You Don't Need More Sales Reps to Move Upmarket | Ben Braverman, CRO of Flexport

I'd love to talk, though, about building sales teams because I think you were very methodical about building the sales team and I think you would get shit for sort of not hiring fast enough. Right. And so could you talk about your approach to building the sales team?

Yeah, I mean, I think we were so lucky that Parker exists, like Parker Conrad, all of us, like all of everybody with a great company right now learned from Parker Conrad, whether they know it or not. Like the whole notion of like modern outbound the SDR structure, all of it, like it being a compound startup. Like there are so many things that Parker taught us when it comes to building the sales org. One of the many lessons we took from him was that you should not add reps to the team until their calendars are jammed, where it's like someone, your reps should be coming to you screaming, I have too many leads. I'm not closing enough business because I'm so spread. Hire more reps. If they're not doing that, it means that their days are actually pretty empty. And it means that anybody you have that is effective is actually being underutilized. And it means that like whoever you add to the team is going to be particularly dilutive because they're going to be taking leads away from people who are already ramped up, who actually have capacity to work more. So like, this is a beautiful lesson. Uh, I think we mostly honored it at Flexport. There was a few times where I think we overhired a little bit. You know, some model said we were supposed to go faster or that a rep couldn't get more productive. But one of the things we saw was what a rep can do in year 1 versus year 5 is just unreal how different the number is, where it's like the company is so much better, our deal sizes are so much bigger, they are a much more sophisticated rep, obviously, like in some cases they're improving, but in a lot of cases it's just like the company is in such a different place. That, that same person can be literally 5 or 10 times more effective for the same dollar you're paying them. And so if you don't believe that, the model says you've just got to hire some insane number of people to keep growing. What happens though is every time you overhire, this horrible thing happens to your machine where it's like, because there's not enough total opportunities coming in for the number of people receiving them, they're no longer fully busy. Therefore their total energy level goes down. Therefore they're less aggressive on the calls that they're on. And like this whole machine slows down because you're not, you're not running it at the right pace. And so, yeah, we got really comfortable with the idea that, yeah, individual quotas could double each year and people would be fine with it because they knew it was possible. And we showed every time and time again, it was possible.

And did you have a specific like hiring profile for sales reps? Were you sourcing from a specific place? Like how did you think about kind of who to bring in?

Yeah. I mean, so I have a couple of recruiting, like third parties that I relied on for years and years and years that I've been super loyal to. I generally don't like using internal recruiting for sales roles. I think internal is not— there are companies that do sales hiring really, really well. And in the first couple of years of a company, you don't have time to figure out like, how do I build a— it's hard enough building your sales motion. Building a recruiting motion is building an entirely second sales motion inside the company. And chances are you're not gonna have the caliber of people working on it that you're gonna have working on the core sales motion. Like that's just, that's just how the market has allocated talent for the most part. And like in some cases that's totally wrong. In some cases you have, you have talent partners that are like way better than their part, their counterpart in sales. But in general, like sales roles are more highly compensated. So people who have sales skills tend to go to them. So you have a lot of folks who have less of a background in building like a systematic sales process in a talent function, especially in a super early stage company. So I like to use third parties. I don't negotiate with them generally on fee structure. Like I have a couple of, I have a couple of partners who I think they charge like a very fair percentage of base. They're able to get me candidates within like 14 days of starting a search that are like to a T what I'm looking for. And in general, like it's so Flexport. Flexport and Hadrian are very different companies, but like Flexport really was 3 businesses in 1. It's an SMB business, a mid-market business, and a key account business or enterprise business, whatever you wanna call it. Each of those sales is a totally different profile. So like the, the SMB motion, what the people we saw that were the best at it, it was purely a function of positivity, energy, project management. Because like one of our SMB sellers might literally do 10 or 12 demos in a day. There are some people for whom that is a nightmare. There are some people that like at the end of that day, they are, they couldn't even talk to their spouse kind of thing. And there's some people who like, that's awesome. Like it's super high volume. They get to, they hear yes a lot. It's super fun. That profile for SMB generally does not translate that well into key accounts. Like SMB, you might get 10 dopamine hits a day. And so therefore you do 10 demos a day, super fun. You don't have to know that much about the client's supply chain. You don't have to be an expert in transportation. You know, the profile for mid-market is very different. Our mid-market profile is a road warrior. So like our SMB seller in office, on the phone, demos on Zoom, super high volume, onboarding your uncle who's selling Moscow Mule party sets on Amazon. Our mid-market seller is a road warrior who is basically like, they're selling to a professional buyer of this commodity. Like their customer, literally their whole job is to buy transportation services. They have no other job in the company generally. It's that, you know, it's that important to a supply chain. You have someone who owns it. They are not gonna buy from someone they don't know and trust. These are 7-figure annual deals. These are, you know, committed contracts where like we're going and signing a contract with an ocean carrier, basically saying, hey, this customer's gonna ship so many thousands of containers with you. The customer's agreeing to do it. You know, everybody believes the supply chain's gonna run smoothly. It's an in-person sale. It's highly methodical, but it's not like a key account sale in the sense that there's no integration. There's no ERP to figure out. The process is pretty much the same on every account. You can onboard, you know, maybe not 20 of these folks a year, but a good seller will have 5 to 10 of these accounts onboard a year pretty predictably that are spending 7 figures. And there it's like, it's a relationship sale. It's really the customer needs to feel like you are an extension of their company because they're not quite big enough to have a size logistics team that they need, and they need Flexport to fill that role. And they're almost interviewing the people we send to be members of their team. Key accounts is like your BCG, your McKinsey, your Bain, your Deloitte, whatever, whatever your, you know, consultancy of choice is. We are mapping an organization. We are onboarding in some cases 30 or 40 people to the, to the software, making sure they all know how to use it. Making sure Flexport has been customized so that when one division logs in, they only see data that's relevant to them. It is like a project launch. And even if they're not buying the software platform, even if it's a purely logistics quote unquote sale, even if it's just someone who wants to buy $50 million a year of air freight from us, it's like, hey, we need to build a process to make sure that we understand how to pick up cargo from their factory, get it to the airport. Make sure we make sure we understand how everything needs to be packed for transport. It's like you need, it's a project plan where you're talking about potentially 9 figures to spend and the timelines are a year. So it's like very low dopamine, very high stress, tons of project management, and the engagement looks a lot more like a consultancy than a sale.