Podcast Pit Stop: Robin Gregg on How to Sell Into Non-Tech Verticals

Traditional digital marketing, sales, and partnership strategies work until they don’t. When that happens, it’s time to get creative! In episode 43, Robin Gregg shares the best strategies for selling into non-tech verticals. Robin is a longtime payments person, with 15 years of experience in both commercial and consumer-related transactions. She is currently the CEO of RoadSync, a digital solutions platform dedicated to the transportation industry to easily and efficiently accept payments. Join us and learn how applying her strategies can open windows in a room full of closed doors.

Take 20 minutes to listen and digest and then head back to the races! 🏁🏆

Pitstop Highlights

Sales Strategies 

Sales can be extremely accessible, especially on the phone. Many of the sales are outbound sales-focused, and while it isn’t the most attractive sales approach, it's one of the most effective. It’s also important to follow up with clients via email or text (with their permission). The key here is to be as accessible as you can. 

Robin suggests making sure to communicate with hires that their job is phone-centric, and that's primarily the medium sales will be made through.

Marketing Strategies

Today, traditional marketing methods no longer work. Consumers are becoming more reluctant to use Google to answer their solutions. Instead, they turn to social media platforms like Reddit and Youtube. 

The consumption of content is only increasing within this digital age, and more are turning towards content that will answer their solutions. A marketing strategy should be geared towards fun and creating content on platforms such as Youtube and Reddit.

Partnership Strategies

When pursuing partnerships, it’s important to look at the main things people are using adjacent to the solution of your company. It’s all about being creative when integrating a value proposition with partners. 

Before pursuing partnerships, make sure you have experience in direct sales before approaching people on selling their products. It can be detrimental when people try to get partners to sell something that they're not great at selling it themselves.

Connect with Robin:

• Connect on Linkedin:  https://www.linkedin.com/in/robingregg/
• Website: https://roadsync.com/

Full Transcript

Brendan: Hey everybody. Welcome to Pit Stops to Podium, the RevPartners podcast where we talk to execs who've competed and won, taking their companies from high growth to high scale. My name is Brendan Tolleson. I am the co-founder and CEO of RevPartners, and I'm delighted to have with me today, Robin Gregg for this edition of Pit Stops to Podium. Welcome, Robin. 

Robin: Hi. Thanks for having me. 

Brendan: Absolutely Robin, I've been excited about this episode. As I mentioned you in prep, I followed your company from afar and watched your progression, which has been really fun to see. So for this audience, Robin serves as the CEO of road sync. But Robin, I'd love for you to give a little bit background on who you are for our audience and also what road sync does. 

Robin: Yeah, so I personally am a long time payments person. I spent over 15 years in payments, both on the consumer side as well as commercial with companies like Capital One and fleet core. And most recently since 2017 I've been running road sync, which is a platform for the transportation industry to easily digitally accept payments and through, you know, basically anywhere where truckers need to pay or get paid. And in what we're really doing is taking making more efficient a market that is very much paper-based in their financial transactions. It's a massive industry, $800 billion industry, and we think there's a massive opportunity to create a vertically specific payment platform that really powers these financial transactions to make it more efficient for everyone. 

Brendan: That's great. I can only imagine during COVID and what's been going on in the trucking industry and the news, it's probably a very interesting time for what you do. It definitely is. 

Robin: I mean, it's definitely chaotic, especially the beginning of COVID as they sort of grappled with things. But you know, the industry is booming and they are looking for ways to make their drivers and their locations more efficient. And so we are very timely in that way. 

Brendan: Well, that's great. Well, rob, before we get into our big idea, we have a tradition here. Pit stops to podium. And it's to get to know our guests outside of work. So you have an impressive background. But what are three fun facts that our audience should know about you outside of work? 

Robin: Sure yeah, the first one is I grew up in Martinsburg, West Virginia, about 20 minutes outside of the Harpers ferry, West Virginia, which is the midpoint of the Appalachian Trail. My dad spent his entire career acquiring land for the Appalachian trail, so I grew up with in a hiking family, so it's a beautiful place to grow up. The second fun fact is I was a Japanese major in college. I went to Washington University and I was a Japanese and econ double major. So that was sort of a fun is different. It is different. Yeah, I have not used it at all, and I probably can speak like 10 words max. But you know, hey, it was fun to study. And then I think the last one is, I'm a skier. I actually learned to ski in my late 20s. I had an ex-boyfriend who taught me and I kept the sport, but not the boyfriend. And I really like to spend as much time as I can out West skiing with my kids. I have kids ages 9 and 14, and there are a lot of fun to ski with.

Brendan: That's great. What's your favorite ski resort? 

Robin: We usually go to Breckenridge because it's pretty easy and convenient, but also spend time out in Beaver Creek and other places like that. 

Brendan: OK, so when you don't see Robin, she's outdoors, likely skiing and maybe practicing her Japanese, we'll find out. So rather, let's transition to the big idea. As you mentioned, you're serving a kind of a non tech market and a massive market. 800 I think it was an $800 billion market earlier. So I think we'll be helpful. You know, based on your perspective and experience, it's really how to sell into these non tech verticals. So, you know, b2b, Sas or technology always is kind of the buzz. But there is these huge markets, as you just described earlier, where people can win just as much, if not bigger. And so I think it's helpful for our audience to understand what that looks like because it's a different motion. And so I think there's some really good practical insights that our audience can understand. So before we talk into the way in which you sell, you market and you build partnerships, let's kind of set the context in the framework as it relates to how you think about these markets. 

Robin: Yeah, no, absolutely. So I got exposure to this when I was working at fleet corp. So fleet core sells a fuel card product into mainly blue collar verticals, any businesses that have commercial fleets. And so that's like things like construction, plumbers and transportation, which is my current market. And what I learned about those sorts of markets is that they're pretty underserved in terms of the financial products and even the software that's being offered to them and they themselves are. Maybe not operating in a very digital way. They may be conducting a lot of their business through, you know, basic spreadsheets or paperwork, clipboards and scheduling work, reaching their employees, managing day to day tactics over the phone. And that's just how they do their business. And so when you think about offering them a new solution, even if it's a digitally focused solution like what we have, you really have to understand how they conduct their day to day business lives. Where are they? I mean, what's interesting about transportation and also the verticals I was serving at fleet core is, you know, they're out in the field. These folks are not sitting in an office behind a desk all day long. They are under a truck repairing it. They are in a truck, driving to a delivery like they are out working. And so thinking that you're going to reach them and that they're spending hours a day in front of email or they're going to be googling stuff during the business hours is just not really how they operate. And so you have to really understand where they are, how they conduct their business lives and, you know, reach them in channels where they're comfortable and they are readily available. 

Brendan: Yeah, the context is super valuable because it's going to inform how you actually engage. And if you rely on to the taxes you just described of traditional prospecting, it's probably not going to be a very successful return on your investment. So with that knowledge, rob, let's talk a little bit about your go to market motions and let's start with sales now. How does that impact how your team sells to this audience? 

Robin: Yeah so because we understood that our market is on the phone and accessible over the phone, we have a very, very heavy outbound sales focus, which, you know, if you talk to other venture backed software companies or payments companies, you know, isn't the sexiest approach, but it's honestly for us the most effective. So we have a pretty massive PR team and account executive team out there calling folks, and that's really most of our customers are the initial contacts will be through an outbound sales touch. And so that just sort of reflects where we are and how our customers can be reached. We also do a lot of follow up, not just through email, but also through texting, because that's also where customers are obviously with their permission. But it's just a different sort of follow up and tactic. I mean, just sometimes it's easier to get these folks on the phone because they might have a few minutes between jobs and it is going to be to get them to respond to you in some written form like email. So that's been really important for us. We actually have a very large outbound telesales team, both our R&D teams, and that's been a huge investment for us and trying to make them as productive as possible. 

Brendan: This is more of a side note, but as it relates to talent acquisition for a BDR you just described because it's more telesales, is that how does that inform how you hire? I mean, is that something that you have to change your job description or like expectations? I'd be curious just to talk with that real quickly. 

Robin: Yeah, I mean, it's been important for us to find people who have sold into similar types of verticals that's been pretty call intensive versus people who are doing spending a lot of their time doing research because it's not the type of thing where you're like, oh, I'm going to research the VP of marketing because I have a CRM system and I could spend half my day doing that it's not. It's not that at all. And so we actually get a lot of our reps will come from other SMB software platforms because that has a similar sales motion or, you know, even like service industries like sometimes trading people fresh is a little bit better, and they might understand the dynamic in the industry. They just I think the main thing for us has been they need to understand that their job is phone centric, which is not the same as a lot of our programs. 

Brendan: No, it's not. But I think it's good to understand. I mean, to your point, if you want something to be successful, it's important to know how to reach the persona. And so it's to your point, is more iPhone centric than email centric. Let's let's transition into the marketing side. So we talked a little bit about the distinction on the sales aspect. How does that inform your marketing tactics? 

Robin: Yeah so, you know, traditionally people would do a lot of paid search. And, you know, we have tested having people buying words like payment platforms for the logistics industry and things like that. But this is not an audience that is googling things or necessarily looking for these solutions online. And so what we found is that's not a really great tactic for us. Just like email is just OK. It's not as great as it would be for some other solutions. And so we've had to be kind of creative. These folks are digital, they're just not digital in the way that other software platform customers might be. So one of the things that we've been focused on is we've discovered that our customers do spend a lot of time consuming content content on how to run their businesses, content on how to learn about best practices. These are folks that are on YouTube watching videos about how to optimize loads as a trekker or how to run the repair shop or to learn a repair. They might be on Reddit looking for information about good people and shippers and brokers to work for. And so as we thought about our strategies, we've really been more content focused and a little bit less sort of paid search and sort of more traditional digital marketing focused because they are digital, but they just are in slightly different places and are more content consumers than anything else, just digitally. 

Brendan: Yeah, I like what you describe being creative, it's the whole kind of concept one size doesn't fit all, and it's not that the approach is wrong, it's just how do you execute it? And so this gets back to, you know, where they consume information. And so while it may not be Google Ads or Google search, but the YouTube aspect which I never would have thought of that makes a lot of sense. And as you describe it. 

Robin: Yeah and it's honestly, it's a lot of fun. So definitely, definitely check out some of the YouTube tracking influencers. They actually are producing some great content, and it's very engaging. 

Brendan: Yeah, as we say, your fun fact should have been something about your browser history and what you've learned about trucking through YouTube videos.

Robin: I will tell you my YouTube algorithm is really, really confused about what content I like. 

Brendan: All right. Well, let's transition into the last aspect of a go to market motion. So we talked about sales, we talked about marketing, and then one of my favorite go to market motions is the partnership side. So how has this creative, creative idea? How do you be creative as it relates to going after partners? 

Robin: Yeah so I mean, I think first of all this, this ecosystem has a lot of legacy software solutions and legacy service providers. And so we've found they have reached and an installed base. And so that was really what made us interested in pursuing partnerships. We anticipate this to be a meaningful piece of our distribution strategy over the next two years and are already building towards that. And so we had to look at what are the main things that people are using their adjacent to our solution adjacent to payments. And it's a pretty long list of stuff. So we've got to be creative about how we integrate with partners with a value proposition of partners, how we can make their product stickier. But it's an important thing because these folks are already people who have a lot of trust back to our earlier two points. This customer base isn't rummaging around looking for new technology solutions on a regular basis, so they're pretty loyal when they get something. And so to the extent that we can piggyback on things they're already using, it's a pretty strong strategy for us in terms of acquisition and retention for customers. So we spent a lot of time there. We're partnering with everything from the legacy fuel card payment solutions in the market, including the one that I used to work for, called fleet core to, you know, various different management systems like ERP systems for heavy truck repair merchants, dock scheduling solutions. I mean, I can't. There's a very long list of types of technology that people are using to run these businesses that have been available to partner with. We do think it's important that we knew how to directly sell our product first before we approach partners. So we have many years of direct sales under our belt before we're approaching people and we know how to work with them on selling the product themselves, which I think is pretty important. I think it's always a mistake when people try to get partners to sell something that they're not great at selling it themselves. 

Brendan: I wholeheartedly agree with that. So just to clarify something, you want to make sure your team knows how to sell before they try to teach someone else how to sell it. So I'd just be curious as we talk about partnerships, are you as is the way you built your partnership model? Are your partners reselling it? Or are you asking them to refer you into the customer base. So that you can sell it? 

Robin: We're doing both. It really depends on the partner. You know, our early partners, we slightly refer. We prefer to we prefer to be referred because we want to have more control over the sales process. But we do have some white label white labeling that we're also going to do. We really like that when it's deeply integrated into the product and kind of be basically lighting up a new feature, which you can actually easily do with payments, especially if it's very adjacent with something like an invoicing solution. So we're open to doing both, but for the most part, most of our early partnerships have been referral. 

Brendan: Got it. OK it makes sense. It's kind of that crawl, walk around approach where to your point, you need to know. As you think about your evolution, you need be able to sell it before you can expect to try and get other people to sell it. Before they can sell it, they probably need to learn from you. So I think that motion makes a lot of sense. Well, Robin, this has been extremely informative for me. I'm sure for our audience too. It's been a helpful guide as it relates to how to sell into non tech verticals. Having that necessary context to then inform your go to market motion from a sales, marketing and partnerships perspective. If our audience wants to connect or engage with you, what are some practical next steps they can take? 

Robin: Yeah well, first of all, I'd like the audience to know that we are hiring a ton at RoadSyn. We raised our series B last year and have been dramatically scaling. Our sales and product organizations, and so if folks are looking for new roles, definitely check us out at RoadSync. We have a pretty extensive careers page, you know, engaging with me personally. I'm on LinkedIn and we'd love to hear from folks and we'd love to hear folks ideas about the content today and, you know, just interest in the business. So I really appreciate the time. 

Brendan: Absolutely well, Robin, Thanks for stopping by. We'll be sure when this goes live to in the comments of the social section to put the careers page. So anybody that enjoys telesales, Be sure to sign up in addition to other aspects of sales and marketing and partnerships. So Robin, Thanks so much. We really do appreciate your time. 

Robin: Great.