How Ben Braverman led sales from 0 to $2 billion at Flexport

“You have to be delusional to do this job well”

Ben Braverman calls himself “the most unproven sales leader in the history of companies that got this big.” 

When Ben joined Flexport as CRO in 2014, he was fresh off a few short stints as Head of Growth at URX (acquired by Pinterest), and Director of Sales at Heyzap (acquired by RNTS media).

Yet, somehow, Ben and the team grew Flexport from a tiny tech startup to a $2 billion behemoth — while navigating one of the most long-winded, bloated, complex sales processes you can imagine. By the time he stepped away, Flexport had hit an $8 billion valuation, and Ben had shifted into venture capital, running the company’s VC fund. 

We sat down with Ben to find out what it really takes to sell innovation in an old-school, tightly regulated industry—and how he turned a complicated sales process into a competitive advantage.

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Top takeaways from Ben: 

• Moving upmarket comes when you start “solving the whole problem,” rather than offering a point solution. 
• Startups can break into heavily regulated, complex industries by targeting SMBs. Even if the CAC doesn’t make sense, it creates opportunities to deeply understand the market. 
• The “land and expand” approach may take longer than you feel it should — but building relationships with enterprises over time is a bet that will pay off big. 
• It’s worth investing in brand marketing, even when the money’s tight — it makes your SDRs job easier. And don’t waste too much time on the nitty-gritty of measurement. 
• Hire slowly — over-hiring can kill your team’s productivity. And consider setting up autonomous sales squads to take on major accounts. 

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How to break into an old-school industry as a tech startup

Flexport started as a software startup. They built a supply chain management platform that connects enterprise resource planning (ERP) data from the many companies involved in a supply chain, so end users can track their shipments from end to end and streamline their freight processing. 

In other words, picture one of the most heavily regulated, old-school industries in the world. Think overseas regulators, international freight forwarding, customs regulations—you get the idea. 

Ben spent the first weeks on the job just trying to understand what the end-to-end global transportation even looked like: 

“It ended up being literally 40 feet of whiteboard across the whole wall of a double loft office in San Francisco.”

So, how did a small group of software engineers ever manage to break in? 

Solve the whole problem 

Flexport quickly realized that to make their business work, they needed to go beyond simply offering a software solution. They needed to “solve the whole problem,” says Ben. 

Customers didn’t want an alternative customs broker. They wanted someone who would take care of the entire process of shipping for them — and they were willing to pay far more for it. 

In fact, they realized that their customers’ core problem wasn’t even about shipping. It was about not feeling in control of their own products. 

“From the moment you pay your factory, to the moment your stuff arrives for sale in the US, or gets to your customer in the US, it can be months. That's kind of nightmarish for a small business owner. So we were like, ‘Okay, listen. Let's give them a map, with their factory on one side and the destination on the other…’ Building this visual totally changed the customer's ability to feel like they were in control of the problem.” 

Start with the long tail 

Flexport didn’t start by going after enterprise businesses from Day One. “We knew we had to be volume players initially,” says Ben. 

And what they realized was that there was an “insane long tail of potential customers:” small ecommerce businesses who “literally couldn't get service from the incumbent vendors.” 

Ben remembers, “We started fishing in the easiest, most well-stocked pond imaginable.” 

Going after the low-hanging fruit didn’t make sense from a purely financial, customer acquisition cost (CAC) standpoint. First-time importers needed plenty of hand-holding, and the team was spending a lot of time explaining the basics of freight forwarding to their new customers. 

But, says Ben, “It got us in the habit of onboarding customers and learning how to serve them, while the stakes were pretty low. That was how we learned and cut our teeth.” 

How to handle massively complex enterprise sales as a startup

So, Flexport was growing “ridiculously fast” in the SMB market. But the team knew they needed to go after the mid-market and enterprise customers, if they wanted a sustainable business. 

For that, they’d need a global network of freighters, their own landing rights, their own ability to consolidate and deconsolidate cargo around the world, their own warehouses…Plus the ability to integrate data from pretty much any ERP into their platform. 

None of which they had yet. 

We asked Ben how he managed to handle enterprise sales in such a tough, technical market, as a small and scrappy startup. His advice: 

Sell the dream 

“You have to be delusional to do this job well,” says Ben. You have to build the relationships with massive accounts, and sell the potential of your solution, even when it doesn’t exist yet. 

“I would visit some of these customers 10, or 15, or 20 times over the course of several years, while their spend just didn't justify it. You can look really dumb doing things like that. You can look really dumb making these kinds of bets. But now Flexport is a nine-year-old company, and the bets are paying off.”  

Think ‘land and expand’ 

The team focused on just engaging with enterprise customers rather than trying to close massive deals right from the off: 

“The time from when one of the large smartphone makers became engaged with Flexport, to the time where we became one of their anchor vendors, you're literally talking about four or five years.” 

For Ben, it was an exercise in patience: “When we were onboarding a lot of these folks, I thought we were going to get that 100 million dollars a year in spend in year two or year three. It turns out, at least as a startup, it takes a lot longer than that. But we always did move upmarket.” 

Invest in branding (even if you really don’t want to) 

“Spending on brand sucks. It's a lot of in-person events. It's a ton of founder time.”   

But if you want to break into a highly regulated and competitive industry, you can’t really get around it: 

“It has to be a core part of your strategy that you care about and nurture. Some of it you do just by having customers love you. But a lot of it is being in-market, and spending the time, and telling your story and teaching, teaching, teaching at every opportunity.” 

“It takes a huge amount of money and effort to do well,” admits Ben. Money that they didn’t really have, at least at first. 

“But the truth is, when we looked at the times when our SDRs were just cranking and way overachieving, it was always at the same time as we were investing in the brand. 

“Even some of the dumb brand spend worked. Just being on the front page of the Wall Street Journal works. We had a bunch of paid Forbes articles that I hated. But frankly, our outbound worked better when those articles were running. It's frustrating to admit, but it's true.”

But don’t get too bogged down in marketing measurement  

Ben started out “trying to do perfect attribution,” but realized that it was more of a time-suck than a help. 

“What I ultimately concluded was: Let's assume the smart stuff that marketing is doing works. As long as the events are good, as long as the webinars are teaching people valuable things, let's assume it's working.

“You can spend forever trying to measure it all and just define every dollar attribution perfectly. But with these enterprise sales, you're never going to do it in a way that's accurate.” 

Hire SDRs slowly 

“You should not add reps until your existing team’s calendars are jammed,” says Ben.  

“Your rep should be coming to you screaming, ‘I have too many leads. I'm not closing enough business because I'm so spread.’ If they're not doing that, it means that their days are actually pretty empty.” 

Plus, it means that any new hires will be taking leads away from SDRs who are already ramped up. 

“Every time you over hire, this horrible thing happens to your machine. 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. The whole machine slows down because you're not running it at the right pace.”

Remember that your reps will get far more effective as your company grows, so you likely won’t need to hire as many reps as you might think. 

“What a rep can do in year one versus year five, it's just unreal how different the number is. Their deal sizes are so much bigger…That same person can be literally 5 or 10 times more effective for the same dollar you’re paying them.”  

Partly, that’s because the reps get better at selling your product. But it’s also because your company has become a more established brand. 

At Flexport, they doubled individual quotas each year. “We showed time and time again it was possible.” 

Create sales squads with high autonomy 

To start handling large, operationally intensive and highly technical enterprise deals, Flexport created sales squads. They paired an operational leader and a sales leader “and had them basically be CEO and COO of their own little business.” 

The sales leader sold the initial deal and then stayed involved to handle the relationship, have difficult conversations with the client, and expand the deal. 

The operations leader handled the nitty-gritty, technical aspects and managed a small team that essentially became part of the key account’s team. 

The operations leader also helped to train the sales leaders — especially important in a highly complex market: 

“A seller who didn't know anything about what they were selling could be Slacking their operations partner, going, ‘Hey, what does this mean? Hey, this customer just asked me this.’”

Prioritize sales managers who are great at training others 

Reps learn technical sales most effectively by shadowing other reps, says Ben: 

“You take them on the road with someone who knows the dance. They get to watch it first, and then they join in a little, and then before you know it, they're dancing on their own.” 

So he saw it as mission-critical to hang on to salespeople who were able to teach their skills to others: 

“We figured out an equity model. Generally, sellers don't get enough equity. And so we figured out, for folks who were able to ramp up new sellers, if you were end-to-end responsible for hiring someone and then they hit their Year One quota, you instantly got a chunk of vested equity. And for the right people, that worked really well.” 

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