Sales Hustle is now Sales Transformation
March 19, 2021

Episode #73 S1-EP73 Enterprise Sales with Paul Lesser

Paul Lesser joins Collin Mitchell in this episode of the Sales Hustle podcast as he digs into the details of how it’s like to be born and raised into a sales culture, divulging into his mastery of the craft and how he’s honed it over the years.

Paul Lesser is an experienced enterprise software sales professional, selling subscription software to Fortune 1000s companies. Part of his expertise is provisioning enterprise collaboration environments that consist of Microsoft, Cisco, Zoom, Genesys, Avaya, or any other platform. Representing Nectar Services, his approach to sealing sales deals stem from adding value to his prospects and customer relationships. Among the many successful deals he has closed is selling Nectar Software to a global financial firm in a 60-month term commitment at $50,000.00 MRR with the opportunity to grow the MRR to $100,000.00+.

With a customer-centric approach, Paul’s passion is about finding the root of his customer’s problems and moving into the opportunity of providing the solution through the sales process that leads to closure. 

You can know more and reach out to Paul Lesser through his LinkedIn -

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Episode 73 - Paul Lesser

Welcome to the sales hustle. The only no BS podcast, where we bring you the real raw uncut experiences from sales change makers across various industries. The only place where you can get what you're looking for too. Uh, your sales game today's episode is brought to you by sales cast sales cast helps sales professionals transformed the relationship building process and win their dream clients.

[00:00:30] I'm your host, Colin Mitchell. What is happening? Sales hustlers. Welcome to another episode today. I've got Paul lesser. He's at enterprise sales, a E, and we're going to be talking about enterprise sales cycles and process. Um, and we're going to have a ton of fun doing it. Paul, welcome to a pleasure to be here, looking forward to our chat.

[00:00:51] Awesome. So before we jump into the good stuff, the tactical items we're going to talk about today, uh, tell us the short version of your sales story. Sure. Uh, well, I was born and raised in a sales culture. Dad was a, a jewelry retailer, grew up, uh, jewelry, retail business, uh, knew early on in my, uh, in my life.

[00:01:13] I did not want. Uh, retail wants to spend time with my wife and kids and not work weekends and long hours, uh, and moved into corporate sales and have been selling, uh, software in the corporate space for over 25 years. It's been a wonderful journey. Yeah. Wow. Okay. So sales was in your blood, huh? As they like to say, my blood Salesforce was in my blood.

[00:01:35] All right. Um, so how did you, let's talk a little bit about, you know, I think. Enterprise sales is kind of like the, a lot of people may think, uh, like the Holy grail of, of sales, right? So, uh, what was the path to getting to enterprise sales? And then let's talk about that a little bit, and then we'll go into like, kind of, you know, what sort of things that you do in the day to day that, you know, people can maybe learn from.

[00:02:00] Sure. Pat Kemp enterprise sales started my career working for 18 T. I was smiling and dialing and prospecting and cold calling for the field sales team. And finally graduated from that and had a territory was selling, uh, 18 T phone systems, uh, and continually worked my way through, uh, corporate. America selling larger and larger deals, uh, worked for a WorldCom, for example, um, worked for 18 T and really about halfway through my career, made the switch from hardware to software, which I think was a very valuable, uh, switch.

[00:02:40] For me, and just always wanted to improve my sales, improve my sales acumen, and always strive to close those bigger deals. So as I matured in my sales career, the constructs became higher and. The deals that I was working on and the customers that I was working with, or the household names that we all do business with today.

[00:03:02] Mm. Okay. And, and was there a learning curve or what was the transition like going from hardware to software? Yeah. Um, well, I I'll tell you, first of all, Uh, selling software is a lot easier because for the most part, you email license keys, as opposed the delivery, the delivery is easier, but delivery is easy, no shipping, uh, definitely delivery a lot easier, less fires to put out, less fires to put on the, uh, the customer can realize the value of the, of their purchase.

[00:03:35] A lot quicker, no screwing, uh, You know, a hardware into a interacts in a data center. Um, I, I just found it to be a much more, um, consultative sale. And I found that, um, much ease, easier, which software, because it's so flexible from a development perspective perspective, to be able to, um, um, distinguish yourself and also, um, actually come up with solutions specific for each individual prospects.

[00:04:08] Needs. Yeah. Now, you know, there's always this kind of debate of people, you know, maybe they've been in sales a while, but never done SAS sales. Right. And there's people in SAS sales, I think, Oh, you need to have SAS sales experience. I think that's BS, but I'd love to hear your take on it a little bit. Yeah, I agree with you.

[00:04:27] I think, you know, the second sales process for the most part is the same, right? Um, it's going through the discovery and making sure that you understand the problems that your prospect is trying to solve and meeting the influencers and the decision makers and having a champion within the prospect account.

[00:04:48] Who's gonna sort of. Deliver your message internally. And the conversations that you have leading up to procurement and contract signing, I think is, I think it's the same for hardware and for software, uh, you know, procurement is a little bit different because now we're living in a world of op ex software as a service monthly recurring revenue, where early in my career, it was that one time.

[00:05:13] Looking to purchase the hardware and we're going to pay you annual for software support. Now everything's wrapped into a monthly payment. What, and, and so, um, I, I'm curious, like what are some things, cause enterprise sales is not for everybody. Right? Um, the, the common things, a lot of people, you know, you hear talk about is, is that the sales cycles are longer.

[00:05:40] You know, maybe some people have a bit of fear about. Working with some of those bigger household brands and don't have necessarily the patients, what are some like required skills to be an enterprise sales. Um, and how does somebody really identify as like, is enterprise sales, the right, you know, path for me or not?

[00:05:58] Well you're right. Collin, you need to be patient. You need to be used to longer sales cycles. You know, there's a saying, you know, loose quickly when slowly make sure that you're spending your time on deals that are winnable. And how do you know if those deals are winnable? You know, I've learned from experience and I continue to learn today.

[00:06:21] Um, one of the main things. If I'm working with a global financial firm, for example, and I'm very single threaded in a deal, meaning I'm only communicating with one or two people and they're not introducing me to other folks within them, the, uh, account, um, other entities, influencers and decision makers of people have different perspectives.

[00:06:42] The chances of me closing that deal at pretty slim, it takes in my sale, you know, somewhere between 12 to 20 people within the organization to get to know. To understand what they'll benefit from the solution that you're selling. So in that respect, they do agree with you. Enterprise sales is not for everybody.

[00:07:02] They are long sales cycles. The losses are tough to take, but you certainly learn in my opinion, more from your loss losses than you do your wins. Mm. I love that. And, um, like what is the, what is the. So let's be, I have a question, but before I ask the question, I want to dig. I want to peel back something.

[00:07:26] You said a little bit first because you've peaked, you've piqued my interest. Um, and, and I love this topic. You learn more from your losses than your wins. Uh, Tell tell me about that. Like, do you have a, do you have an experience where it was a painful loss and let's talk a little bit about what that was and what you learned out of it and why that was so beneficial.

[00:07:47] Yeah, I hear you, you know, I think just to start the topic, I just want. You know the audience to understand that, you know, losses aren't important. And if you've put it into context, right, I'd rather be involved in 10 opportunities and win seven than be involved in four and went four. Obviously I'd rather win seven than four.

[00:08:06] So you're going to lose, um, as far as those losses go, I think you really may need a couple of things. You need a good team around you. You need a good leader, you need a good sales team, other colleagues of mine, or their enterprise, ease of upline, who we can actually talk to and then dissect the opportunity and be humble in the fact that we might not have done everything.

[00:08:36] Properly. And maybe it's not communicating with the right person. Maybe it's not understanding budget and budget requirements. Maybe it's not understanding the competitive nature of the deal. I think in many organizations. Salespeople are so scared to talk, scared to talk about their losses, cause their losses that they don't really learn from them.

[00:09:00] But if you really spend time with your team and your leader discussing the loss, I think there's a lot to learn. Yeah. I mean, I'm not a big sports guy, but it's the equivalent of equivalent of like a, a team let's say football team losing the super bowl and then not watching the game tape. Yeah, no better believe they're watching that game tape over and over and over and over again and learning from every little single step and play of what they could have done differently.

[00:09:31] Yeah. And, and sales takes a playbook. That analogy is awesome because sales. There is a playbook to follow regardless of vertical market, whether it's an insurance company, a financial company, a healthcare company, if the deal, and some of these sales cycles can be eight months to a year and a half, if a deal isn't taking on a certain feel, it's sometimes it's hard to explain it's natural.

[00:09:58] Um, you know, it might be time to look at yourself or to ask some very, very difficult questions to understand exactly where you stand. Hm. Yeah. I mean, there is a playbook you need to follow. And so, you know, I think I know a topic that you like talking about is discovery, uh, which I enjoy talking about discovery as well.

[00:10:20] Cause I think you, like, you mentioned early, you, you win or lose early. Right. Um, discovery plays a big role in that. Uh, but um, I'm curious to kind of peel back a little bit. What. Discovery in enterprise SAS sales looks like because that in itself, uh, is a pretty lengthy process. Right? I think you're discovering throughout the entire sales process to close.

[00:10:43] And sometimes after the close you're even discovering because there's more stuff you can potentially sell them. Uh, you know, I think from a discovery standpoint, if a customer doesn't have. Problems that you can solve if they don't have any pain points, if they don't have a point a and a point B and a plan to get from point a to point B, what, what I refer to as the gap, if you can't fill that gap with your solution, it doesn't matter how many customers you have.

[00:11:13] It doesn't matter how wonderful your marketing is. It doesn't matter. The rapport that I have with them. The prospect. And that's why the discovery is so important because once you identify those pain points, once you identify those problems, and once you identify the gap after the discovery, the conversations.

[00:11:34] Become very specific to the customer's pain points. I sort of attributed to, instead of me giving a demo and just throwing up all over a customer dome, demoing, everything that we do, if you've done a proper discovery. Now your demonstration is specific to the customer's needs and objectives. Yeah. I mean, in enterprise sales though, you know, aside from, you know, Figuring out what the problem is, what the pain is, what the impact of that is.

[00:12:03] What's the impact of not solving that, what the, what you're competing against the status quo in most cases, right? Like even just a discovery around making sure you have all the proper stakeholders. Right. And the enterprise sale is probably a whole task in itself. Many times when you start the process, obviously you want to start as high up in the organization as you can.

[00:12:25] Right. I'd love to be speaking to the decision makers immediately, but a lot of times you're speaking to, um, Influencers and sometimes major influencers sometimes not, but that's critical because that's where you can get all the granular information about the environment and Collin, listen, relationships are very important too.

[00:12:47] Once you have earned that credibility, you need to have a champion in the account regardless of their influence or power so they can help navigate you. Um, around the cultural, the political, the social climate of the customer. The last thing I want to do as an enterprise salesperson is propose something to somebody and that person is going to be either put off by it or threatened by it.

[00:13:18] And that's where the politics come into play. Yeah. How, what are some tips that you have? You can give people that are maybe new to enterprise sales are still struggling around figuring that piece of the puzzle out. So my first tip is start. The engagement and continue the engagement by talking about the prospect, the prospect's needs, the prospect's problems.

[00:13:48] Don't make it about yourself, your company and your company's features. Um, I think. You know, early in my career, my sales, it was a very feature sale. The phone system can do this. The phone system can do that. I think the world of sales has changed a lot because a lot of times prospects engage with people like myself.

[00:14:11] There were already 30 to 40% of the way through the sales process because they've done research on me and potentially done research on my company. So my first is make it about. The customer and the problems that they can solve. Number two is before any engagement. Do research on your prospect. You can learn a lot by reading their financial forums, especially if they're public, you can do a lot of research on the internet by viewing their website, and maybe you pick up a nugget of some charitable activity that they're involved in, or maybe they just crushed their quarterly earnings.

[00:14:51] You bring that up early in the sales process, especially on a first call. You immediately gain credibility with your prospect. Um, and, and this takes a lot of, I mean, it's a lot of what sounds like a lot of work. Right. Um, but doing that work and putting it in before you even really know if, you know, if, uh, Prior to even discovery, right?

[00:15:17] Like not even knowing, like, do they have a problem? Are we the right fit? Can we solve it? Um, and I have, uh, interviewed before a good friend of mine, Ian Coniac, he's an enterprise sales rep, top enterprise sales rep over at Salesforce. And he, you know, one thing that he said that has always stuck with me, which I think is so relevant, obviously for enterprise sales is it's a lot of just doing more with less people.

[00:15:41] Right. And that's kind of been the recipe success. So, you know, reading those annual reports, doing that research, doing all those things that you talked about, those things make the biggest difference in those relationships, especially early on. And I think you also have to be, have a passion for it and your icon.

[00:15:58] Listen, it's difficult work personally, for me, it's not work because. I enjoy it. I feel like my sales career is as much a hobby as it is my career. You know, I enjoy doing the research. I enjoy learning about these financial firms and these insurance firms. Um, the other advice that I would give with, which I think is a good tie in to the question that you asked this from a prospecting perspective, you know, it's better.

[00:16:26] To find 10 targets and touch them 10 times, then find a hundred targets and touch them. Once I think statistics will show that you need to touch a prospect, you know, five to 10 times, whether it's LinkedIn, whether it's email, whether it's a cold call before you can actually get their attention and get that first appointment.

[00:16:49] So that would be my. My perhaps, you know, my number one for, for new salespeople, just because you don't hear back from a potential prospect while you're prospecting, um, don't give up, don't give up if they were in a vertical market and you've solved problems for their competitors, there's a chance that they have the same problems.

[00:17:12] They just don't know it. And how do you reach out on what channels. And how do you stand out to be different? Um, when, you know, going after the C-suite for, for, in an enterprise of the size that you work with. Yeah. Great question. Colin. Thank you. I think first and foremost, um, you know, I never just check in with a prospect.

[00:17:36] I never, um, uh, you know, make it about, you know, we have this incredible. Feature, um, it's every reach out is strategic in nature and about them. I might say something like we're working with one of your competitors and we solve this problem for them. I'm curious to know if you like to engage in a conversation, um, or, you know, We were able to accomplish this return on investment, um, um, during our relationship with X, Y, Z client, um, perhaps that's something that you'd like to have a conversation about.

[00:18:21] And also in, in today's world. Unlike when I started my sales career, not to age myself, Um, you know, but there is, uh, there is the internet, there is LinkedIn. I can go into LinkedIn today and go to XYZ company, do a search under a title, for example, collaboration or voice or video, pull up the people within that organization that have that wording in their title and actually find the people very easily that I want to target.

[00:18:52] Yeah. Yeah. And so when you reach out. Are you using phone, email, LinkedIn video. Talk to me a little bit about that. Yeah. Um, sorry. I don't think I answered your question specifically. So yes. Um, the phone is absolutely critical. There is a lot of debate. Weather today. There's a lot of debate, whether the phone is gone away and it's, you know, I think having those conversations are important.

[00:19:20] So the phone I leave voicemails, I send LinkedIn InMails, not from a spam perspective, from a very strategic, uh, perspective. Um, I'll send. InMails. Um, LinkedIn is great to see who you're prospecting. You might share connections with. Maybe you can get an introduction from, um, one of your friends. Who's done business with them in the past.

[00:19:51] And I think it's just human nature that, you know, if you've left a voicemail, if you sent an email, if you sent a LinkedIn in mail and then you call again and the answer, the phone. In the back of their mind, they, they don't know that they've heard from you before maybe, but subconsciously they sort of know you because you've reached out three, four or five times prior to getting them live.

[00:20:17] So, um, all means possible. I used to knock on doors. Don't do that anymore, but yeah, no people might, uh, My like might get scared if you knock on their doors. I hear. Yeah. Um, all right, awesome. So we talked a little bit about reaching out, using different channels, doing research. You know, we talked a little bit about discovery, how in enterprise sales environment, how do you move along?

[00:20:48] You know, Yeah. I mean, full disclosure, enterprise sales is not for me. I'm not the most patient person. I know that about myself and I'm okay with that. Um, so, so, but you know, for some people that, that have. The ability to be a little bit more patient and deal with those longer sales cycles. Um, I I'm in the sales cycle.

[00:21:10] Um, you know, how do you move along some of those stalled deals? Yeah. Um, that's a great question. And it. It, it really is very challenging because you know, the deals that I have found that in, even in even the ones that are potentially a year sales cycle, you know, you sort of go through the sales cycle naturally a lot of times.

[00:21:34] And the next logical step in the process is to have a conversation with procurement. And then you never ask for the business. It just sort of. Valves as the logical next step, but deals that are stalled that you've worked on. It's hard. And I lean on, you know, people who mentor me in sales. Um, I lean on leadership that.

[00:21:59] Nectar services, Corp, where I currently work. Um, I think it involves the conversation and a strategy for, um, figuring out whether those opportunities are opportunities, whether you should spend more time on or not. And I think a lot of times you can ask some key questions. One of them being. Ask for introductions to people who you haven't met within the prospect's account.

[00:22:25] And if the people that you're talking to are unwilling to advance you and introduce you to other folks, uh, that's indicative of an account. That's probably not worth your time to continue with. Yeah, no, that's a, that's a, that's a great piece of advice. Um, Hey Paul, thanks so much for coming on. Uh, I really enjoyed this topic.

[00:22:51] Any final thoughts? Anything, you know, where can people find you? Uh, anything else you want to let everybody know? Nah, I appreciate it. You can find me on LinkedIn. Uh, Paul lessor. Uh, I am, uh, very accessible and, and quite responsive. And, um, I love talking sales, so reach out and I will definitely respond.

[00:23:14] All right. Awesome. Thank you so much. If you are listening to the podcast, please, if you enjoy today's episode, write us review. Uh, share with your friends and as always, we're listening for your feedback. Thank you for tuning in to this episode of sales hustle. Are you a sales professional looking to take your sales career to the next level?

[00:23:35] If the answer is yes, then I want you to go over to sales, check us out. And if you feel that you are ready, set up a time to talk with me and my co-founder Chris. I'm your host collum Mitchell. And if you enjoyed this episode, feel free to leave us a review and share the podcast with your friends.