Flexport's CRO Ben Braverman explains why the company pairs a sales leader with an operations leader for each customer account. Freight forwarding requires handling documents, trucking, warehousing, and customs, so one person can't manage both selling and operations. Squads act as the customer's de facto CEO and COO, giving them a single trusted contact while keeping the salesperson focused on strategy.
I think one of the things you did that was really smart was you had this like squad model. I think I've heard you talk about this where you gave sellers a lot of leverage and it kind of helped them with this big project management component of things. Can you, can you talk a little bit about that?
Yeah. So what, what we figured out pretty early on is the customer didn't want to talk to anyone about like an operational problem that couldn't actually solve their problem. So like you couldn't separate customer service from the actual operations of the company that easily. And so what that meant was if you're a seller, if you didn't have a team supporting you, like even though obviously like it's other people, like we're not driving the trucks, it's not, it's, you know, for the most part, we're not driving the boats or the planes either. Even though we are this non-asset-based business, there's a whole workflow of operationally moving the cargo, which is uploading documents, talking to trucking companies, talking to warehouses, all this stuff. That has to happen. And then if you have the person who's doing onboarding, who's like actually selling net new, if they get bogged down in trying to communicate that world of operations to the customer, their ability to sell net new goes to zero. Like truly it goes to zero. One, because the same person who's good at selling net new is generally not that good operationally. And two, because it is just, it is to serve the customer is so operationally intense in freight forwarding customs brokerage that you just, you're almost forced to give the customer a direct line to the people that are doing the operational work. So what we found was, okay, let's pair up an operational leader and a sales leader, or, you know, a seller and an operations person, and have them basically be CEO, COO of their own little book of business. We had, you know, the squads had their own swag budgets. They all had cool jackets and patches. They were, and on the monitors, it wasn't like individual names, it was names of the squads. And so you had this very healthy internal competition. They all had equal access to the resources that were Flexport or that are Flexport. So obviously they all had equal access to our air contracts, ocean contracts, whatever it may be, but everything that their customer needed. So if let's say you and I were the squad, everybody that Ben and Alex had onboarded knew that whatever they needed from Flexport, they could get from Ben and Alex. Like they didn't have to think about anyone else. They didn't ever know anyone else's name. They didn't have to go, oh, if it's a customs brokerage question, who do I call? If it's an air freight question, who do I call? They just know. Let's, let's say you're the account manager and I'm the seller. They know day to day for a question, they're going to call you because you're literally the one moving their cargo. And they know if there's a huge problem and they're like, man, Alex really is not doing what I need for him right now. They're going to call me and go, hey, Ben. You sold me on this fucking thing and it's not working the way you promised. What do we do? And so it's like, you're, you know, the operations leader is like day-to-day point of contact. The salesperson stays involved and like we cop the salesperson for years in the case of our mid-market and key accounts, even though a lot of the work is being done by the squad because you need that relief valve. And because the squad itself basically becomes an extension of the customer, they almost think of the people operationally serving them as their own employees. And you can't have your own employees telling you that something costs more or you've got to pay a penalty because you didn't pick a container up on time, whatever. It's like nice to have a seller who can come in and do some of that more unpleasant work or some of the work that requires a little more brute force. So yeah, the model worked incredibly well. Building something very similar at Hadrian. I mean, I'm trying not to be the general who just fights the last war over and over again, but I think in these ops-heavy businesses, like this model just works.
It must have been really intimidating for new sellers to join Flexport. I mean, there's just so much to learn, especially like, I don't know, most people probably don't know much about freight forwarding. Like, how did you get the best sellers to even care about training other sales reps? Because those sellers are trying to hit their number too. And so, yeah, what did you do there to kind of incentivize them?
One, the squad model helps tremendously with this because generally it would be an account leader who knew the industry. And so even if you were a seller who didn't know anything about what they were selling, literally during the sale, they could be slacking their business partner going, "Hey, what does this mean? Hey, this customer just asked me this." And as long as the seller had a good poise, they could say to the customer, "Hey, I think I have this answer for you, but my operational leader, who by the way is the best and you're gonna love, and they're gonna serve you end to end once you buy from us, let me just check in with her 'cause she's so good and then I'll get you a hard answer." Like that model allows you to hire people who don't know the domain and still crank in a way that if they were left to their own devices, it would have been impossible. The other thing we did was we had a few really special folks who were great at ramping other leaders. Probably the most well-known is a guy named Justin Schaefer, who actually now is VP sales for a company called Expedoc that sells software that arms legacy freight forwarders to compete with Flexport, which is hilarious. But Justin, we basically realized that Justin would do anything. Like, he was an ex-pro baseball player, blown out his shoulder, like the most competitive person on planet Earth. He would just do anything to make a person that he hired succeed. Like, if he had said, this person's good, I'm hiring them, he just couldn't live with the idea that he was wrong. And he would go to the ends of the earth to help these people ramp up, even if that meant just like going on the road with them and doing the deals for them. And ultimately, like, there's a few folks we had to let go because, like, Justin was just doing their jobs. But really, like, that's how you ramp sellers. Like, the way you ramp a seller is you take them on the road with someone who knows the dance and they get to watch it first, then they join in a little, and then, you know, before you know it, they're dancing on the road. And that's what worked for us. And we figured out an equity model. Like, generally, sellers don't get enough equity. And so we figured out for folks who were able to ramp new sellers as sales managers, If you were end-to-end responsible for hiring someone and then they hit their year 1 quota, you just instantly got a chunk of vested equity. And that for the right people, that worked really well.
