Ben Braverman is the CRO @ Flexport, one of the world’s fastest growing startups combining technology, infrastructure and expertise, to build the operating system for global trade. To date they have $1.35Bn in funding from some of the biggest and best in the business including Softbank’s Vision Fund, Founders Fund, DST, Susa Ventures and Y Combinator, just to name a few. As for Ben, he spearheads global sales and go to market teams. Prior to Flexport, Ben helped drive two high-growth companies to successful acquisitions: URX (acquired by Pinterest) and Heyzap (acquired by Fyber).

In Today’s Episode We Discuss:

* How Ben made his way into the world of startups and came to be CRO of one of the world’s fastest growing startups in the form of Flexport?

* Why does Ben fundamentally disagree with the specialization of roles within SaaS companies? What does he believes this does to the customer journey and relationship? How should one thing about role segmentation and allocation of accounts with this in mind? Where does Ben see many people going wrong here?

* Why does Ben believe it is “total horseshit to say the best sellers don’t make the best managers”? What must founders try and figure out before hiring their sales leader? What are the leading indicators that suggest a sales rep has the ability to be a sales manager? How does Ben determine between a stretch VP and a stretch too far?

* What does Ben mean when he says, “there are 3 distinct buckets of sales management”? What are they and what is their relationship between one another? Why does Ben believe one does not need sales management in the early days? What is the best way to train reps and determine payback period fast? Why does Ben believe sales ops is the most underappreciated role in the valley?

60 Second SaaStr:

* What does Ben know now that he wishes she had known at the beginning?

* What is the optimal relationship between CRO and CEO?

* What does Ben believe in SaaS that most around him disbelieve?

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Jason Lemkin
Harry Stebbings
Ben Braverman


Harry Stebbings: We are back for another week in the world of SaaStr with me, Harry Stebbings, you can suggest both questions and guests for the show on Instagram at H Stebbings 1996 with two B’s and it would be so great to see you there. But to the show today and I have to say some guests, well, they’re just so brilliant that they just roll in this kind of stream of thought and consciousness. That’s just awesome for me to see and that very much is the case today as I’m thrilled to welcome Ben Braverman, CRO at Flexport, one of the world’s fastest growing startups, combining technology, infrastructure and expertise to build the operating system for global trade. To date, they have $1.35 billion in funding from some of the best and biggest in the business, including the likes of Softbank’s Vision Fund, Founder’s Fund, DST, our friends at Susa Ventures and Y Combinator. Just to name a few.

Harry Stebbings: As for Ben, he spearheads global sales and the go to market teams at Flexport and prior to Flexport, Ben helped drive two high growth companies to successful acquisitions. Both URX, acquired by Pinterest, and Heyzap, acquired by Fyber and I do also want to say a huge thank you to Ryan Peterson, founder and CEO at Flexport for the fantastic intro to Ben today. Ryan, I really do so appreciate that and mojitos on me to thank you for that.

Harry Stebbings: So now I’m very, very excited to hand over to the wonderful Ben Braverman, CRO at Flexport.

Harry Stebbings: Ben. It is absolutely fantastic to have you on the show today. I’ve heard so many great things from the main man, Mr. Peterson, so thank you so much for joining me today, Ben.

Ben Braverman: Oh yeah, of course. Thank you so much for having me. Ryan said wonderful things. I’ve obviously been listening to the show. Unbelievable what you guys are doing over here. So just thrilled to be a part of it. Thanks for having me.

Harry Stebbings: Well I bear a huge amount to Ryan, but I would love to kick off today with a little bit about you, Ben. So tell me, how did you make your way into the world of startups and come to be CRO for one of the fastest scaling, I think it’s eighth fastest scaling of all time in Flexport.

Ben Braverman: Yeah. Yeah, totally traditional story. Dropped out of Vassar College when I was 19. Went to India and volunteered and then wandered around wearing a blanket as pants for a few months. Ultimately came to the conclusion that as a lone individual could impact the world, not in quite in the way I wanted to. I decided, alright, let’s come back and start working on something bigger. So I came back to the US. Moved out to Silicon Valley. Got linked up with a guy who had taken a company public on the Frankfurt Exchange in the 80s. We ended up founding a company together called FortKnock, which was a touchscreen authentication system. Made every mistake under the sun, lost a little bit of angel money, but ultimately parlayed the whole thing into a job leading sales at Heyzap, which is one of the early YC companies.

Ben Braverman: I worked for Jude and Ahmad who, you’re a brilliant Brit. They are brilliant Brits. I worked for them for a little while. Helped them go from being a social network to an ad network. Some of the same investors ended up placing me at URX, which was sort of the deep linking standard of 2014. Raised a big round from Accel right out of the gates. Ultimately we sold to Pinterest. I met Ryan at the dog park. Like all great romcoms, our story starts the dog park, and I met Ryan Peterson and was just blown away by the almost clairvoyant nature, in retrospect, of his conviction. I don’t know if you know this about Ryan, Ryan’s previous company, ImportGenius dot com actually spits out money. He and his brother have done very well in that business and very few people in Silicon Valley build profitable companies. There’s lots of people who raise money. There’s lots of people who do things that are impressive in the press.

Ben Braverman: Very few actually profitable businesses. ImportGenuis is not only profitable, it’s never raised a dime of venture. To the these two brilliant brothers, they just effectively run it for the fun and for the cash that it spits off. So when I met Ryan though, he had totally abandoned this business. This is six, seven years ago at its height. ImportGenius was doing as well as it’s ever done. And I was just blown away that this person had walked away from such a massively profitable business that they owned all of. And I said, “Ryan, first of all, why didn’t you take any venture? Why didn’t you want to keep working on this business?” And he said, “Look, the terminal value of ImportGenius is zero.” And to have the resolve to say this out loud about a business that’s cash flowing millions of dollars a year is pretty powerful.

Ben Braverman: The terminal value is zero. Potentially, someone comes along and decides to offer this publicly available dataset for even lower than we do in terms of costs. And when that day comes, the value of my business goes to zero. There’s a business called Flexport though. It’s going to change the way cargo moves around the world. The biggest companies on earth spend billions of dollars on this service no one’s ever heard of called freight forwarding and they all hate their vendors. My life’s work is to build this company, Flexport, and it’s so much more important. It’s going to be so much bigger that I don’t care about that ImportGenius business.

Ben Braverman: And at that moment I was just so captivated by this story and not only a guy who built a massively profitable business, but one that he didn’t give a shit about anymore. That to me is just … you’ll never meet anybody else in Silicon Valley about whom both of those things are true. So I was just, “Okay, whatever the new thing is must be the biggest thing in the world.” I put my life savings into the company trying to convince Ryan that I was a serious enough sales leader to be worthy of being his partner to some degree. Now I use that term charitably about myself and in over the course of a year after I made the investment of just going on walks with our dogs and talking about this business, I slowly convinced him to let me in the front door.

Ben Braverman: June, 2014, when I started, we had an $18,000 month. The year of 2018 as a whole was 472 million in sales, but we’re targeting a billion this year. I’ll be thrilled at 950. It’s been a great run and I’m just, again, just that I’m thrilled to be on the show. Thrilled to be a part of it.

Harry Stebbings: I mean, it’s just been such an incredible journey. I have to say, when you look back now, do you ever kind of pinch yourself and also give yourself a bit of a tap on the back? I’m not saying a congratulations of it, but just appreciate the incredible journey it’s been. Do you ever sit back, and go, yeah, we’ve done well?

Ben Braverman: I more sit back and think, “Oh my God, everything had to line up.” You couldn’t replicate this, necessarily, if you tried. We’ve had the right people at the right moments in history time after time after time. When you look at the historical backdrop of Flexport, we got started during the port strike. So we never should have even been a, we’re in multi sided marketplace. Not only do we need to get our customers to agree to ship with us, we need to get the asset owners, the folks with airplanes and boats and trucks to agree to carry our cargo.

Ben Braverman: And in our first year there was plenty of customer demand. I mean people really, there’s not unlimited app that’s for a job well done in this industry. And there’s very few people who are doing a really excellent job. So we have this enormous market. We knew people were going to be engaged, but the other side of our marketplace, the asset owners, they really should never have taken us seriously. And they certainly never should have served us in any real way. And yet because there was this port strike, everybody was in the same boat where the entire west coast of the United States was shutdown. No cargo was getting in. It was pandemonium for everyone.

Ben Braverman: So, effectively, everybody was playing against the same stacked deck on the supply side of the market. Everyone on the demand side of the market was rushing around frantically trying to find a solution to this horrible problem and that sort of is a recipe for the perfect way to start a new business. Great companies are born out of chaos. Yes, I do look back and go, “Okay, this has been a wonderful experience.” But I more look back and go, “Oh my God, we couldn’t do this again if we tried.” Everything had to line up.

Harry Stebbings: I mean that is just such an amazing journey of how the right thing happened at exactly the right time and I love that with the port strike. We have chatted before though, Ben, and I did want to start today on some conventionally held wisdom within the SaaS world and it’s on the theme of specialization. It’s often said that the specialization of roles is always an inevitable part of company scaling and leaders must know when they are and act fast. How do you respond to this conventionally held wisdom on the specialization of roles and would you agree?

Ben Braverman: In a perfect SaaS business? Yes. It would be wonderful to have everybody specialize to the nth degree where you have a pure SDR role that all they do is outbound. You have a pure closing role that all they do is get on and can say the right things to the customer and find out their pain points, explain how the product solves their problem, and then the next day an account manager takes over the relationship and that AE never has to interact with the customer again. If that really fits your business, if you’re selling a product that is so transactional that the customer really doesn’t care about being put through this experience that has been optimized for you, than sure, specialization works. I believe that that environment, it may produce an indiscreet skillsets, a little bit more productivity per day, but the customer journey is horrible.

Ben Braverman: And all of these handoffs and all of these people who feel like they’re only responsible for some subset of the customer experience with your company. It does not necessarily add up to the ideal customer experience. And what we’ve found is that you can fly in the face of this conventional wisdom to a pretty high degree and still have efficiency that’s just fine. Still have all of your employees on a unit economic basis delivering what they have to deliver. But your customer journey, if you’re more flexible and you design the specialization to only really kick in and for the handoffs to only happen when it’s absolutely necessary, and when it benefits your customer, you dramatically change the way they interact with your business. So for us, whenever someone new who’s really smart comes to Flexport, the first thing they see is that, oh my God, 90% of your quote unquote sale happens after the first shipment.

Ben Braverman: The reality is most of our customers, if you’re a Georgia Pacific, who this year, they’ll trust us to book about 65,000 containers to their cargo, outbound from the US, that relationship started with a small test. And so if we had just had a traditional model where our salesperson rolled off the moment Georgia Pacific booked their first piece of cargo with us, A, it would have been a horrible experience for them because our salesperson, in this case, our VP of sales, Julie Harris, she spent a year getting to know them, getting to know their team, deeply understanding everything about their process. If the moment they had started actually spending money with us, all of a sudden an account manager was just thrown into the mix and Julie was able to roll off completely, it would have been a horrible experience for them. All that value that Julie had cultivated in the course of a year would have been lost.

Ben Braverman: You just can’t hand it off to another person that seamlessly. And the reality is we’re in a service business. So for us, our account managers, they’re effectively operations managers. We even call them operations managers. They’re responsible for moving cargo. And so it’s a lot to ask of someone, okay, not only do you have to move cargo, but you’re responsible for retaining this customer spend, for increasing their spend over time, for understanding the pain points of all of their senior leadership. I mean that’s a lot to ask of someone on top of actually moving thousands or hundreds of thousands of kilos air freight and the given year or whatever it may be. So what we’ve found is we more designed around the customer. We want everything to be a total partnership between sales and accounts. So we have this squad model where every customer is served end to end. Our squads are effectively CEO, COOs within the company.

Ben Braverman: Everything that the customer is going to need to experience in their life at Flexport is underneath this squad. So its operations associates to move freight. It’s a customs broker to keep everything in compliance. All of this stuff happens underneath the auspices of these two leaders. And the lines between them are not totally clear. They’re both responsible for getting the customer onboard. They’re both responsible for making sure the cargo moves smoothly. Because the salesperson has to understand the customer need. The operations manager has to actually execute against it. But the lines between the two of them, who’s actually responsible for the revenue? Who’s responsible for that customer having a wonderful experience? The answer, ultimately, is both and it’s everybody on their team. And yes, every consultant who looks at Flexport goes, “Oh my God, this is so inefficient. Oh my God, how have you guys managed to scale this way?”

Ben Braverman: And the reality is if your customers love you and our customers do love this end to end experience of the same people who take them through this journey of what is Flexport through being in love with Flexport and us being their primary provider. If your customers really appreciate you, you can get away with a lot that’s imperfect. And yes, we can probably do more calls per day in a different model, but this model suits us. I think it suits most service businesses better than the traditional SaaS dogma of every role must be hyper segmented and you need to have all these handoffs that your customer is just going to endure.

Harry Stebbings: There is one particular element you said there, Ben, that I just can’t not jump on. You said that, surprisingly, it works on a unit econ basis for each individual. I’m super intrigued. When you look at economic productiveness of people within the team, often we hear about kind of sales payback periods. For you as CRO, how do you think about unit economics with relation to people in particular and in terms of ensuring maximum productivity and the output from team?

Ben Braverman: So this is one area that I actually do think the conventional wisdom is pretty good, which is if you have a complex sale by the end of a person’s first year, they should be paying for themselves. If you have a simpler sale, I think you can almost certainly compress that time horizon. For us, a major transaction is going to take between three months and a year to fully come to fruition. It may be that they ship for the first time 45 to 90 days into the relationship with Flexport, but by the time they’ve seen a container delivery and it takes 20 some odd days just to go from Asia to the US in a shipping container. By the time they’ve seen the quality of the service, by the time they’ve seen that the platform does everything we say you can do, they’re well into their second or third month of Flexport.

Ben Braverman: So really, our sales people are effectively shepherding people through this initial journey. And then once they’ve seen how amazing Flexport is, they have to make a plan together for okay, how do get your entire business that’s running today between some combination of email and disparate websites into this one platform? How do we onboard all your vendors? It really is sort of a year long transition where we take a company that’s working in their old way to working with Flexport and it would be foolish of us to try to artificially accelerate that cycle too much. Having said that, most of our salespeople do come into our SMB segment, and this is intentional. One, it’s a training ground where the sales cycles are shorter. So even though our focus is the mid market, the vast majority of our revenue is in the mid market.

Ben Braverman: We have a lot of success graduating SDRs into an SMB segment that has a shorter cycle so that you can really see by day 90, day 100, they should have a few new logos in their name. From a unit production perspective, we’re not at all expecting these people to be break even, but we at least want to see, okay, based on the historicals, are you adding enough logos? Do you have enough pipeline on day 100 that we think you’re going to be where we need you to be at the end of that first year? And if not, we can course correct. But we all ultimately, our model is to break even by the end of year one and then track a whole bunch of milestones between when they onboard and that at the end of that first year to make sure they’re on course to do it.

Harry Stebbings: So if there are kind of pieces of conventional wisdom that do work well and then those that don’t, another area kind of related to the specialized roles element. And I loved it when we were chatting earlier, ’cause you said to me, “It’s total horse shit that the best sellers don’t make the the best managers.” Which again is something that I’ve heard often on this show. So debunking another quite commonly held opinion in SaaS. Why is this statement BS on sellers not making good managers?

Ben Braverman: I wish this were true because it would make it so much easier to hire sales leaders. But the reality is we all want to report to someone who was already gone on the journey that we’re on, particularly salespeople. We’re doing this thing that feels like alchemy. It feels like it’s impossible. You’re walking into someone else’s company who has their own problems, their own issues, their own goals, their own time horizons, and you’re trying to get them to align with you that they can accomplish everything they want to accomplish under the sun. And then you can also accomplish your goal. And in many cases it’s true. In many cases, the product that we’re offering does actually accelerate my customer’s ability to take their goal. But the reality is this is a hard thing to do day in and day out. And it’s a hard thing to do at scale and it’s a really hard thing to do in a complex industry, which, frankly, that’s all that’s left.

Ben Braverman: All of the easy software products that you can train somebody to sell in a week, those are gone. Those are opportunities someone took in 1996. What’s left are really big, hairy problems to solve with really complex solutions to deploy to solve them. And so, effectively, when you try to take someone who’s just a great quote unquote leader or a great pure manager and pluck them on top of salespeople who are out in the field doing the Lord’s work day in, day out, getting their asses kicked a lot of the time ’cause that’s just part and parcel of the job and they have to then go report into someone who doesn’t have answers to the same existential questions that these people are asking themselves every day. That doesn’t deeply understand why a customer is behaving a certain way. That hasn’t seen a certain procurement teams posturing before. That there’s really very little they can offer them tactically to help move their deals along. Effectively, they lose the sales team very, very quickly.

Ben Braverman: And sort of the more positive way to look at it is when you have someone who embodies all of the skills that fall into a sales leader, which is rare. When you have that person and they come up through your system, they make your sale, they understand your customer very deeply and they naturally graduate into a leadership position, the level of authority that they can speak with, the level of confidence they inspire in the team. it’s an order of magnitude different than what you get when you bring someone in off the street and they’re trying to fake it. Because that’s effectively what it is. Let me take a step back. Right? I think the reason that this commonly held wisdom applies or that people have bought into it so deeply is that we’ve taken three discrete skill sets and we’ve tried to say this is what a sales manager is.

Ben Braverman: The traditional wisdom is a sales manager is a person that does pipeline reviews. That asks reps how they’re tracking towards their number. That checks in on commits and yeah, if you’re a multi thousand rep organization, if you’re Palo Alto Networks, yes. The job of being a sales leader there is almost as much a COO as as it is a sales leader. So much of what you’re doing is tactical. It’s operational, it’s tracking against the number, but when you’re in any sort of scale up environment where there’s still real learning being done and where there’s still frankly a customer that demands a certain level of seniority to come into the sale, you really have three discrete buckets of sales management that I think are equally valuable. The first camp, I call this the zero to one leader. This is a hiring manager.

Ben Braverman: For us at Flexport, we’ve sort of chunk this out into a discrete role. All this leader does is hire the best talent. They refine the hiring profile, they figure out exactly what attributes sum up to success at your company. They go and find those people, they hire them, they onboard them, and they see them through that first year of their journey at your company, and this is really an in office role. This is a role that is sitting next to the rep that’s listening to calls. That’s giving feedback in real time and in a really scaled up organization, maybe this lives in enablement. I’ve literally, coming back to this specialization thing, I’ve never seen this done well. I’ve never seen a company that actually has an enablement function that’s this hands on. So I’ll believe it when I see it. In our case, we’ve breeded a sales management function that all they do is hire and train.

Ben Braverman: And so to your point about the ramp ups, effectively, this person is responsible for overseeing year zero to year one in the salesperson’s life cycle at Flexport. They are there to oversee them from their ramp to their day of break even and on the day they break even, they need a different kind of sales manager. That same person who’s been sitting next to them, guiding them through the calls is no longer useful. So at that point they graduate at Flexport, they graduate into mid market and they get a completely new kind of manager. And in this case we call this manager a swat team leader. So they are now graduating from our SMB segment into our midmarket segment. I think this is applicable to tons of companies. I’m talking about Flexport here, but I think this is universally useful. At least, I hope it is.

Ben Braverman: When you graduate into the mid market and you’re selling bigger deals, which for us is anywhere from 500,000 a year to 10 million in spend. And for our client, this is a major line item. This is the arterial system of their business, the company that they hire as their forwarder, they are hiring us to move all of their products from their factories to their customers. This is sort of a sacred role, but I think there’s a, in this deal size, everything is sacred. You’re not touching anything minor in someone’s company for $10 million a year. And so if that’s the nature of the sale, you’re going to have multiple stakeholders. You’re going to end up having more senior and more junior stakeholders and you’re going to want to mirror that same structure on Flexport side or on your company side. And so, effectively, when you have people who now know the basics of your business and they’ve stepped into this more serious seasoned sales role where they are hopefully more than breaking even for your company and they are in the field versus being in the office, they need a totally different kind of manager.

Ben Braverman: In our case we call it the swat team leader. The swat team leader is by definition someone who came up through our system. It is someone who deeply knows the sale, who has sold the biggest deals at Flexport, that has the biggest reference customers on speed dial, and that is willing–This is a purely out of office role. This is a road dog role. This is a manager that as our reps are traveling around the country, this manager is traveling with them, sitting in the meetings with them, acting as the level up for the client. So the client knows that if they want to bring a senior stakeholder into a meeting, they have a mirror on Flexport side and they effectively own the number that is a roll up of their reps. And yes, part of what they have to do is track their reps’ performance because ultimately it is their performance.

Ben Braverman: But in terms of what’s actually driving the value in that job, it’s 5% admin and tracking. It’s 95% being in front of customers doing the Lord’s work of closing bids. And so you’ll notice I’ve talked about two of our sales primitives. The foundation of our sales management philosophy and none of it sounds like traditional sales management. Now the third camp is really what you need when you’re a large organization, particularly a larger matrix organization, which is what everybody thinks of as being traditional sales management. This is understanding the pipeline. This is conducting the pipeline reviews. This is getting salespeople to commit. This is partnering with the GMs and our in your different GOs who are managing the local P and Ls. This is a valuable role particularly for a high growth company. It’s the role that if you have to sacrifice on one of the three, that’s the one I’ll give up every time.

Ben Braverman: Because, effectively, your two leaders that are doing the most important things, hiring and training in camp A. Closing with your seasoned reps in camp B, they’ll fill the gap for a long time and, effectively, as long as those two people are doing their jobs well, you can get away for a long time without having necessarily a traditional sales management function in your company that sort of is doing the coagulation. And you can really get away with it for a long time if you have a strong sales ops leader who was willing to fill in. So if this is your worldview and you believe the most important thing someone can do are deeply understand your customer to the degree they understand what kind of rep is going to resonate, they understand how to train that rep to make them excellent in 12 months and then they’re willing to go on the road with them and close business full time after that.

Ben Braverman: All of this to me says this is someone who has to come up through your system or it’s someone who has to come up through a very similar system that you then onboard and and indoctrinate with your DNA, and again, these are people who were great at the job. There is no one who’s going to be a great level up going on the road with your reps five days a week who was just a mediocre seller herself. All of our sales leaders at Flexport, all of them were top tier AEs when they were ICs for us, whether it’s the people who were doing the zero to one because they just really fall in love with the craft. They fall in love with the architecture of the sale and then so they just want to train and ramp people over and over and over again. Or maybe they don’t want to travel quite as much.

Ben Braverman: But the reality is they can get on the phone just as well as one of their reps and bring the business home if they needed to. And so, yes, I very much disagree with this dogma. I think it’s held back a number of amazing salespeople from going into management because they think that their skillset isn’t applicable and yeah, you need to learn to care about others. You need to learn that your success is their success. But as long as the people have that basic EQ, the best sellers make the best managers until a really high degree of scale.

Harry Stebbings: Ben, I’m enjoying this so much sitting back and listening. I do have to pick up on two elements that you said there. When you look at kind of that cohort that could be making the move into kind of that management function, so to speak, and that they’re top performing AEs and there’s three or four of them and they’re consistently crushing it, they’ve come up through the ranks successfully, what makes the one that scales successfully to that management function the one? Are there leading indicators that suggest one is better or more suited than another?

Ben Braverman: Yeah, absolutely. It’s the desire. We have people on our team that are just super ICs. One of the guys told me recently, a previous company that he worked at tried to make him a manager and all 10 of the reps quit. And so that’s a very specific flavor of salesperson who ultimately, he is in this game because he likes driving fast cars. He likes flying around the world and that’s, that’s a very specific varietal of salesperson. I think it’s probably more representative of sort of a different generation of salesperson when it was less of an intellectual pursuit. But the modern sales role is such a philosophical, intellectual endeavor that you have to deeply understand not just what other humans want but what entire organizations want and then you have to have the patience and persistence to define that strategy with your customer to build a real partnership and to develop it over the course of a year or multiple years.

Ben Braverman: The kind of person that’s willing and able to do that, is almost always going to be willing and able to become a great manager. Now some of the traditional sales people, like, this guy I’m talking about, who are more hyper transactional, they end up as they scale in their careers, they become door openers, so they don’t actually manage accounts themselves, but you rely on their network and the fact that they’re just so damn likable in that first meeting that you keep them on the team as door openers and sort of, we call them senior BD staff, but effectively they know the industry really well. They know the customer base really well, but they don’t want to own the relationship with the customer forever or it doesn’t give them joy.

Ben Braverman: Whereas we have some people on our team and frankly the vast majority of our of our sellers fit this sort of this new mold of sales, which is a relationship sale. Which is deeply understanding and empathizing with your customer to the degree that you can design a solution around their needs. That kind of person almost always translates well as a manager because the same path that they’re taking with their customer of, “Hey, where are you trying to go? What has to happen this year for it to be a successful year for you? What do you want out of your time on Earth?” All of the same questions that you have to answer with your customer. If you’re willing to ask them and answer them with your reps, they’re going to be bought in and they’re going to be successful.

Harry Stebbings: I totally agree and my word, I’m so thrilled I asked that question, Ben. The other one that I wanted to unpack was when you said about camp B there and the three functions that we distilled, kind of sales management down to being the closing element. I’m always really interested, how do you create a culture of ambitious goal setting and targets, but then also not a fear of not hitting quota? How do you navigate that very difficult balance of ambition without fear?

Ben Braverman: It’s very difficult. This is sort of my shout out to the sales ops team. I think sales ops is one of the most under leveraged, underappreciated functions in all of Silicon Valley. One of the best arbitrage plays there is right now is going and hiring senior sales ops leaders and then converting them to run other functions because sales ops really is at the heart of a functional sales org. If the quotas are wrong or if the quota design doesn’t mirror the behavior that you want it, that you’re trying to elicit from your team, the whole game is pretty much shot. It doesn’t matter how good your go to market is. Doesn’t matter how good your strategy is. So fundamental answer here is you need to have a good quota system that aligns with reality and you can’t try to force the reality to be what you want it to be.

Ben Braverman: You have to sort of go, “Okay, objectively, what can this team actually deliver? What is the capacity that I actually have to hit the targets? Where does the company need us to go? What are my levers as a sales leader to fill whatever caps there might be?” But to always have the sales team goaled accurately and to always have them be goaled in such a way that if they show up and they do all the right things for the customer every single fucking day, that they will succeed. If you ever designed a system where people can do that or they can show up every day, do all the right things for their customer, genuinely act in the best interest of both their customer and Flexport and they still are 65%, you’ve designed the goals incorrectly or you’ve hired the wrong people. The bargain has to make sense. This economy is too good, especially for high caliber talent.

Ben Braverman: There’s so much opportunity in the world right now that the bargain has to make sense for everyone on your team at every level, all the time. And whether that’s an SDR who you’re saying, “Okay, yes, you’re maybe two and a half years out of school, this is your second sales job. You’re making 100 phone calls a day. But if you succeed in this role over 18 months, we’re going to turn you into a real salesperson. And at the end of it, you’re going to be a full quota carrying AE. Does that bargain? It make sense to you?” Yes. If yes, that person will make that 100 calls a day for 18 months and they’ll give you everything. So when we look at how we’re goaling our team, we try to live somewhere on the ambitious end of what’s plausible.

Ben Braverman: We try to design quotas, and I, our shout out to Sarah Harrison, my sales ops leader, we try to design quotas that if people really look at what they’re trying to deliver and try their best every single day to, to take action against that goal in a way that those two things are connected, that the company will move forward. For us this year, that meant switching to an annual comp plan because we didn’t want people, in Q four trying to get those last few deals over the line when we know our customers bid in Q one and Q two. So instead of going for max revenue in Q four, you should actually be going for the maximum number of trials. You should actually be going for the maximum number of new customers that are trying you out and falling in love with you in advance of their formal bid. If we had a quarterly quota system, we were effectively getting people mixed messages and saying, “Yes, go chase short term revenue, but also make sure you’re getting ready for next year.”

Ben Braverman: And so we said, “Okay, you know what? We’re going to make all of our quotas annual so that people can just do what’s right for their customer and for Flexport and not worry about what day of the week it is.” So yes. I don’t know if I answered your question. I just believe that that the key to all this is having the quotas be correct in the first place.

Harry Stebbings: No, you totally did. And I love that in terms of transitioning to the annual quotas. I love that. This where I slightly wish I allowed the show to go on for hours and hours ’cause I feel that we could chat with a mojito for a much longer time. But, I would love to move into my favorite, Ben, being the quick fire round. As you know, I say a short statement. You give me your immediate thoughts about 60 seconds per one. Are you ready?

Ben Braverman: Yeah, let’s do it.

Harry Stebbings: Okay, so your hardest element of your role as CRO at Flexport.

Ben Braverman: Constantly having to fill leadership roles. The brutal thing about growth and also the blessing of growth is that every single month you come in and there are gaps in your org because you’ve opened a new office, you’ve entered a new segment, one of your best AEs has been promoted. One of your best sales leaders has become a manager of managers. So every single day I look at our org chart and go, “Okay, who are the five most important leaders we don’t have in place? How can we go get them?” And so there’s never a day where the team is set. That is by far the hardest element of the job.

Harry Stebbings: Listen, I totally agree. And when I look at your Linkedin versus to the office openings, I do feel sorry for you in that regard. I can’t talk though. The optimal relationship between CRO and CEO.

Ben Braverman: Yeah, well hopefully the CEO likes you. That’s step one. But ultimately the CEO has to trust that as a CRO I can be out in the world to whatever degree I’m capable of living up to this as Ryan’s proxy and that when I take an action for Flexport that I am doing, not at what is best for me, not what is best for the sales org but what is fundamentally the right thing for our company and our customers and our engineering team and all of the people that are powering this engine behind the scenes that I would make the same decision, the same high quality, high fidelity decision that Ryan would. If you can have that level of trust between your go to market organization and your CEO. I ultimately think you can solve every other problem.

Ben Braverman: The issue is sometimes that’s hard to do. It’s not always that my interest as far as hitting the goal this year are aligned with our engineering team’s interest in building a platform that’s built for the next 100 years. So the fact that Ryan can trust that every single time I will make the trade off that I believe is best for Flexport as a whole. Even if it means that quote unquote my org or the org that I am associated with may not be thrilled with me, that sort of is the key to relationship.

Harry Stebbings: What do you believe in Saas, Ben, that many around you disbelieve?

Ben Braverman: We’ve already talked about a few things. I believe that sales really is a quasi religious function. I believe that a great sales org is like a heat seeking missile for product market fit and that is probably the more important function than delivering a number. I believe that if you have a sales org that is really well calibrated and totally in tune with the needs of the customer and resonating in real time with your customers and you have a sales org that’s also able to live in a core version of reality and cannot delude themselves about why people are buying, I think a lot of times your ego gets in the way as a salesperson.

Ben Braverman: You think that somebody wants to work with you because you’re so wonderful, but if you have a sales org that can get out of the way and it can just say, “Look, we are the entire company’s conduit to the customer. How can we translate their needs, their wants, their frustrations back to the organization in the highest fidelity way possible?” That is way more important than hitting a number and that if you’re constantly doing that in real time and all of your sales teams are seeing themselves that way, it’s effectively a two way consultant for the customer to try to understand how Flexport helps them meet their goals and their consultant for the company to help understand what we need to build to hit to serve the customer even better tomorrow. If all your reps are acting that way and they’re doing the job day in, day out, you’re going to just sort of wake up having to hit the number.

Ben Braverman: One of the things Ryan says all the time is no one ever gets rich trying to get rich. You get rich by creating value and then one day you wake up accidentally rich. I think it’s very similar in a sales org. If you have a team that’s calibrated towards value creation both for the customer and for the company and they keep showing up every day, you’ll wake up having hit your goal. I think there’s an over–sort of this militaristic focus on goal setting and goal tracking and I get it if you’re public, I totally understand it, but I don’t think that is the core value driver in a sales organization.

Harry Stebbings: No, I do agree with you there as well, I have to say. I do want to finish though, Ben. This one’s probably the hardest of all. What do you know now that you wish you’d known at the beginning of your time with Flexport? Take yourself back to the dog track. First meeting Ryan, what do you know now that you wish you’d known then?

Ben Braverman: I wish I’d known that there is never going to be some miraculous milestone and there are no messiahs. There is no one person that you hired who solves all your problems. There is no one round of funding that you just come in, everything’s perfect. There’s never going to be a version of Flexport where we come in one day and go, “Oh, it’s finished. The company’s done. We built it. The software is perfect. We have all the right team in place, our customers are thrilled 24 hours a day. We have the lowest prices in the market and the happiest customers in the world.” I think maybe we’ll get there on a 100 year time horizon, but even in 100 years, there’s going to be a new mode of transportation and we’re going to have to totally rebuild the company around it. And so I think early on, especially in the really early days when you’re burning through that first 3 million bucks that you’ve raised and you can’t hire some of the senior people you wanted because you can’t afford them.

Ben Braverman: There’s this tendency to start thinking in terms of milestones and you start thinking that, oh, everything’s gonna be great when, and you have to just sort of deeply internalize that things are already great. That the fact that you are on this journey, that you’re getting to see this miraculous thing come together, things are already great and yes, whatever goal you’re trying to accomplish, raising $1 billion, whatever it is, it all feels good. It all feels rewarding. It is wonderful when you can afford to hire the smartest, most senior people in a given vertical. But ultimately you got to just show up everyday and be psyched to be here and be psyched about the problems because tomorrow, although you might have a nicer office, the company might have more employees, you’re still going to be playing the same game.

Harry Stebbings: Ben, listen, I think you can tell from my voice just how much I’ve enjoyed it. I’ve never had to ask so few questions in one interview. It’s been the most wonderful for me and I’ve so enjoyed it. So thank you so much for joining me today, Ben.

Ben Braverman: Well, I think that was a very nice way of saying that this guy sure rambled for an hour, but I appreciate it. I look forward to meeting you in person.

Harry Stebbings: What did I tell you? Extremely special guests and if you’d like to see more from Ben, you can find him on Twitter at Braveben. Likewise, it’d be fantastic to welcome you behind the scenes here at SaaStr. You can do that on Instagram at H Stebbings 1996 with two B’s. I really do love to see you there.

Harry Stebbings: As always I so appreciate all your support and I can’t wait to bring you another exceptional episode next week.


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