SaaStr 222: Flexport CRO Ben Braverman on Why It Is Total Horseshit That The Best Sellers Don't Make Good Managers, Why Specialisation Does Not Lead To The Best Customer Experience & Scaling Revenue From $18k MRR in 2014 to a $472m Year In 2018

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 @hstebbings1996 with two Bs, 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, Founders Fund, DST, our friends at Sousa Ventures, and Y Combinator, just to name a few. 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 HazeApp, acquired by Fiverr. 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 mojito's on me to thank you for But before we dive into the show today, I want to ask a question. Who has never had a bad service experience? I know I do all the time. That's why you need to consider Kustomer. That's Kustomer with a K, the next generation customer management platform that gives you a full view of your customer journeys, business process automation, and the ability to know everything about every customer, driving informed actions. Kustomer tracks every purchase you've made, product you've returned, ad you've clicked on, or item you've tossed from your cart, presenting it on a beautiful, always-in-context, omnichannel timeline view for the agent so that they can consistently instantly and effortlessly deliver a white glove service. But don't just take my word for it. People-first companies like Away Travel, Glossier, Ring, and Rent the Runway all choose to work with Kustomer and see significant improvements in customer satisfaction, retention, and agent efficiency. Simply go to kustomer.com— that's Kustomer with a K—.com to learn more and ask for a demo. And speaking of great products, as we did there, we all know that hiring is the crucial element in building any company. But let's be honest, the process is not great. So if you're currently spending a lot of time on phone interviews in your hiring process, there's an awesome solution called Sparkhire that's here to save you. Your candidates record video responses to your interview questions on their own time. Watch, share, and collaborate on the video interviews at your convenience to make better and faster decisions on who to invite for an in-person interview, saving time and money. And with over 5,000 organizations seeing significant improvements in their hiring process, Sparkhire is the leading video interviewing platform in the world and is giving away 20% off for 2 consecutive months when you sign up at sparkhire.com/saster using the promo code saster. That's S-A-A-S-T-R. That's sparkhire.com/saastr. It really is a must. Finally, as you know, every week we talk briefly to a WePay customer about how they achieve success. This time we'll hear from Justin Goodhue, founder and CEO at Trellis. Trellis is an event management platform for charities and nonprofits to create, manage, and grow their fundraisers. Trellis enables event organizers to easily build beautiful event and fundraising pages to sell tickets, collect donations, and automate their workflows. Hi, Harry.

My one piece of advice is do less. I know that sounds crazy, but the SaaS platforms that try and do everything end up failing every single time. The ones that can do one specific pain point the best in the world always win.

Thank you, Chad. And I absolutely love that maniacal focus, and it's very important to maintain success. And to find out how to successfully grow payments revenue by over 100% in a year, check out our case study with TeamSnap by visiting wepay.com/harry. That's wepay.com/harry. But you've heard quite enough of me, so now I'm very, very excited to hand over to the wonderful Ben Braverman, CRO at Flexport.

Good. That's perfect. Okay.

I think we're warmed up. 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. Oh yeah, of course.

Thank you so much for having me. Ryan said wonderful things. 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.

Well, I pay 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 8th fastest scaling of our time in Flexport. 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 quite in the way I wanted to. I decided, all right, let's come back and, and start working on something bigger. So I came back to the US, moved out to Silicon Valley, got linked up with a guy taking a company public on the Frankfurt Exchange in the '80s. We ended up founding a company together called Fort Knock, which was like a touchscreen at communication system. We 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. I worked for Jude Namad, who, you know, you're a brilliant Brit. They are brilliant Brits. 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 was sold to Pinterest. And I met Ryan at the dog park. Like, like all great rom-coms, our story starts at the 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.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. Very few actually profitable businesses. ImportGenius is not only profitable, it's never raised a dime of venture. So these two brilliant brothers, they just effectively run it for the fun and for the cash that it spits So when I met Ryan, though, he had totally abandoned this business. This is like, you know, 6, 7 years ago at its height. Import Genius 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 Import Genius 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. The terminal value is zero. Eventually, you know, someone comes along and decides to offer offer this publicly available data set for even lower than we do in terms of cost. 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 import jeans business. And at that moment, I was just so captivated by this story of 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 like, 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 over the course of a year after I made the investment of just going on walks with, with our dogs and talking about this business, I slowly convinced him to let me in the front door. June 2014, when I started, we had an $18,000 month. The year of 2018 as a whole was $472 million in sales. We're targeting a billion this year. I'll be thrilled at $950 million. It's been a great run. Again, just as I'm thrilled to be on the show, thrilled to be a part of it.

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

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 with 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 able— you know, we're a 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, you know, the folks with airplanes and boats and trucks, to agree to carry our cargo. And in our first year, there was plenty of customer demand. I mean, people really— there's an unlimited appetite for a job well done in this industry, and there's very few people doing a really excellent job. So we have this enormous market. We knew people were going to be engaged, but the other side 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 shut down. No cargo was getting in. It was pandemonium for everyone. 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.

I mean, that is just such an amazing journey of like how, uh, 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 In a perfect SaaS business, yes, it would be wonderful to have everybody specialized 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 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, then sure, specialization works. Like, I believe that that environment, it may produce in discrete skill sets a little bit more productivity per day, but the customer journey is horrible. 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. The reality is most of our customers, you know, if you're Georgia Pacific, who this year they'll trust us to book about 65 5,000 containers of 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 All that value that Julie had cultivated in the course of a year would have been lost. 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 of air freight in a given year, whatever it may be. So what we've found is we more design 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. Everything that the customer is going to need to experience in their life at Flexport is underneath this squad. So it's 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 of them. 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? 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 could probably do more calls per day in a different model, but this model suits us, and I think it suits most service businesses better than the traditional SaaS dogma of every every role must be hyper-segmented and you need to have all these handoffs that your customer is just going to endure.

There is one particular element you said there, Ben, and I just can't not jump on. You said that, like, you know, 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? Productivity and output from team?

Yeah, 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. You know, for us, a major transaction is going to take between 3 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. Flexport. But by the time they've seen a container delivery, you know, 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 it can do, you know, they're well into their second or third month with Flexport. So really, our salespeople 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 we get your entire business that's running today, you know, between some combination of email and disparate websites, into this platform, how do we onboard all your vendors. And so 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, 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 breakeven, 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 ultimately— our model is to break even by the end of year 1 and then track a whole bunch of milestones between when they onboard and the end of that first year to make sure they're on course to do it.

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 because you said to me, it's total horseshit that the best sellers don't make the best managers, which again is something 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?

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 has 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 know, 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 hit 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 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. All of the easy software products that you can train somebody to sell in a week, those are gone. Those 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, if you, 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 their ass is kicked a lot of the time because that's, 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 team's 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. And sort of the more positive way to look at it is when you have someone who embodies bodies 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 3 discrete skill sets and we've tried to say, this is what a sales manager is. 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 it is a sales leader. So much of what you're doing is tactical, it's operational, it's tracking against a 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 3 discrete buckets of sales management that I think are equally valuable. The first camp, I call this the 0-to-1 leader. This is a hiring manager. For us at Flexport, we've sort of chunked 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, it's listening to calls, it's giving feedback in real time. And at a really scaled-up organization, maybe this lives in enablement. I've literally, coming back to the 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 created a sales management function that all they do is hire and train. And so to, to your point about the rep, ramp-ups. Effectively, this person is responsible for overseeing year 0 to year 1 in the salesperson's lifecycle at Flexport. They are there to oversee them from their ramp to their day of breakeven. 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 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 to our mid-market segment. And I think this is applicable to tons of companies. I'm not— I'm talking about Flexport here, but I think this is universally useful. At least I hope it is. 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 customer. This is, this is sort of a sacred role, but I think there's— 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's side or on your company's 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. 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 clients. So the client knows that if they want to bring a senior stakeholder into the meeting, they have a mirror on Flexport's 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, you know, ultimately it is their performance. 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, closing deals. And so you'll notice I've talked about two of our, our sales primitives, like the, 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 in your different geos who are, who are managing local P&Ls. This is a valuable role, particularly for a high-growth company. It's the role that if you have to, if you have to sacrifice on one of the three, that's the one I'll give up every time because effectively you're two leaders that are doing the most important 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's willing to fill in. So if this is your worldview and you believe that the most important things 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. 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 indoctrinate with your DNA. And again, these are people who are great at the job. There is no one who's going to be a great level up going on the road with your reps 5 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 are 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. 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 skill set 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.

I mean, Ben, I'm enjoying this so much sitting back and listening. I do have to pick up on two elements that you said there. So when you look at kind of that cohort that could be making the move into kind of that management function, so to speak, and they're the top performing AEs, and there's 3 or 4 of them that are consistently crushing it, they've come up through the ranks successfully, what makes the one that scales successfully to management function the one? Are there leading indicators that suggest one is better or more suited than another?

Yeah, absolutely. It's the desire, right? It's— so we have people on our team that are just super ICs. One of the guys told me recently, you know, 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, you know, he is in this game because he likes driving fast cars, he likes flying around the And you know, 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. 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 salespeople, 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 so 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 they, or it doesn't give them joy. 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 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.

I mean, I totally agree. And my word, I'm so thrilled I asked that question, Ben. The other one that I wanted to unpack was you said about Camp B there and the three functions that we distill 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?

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 underleveraged, underappreciated functions in all 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 doesn't mirror the behavior that you want, 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. 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 gaps there might be? But to always have the sales team gold accurately and to always have them be gold 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've ever designed a system where people can do that, where 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 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 2.5 years outta 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 gonna turn you into a real salesperson. And at the end of it, you're gonna be a full quota-carrying AE. Does that bargain 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. We try to design quotas, and I— 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 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, you know, in Q4 trying to get those last few deals over the line when we know our customers bid in Q1 and Q2. So instead of going for max max revenue in Q4, 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 giving people mixed messages and saying, yes, go chase short-term revenue, but also make sure you're getting ready for next year. 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 the key to all this is having the quotas be correct in in the first place.

No, you totally didn't. I love that in terms of transitioning to the annual quotas. I love that. This is where I slightly wish I allowed the show to go on for hours and hours because 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 quickfire rounds. As you know, I say a short statement, you give me your immediate thoughts, about 60 seconds per one. Are you ready? Yeah, let's do it. Okay, so your hardest element of your role as CRO at Flexport?

Constantly having to fill leadership roles. The brutal thing about 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 5 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.

Listen, I totally agree. And when I look at your LinkedIn posters to the office openings. I do feel sorry for you in that regard. I don't want to talk about the optimal relationship between CRO and CEO.

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 when I take an action for Flexport, that I am doing not 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 engineering team and all of the, on 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. The issue is sometimes that's hard to do. It's not always that my interests, as far as hitting the goal this year, are aligned with our engineering team's interests 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 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 the relationship.

What do you believe in, SaaS, Ben, and that many around you disbelieve?

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 intune 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. A lot of times your ego gets in the way as a salesperson. 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 they 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? Possible, but 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, that they're effectively a two-way consultant for the customer to try to understand how Flexport helps them hit their goals, and they're a consultant for the company to help understand what we need to build to hit, to serve the customer even better tomorrow. If all of your reps are acting that way and they're doing the job day in, day out, you're gonna just sort of wake up having hit the number. It's sort of like one of the things Ryan says all the time is no one ever gets rich trying 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— there's sort of this militaristic focus on, on goal setting and goal tracking. And I get it if you're public, I totally understand it, but I, I don't think that is the core value driver in a sales organization.

No, I do agree with you there as well. I have to say, I do want to finish though, Ben, And 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?

I wish I'd known that there's never going to be some miraculous milestone, and there are no messiahs. There is no one person that you hire that solves all your problems. There is no one round of funding that you just come in and 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. You know, 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, you know, especially when the really early days when you, you know, you're burning through that first $3 million that you've raised and you can't hire some of the senior people you wanted because you can't afford them. There's this tendency to start thinking in terms of milestones and to start thinking that, oh, everything's going to 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 every day and be psyched to be here and be 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.

Ben, listen, I think you can tell from my voice just how much I've enjoyed it. I've also— I didn't— 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.

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

What did I tell you? Extremely special guest. And if you'd like to see more from Ben, you can find him on Twitter @BraveBen. Likewise, it'd be fantastic to welcome you behind the scenes here at SASTA. You can do that on Instagram @hstebbings1996 with two Bs. I really do love to see you there. But before we leave you today, hey, I want to ask a question. Who has never had a bad service experience? I know I do all the time. That's why you need to consider customer. That's That's Kustomer with a K, the next-generation customer management platform that gives you a full view of your customer journeys, business process automation, and the ability to know everything about every customer, driving informed actions. Kustomer tracks every purchase you've made, product you've returned, ad you've clicked on, or item you've tossed from your cart, presenting it on a beautiful, always-in-context, omnichannel timeline view for the agent so that they can consistently and effortlessly deliver a white glove service, but Don't just take my word for it. People-first companies like Away Travel, Glossier, Ring, and Rent the Runway all choose to work with Kustomer and see significant improvements in customer satisfaction, retention, and agent efficiency. Simply go to kustomer.com— that's customer with a K—.com to learn more and ask for a demo. And speaking of great products, as we did there, we all know that hiring is the crucial element in building any company. But let's be honest, the process is not great. So if you're currently spending a lot of time on phone interviews in your hiring process, there's an awesome solution called Spark Hire that's here to save you. Your candidates record video responses to your interview questions on their own time. Watch, share, and collaborate on the video interviews at your convenience to make better and faster decisions on who to invite for an in-person interview, saving time and money. And with over 5,000 organizations seeing significant improvements in their hiring process, Spark Hire is the leading video interviewing platform in the world and is giving away 20% off for 2 consecutive months when you sign up at sparkhire.com/saasr using the promo code saasr. That's S-A-A-S-T-R. That's sparkhire.com/saasr. It really is a must. And finally, as you know, every week we talk briefly to a WePay customer about how they achieve success, and this time we'll hear from Justin Goodhue, founder and CEO at Trellis. Trellis is an event management platform for charities and nonprofits to create, manage, and grow their fundraisers. Trellis enables event organizers to easily build beautiful event and fundraising pages to sell tickets, collect donations, and automate their workflows. Hi, Harry.

My one piece of advice is do less. I know that sounds crazy, but the SaaS platforms that try and do everything end up failing every single time. The ones that can do one specific pain point the best in the world always win.

Thank you, Chad. And I absolutely love that, Manoj. Focus, and it's very important to maintain success. And to find out how to successfully grow payments revenue by over 100% in a year, check out our case study with TeamSnap by visiting wepay.com/harry. That's wepay.com/harry. As always, I so appreciate all your support, and I can't wait to bring you another exceptional episode next week.