Cracking the Enterprise Code: Strategies for Moving Upmarket

Hello, Dave. How you doing? I'd say this afternoon, but it's morning for you now. How are you doing? You okay?

Well, Simon, how's it going? Good to see you again.

Yeah, everything's everything's good. Thanks. Yeah, really really appreciate you sort of taking the time to, uh, I'm sure you're busy schedule, to to make time to record the session today. So, yeah, really looking forward to, uh, to kind of digging deeper into this exciting topic.

I'm very happy to do it. No worries. Great stuff.

Okay, so look, the title of today's episode is cracking the enterprise code, strategies for moving up market. Okay, so for people that haven't tuned in to this, uh, series of episodes, um, you know, welcome. Um, my name is Simon Gregory. I'm a director of a recruitment company based in London, um, called Thornton Gregory. My background's, uh, 10 years focused on hiring for software, uh, vendors, uh, a lot of which have been in the martekch space. Um, you know, we work with those companies and help them build sort of, you know, stellar, a, uh, sell a player sort of GTM teams across Europe and North America.

Um, the kind of the premise of the series was I worked in the space for 10 years and met some amazing minds like, you know, a crazily good like, uh, operators and heard their stories firsthand, whether it be in person or on Zoom, and just kind of dawned on me that it was a little bit of a shame that really it was really only me listening, right? And I was talking to these people that were operating in revenue leadership, like we're talking about today, and and really turning the dial on the space, but also equally in things like revops, sales enablements, customer success, pre-sales and all these kind of things that, um, really, um, are evolving in our space, um, driven by technology and, um, you know, there are some fantastic people in there. So I wanted to give back a little bit and sort of trigger some of those people to come on the show with me for an hour, talk about a topic like this and really kind of give back in terms of a little bit of gold to our listeners. So, you know, we're on Spotify, YouTube, and Apple Podcast. So, just check us out. There's other episodes. Um, you know, none of them are the same. Different questions each week.

Okay. So, and today's all about this going up market and and and Dave truly truly is a subject matter expert in this. Just off air there we were talking about, um, he was doing a, uh, a roundt a discussion to another audience about the topic which apparently went really really well, so no pressure today, as, uh, but, um, I guess look, I always give a little bit of a prelude about why I brought people like Dave on or the guest of the week. I met Dave, uh, maybe Dave doesn't remember, we sat and had lunch together in, uh, in London, uh, when I worked for you before.

Yeah, we had a nice lunch and it was off the back of some good work that we did, um, more than 10 years ago, which is a bit crazy, um, for Dynamic Yield, uh, which is, um, if you don't know, one of the kind of the initial trailblazers in the personalization space, and and Dave with the chief revenue officer there, um, they've subsequently gone on to, we'll talk about I'm sure later, but get acquired twice and, um, some of the frameworks and the people and the processes and the logos that they've pioneered within that organization, um, set them up set them up undoubtedly for the growth that they saw which took them to the eventual exit. Also companies like Verasign, sell through and its different carnations, and then after DY moved into Hitachi RSA and then back into the startup world. So real breadth of experience that we're like really excited to kind of like talk through and just understand a bit more about and, um, you know, thanks again. So you know that's the the drum roll and you know little intro, but you're welcome and it's my pleasure.

I also want to say I think you do very high caliber work. The individuals that you introduced me to were were really excellent candidates and I hired a few of them. So thank you for that.

Praise indeed. Thank you very much. I didn't tell you to say that. So thank you Dave. That's really great.

Thank you. Okay. So, look, I know I've given you a little bit of a high level intro there. Um, so sorry to steal your thunder slightly, but for the people that don't know you, would you mind just telling them a little bit about your career to date?

Yes. Um, so, as I say, it's quite a long story, but I'm going to sum it up and say, originally, my mother had my whole life planned out for me. Was to be a chef, go to Culinary Institute of America and, uh, work in her restaurant for the rest of my life and marry my first girlfriend who she loved. Uh, instead, I ran away to college and, uh, joined the tech industry. Uh, always always loved a technology. Uh, and that move, uh, I stayed very close to my mother of course, but that move improved my life significantly. Um, so I'm going to use a few industry acronyms for the audience that they will understand them. So I've been a TM, a NAM, a GAM, an RM, an AVP, an SVP, and a CRO. I've also been a consultant, strategic advisor. And in those roles, I've been an acting chairman and CEO roles and, uh, CRO kind of helper. So I found a lot of worn a different lot of different hats, but that's allowed me to actually be very focused on the whole go to market area. So I haven't moonlighted in finance or moonlighted in in product or any other areas. I've always been very focused on the front office as they say.

Okay. Fantastic. Yeah. Okay. And look, in terms of milestones there, like have you got any particular, um, you know, really pinnacle milestones in your career apart from just going into software and if so can you talk to them and why?

Sure. Uh, so I'll put them in two categories. First as an individual contributor, uh, as a rep I actually closed two $20 million sales for two different companies, uh, within a global 100 account. Uh, one of them actually pulled Andy Grove into the sales cycle, who some will recognize was the chairman and CEO of Intel. Uh, and thought I was a kind of interesting 20some rep at the time who cold called Andy Grove's office and said, "Hey, Andy, would you help me on this opportunity with the CIO and his team?" And she's like, "Yeah, sure. I'll help you." So, anyway, that that was fun. Everyone was kind of looking at me strange like, "You just hosted Andy Grove on a call." All right. Um, and then the second one, uh, I was at Oracle at the time. And by the way, when you do when you work on some of these large opportunities, there's a lot of people telling you not to do it. Like, don't do this. Uh, this is this is going to be bad. You know, there's a lot of people that are very, uh, fearful for some reason of taking risks. And I always take like calculated risks. So, it's not like I wasn't looking to risk my company's reputation or business or anything. It's just, you know, you take some personal risk to win. Anyway, uh, so I closed a a $20 million software and support contract for Oracle, which was, uh, locked out the competition in a major account for five years and was, uh, announced by the president on the investor call. As a result, I got the Oracle's executive committee awarded me global account manager of the year and I received a two-level promotion to lead a region and manage managers. Uh, so that was that was quite a milestone as an IC and then as a leader I would say it's been the transformation that I've been able to help drive in companies. Uh, so a recent example is RSA security when it was part of DELMC. I was recruited to lead the America's sales or which was 60% of the global revenue and there was a few hundred people in there. Um, they had been missing their numbers for two years in a row had very low morale and high attrition. I came in and worked with my VPs on the team and the rest of the org and rallied everyone and reversed that trend. Uh, we focused on training improving sales excellent execution as well as recognition. We made both of the next two annual numbers which reversed the trend and it put DELMC in a position to sell the business for $2.1 billion. So those are two, uh, you three, uh, examples that I think of.

Yeah, I love I love those. They're brilliant. Um, some no doubt amazing, uh, company names, some of the biggest in the world you mentioned there. Um, is there any particular reason or or rhyme or reason about why you chose those roles or why you kind of, you know, landed in those particular companies among maybe many options?

Well, at the beginning of my career, I wanted, uh, really to get as much training as I could. So I joined great companies like deck and Oracle, uh, and received amazing training and and tremendous experience and later all the moves were based on a perception that the product was innovative and highly valuable to customers and could fuel high growth and I also of course felt, uh, strong chemistry working for the hiring manager. I would say the common thread in all my jobs is has been a focus on the enterprise segment. I've had SMB responsibility in mid-market as part of inside sales teams or startups, um, and you know, fine with covering those, but my sweet spot is really up market that leads us perfectly into the body of the, uh, discussion that we're, uh, we're going to talk about now. So, um, if we go back to the kind of the the title we're saying about cracking the enterprise code strategies for moving up market. So the first question I had on that was what are the most significant differences between selling to SMBs versus enterprise customers and how do you adapt your goto market strategy for each?

Uh, yes, great question. So I would say in SMBs there's just simply less people and, uh, so there's less people to sell to and then the vendor credibility hurdles you have to clear in the enterprise are less. I mean you have to be credible but they're not as stringent, uh, most upmarket companies for example have like very stringent, uh, data security, uh, documents that you have to have legal review in your CISO review and sign sizing that that typically doesn't exist in SMBs. The opportunities are smaller as well and it's the opposite to all those in enterprise. Um, so the go to market for either of them should always start with a lot of discipline around your actual account targeting, um, aka segmentation, uh, whether enterprise or SMB this is critical. So, it's best to define that ICP and filter your targets. Really thinking about the propensity to buy what you're offering. It's different than when you're raising money. So, if any founders are listening or CEOs and early stage companies, when you raise money, you want to tell a story that you have grasped green field, vast green field for your, uh, offering, meaning everyone could buy it and use it. And that's great to raise money. When you actually go to sell it, it's not great. You actually have to have really strong filters for who realistically would be buying from you based on the size of your company or the maturity of your solution or the value it's delivering. If you you could be a young company and the nature of the solution is such that a large enterprise could actually buy it right now or you could maybe not be be ready yet. So you really have to kind of think about that and then which job titles in wi in which vertical industries would have the highest propensity to buy what you're selling. Um, and then the main difference on the execution is the SMB should seek to generate a significant amount of inbound leads and then use a web channel or inside sales resources to accomplish that. I'm not saying those folks could you visit in person with customers. Most selling today is done on Zoom anyway or whatever, uh, video and in enterprise the motion should be primarily an outbound motion and I firmly believe that account-based marketing and selling is the way to go there. Enterprises then should once they determine that sort of universe of accounts that they've segmented, they should go about the work of account development selling because the the premise is that these accounts are pre-qualified to be great, uh, customers for you. It's just a question of timing. So if you take that mindset, you've already done the filtering on, yeah, based on, you know, logic and and these principles, this customer would be a great customer, would get tremendous value from what we're selling. Um, and focus on those versus trying to respond to every single inbound lead that comes in, you know, turning taking you left and right and center, uh, which may completely be out of your ICP, but they're, you know, they think they can use it and spend money on it. That really, uh, hinders scale and velocity because you're wandering all over the place. Um, it may not be bad if you're doing like a sort of the concept of early release or you know what we used to call beta back in the day. Uh, but when it comes to actual executing go to market, it's not. So those are I think are the key differences in my opinion.

Yeah. Okay. Okay. And so, um, you touched on one one maybe there but what are the common mistakes that you see from companies that are transitioning up market from the SMB into the like upper segments?

Yes. So when I was leading, uh, the front office for a few early stage venture companies I actually went immediately up market and there were reasons for doing that that were vi, you know, viable logical, u, many, uh, SAS companies actually start down market in the SMBs and I think they should reconsider that, but let's say that they have and now they have traction and they, you know, a decent amount of revenue building. The biggest mistake I've seen those companies make, and I've at this point I've advised somewhere around 50 different startups, um, they fail to train the sales reps to grow into that enterprise rep and or staff reps who have enterprise experience. So, in other words, they view it as an expansion of the accounts that they're assigned. They don't actually recognize the resource requirements that are different. Uh, and then the other mistake is they use the same sales process for both. And let's say you have, uh, you're calling on SMB and you have a six-step sales process or eightstep sales process. Highly likely that doesn't actually fit for the due diligence an enterprise is going to need to do. You're probably going to need a 12 or 14step sales process. um, enterprise needs its own sales process.

Okay. Okay. What what's the role that customer segmentations plays in in crackling the enterprise market and how do you identify the right enterprise prospects?

Yeah. So I touched on the first part just before. So it plays an important role. The identification you have to think of it as a market map. So a linear flow of a map which starts with the voice of the customer and then goes into your the design of your solution. The marketing and sales execution are later to the right. So right out of the gate it plays a massive role right out of the gate. You should make sure that your solution design is actually aligned with that enterprise voice of the customer. Uh, or you shouldn't actually go there. uh, and if it does align then you filter and create micro segments within enterprise again touching on the propensity to buy filters right like so what size enterprise there's quite a disparity in terms of the sizes of enterprises, u so what size enterprise what vertical are they in what job function are these people in what do they care most about what what's the most acute pain you can actually solve or address for them and then you filter, uh, accordingly.

Okay. Okay. And how do you align sales, marketing and product teams to successfully approach and close those enterprise deals?

That that's another great question. There are so many silos in companies that aren't even that big. And that's like I can understand it in really large companies I've worked in. uh, there's ways to to bridge those silos and and bring people together in large companies, but also in small. But I've worked in some fairly small organizations like, "Wow, we're way too small to be this siloed." And really what it comes down to is shared goals. So the first thing I would do is I'd have shared annual OKRs. So each of those functional areas has skin in the game from a, um, performance review and a bon performance bonus standpoint to cross-pollinate to help the other functions. Then operationally, uh, bring people together have weekly crossf functional team meetings and cascade it, uh, downward. So started at the ELT and then moved down to, uh, VP level, director level, manager level and then to the actual individual contributor teams like teams of reps and SC's and customer success people and product management meeting to discuss accounts or territories, opportunities etc. And then the last is use Slack or Teams and just have highly open frequent visible communication going on. Be specific to accounts or specific to a vertical specific to a market segment, uh, whatever specific to a product like make sure that that communication is visible and is flowing. So I think if if you just think it's just common sense, right? If people have shared goals and they have open and honest communication and they have frequency of contact and you have decent people, then they're going to be aligned.

And do you think that's something that within the organization you've really got to proactively work on like to to make good? That's like it's an ongoing journey. Is it? I mean some companies are lucky enough to have that organically form but I wouldn't rely on that in a business you're you know we don't want to just hope, uh, so yeah I think it's very it's structural and it's very easy to put in that kind of structure I just you know it's part of the way people are managed and and then the kind of culture that's operational execution and the communication that's part of that becomes part of that culture is something that I talk about a lot with, uh, candidates and clients is this over here.

Um, uh, you know, the return into the office situation seems to be a bit more of a movement certainly in the last four to six months. I guess that whole water cooler moment that you're talking about, you know, is probably easier in person, um, but sometimes not practical especially in the startup space. What's your viewpoint on, uh, trying to get people together or not, working remotely or not? What's your kind of viewpoint there?

I think there, you know, obviously there's no substitute for in-person human interaction. However, I'm, you know, a veteran of the tech industry and have been working remotely for decades. Um, you know, there has been offices that I've had been part of which I would go into frequently, some cases, you know, four four days a week. Some cases five days a week. But I honestly think that people have evolved in the dynamic workforce, remote work forces is just, you know, it's I don't think as long as you have like some recurring meetups in person, whether it's, you know, once a week or once a month or, you know, at least once a quarter. I think that like just the nature of what how we communicate today, what we do is fine. Like I don't I don't think people have to be forced I don't think people should be forced to go back into the office so to say, um, and it depends on your business too like I'm I'm referring to, you know, go to market functions in the tech industry so for our business we work anywhere. I mean have a mobile phone I'm I have teams and Slack on my mobile phone I'm constantly in touch I'm more in touch than, uh, many times when I'm in an office in meetings. But I have no problem going into offices and working and I I love seeing people in person and I do feel you should have those in-person meetings like I mentioned but, um, and particularly like we actually, you know, it's been harder for reps to get in front of customers. Those customers wanted to do Zoom and that's that's fine, but this should also still encourage a lunch meeting here and there, some coffee meeting to to, uh, to see each other, but in our business I really don't think that it's as big a deal, uh, as long the the more important thing is like how are people gold are they regularly aligned in, you know, speaking and I don't mean meetings for the sake of meetings by the I mean like really getting into substantive conversations about like this customer satisfaction issue or this opportunity or whatever. Um, because the reality is it takes teams to win and it's not a soloist, uh, business. Uh, I have had experiences in working with people and people working for me that are more soloists and, uh, they don't do as well. It definitely takes, uh, a team to to win. So, but with Slack and Teams or whatever you're using, um, there's just like I don't know, it's the collaboration capability still there.

Yeah. Yeah. It's a it's an interesting topic that that you could do a whole episode on. I mean, constantly being debated over here, but so we if we flip flip it slightly in terms of the the overarching topic, but we're talking now about the people. Okay. So what qualities do you look for in, uh, the sales leaders and teams to succeed but particularly within the complex sort of enterprise segment?

That's a really great question. So the first thing I think you have to ask yourself is with whom am I interacting and who you know my organization interacting? What are what are these customers, buyers, evaluators? What are they like as people? Like are they very formal, very senior? Are they completely informal? Um, lots of, you know, young newer employees like what is that? Who are they actually interacting with? And, uh, you know, birds of a feather flock flock together. So you you have to align for that. So even though it's an enterprise solution like it could be a very deep AI technology that is a highly technical sale that is being sold to engineering developers of AI and it could be a lower because it could be an enterprise solution but it could be a lower ticket enterprise solution. So in that case, maybe there's only one or two job titles involved in the decision, unless there's like a mega deal. In that case, like you're looking for someone that's, you know, super smart, highly technical, uh, as an individual contributor and a leader and someone that's pretty like informal and casual because all those folks for the most part, you can't stereotype every role, but like they're going to be more casual, you know? So, if you have someone coming in there and acting like super fancy and and posh, uh, it's not going to work out. You know, they're just not going to it's they're it's not going to they're not going to bond. And in the opposite, if you have an enterprise solution that's being sold for hundreds of thousands or millions of dollars to CIOS or, you know, you know, CM global CMOs or or CFOs or whatever or, you know, CEOs, you need a highly professional person. You need someone who's very polished, has excellent communication skills. Uh, so you have to match culturally against who you're selling. Then there's other attributes that I think are important across all you know of those situations. And that's an agile thinker, uh, someone who can actually think big and is inquisitive and can doesn't have a fixed mindset more of a growth mindset because this our technology industry is evolving at such a fast, uh, pace that the brain of the people that are leading people has to be flexible. H you have to be, uh, able to consume a lot of information and have an open mindset as to embracing new approaches because if you're fixed on what happened you can imagine in my career how many technology shifts there's been right I have embraced every new technology shift with passion and gusto because I understand the value that it can drive and I'm not fixed on oh like I really miss selling this or I miss like marketing that right or I missed the old way we we did it. Um, you can't have that mindset. You have to be highly adaptive. And, uh, and then also too, the reason I mentioned big thinking is, uh, you know, if you think small, you're going to actually play small. But if you think big, you'll play big. And I could use lots of sports analogies, which I won't bore your audience on, but, uh, it is that case in business. If you go if

You go into a situation, yeah, you know, we're happy with just getting, uh, 200,000 a year or whatever from this, uh, account. Meanwhile, you found that the value you're providing is really high, and it should actually be, uh, the technology should be used broadly inside the account. You need people that are leading; people that should be thinking like, "Yeah, I think, uh, you know, $10 million or $5 million would be an appropriate cost value alignment with what we're providing." Or let's say there's some account that is really hard to crack, and, uh, it's never been cracked by this. Let's say it's a startup. Uh, you need someone who's willing to embrace that challenge and say, "You know what, we're going to crack that account. We're going to get into that account even though it's never been done. We're going to find a way to do it." And so I look for leaders, uh, to have those attributes, and I look for team members, um, to also have that. And, of course, the last thing is like good team players, people who actually work well with others.

One of my former managers who hired me, uh, when he was briefing me on my organization, he said, "You know, this one guy is a really strong rep, but he is the person most likely to be killed by friendly fire. He doesn't get along with anyone. You'll understand when you meet him." And sure enough, I met him, and right from the get-go, I was like, okay, I could understand that it's difficult. So he was more of a soloist, but in most part, you need team-oriented folks. Yeah.

You talked about the, the, the kind of seeing big, you know, going big type mindset. Um, do you think it was just like exuberance of youth getting into that $20 million account that you did in your 20s, or do you just naturally have that kind of, you know, that kind of like bigger mindset than maybe some others?

That's a really great question. No one's ever asked me that before. Um, of course, I was guilty of being an exuberant youth, but I don't think it was actually that; like it was actually a competitive, uh, element. So, an account that I was selling into announced that it was going to have a very large project, uh, and were looking for, you know, top vendors to compete for it. So for me, it really was more about competing for wallet share in the account that I was in, and that the product—I won't go into the details—but it was actually a new offering; the product, uh, was a new offering of a type of product that the company had failed in previously, which was very public. So very publicly failed in a product area. I mean, everyone knew, like everyone in the industry knew, um, because this was the second, the second largest tech company in the world at the time. And so they re-entered the market, uh, and partnered with Intel on that. And I just thought like, you know what, I have to really understand this customer's business. I've forged some really great relationships here. I understand the type of support that this company needs, and this product we announced actually seems like really competitive. So, uh, I got a seed. Uh, there were only like a handful of seed models that were available, and I got one, and I put it in inside the innovation lab inside it in this account, and then I spent time briefing people on it and sharing information, and, uh, they really took to it. They really thought, "Wow, this product actually does seem really strong." And so then I just had to like compete against the brand, u, equity of the stronger other players that were in that market. And that's why I pulled Andy in, and and you did some other things, uh, to win the business. But it was, uh, I literally had—I was—you to mention—I think I was like, I don't know, 27 or 28 years old, something like that. And, uh, the team lead that I was working with was actually very against the sale. He was like, "This is going to risk some other areas of our business if it doesn't go well, and you know, there's quota implications and such." I'm like, you know, I respect all that, but like how can we turn our backs on, you know, a $20 million opportunity? And, um, and then as I started winning, then he jumped on the train, and he was then he was like, "This is great." You know, I, and I, I let him get his, his glory, of course, uh, for what he, he, he, you know, he, he, he was doing in his role. Uh, I didn't stand in the way of that at all. That's not what I was interested in. But, um, yeah, it was it was very exciting. It actually came down to there was a short list of like four, and then there was a short list of two, and the final two were head-to-head, and, uh, and I was able to, uh, you know, to win that. So that was that was really exciting.

And then the other one I'll just mention that wasn't youthful exuberance, I don't think anymore. Um, that was also like how do I maximize my, uh, you know, my economic opportunity here and and lock out the competition. So that, and that was another situation where people told me I was crazy. This account only needed to spend, you know, one-tenth of that, uh, amount. The account was—I was originally told the account was sold out, uh, for Oracle licenses. Why are you doing this? It's crazy. And I literally just went around—I had a vision—and I went around and I met with dozens and dozens of, uh, IT directors and, um, and shared that vision and just said, "Hey, what if this type of agreement existed? What, what could you be able to do that you're not able to now?" And they really opened up and shared a lot of information, and I collected all that information and I went back to, uh, the, you know, the customers who, like, procurement who basically said we don't, we don't need all that, you know, and I showed them all this information; they're like, wow, we didn't know that, we didn't know that information. So yeah, uh, and then, you know, I just smiled at the internal people and just said, "Sorry, guys."

One other funny story for the audience: I closed that sale on a, uh, two-page proposal. So, I, I had—I had peers that put together binders. Like, there was a guy who—Yeah. Yeah.—who, uh, I was in a cube at the time, and there was a guy who had like a fancy office right across the way because he, he was more in favor with local management, or I don't know, he had a same-level job, but he had like this big office cube. And so, he was—he had binders. He was putting together like these giant proposals and binders and sending them all over the place. And I had literally put together this two-page abstract, um, to close the sale. Now, of course, we, you know, we had to put it into an order form, and there was already an MSA in place, but we actually had to rewrite the MSA, which was—that's another podcast in its own if you ever want to have a session—because I worked 80 hours a week for the last two weeks of the quarter to actually finish off the 12 sticking points on the MSA that were—we were stuck. Um, but anyway, I think it's kind of, kind of funny that the customers really got a lot of value from that agreement. I mean, they really were able to, to, uh, leverage Oracle's, uh, database technologies and web technologies and tools in a much bigger way for the benefit of this very large company. Uh, and then certainly we benefited because we locked the competition out for five years, and it was, you know, it was a sizable transaction. So, it was it was a really cool—that that that was a nine-month, uh, from conception to closure. That was a very cool, uh, experience. I can only imagine. I mean, very few people on the, in the world get the, the pleasure of closing a $20 million deal. So, that's amazing insight. Thank you for that, D.

Um, so look, how does an organization start to prioritize larger deals while also staying consistent and focused on executing the deal ranges that ultimately made them successful at the start?

Yeah, it's pretty—I think it's actually a pretty simple answer. It's—you have to create a separate, uh, team to focus on it. You can't—your current team is already burdened on what they're doing, and it's not something you can like just moonlight in. You, you really have to, uh, you really have to focus. So what I would do is I create separate teams that focus on larger accounts/deals, and that would have a rep or reps depending on how many you have, and, uh, SEs for pre-sales and customer success would be looped in there also. Um, it's an expensive proposition for startups, so you know, you have to be careful there, uh, in the startups I actually segmented the jobs. So I had—it pulled—I would in the beginning I would pull like just a couple folks out of the normal role and train them to focus, um, and in larger organizations where you have to cover like, you know, lots of large accounts but also territories, then you just—you have different roles. You have territory managers versus named account managers. Um, I'm not like a really big fan of territory managers in most organizations unless there's some reason to have that. There are some reasons, like if you have—you know, take a company like Microsoft that just has so many products and, um, you know, that that's different, but like in most companies, uh, you're better off having everyone being named account reps and handling, you know, 30, 30 named accounts, uh, which could dynamically change—that you could change that list as you're executing, and an account gets, uh, qualified out, you could add another one in, but but it's better to have focus—focus. And then the other, Yeah. So that's it. So it's basically just keep, keep the other folks focused on the flow of deals and then, and then create a specific team. Yeah.

Okay. I mean, you touched upon it there. Some deals can be very long and complex. Sometimes I hear, you know, 12–18 months isn't unusual. Sometimes longer—depends on where you catch them, I guess, and, you know, various factors. What are the best practices for managing these processes effectively while keeping the team motivated and focused?

So, if you hire experienced enterprise sellers, this is a non-issue. They're used to this, and you tell them truthfully during the hiring process what your sales cycle length is, and they can choose to participate or not, right? Um, but if you are converting reps that are used to shorter-term, quicker wins in sales—also commission—one of the things—but you train them on the different way to sell there and expectations—but, uh, you can also offer commission draws. So, you know, think about you have this like young rep who's an up-and-comer who's been crushing it and really knows your product. So, it's very logical. You want to leverage that person in a bigger way; it probably will work. I've done this; it's worked. Um, and then if they're okay with, uh, you know, the current flow of commission, then you're, you're cool. You don't need to do anything other than train them and support them. But if for some reason they're in a certain circumstance and that would be very disruptive to their family's income to switch to that job, and you really want them, then you can offer a draw, uh, you know, a recoverable draw against future commissions. So they're, they're getting—not maybe the full flow of commission variable income, but they're getting, you know, some buffer there. Okay. That's all right. Okay. No. Yeah. No. Cool.

Okay. Uh, how do you overcome challenges such as gatekeepers, procurement hurdles, and navigating large organizations in the enterprise space?

Okay, so this is a podcast all into itself, but I'm going to make—Yeah, I thought so.—yeah, as briefly as possible. The key is to create what's called a stakeholder analysis. So stakeholders are these different roles that you mentioned. Uh, stakeholders are gatekeepers. They're evaluators. They're recommenders. They're people making the decisions. They're people influencing the people making the decisions. They're approvers and the signer. And so you should have a simple opportunity plan and/or account plan that this opportunity plan is a part of. And so I'm not talking about 12 pages or 10 pages. I'm talking about two pages. Um, and of course, you need to make sure you know who the economic buyer is. Follow your qualification filter using MEDDIC or whatever you use and any challenge or sales approaches you're taking to make sure you're, you know, you're influencing the right people. Um, because you—if you're not dealing with someone who's funding the project, whose cost center is funding the project, then if you don't have any contact with that person, that's—and you're selling something that's larger. So, if it's small ticket, not a problem. If it's a larger buy and you are not being allowed to interact or engage with the economic buyer, then you should qualify out because you're—there's no chance you're going to win the opportunity. But getting back to the question, so imagine like a mapping out those roles. So you, you know, take a spreadsheet. What are their, uh, names, their job titles, their roles, and then you're looking at, um, do they have any experience dealing with your company? Do they have a position related to favoring or not favoring you because maybe they have an alliance with a competitor? Are they neutral? Um, and your actual, uh, tactics should, um, be your map to navigate who you need to spend time with and influence to support your selection to win that opportunity.

Um, you mentioned procurement hurdles. Include procurement in the stakeholder analysis. And once you know that you have a qualified opportunity and you're competing for the opportunity, include a courtesy briefing with the VP or director of procurement responsible for your area. Uh, most vendors try to avoid procurement until the 11th hour. That's a huge mistake. They really appreciate when you, uh, approach them and say, "Hey, we haven't won this opportunity; we're competing for it. But I wanted to take the courtesy of briefing you on what my company does, what we're about, and how committed we are to the potential future of this relationship, this future relationship." Uh, that actually—and then you can learn in that call how they work. So when it—when you're—when, uh, your economic buyer is ready to transact, what is the procurement process like, hearing it from the horse's mouth? Many, uh, economic buyers and—act—not many, but some economic buyers and their direct reports will actually not know some certain steps that may occur in procurement that procurement certainly knows. So it's best to, you know, to know as much as you can, u, and and that helps you accurately forecast the timing of the deal when you do win it.

So, sum that part of the answer up: create a stakeholder analysis, map out who these folks are, and then your action plan every Monday should be, uh, who—which one of those individuals do I need to actually meet with and influence. Um, the next part of it, it's—it's, uh, if you're—it's leveraging your team. So, if you're a smaller vendor and you're selling something larger in terms of the deal amount, then you have to think about like what potential issues am I going to come across? And vendor credibility is always one of them. So, I always recommend trying to get to the CFO of the buying company, or if it's a massive company like one of their direct reports, a VP, and having your CFO join you on a call with that CFO to brief them on the financial wellness of your company, your financial standing. That can actually help—one, it creates another relationship, and two, it helps, uh, you know, build your credibility. Uh, same thing with your CTO. So if you, you know, have a CTO, uh, your CTO aligning them to meet with their CTO or their CIO. That's pretty common. You'll see that quite a bit, and that's that's a good move. U, and then the—I always—if it's a large enough opportunity—always recommend having—hosting—your CEO to meet with their executive-level economic buyer. Uh, it shows professional courtesy. It shows commitment; there's an ultimate, you know, the buck stops here name associated and a person with to that economic buyer, so it gives them a certain psychological comfort level. So that's what I mean—this is a team game, right? Certainly you have your, the rep and the SE and CS and the consulting folks, uh, but these are these other execs in your company can actually be part of your selling team, and I've, I've done this personally, and it's worked really well, and many other people that I know do it. Um, and then last thing to mention on that, some teams make the mistake of spending too much time with the people that are supporting them the most. Uh, and the reason why that's a mistake is you want to spend the most time possible with people that are on the fence, in a neutral place, or even people that are leaning away from your solution if you can get to them to win them over because at the end of the day, most of these decisions are—really someone makes a final decision, but the input on it is truly a consensus. So if people love your solution and are kind of like your champion or coach, then you should support them. You should definitely have regular contact with them. But don't cling to that coach. Don't cling to that champion. Make sure you're spending time with the people that are, are need to be moved in your direction. Uh, and then if you come across someone that is just absolutely hates your approach, doesn't like your company, is in bed with a competition, um, after you meet that person and figure that out either directly or indirectly through other intelligence in the account, don't waste your time trying to win that person over. If they're too far gone, if they're too far, uh, uh, distanced from you, and it's pretty clear, don't waste your time trying to win them over because you're not going to be able to. What you should do is try to get them outvoted. So, if you have more open-minded people who are not as far-leaning away or more on the fence, you spend time with them and your supporters, then that other extreme opinion is going to be, uh, outvoted in most cases, unless it's actually the economic buyer. If it's the economic buyer, then you should figure that out soon and qualify out of that opportunity. So, that's as concise as I can make that answer. It is an entire podcast, but—

That's fascinating. Those are some, those are some, some—Yeah. Yeah. Yeah. No, thank you there.

Um, what are the strategies? So you talked about, um, influence and I guess trying to build trust in this buying community. But what are the strategies for building trust and demonstrating value to enterprise clients that already have a pretty entrenched vendor?

Excellent question. This is a very common situation, and it can be overcome, uh, and and many examples of where it has been overcome in my career and and colleagues as well. So first, uh, you have to be as professional as you possibly can be. So when you engage with someone, think about who they're measuring you against. They're measuring against probably a, a strategic vendor who's very established, who they've met many different people from the organization. They're probably all very professional. So, this isn't the time to like, you know, let your hair down and be super chummy and casual. This is a time—not that you want to be like super formal—but like, again, align for the type of buyer they are. I should go back to that. So, if they're—if they are casual, then you want to be there. My point is really more—you want to be—you want to give the best impression you can about your company and yourself and keep in mind that you're there to help them. Uh, not the opposite. You're there for them. They have to feel like you're there for them, and you're not just there to get something from them. Secondly, do not bash the competition that you're doing business with. It will not work. Uh, you can accentuate certain strengths that you have, um, and we'll talk about that in a moment. But do not go in and bash the competition. The door will slam quickly in your face because some set of people, over some period of time—years typically—have put a lot of time and effort into building a relationship that has—has this vendor entrenched. Next, you want to be credible. So when they ask you for information, make sure it's accurate. Deliver quality responses very quickly. They're going to then see that, wow, this person actually is someone who's professional, likable, credible, fast, and giving me what I need. Very supportive. So like you just—you're going to start to grab some share of their brain, you know, some mind share by acting this way. Um, when you're talking with them, you want to challenge the status quo. All challenger sales—to get them thinking about what you do—but you need to show empathy while you're doing it, right? Like you empathize with—I can—I'll give you an example. I can fully understand, Simon, why you've made the decisions you've made based on your business needs. Um, and that's, you know, it's completely logical. What we found is that there—it's a new approach that companies like yours are taking to actually complement many of those approaches and drive significant additional value, incremental value, or or eliminate this problem that those approaches have. So you see in that what I'm basically done is I haven't insulted what you've done already. I've, uh, affirmed and supported that you've made those decisions for probably very good reasons. And then I'm starting to educate you on—there's actually a new way, right? But I'm doing it in a way that's empathetic. I'm, I'm educating on the fact—there's a new way that could actually, um, help you. And that brings the next point. So your strategy in—mo—like if the entrenched vendors have something that's awful or known to be like ridiculously costly, and you have something that's so much better, then you take a frontal assault strategy. You go head-on, head-to-head, and you either like win or you blow up. That's one approach. In many other cases, it's not that stark of a contrast. In many other cases, it's like more of—with what they have, you could replace part of what they have, um, and drive more value. And in that case, you want to take what's called an augmentation strategy, which is complementing what they've already have in place. So you would, for example, I'd say, "Simon, so the good news is you don't have to throw out everything you've invested in in the last three years. Um, however, you can invest in addition to that in what we do because it's going to actually drive these benefits for you at a strategic, a financial, uh, an operational level," and—and that's a flanking strategy, right? Obviously, I want to get a foothold. I'm thinking long term. Once I get a foothold, then I want to increase my share. So, I want to continue to offer them more value and eventually displace the competition. So, I'm not satisfied with just the slice of the pie. I want the whole pie if doing so would actually deliver value for the customer. If it doesn't, then I should be satisfied with my slice of the pie. Um, so that is—those are some, you know, some approaches for, for that, and that's, you know, most of that is like age-old, you know, knowledge in our industry that I've accumulated—not, you know, originated—um, but accumulated from working in different companies.

Yeah, I know some of those—some of the questions may have—could have 30-minute answers, you know, because there's so much depth, isn't there? Right. So, appreciate you paraphrasing some of those learnings. The—we've got the last question here. So, can you share a success story where you helped a company focus up-market and achieve significant growth? What lessons can others learn from that?

So the other day I was thinking about like my career and, uh, I was doing some rough math, and so I'm going to answer it in this way. So conservatively, I've spent—I estimate—um, that I've spent as an individual contributor, uh, and as a leader, uh, about six years of my lapsed time of my life in meetings with customers. So that's about 12,000 hours. So I calculated, you know, the hours I've been in ROS and a 45-hour average work week, uh, and, um, you know, what percentage of time, and then I've spent about three times that amount of time, uh, discussing opportunities, coaching, uh, teams and and direct reports, forecasts, uh, account strategy reviews, quarterly business reviews, you know, all that other work that we do. Um, and that adds another, uh, 18 years to the…

Equation or 36,000 hours. So, I've spent about 24 years of my life, uh, elapsed time in either either in front of customers or discussing opportunities, forecasts, and accounts. And you know, as you probably recall, the book *Outliers* by Malcolm Gladwell, he talks about the concept of an expert having 10,000 hours or more. So, I, I, uh, digress because I think I'm an expert at this point on the subject.

So, you are. Thank you. So, um, I'm not going to get into specific success stories. Um, you know, some of them are listed in my LinkedIn profile, which your audience can see, but what I wanted to actually share is um, the common theme or sort of area where uh, the teams that I've worked with or, u, you know, opportunities I may have lost uh, was, was lacking, and that was approach and execution of the accounts. Um, and the opposite obviously, like when the approach and execution was strong, then that was successful. So, uh, so it's I think it's more valuable rather than talking about like one account or, you know, two accounts or something like that. I think it's more valuable to reflect on what companies can do to, when going up market, to actually be successful.

And so I'd sum it up this way. Um, as I mentioned before, up-market accounts, they're used to be h, they are accustomed to being handled by highly professional, empathetic, responsive AMs who have really good soft skills. That's the way they're ex, used to being treated and expect to be treated, and they expect value from those interactions. So if a person or team schedules a meeting, they need to make sure that they are going to deliver some sort of information or insight or handling some aspect of the customer's business issue for them, that there's value there. So always delivering value. They also want to know the vendors are there for the long haul.

Now, if you have a product-led growth business, low-ticket item, um, this doesn't really apply. You know, you're basically doing high volume, low ticket, and people are, they're either going to like love the product or not like the product. They're going to use it or not. And, you know, it's the way it is. But for the rest of enterprise-focused, um, venture-backed companies, PE and public companies, um, they want to know that vendors are there for the long haul. They're putting their reputation on the line when they buy something. So what happens, even if you hire the wrong people, these short-sighted leaders and managers and individual contributors are going to get screened out by the customer because they can see it coming a mile away. On the other hand, if you hire the right people, train them and support them, those customers will spend large sums of money for value for their company. It's their job; their job is to deliver value for the company; they need technology and services to do that. So if they believe the issues are being addressed and um, and it's the type of issue that there's a high sense of urgency around and your product works as advertised, uh, you it doesn't matter what size company you are, you can uh, win and close very large opportunities if you go about it the right way.

Uh, if you have a weak product or it's just very immature, then you're better off just telling the customer you have a new product and you'd like to sell a small proof of concept or a small project and start working with them to get value from it and also take their input to develop it. Um, but if you have a strong product and you can back it up, you can be wildly successful. And uh, even like many large organizations even need to think bigger about the value they can provide because people are so like uh, sort of sometimes there they don't, they want the quick hit, you know, they, they don't have the patience to invest. But if you invest time uh, in the account and you really connect all the dots, you can actually build up uh, the opportunity for yourself and your company and and provide more value to your customer, which at the end of the day is the most important thing.

Yeah, those are those are, it was a different answer to your question. No, no, it's brilliant, Dave. That, that has been absolutely brilliant. Thank you so much for sharing all of that fantastic knowledge and wisdom and and just like real-life insight and examples. Exactly why we wanted to do it. Um, before we dive into the quickfire questions, which will just finish up as uh, very quickly, um, anybody that's listening today that got this far, you know, love what you had to say. How's the, what's the best way to get in touch with you? Is it LinkedIn or email or what's the best?

Yeah, LinkedIn. LinkedIn is the best way. Feel free to reach out and and uh, message me or send a connection request. Happy to, happy to engage. Okay, cool. All right. Well, last, last but not least, just little quickfire questions we do with all of our guests. So, first answer that comes to your head, please. Not too much thought, but favorite piece of tech or app you're using at the moment.

So, I have to put a plug in and I have no vested interest in this company whatsoever. Um, it's a, it's a company called Clary, C L A R I. Yeah. And they sell AI for forecasting and viewing customer opportunity and customer health. And I purchased it in my last uh, job and absolutely love the product. I think it is incredibly valuable. They have, they have a "what's changed" um, simple query that you can run just by a few with a few clicks and you can really see what's going on in your pipeline and in your forecast. They basically plug into your email and they can see the volume of email and the uh, cadence of email interaction with prospects; uh, they can see what if there are quotes attached, the nature and subject of meetings in your calendar. They can see all of that and is incredibly helpful. It's also for reps uh, much easier to update forecasts. So you have a mobile app on your phone or you know, you have the app on your laptop, you can easily update status, next steps. It all plugs into Salesforce.com or whatever CRM you're using. So the forecast of system of record is still intact, but it's absolutely amazing. So I have to, have to put in a plug for Clary, that people who now are tired of hearing me like really.

Yeah. Know at the disco or night at the restaurant? Both. Both the restaurant then the disco. Yeah, that's a good answer. I've heard that before. Yeah. Love live uh, cover bands. You know, being a resident of the New York metro area um, and particularly living in New Jersey, we are we have a certain culture for music that uh, is really strong. So, there's really a lot of excellent entertainment all the time and I'm uh, always busy dragging my wife out in uh, on the dance floor. What's your favorite food?

Uh, I'd have to say it's Italian food. Uh, really love, really I love all food. Um, but, uh, I have to say it is Italian food. Okay. Favorite movie. Man, that, that is, that is a hard question because I love so many genres. Um, I'm, I'm gonna have, I'm gonna embarrass myself and just say there's a goofy movie that was made back in the 80s called *Moonstruck*. Oh. And uh, it has Cher and Nicholas Cage uh, in it as you know, the stars. Uh, and it's just, just a funny comedy about a family in New York and it's just really, I would say that at it's, I don't know if it's my favorite movie, but it's definitely one that comes to mind as one of the Okay, cool. Silly movie, but, but uh

All right. If you were to describe yourself in two words, what would it be and why? Uh, two words. Inclusive and goodwill, I would say. Cool. Um, yeah. Proudest moments or moments of your career to date. Uh, I've talked earlier about this. Um, I would just say that I'm humbled by the amount of great people that I've had an opportunity to work with and learn from over the years. And uh, I would not have the type of life I have had and have now if it weren't for uh, all the great people that I worked with and the customers and partners that I've worked with and will continue to work with uh, for the next, you know, dozen years or so. So I don't really have one particularly, particularly proud moment. I just, I would say I'm proud to be part of the overall industry that I've, I've been in. Um, I would say it that way. It's a lovely warm answer. I like it. The um, what's your favorite place that you've ever visited on holiday or just visited in general?

So this is actually true. I'm, I'm a big fan of um, the UK. Yeah. Um, I've really, London is a very special place. Uh, I've really enjoyed visiting there. Uh, I've also, uh, spent time in Western Ireland and it's amazing. Um, and but if you were to ask me, say I could go anywhere in the world uh, tomorrow for take a break for a week or so, it's going to be an island somewhere. So big fan of Aruba, Turks and Caicos, you know, that picture uh, warm weather and uh, nice beaches and clear blue water which you will not get over here on in Ireland. So yeah. Okay, cool. Um, last question. Um, and I get an assortment of answers to this one, but if you have a guilty pleasure, what is it?

So, I'm very focused on uh, my personal nutrition and diet. So, it's going to be a violation of that. Okay. Holly would be a night of pizza and ice cream. Oh, be my, my guilty pleasure. Overindulging and eating too much of both of those things and then passing out on the couch. Right. Food coma. Great. Dave, thank you so much for all of your uh, all of your wisdom. As I say, golden nuggets in there. I'm sure there's loads of value to the audience. Um, you know, again, thanks again for, for taking the time. My pleasure, Simon. I enjoyed the conversation, your excellent questions, and appreciate the opportunity to share. Yeah, lovely stuff. Okay, thank you so much. You're welcome. Take care. You too. Bye. [Music] Heat