How to win massive deals by playing the long-game

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This is a podcast episode titled, How to win massive deals by playing the long-game. The summary for this episode is: <p>Enterprise selling is a team sport. In order to win bigger, you have to get more people involved, which means longer deal cycles and deeper relationships. Learn how to handle complex deals with ease, according to <a href="" rel="noopener noreferrer" target="_blank">Will Urban</a>–CRO at Flexport, a supply chain and logistics organization.</p><p><br></p><p>In this episode, he’s sharing how despite pandemic challenges like longer sales cycles and more complexities, his team actually thrived.&nbsp;</p><p><br></p><p><a href="" rel="noopener noreferrer" target="_blank">Sign up for The Edge newsletter.</a> </p><p><br></p><p>KEY TAKEAWAYS</p><p>[7:50 - 8:25] How Flexport embraces the long game</p><p>[18:12-19:07] A dive into their "deep selling" process</p><p>[26:44-27:03] Empathy + flexibility = the long game secret</p>
How Flexport embraces the long game
00:52 MIN
A dive into their "deep selling" process
00:58 MIN
Empathy + flexibility = the long game secret
01:12 MIN

Will Urban: We had some really big deals that resulted out of that because of a small thing they helped that customer with, they remembered us now that things are opening back up and we can open up more capacity. The deal now, maybe 10X what it was originally because of our approach through it, maybe compared to our competition.

Devin Reed: This is Reveal, the Revenue Intelligence Podcast. Here to help go to market leaders, do one thing, stop guessing.

Sheena Badani: If you're ready to unlock reality and reach your potential, then this show is for you. I'm Sheena Badani.

Devin Reed: And I'm Devin Reed coming to you from the Gong Studios. Enterprise selling is a team sport. In order to win big, you have to get more people involved, which means longer deal cycles and deeper relationships. But our guest today, doesn't shy away from these sometimes grueling, often taxing sales cycles. In fact, it's their go- to sales motion. Will Urban is CRO at Flexport, a supply chain and logistics organization. And today he's sharing how despite the many challenges the pandemic presented, including even longer sales cycles, his team actually thrived. But before we dive into this week's episode, I want to let you in on a little secret. Every successful revenue leader has a competitive edge that no one knows about. It's how they go from meeting expectations to exceeding revenue targets. That's why Gong launched The Edge, a monthly newsletter specifically designed for growth- minded executives. It's written by Kelly Breslin Wright, Gong's President and COO. She's taken three different companies, public. She's a five time tech advisor, and she's been a board member to six different companies. Every newsletter will give you insights into how to gain a competitive advantage, both in your career and for your organization, and you'll get data driven posts on the topics that senior leaders care about most. These are quick five minute reads, delivered monthly and always 100% free. To sign up, go to gong. io/ theedge, that's gong. io/ theedge, or click the link in the show notes to sign up now. If you like what you hear on Reveal, you are definitely going to like this newsletter. So make sure you subscribe to The Edge, today. Okay. Back to our show. Let's go hang out with Will. So you are the CRO at Flexport, a supply chain and logistics company. I have a feeling the last two years have not exactly been business as usual for you and Flexport. So can you kind of share with me a little bit high level, what's changed for you in your business in these last couple chaotic years?

Will Urban: I've been in this industry for, kind of dating myself now, but going on 26, 27 years, first job out of college and worked for one of the really big players for years and years, and then moved over to Flexport only in the last, I'm going up on my second year, and I've never seen the marketplace like this. And a lot of it started with the pandemic and the factory shut down in China and the whole bull up effect of all that going around the world. So you had everything stop in China from a production standpoint and then restart, and when that restarted months later, there was two things that happened. Things work on a schedule with shipping, so capacity and liners and things like that. When those things get out of sync in a massive way, it disrupts the whole global supply chain. And then certain places around the world became corked, essentially, because there wasn't room for new containers or freight to come in and empty containers to go back to origin to be reloaded again. On top of which consumer spending and habits became very different, meaning where people had that money and they were going out and going on vacations and restaurants and things like that, everybody was stuck at home. So they actually started turning that discretionary spending on, we'll paint the house or we will buy new furniture or we'll put a home theater in our house. And those commodities became not only scarce, but just corking the whole supply chain and their big physical items, which actually took up more space and more containers, and all those things kind of combined, have led to where supply chain now is sort of on the daily Americans vernacular. You go to the store, maybe there's some things there that used to be able to get right away. Maybe you're ordered something that would've taken a month and now the company you order from is telling it's going to take six months. So we've never kind of seen it so deep in American lives. I think everybody just kind of feels like the clothes they're wearing or the stuff they buy every day, just magically shows up on a shelf and it kind of does, but now it's all delayed because of all these things that happened with the pandemic. So dealing with that in the last couple years has been challenging.

Devin Reed: I can imagine. And it's true because as someone who has ordered one of said couches, and it did take a lot longer, the supply chain was never in my vocabulary, maybe back ordered was as close was as kind of close to it. But it's interesting because logistics did become a bit of a forefront topic for people, even if they don't quite understand the depth of what is it is y'all do, and to get things from point A to point B, it has been interesting to experience that. I imagine it's had a pretty big impact on your sales team. So how did you enable your teams to thrive through this chaos?

Will Urban: It's really been tough on our sales team and they've done an absolutely excellent job navigating this. But you know what was interesting is when we were just kind of leading up to the pandemic before all this happened, we were closing all this business and making commitments to customers, and then essentially we had to say," Well, we've only got so much capacity we can offer you." And so having to backtrack our ability to service our customers and then making tough decisions on how do we allocate, when I say capacity. I mean literally the space that we have is Flexport on a steamship, one of the ocean liners or air freight capacity on a plane, because that all became so constrained. Those carriers could only offer us so much space and thus, we can only offer so much space to our customers. Really tough position for a salesperson to be on. And in some points, we had to slow down sales cycles, meaning, we closed the deal, but we've got to try to put it off to the next quarter because we simply can't service it. So then you've got all these issues of keeping the relationship warm and alive. All that work just from a Tomo perspective of if you're a sales rep and we're definitely a deeper sell and a longer sell kind of process than a lot of companies, it takes us longer through those sales cycles to get companies on board because it's a very deep domain expertise kind of sell. And a lot of our clients, it could take two to three years to get their business, sometimes because it's a building trusting thing, because we're moving really literally their assets around the world, and/ or they have a bid cycle that they go through. And sometimes you get on the bid the first time around and they don't know you that well and that's how they get to learn who you are, they might give you a little bit of business or no business, and then the next cycle, maybe you're more successful. So the time that these reps put into this, and then we had to turn the faucet off at different times, so we could operationally choke it down, really tough for a salesperson. And then you have issues with their comp and commission and all those things. And I think we did a good job of making everybody whole and weathering the storm there, but really tough for a person that's out hunting all the time to be stop, start, and then keep that relationship hot with the customer, because every salesperson that's the dreaded thing, they get up to the finish line and there's some outside thing, they don't co control that keeps them from closing it. It's really hard to stay motivated. So I think what we did, we talked a lot about it. We talked a lot about one of our core cultural elements is we say we play the long game. So we play the long game in terms of how we're building Flexport. We play the long game in our customer relationships and our team buys into that, and so they weathered it really well with a lot of maturity, which I was super proud of them. And now that's paid off because things are opening back up. Our pipeline has never been stronger and these relationships that these guys and gals put together are really starting to see the fruit of it. So I think the really cool thing about this come up the backside is they're like," Hey, we weathered one of the toughest things ever as a sales organization and that perseverance and being resolute on our plan really paid off." And it was a really great lesson, so for some of our younger salespeople as well. Because there's always going to be blips in the business, there's always going to be things that come up in adversity and things that you have to get through. So I'm not saying we did it perfectly, but we pushed our way through it.

Devin Reed: That's interesting. Because it gets kind to the crux of our conversation focus, which is how relationships fuel predictability, which is things that probably people view as kind of different. Relationships are not very predictable. They're usually like, it's not transactional, but predictability kind of becomes more of a transactional concept and X input, Y output, continue, repeat, optimize. So I think it's interesting the way that you're viewing both these. I don't know if you have an example. I'd love to zoom in a little bit more to what it was like during that time of," Hey, got a client that wants to buy, I'm at the finish line. I need to hit quota or maybe the team goal." What were some of the how's of, how do you balance that? Or maybe what was some of those relationships like to be able to smooth this out and do right by the customer and fill your business?

Will Urban: What we realized right away is we had to kind of keep both relationships cooking from a management team, meaning the relationship with our AE is to make sure that we understood how frustrating this was and be empathetic to the situation because sometimes that gets lost, because everybody's so focused on closing the business. It's like," Hey, this is a person, trying to pay their bills, trying to move forward in their career." We're saying," Hey Devin, you're doing all the right things, but we still can't close this business. Nothing that you did, just the whole outside world kind of converging on you." So it was a lot of talking in one on one with a lot of sales people just to make sure that one, that they knew we appreciated what they were doing. And then two, really trying to help strategize with them, how we could keep these relationships alive. The flip side was when during that period of time, it wasn't just about, could we get space or capacity, it was, how could we execute through that? Even though there's a whole operations team behind that salesperson that's actually managing the day to day shipments and all that, the face of the customer is always that, AE, and how that AE is perceived is essentially how that AE is working with our operations team to provide a great service to the customer, even in the toughest market conditions. And so what we really encouraged our AEs to do in that period of time was double down on that, really be over communicative, almost getting the operations a little bit more than we would like them to, but to be that face to the customer because the customer was struggling so much. If you think about it, if you're a smaller importer and you import 10 containers a year and your whole livelihood, everything you're going to sell, is in those 10 containers, it's incredibly impactful, if that thing's delayed a month. You've paid your supplier. You haven't gotten the goods to your customer, to their store or distribution channel, whatever it is, and then they don't get paid usually until that stuff hits the shelf. And so there was cashflow issues in there, it's just not timing, there was the whole thing around all of it. And so we just really put a lot of focus with our AEs about talking to customers about those things. And we had some really big deals that resulted out of that because of a small thing they helped that customer with. They remembered us now that things are opening back up and we can open up more capacity, the deal now, maybe 10X to what it was originally because of our approach through it, maybe compared to our competition. And I really give the credit to our AEs being the face of that. And it wasn't easy because they were getting yelled at a lot. Every conversation with a customer during that period of time was negative, which is really hard to deal with. I think most salespeople are great, can handle negativity, because otherwise how could you? People say no a lot more than they say yes, right? If you can't deal with that, then you're not probably going to survive in sales. It's not like they couldn't take it, but when every interaction's negative, just because of everything going on in the market, nothing we've done, it's tough. So we talked a lot about that too, about, how do we show our value even in the most negative situation, how do we show empathy to that client? A lot of it's just saying," Hey, I understand how you're feeling and I understand why that's so impactful to your business." So that's kind of how we weathered through it.

Devin Reed: If you really think about the deepest relationships, that's kind of what they are. I wrote two things down as you're talking through that, one was empathy. That's definitely something that surfaced as you were mentioning this, but the others kind of reciprocity. You said," Hey, other people weren't doing this and now our deal sizes are larger," other people being your competitors. And so it's doing the right thing for your customer right now, even though it was not easy, and even though you might not have had much to show for it at the time, definitely paid off later.

Will Urban: Also, during this time is important to understand that prices are skyrocketing. That container was costing literally sometimes 10X what it cost a year ago, just because the market was driving the pricing up, because the scarcity of capacity. And our AEs being very strategic and coming to us and saying," Hey well, if we can cut our profit here by 15, 20%, really play the long game with this customer, being empathetic to their financial situation," none of them expected us to take losses or not make money. But also, you had to be really careful that you didn't profit on their pain. A lot of the team was coming to us going," Hey, listen, I need a break here in the pricing very strategically, because later I think, this will really show a lot of goodwill later and they know that we're playing the long game of the client." That led, the reciprocity thing, kind of led to a lot of great business now and trust. And so I really credit our team again, about being very strategic at how they approach these relationships.

Devin Reed: I think then it kind of goes to, well, how do you track that? You can't track empathy. It's not going to show up in a dashboard anywhere. So I'm curious, three to five year sales cycle, extremely complex, relationship focused. What buying signals are you looking for to know that a deal is on track?

Will Urban: The buying signals for us are essentially, we kind of look at this 60, 70% range. We have kind of a defined sales cycle. When we get to the 60, 70% range, we're getting all these buying signals. Those signals are really more about, have we gotten by price? No matter how good your tech is and your process is, you've got to be competitive in the marketplace or no one's going to talk to you. But we're never usually the lowest cost provider, from a transactional price standpoint. And so the buying signals for us are when we really start realizing the customers buying in on our value prop, which is two things, we as Flexport compared to our competition are super focused on being the most tech enabled, freight forwarding company in the world. And we use technology not to just drive down our cost to serve, but our more importantly, our customers cost to serve. We spend a lot of time in disco thinking about and iterating with our clients about not trying to push them through our structure, but designing our structure around what they need to have happen. So, the first step for all of us is," Hey, what are your goals? What are you trying to achieve?" What's really important to our client, not barfing up a bunch of sales stuff, but really listening to them about, what's driving their business, and more importantly, the person you're talking to, how are they measured and created in the company? How do we make them successful? When we kind of establish that, the walls start going down and they realize," Hey, we're much more of just a supplier, but an advocate to make them successful in their organizations." People with us don't buy subscriptions, clients of ours spend millions and millions of dollars. We don't necessarily make millions and millions of dollars. We make a margin on top of it. But when you talk about freight spend and distribution channels and things like that, you're not handing over a simple spend. You're handing over a very complex, very expensive spend. We have to really exhibit one domain expertise. But two, we understand what that organization's trying to achieve. When we get to that point where they're buying in going," Yeah, I can see how your technology would help us do that," or," Lets strategize on a lane or one of their customers and how would we best serve that customer?" Then we feel like, we've really turned the corner. You're kind of up on the top of the S curve. And then that's where we see the buying signals happen. And quite frankly, that's where we turn all of our leadership inward towards helping that AE, close that account because now, the AE has done a great job of opening the door and then all SMEs and all the people like me go in and go," Okay, how can we help you push this over the line?" But those are our true buying signals when they buy into our technology in our process. Which takes a lot of time because the customers got to devote time for us, to us, to have those conversations, because they're kind of deep, long conversations or they could be a two day workshop or it could be them having us interview a whole bunch of their suppliers. It just takes a while to get to that point, and that's why the sales cycle sometimes is quite long as well.

Devin Reed: Well, it sounds like a few things? It sounds like you led up with you need to be competitive in the market, but it sounds like if you're not the cheapest solution, that's where the trust is really going to step up. You'll pay more for that trust. You're listening to what your market, what your audience is asking from you versus trying to funnel them into your specific sales process. And then kind of sealing the deal with team selling. Now that we know this is real and we have a lot of trust built up, let's go all in and really close this thing out the right way.

Will Urban: That's exactly right. We believe that transactional price, whatever it is per kilo or per container, we just have a margin on that, that floats up and down the marketplace. So as the market goes up, we try to keep the same margin, when it goes down, we keep the same margin, pass the difference off to the customer. And we're very specific about where those margins should be. But that's transactional price. The more important thing to our client is getting to understand that our tech and our process, the goal is to drive down their overall cost, to serve, and provide a better customer experience for their customers. It's an interesting thing in our business because the importer or the shipper is our customer, but we're both serving their customer. It's all about, how their customer received the shipment or got their goods on time or the visibility or predictability that we provided to them. And so we always are serving two masters, even though one of them is really our first client. And so we really have to understand what they're selling to their customer, otherwise, we can't make them be successful. When AEs get to that point and realize that, that's when they become really powerful within our organization. Because really what's ultimately most important, making the person that we're talking to successful, but bigger picture, making their customers want to keep buying from them, based on the service that we provide. When we get to that point, when AEs understand that, I've seen just really incredible things happen. One, they close more deals. Two, what we do is we have longer deeper relationships, and a lot of times, that second tier client becomes our first tier client because of the experience with us. Because just because they're buying from them, doesn't mean they also don't source their own products and do their own things. So it's so important that we hit both things. So it's pretty interesting. It's why it's a really dynamic sell, a really deep selling process.

Devin Reed: Let's dive into the data behind the dynamic selling process that Will is talking about. According to Gong Labs research, bigger deals are going to involve multiple stakeholders. After analyzing 10,000 sales deals, we found that the average deal value with the team of around five buyers, is around 25k, but that increases dramatically because the average deal value for a team of 25 buyers is$200, 000, so the correlation is very clear. This holds true for the number of people involved, both on the buying side and the selling side. Selling teams that include three or more personas, have a 50% win rate, as compared to teams who don't use team selling, have a win rate around 15%. So what's clear that team selling both helps you increase your win rate and your deal size. Selling is a team sport and Will's stories of long game success, involve teamwork on all sides, which brings complexity to the sales cycle. Here's Will on how his team avoids pitfalls during enterprise deal cycles. We just talked about the positive ways. What about, to tell a deal is on track, what are the deal warnings or the risk flags that pop up and you go," Wait, hold on a second, something's not quite right, and we need to take action."

Will Urban: When it gets really transactional. When it's all about great on your value ad, but what's the price per kilo? There's definitely just price buyers in the industry for sure. And some of it is because a lot of it's based on their commodities. So some commodities, if you're importing a full router, there's a lot more margin in that. If you're importing peas or vegetables or something, there's very little margin on it, so that transactional price is super important. So you got to kind of know your audience and who you're selling to and what they value and what they don't. But when we go to that, it's all about the transactional piece, I don't know that there's enough margin in it for us to be interested. And so we have to be able to show them the overall value again, from the cost of serve standpoint, to make it worthwhile for us. Sometimes with really big volume things, it makes sense for us, cause it helps us build a lane or it gets us buying power somewhere else. We've made some of those kind of deals or trade offs. But the other thing more importantly is, it doesn't really fit in what we're trying to do. And so the one thing about our business is we're creeping up on a four and a half,$ 5 billion run rate this year, we've just had huge growth. But at that size, we might not even have 1% of worldwide market share. That's how big this industry is. And so my point is, there is plenty of business to go after that's a better fit. So when we start getting those signals, it's like," Hey, it's nothing personal, it just doesn't align with what we're trying to do. And yeah, keep the relationship warm and alive, but let's not devote thousands of hours into it, because we know we're never going to be happy with it even if we get it. It's not going to work." And that's sometimes a tough lesson, I think every AE in any sales thing goes through that. When you're young and you're new in a job, you're just trying to grab everything you can to be successful. And then you start realizing, not only the company won't be successful with that, you spend all your time trying to keep that relationship alive, because you're never going to make them happy because it's strictly a price buying scenario. And then what does that do? It takes you away from developing your pipeline and your book of business. And I think every younger salesperson goes through that. And so it's just kind of a learning curve you have to go through and then they get a really good nose for," Well, that business doesn't make a lot of sense unless it's under some really specific parameters. I'll keep talking to them, but I'm going to spend 90% of my time on the client that does."

Devin Reed: How does this transactional risk flag hit your radar? Is it hearing the customer conversations? Is it maybe in a pipeline review or deal review?

Will Urban: Well, one, not to make it a pitch about Gong, but that's really helped us a lot. So we listen to these calls. So I try to make a point of listening to a few a week from different people and different geographies. But our sales managers, kind of our frontline sales managers, most of our clients allow us to record the calls, some don't. We're actually getting better at kind of getting through those objections with your help about," Hey, it best serves everybody if we can record the call. We can provide a better product for the customer." But we're looking for those key words. So if half the conversation is keyed on pricing, then it's one of two things. It's, how do we break through to decision makers at that client that are kind of seeing things more in the macro level, and/ or is our sales rep going strictly for the price play to open the door versus playing more the longer game to understand their business and really sell more of the value? And so Gong's helped quite a bit. We also just know if right at the beginning of a relationship, if they just push right away for pricings, like" No, well show me your pricing and then we can talk." We have to be resolute enough to say," I don't feel comfortable giving the pricing because I don't know enough about your business." And if they scoff at that, we can't just barf up pricing. We have to be disciplined enough to say," Well, I get it, and that's important, but maybe this isn't the right time yet to have this conversation." Still always keeping the relationship warm because you never know what's going to happen or that person jumps to the next customer. And so you want to always stay friendly and not be Dr. No. But at the same time, rarely does it work for us where we lead with pricing and we're successful. And so just when those things bubble up, it's really coaching our team to be disciplined. And what that really speaks to is why you always have to have a very, very robust pipeline. You got to have more deals to go to. We have to have more warm leads for our people because it kind of goes and droves, based on what's going on in the economy, and it's really easy to get sucked down this just transactional pricing hole in our business. It's super easy. And also praising people when they make those decisions. I think that's the part about it, it's like," Hey, that was a great decision. Maybe you're not quite hitting your number this quarter or your pipeline is not as robust, but I also think when we look back and reviewed these deals, you're making the right decisions with these deals." Because the other part we want to impose on everybody, if we go down that path, there's a lot of costs that goes with that. We tie up a bunch of our pricing analysts. We tie up a bunch of our people that are negotiating capacity for that client. With a carrier, we're tying up that capacity that we could be possibly giving to another client that would pay a much higher margin. And so it's not just about that AE and the relationship, it's how it impacts the rest of the organization and making sure that AE understands that, and it's playing the long game and making the better decision for Flexport.

Devin Reed: How has what you've learned in the last year and a half, two years during that period, shaped how you'll continue to lead into the future?

Will Urban: I think the first thing is, and it was actually funny because my counterpart, our COO and I, actually have a whole bunch of our leadership in Seattle this week and we've been talking to everybody and the point we made to them was," Hey, listen, I don't think the market's ever going to go back to," Normal," this is the new normal." And one of the things that we have learned, and I think has really helped us grow during this time, because we've actually had pretty phenomenal growth through all this market strife. There is tremendous opportunity in the chaos, meaning, when you're willing to listen and be empathetic and be creative and really go out of your way to understand what the customers dealing with, so many of our competitors I think were just telling our customers," No, can't do that. No, sorry, I don't have any space." And sometimes, we had to say the same things because we couldn't physically make it happen. But our willingness to kind of go the extra mile and help people out, and really again, I keep keying on this word, but I think it's so important, is being empathetic to the customer situation, has really helped us come out on the other side of all this chaos, quite strong. Because people remember, they remember how we treated them. They remember how we listened to them. And even if we weren't successful, we gave our best efforts to make them successful. Because there are some things that just no one could possibly change in the marketplace right now. If there's a ship that can't get into birth, sitting off the Port of Long Beach and your container's stuck on it, I can't physically make anything happen any faster than it is. But once that container's available, how can we do everything within our power to get it delivered as fast as possible and constantly giving customers updates. And then I think the second thing is our sales team proved to themselves that they could still close business and be successful in a crazy market, which gave them a lot of superpower strength. I think it builds a lot of confidence. I'll give you a kind of, I ran into one of our younger salespeople a couple days ago and he says to me," Hey, the deals are just now closing." And he goes," I learned so much of getting the crap beat out of me the last six months, that now nothing kind of phases me. I go into everything really, even more prepared. I go into everything kind of understanding every objection I could possibly get, and now I'm not getting all those objections and I feel so confident closing business." It's like," That's pretty cool." What a great outcome and a great attitude by that young guy that is going," Hey, I learned so much from this, it just made me tougher, essentially."

Devin Reed: There's no shortcut for resilience in sales, except for getting your teeth kicked in a few times, going through the fire.

Will Urban: It's all about grit.

Devin Reed: I'm going to ask the final question that we ask all of our guests, but it's an easy one, at least I think it is. Will, how would you describe sales in one word?

Will Urban: Fun. To me, it's the best part of my job. I've got a really big, my part of the org is almost 1300 employees. I still, the most one I have is sitting down with customers and just talking to them about our business and their business and the relationships with that. It's just to me, the funnest part of the business and that's actually what I really look for. I think that people that really find it fun and fulfilling, are the very best salespeople.

Devin Reed: It kind of goes back to playing the long game. When you play the long game and you let yourself have fun and really enjoy the process, good things happen. When you cut the fun, try to be too transactional, fixated on goals, not only is it, burn out faster, but the results don't follow.

Will Urban: Well, and we as sales leaders have to make it fun. There's pressure and numbers and you got to perform, there's no question, but we can also do it in a way that encourages people to have a good time with it. And I think when you get everybody kind of working, it gets to be magical and people are really having fun, they're really successful, generally, and everybody wins.

Devin Reed: If you want to learn more about how revenue intelligence can help you win record setting, complex deals, head over to gong. io. And if you like what you heard today, give us a five star review on Apple Podcasts, Spotify, or wherever you're listening.


Enterprise selling is a team sport. In order to win bigger, you have to get more people involved, which means longer deal cycles and deeper relationships. Learn how to handle complex deals with ease, according to Will Urban–CRO at Flexport, a supply chain and logistics organization.

In this episode, he’s sharing how despite pandemic challenges like longer sales cycles and more complexities, his team actually thrived. 

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