For Founders

What To Get Right When Building a Sales Org

Ben Braverman, managing partner and former CRO at Flexport, shares his experiences as a sales leader and tips for how to hire great salespeople and build a strong sales organization. 

7
 min read
Published: 
July 18, 2022
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Note: This article is adapted from a live discussion for the On Deck community featuring On Deck alums Ming Lu and Vik Duggal. If you’re an early-stage founder, angel investor, or exec interested in joining our community, consider applying to one of our programs - you’ll be in great company.

Note: If you’re an early-stage founder anywhere from pre-idea through pre-seed, consider applying to On Deck Founders.

Note: This article is adapted from a live discussion for the On Deck community featuring Josefin Graebe. If you’re an early-stage founder, scaling founder, or senior exec interested in joining our community, consider applying to one of our programs.

Ben Braverman is a co-founder and managing partner at Flexport Fund, a platform for global logistics. Prior to serving as managing partner, he was their Chief Customer Officer for two years and their Chief Revenue Officer for six years. In this post, he shares his thoughts on how to hire great salespeople and build a strong sales organization. This is an abridged summary of Ben’s interview on Execs, our podcast where we interview executives from high-growth companies. 

What’s the most important thing to get right when building out a sales organization?

Ben: The most important thing to understand about building a sales machine is solid list construction. I originally got this advice from Parker Conrad when he was the CEO of Zenefits. When I first started as Flexport’s CRO, Zenefits was known as one of the fastest growing companies of all time. Their go-to-market machine was something truly special. This was in the early days of high-quality outbound sales when you weren’t dialing for dollars, but rather doing outbound activities that could generate high-quality opportunities in great volume without alienating your customer base. 

Parker said: “Look, it comes down to list construction. You start with your concept of a customer and end with your concept of a happy customer for whom you have a full share of wallet.” You need to figure out a way to automate this list construction and the enrichment that goes out to it so that every single month you’re working from a larger and larger data set, then you can further refine your ideal customer from that data set and automate assignments out to your salespeople. 

As you get better at building the list, and the list gets bigger, and you get better at assigning the right leads to the right reps, there’s just this positive momentum that starts building. If you’ve put in good guidelines for how sales development representatives (SDRs) work those lists — the copy they use, the tooling they use — you’re going to enable them to do great work quickly. 

How do you think about the SDR role?

Everyone we hired to become an SDR, we impressed upon them that their job was to generate 8-12 high quality opportunities. We gave them a list of 100 and the only way to move someone out of the list was to convert them to an opportunity or say that they’ve failed. If an SDR failed to convert an opportunity, it went back to the central pool and was reallocated to another rep. 

We did our best to ensure that list of 100 was great. We enriched it with contact info, titles, org charts, and whatever we were able to get from public data sets. But then their job was to fill in the rest and decide how they were going to spend their time and efforts. 

Every company has a different playbook and I don’t want to be too prescriptive, but I think that being an SDR is really a creative role. Your job is to look at this list and think: which of these customers are the best fit for our company? How do I get them to know who we are, and be curious enough to take a meeting? 

SDRs need to do this scalably every single month. For our sales machine, our promise was that our salespeople would do this for 12-18 months before being a full cycle sales rep. It’s not so much a promotion as a graduation. They’ve learned enough, generated around 150 opportunities, and they’re ready. 

What about account executives (AEs)? 

Ben: AEs can handle a lot of volume. You don’t need as many of them, but they have to be great. At Flexport, our AEs were fully booked with meetings because we didn’t have our ideal customer profile (ICP) yet and we didn’t know what was going to close — the only variable we had control over was our total number of interactions with leads, so we maximized that. We learned this amazing lesson early on, which is that a few sellers with a lot of opportunities can generate a tremendous amount of volume. 

If you look at the first thousand days of Flexport revenue, you can attribute almost all of it to four humans. That’s four people that got a company to a unicorn valuation in sales because we built this enormous system that was generating meetings for them on the back end. 

Our best sellers also say no to customers. For example, when a customer wants to do a single transaction with us, our best people have the courage to say no. The whole idea of Flexport is that it’s a single source of truth, and the more data you put through it, the more transactions you’re doing with us, the richer that data set becomes. And yet, if your job is to make sure you’ve minimized risks for your company, putting all your eggs in one basket with Flexport can feel like a high risk decision. Our best sellers addressed that challenge head on. 

They’d say: “Look, I fully understand that you’re good at your job and you would never expose your company to the risk of giving us all your business overnight with no understanding of our ability to execute. I understand that. How can I assuage all of your concerns through the course of a trial with us?” 

We set goals with the lead during the sales cycle. We say: “If we do X, Y, and Z for you during this trial, then you’re going to give us this portion of your business.” We lay it all out on the table. If you’ve built enough mutual trust with a customer, you can have that conversation directly. 

What is your attitude towards compensation for salespeople?

Ben: People with skin in the game outperform almost every single time. One of the things that we forget in sales is that the way to give people skin in the game is not always to give them a bunch of cash, it’s to give them a way to earn ownership of the business. 

The spectrum of outcomes for a salesperson is different from a normal employee’s. Their salary in a given year can fluctuate from “I’m going to get fired if I don’t sell more” all the way to 3-4x their base. It can be uncomfortable for a company to give equity in addition to this potential upside, but what we’ve found is that the people who have stuck around and consistently made decisions that were aligned with the best interests of Flexport were always the people who were fairly compensated in terms of equity. 

We tell our sales leaders that their goal is a roll up of their team’s goals. So if you have eight people on your team plus yourself, and each person can reasonably generate X dollars, then your goal is 9 times X. We don’t believe that we’re losing sales capacity by promoting someone to leadership, we’re just allocating that capacity differently. 

We also tell people: we don’t care how you hit your goals. Any constellation of your team can generate the revenue. You can do it all on your own if you want. But everyone who achieves about a certain threshold that we set can receive an equity bonus as well. This combination of short term cash and long term equity keeps people around who are going to move the needle for you. 

What attributes do you look for in a great salesperson?

Ben: Curious people are great sellers. Those are the people in the interview process who ask about the business, the industry, the competitors, the company’s history. You can tell when someone is genuinely curious — you can tell when someone is just trying to fluff you up versus someone who is actually invested in discovering what the company does and where their place is within that. 

We found that the salespeople who consistently succeed are the ones who are just dying to learn more about the company during the interview. It’s almost to the point where you’re like: “Hang on, I have to ask some questions, too.” I don’t want to tell people who are applying for jobs to go in and ask questions nonstop, but if you are genuinely curious about how the puzzle fits together, about all the why’s, it will come through. And we’ve found that those people tend to be really high performers overall. Part of it is because our business is so complicated; you couldn’t succeed at Flexport if you aren’t willing to do the work of understanding the fundamentals. 

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