard job to get into right? It's a hard job to get that first product role. I do a lot of mentorships both in and outside of my company. And I'm always happy to help people get to get that first step or at least, help coach them on how to get that first step. Because a lot of times, there's people in the company that are looking to get into product, right? It's a hard role. It's a fun role. It's a visible role. A lot of responsibility, but a lot of, a lot of fun that comes with that, and you get to interface all the departments. It's a fun role. So when people are posting kind of those [00:19:00] junior or those entry level product roles there's usually you're going up against the line of people inside the company, that are interested, that are known quantities. So you've got to demystify yourself a little bit. You've got to make yourself less risky than the people that are in there. So one of the biggest things I tell people is, make sure, enough about the role. So go and research, listen to podcasts like this, read books, read blogs, whatever you can. So you can go into an interview really well informed on What the role is because, that's something that the person inside the company may not know as well as you, right? There may be known as, hey, you're really good on the ops team or you're, but you don't know anything about product either. The other thing is to spend time thinking about what you do and how it relates to product. So after you've read the blogs or you've listened to podcasts or what, Read a book. Think about your resume and think about how a product person would tell that story. And again, great idea to go reach out to somebody like me or somebody else in the industry that's willing to help and have them help you rework that resume into something that [00:20:00] is more talking about metrics and impact or how you work across team or the things that we're looking for in product people, right? Which is that ability to deliver the results, that ability to. Talk to all different facets of the business, the ability to make decisions. So while your role may not include all of that today, find the projects that you did do that on, or find the examples where, yeah, I worked with engineering on this thing for three months. Yeah, I was an analyst over in the finance department, I was working on this tool and, I was giving them feedback every day and I was helping us get to a better resolution. And when we were done, we were like, We cut month end close down by three days, like awesome story. That's a product story that you didn't realize was a product story. So you've got to take that risk out of yourself. The other thing is is don't be afraid to go to a company that you want to get a product role with. In the current role you have, right. So move sideways to then move up come in a good company. If you tell them on the way and Hey, yeah, I'm happy to come over and be a financial analyst. Like you have this opening. I'm really excited to be here. I love this [00:21:00] company. I want to be here, but my goal in two years is to be in the product department. Like no one's going to. No good company is going to wash you out of the process at that point, right? They're going to be happy to have two years of a kick ass finance person that is then also going to move on to be a kick ass product person. That's a win for the company. But sometimes, yeah, you do have to become one of those insiders, but if not, you can definitely tweak and work your resume and work your interview questions and practice to where you're giving. Very product the answers to help you get in. The other side is The kind of the first part of your question is b2b b2c There is a personality type for that right and we don't necessarily screen you out because of that At least I never I hope I never have. But like we were talking about earlier Being risk adverse, you're probably better on a B2B role. So when you think about what you're applying for, the type of questions you're gonna get asked, the type of day-to-day job, you're gonna have, you're gonna be happier in a B2B role. If you're somebody that loves talking to, a handful of customers and getting really deep with them and building relationships over years, [00:22:00] b, B2B is gonna be a lot better for you. But if you're someone that's, hey, I love e commerce. I love moving fast. I'm super cool with risk. I'm really creative in the fact of like visual or just I like thinking off the wall ideas. Hey, I've built my own little mini business. You're probably gonna do better on B2C as a way in. Over time, I think PMs naturally will fall into a side of the camp that they're more comfortable with, but I definitely see a handful, whatever it's 30 percent that do ultimately bounce back and forth because they like, Sometimes they feel really happy about the speed and the you get extra eyeballs on the B2C side and then sometimes they want a little break and they're like, Hey, I can take things a little slower, be more deliberate, and I'm going to go to B2B for a year. And I've got people on my team that they are happy to, or people in previous companies as well, that have been happy to bounce back and forth. But you do get some people that are like, no, I only want to do the B2B. Crazy B2C lifestyle where I'm throwing up tests every week and we're moving. And with a little less pressure and a little less risk, right? Because the cost of a mistake isn't as bad. Fair [00:23:00] failure definitely falls more on the B2C side. Matt Arbesfeld: For sure. Yeah. It's amazing. The role is called product manager, but it's so Wildly different between B2B and B2C that you almost need a different title for the different roles. And yeah the fact is almost everyone working in some ways is doing product because they're planning out a project, they're executing, they're measuring the results. And so everyone can connect to the product job. I'd be curious though, if. If you're breaking into a company with a goal to be a product manager, are there any best kind of initial entry jobs for on the B2B or B2C side. that you'd Suggest or guide people to? Matt DiBari: Yeah, I think I've seen some of my most successful PMs in my career. Myself included. Came out of ops. Right? Because You do spend time really, close to the customer. You really, you do end up getting really close to where value is created and you understand when something's not happening for them, you start learning, hopefully, if you're good at it, you start learning that empathy skill, right? [00:24:00] You start building that. Oh I can completely put myself in your shoes of why you're that frustrated and maybe yelling at me. Or why, Hey, you're trying to go live and we're just, it's not happening because there's this data issue or this integration issue or this, whatever. So I find that those, people with that background tend to move into the role quicker or settle into the role quicker because they have empathy. And they also know the systems, right? They know, they typically know a lot of people in the company, right? Because they probably had to at one point or another interface with a lot of the other departments. Salespeople also are great at that. The problem is the risk with a salesperson or somebody that came out of sales is the reward system is so wildly different, right? In sales, you do a task today. You hopefully get paid on that task relatively soon. In product you do a task today. That leads to another task tomorrow that leads to another test tomorrow leads to a software release in three months that leads to user adoption and growth over the next three months. And it's just your time horizons are wildly different. So you got a screen for [00:25:00] that. But at the same point if you're in sales, you know what you're getting into, like those are some Some of my favorite product people to work with because they're just so empathetic for the market, right? They really know what's happening out there. They also know the competitive set really well so those are two that I find Because of the customer focus and the empathy that do great. Otherwise, the hardest one is the hardest one to break in, I should say from talking to all my friends and other product leaders is somebody for the consulting background, because the question becomes, you're great at Probably building empathy. You're probably really curious and really knowledgeable, and you can understand a new industry or a new problem set really quickly because that's the role, but you don't know what good looks like because a lot of times you're getting the company started or you're getting the project started and then you're off to the next one. So what does it mean to be on something for two years and four versions? And how do you know how to not just innovate, but also iterate and extract full value out of things? So that's another one where if you're in a company in that [00:26:00] role, try to sink yourself into bigger, meatier projects. Or if are in a role where they force you to roll on, check back in on things, show that you have that skill set that yeah, I can, I want to stay with things. I want to stay curious on a thing I already did. I'm not just going to go chase shiny objects or go onto the new thing because that scares all of us in leadership, right? We want people That want to extract maximum value and spend time back into the, going back into the well and back into the weeds on things over and over again. So that's something where, you know, On the surface, the skill sets look perfectly matched, but then, there's that fear of, Can you, stay in there? But it's an easy one to show as well, it's just by spending some of that time of revisiting your old projects or showing kind of that. Another fear with people with consulting background is that they don't. They're not the best at saying no, because part of, that, that role is you win by agreeing and you win by saying yes, and aligning to the company goals and sometimes in product, that's the last thing we want you to do, right? We want you to challenge the status quo. We want you to push back. We want you to tell [00:27:00] the CEO, Hey, your idea is bad. And here's why. And here's all the data that supports that. And sometimes in a consultant role, you don't get that freedom. Being able to show those two skills of kind of that ability to stay and that ability to push back are really critical. And if you can do that. Sky's the limit, but you've got to be able to prove that. Matt Arbesfeld: for sure. Some of the best products have come out of heated disagreement with me and a product manager or the product manager and designer. So, having that's really important. Awesome. Super great conversation. Some really actionable advice across the board for both established product leaders and also new folks. Yeah, really appreciate the time anywhere folks can find you Twitter, LinkedIn. Matt DiBari: Yeah. The best thing is just go to my LinkedIn Matt Tabari, Find me, send me a message if you want any, like I said, I'm happy to, help you just do like a resume review or anything like that. I can find time for you. So just hit me up on LinkedIn and I'm glad to help. And this was a lot of fun. I appreciate you having me on this. Thank you so much. Matt Arbesfeld: awesome. Thanks Matt.