REGARDLESS OF EXPERIENCE WE ALL FACE THIS ONE LIMIT

Today we've got a great interview for you, kind of a rags-to-riches story. A rep who started off selling internet connections to small businesses and office parks, door-to-door essentially, B2B but still door-to-door, and grew into an enterprise rep with great success. And we're going to be talking about what that took. How do you do these large deals? How do you think about them differently? How do you use your judgment skills instead of just being busy, being busy on the things that matter most? He makes some great points that we all get the same amount of time every day. It's how well we use it, how well we apply it on the things that are most likely to close.

Hey, Tim, thanks for joining us today.

As a way of getting started, give us a little background on yourself.

Yeah. I'm speaking to you right now from just outside of Nashville in Tennessee. We just— the family and I moved here just about 2 weeks ago from outside of Chicago. So, and it's coincidence, I'm running away from the Cubs when they're doing a massive sell-off right now.

Yeah.

But no, I'm joining the bandwagon and the exodus from Illinois and states like California and stuff and heading down to Tennessee.

What attracted you to Tennessee? Family or no state tax?

No, just, yeah, no state income tax. As a sales guy, that's always interesting. And just the weather and stuff, got kind of sick of dealing with the brutality of winter outside of Chicago. So yeah, we bought a piece of land about 25 minutes northeast of Nashville on the lake. And yeah, gonna enjoy, enjoy better weather and being on the water.

Perfect.

Hey, so what motivated you to get into sales?

Yeah, so, you know, I grew up outside of Chicago and kind of got this like perfect blend with with my parents. But I'd say probably the thing that originally drove me to it is my mom. She owned a children's theater, so it was like her her mission to instill you know kind of building up children for success in life through theater. And so through her influence, I got to you know. Participate in that stuff that got me really comfortable, you know, kind of being on stage. And I think as salespeople, right, we're on stage, right? So that was part of it. And then on my dad's side, you know, he was an athlete. He, you know, coached my sports teams and kind of instilled this competitive drive, you know, in me. So I think, you know, it was that really unique combination that Kind of built the foundation for me. My first sales job, so I went to University of Iowa and originally I thought I wanted to be a lawyer, so I studied journalism and political science. And when I graduated, I took the LSAT and was kind of looking down the barrel of a huge amount of loans going into law school. And yeah, at the time I was seeing some friends who had graduated before me already doing it. And I decided to, you know, to take a sales job and just take some time, right, before doing that. And, you know, my first sales job, I made $100 grand out of college and I was like, well, forget this. Like, I'm just gonna— I'll be a sales guy. And yeah, but my first sales job before I got into Enterprise software sales. I was selling internet to small businesses door-to-door, T1 lines. And I think that there's got to be a great potential TV show on like that time period for anybody that was in that business is, you know, we'd literally go cold calling, you know, through business parks, you know, across outside of Chicago and You know, and, and we were selling T1 lines, which is like, you know, 1.5 meg, you know, download and upload speed at a time when, you know, Comcast was really— and, you know, DSL lines were becoming popular. We were asking people to spend like 10 times more money on something slower, you know. So it's like, it was a bad business to be in. I'm glad I left. And yeah, and I went into software sales. Yeah.

But it built up that resilience in that.

Yeah, I was, I was thinking actually, you know, about 20 minutes ago, just like before I was going to get on the phone with you, is, um, I remember the right when I got out of the training, because I attribute a lot of the foundational selling skills that I have like from that time period. But I remember the first day I got out of training, I went to this office park, um, you know, right by O'Hare. airport. And I just went through knocking on doors trying to get people to sit down with me so I could sell them internet. And the first couple doors I went through, people were just screaming at me. These office parks had gotten hit up by everybody selling everything. And I remember at the time, I used to smoke cigarettes and I went down to my car and lit up a cigarette and was like, man, I don't know if I can do this. Is this what it's like? But, you know, I pulled it together and, you know, I ended up never missing my quota actually in that job. And I was managing, you know, 10 salespeople inside of 8 months doing that job. So ended up being very successful. Cool.

And what do you like about software or enterprise selling?

Yeah, I mean, it's very different than that. That was a very transactional business. This is the opposite. You know, for me, I've been lucky enough to work for 2 companies that sell software that aligns with like a transformational vision about like, you know, revolutionizing the way that you run your business. And so I really enjoy you know, selling transformation, right? Engaging with, you know, cross-functional leaders at senior levels and, you know, having passion. You know, firstly, you have to have like passion that your wares like actually work and stuff like that. And I've worked for 2 companies where their product actually, you know, works. It does what we say it does, which is good. Like, you know, you want to be selling something you believe in. But I really enjoy working with the biggest companies in the world, being passionate about a fundamental change to how they run their business and knowing that it's going to make their lives better for them, for the employees, and for their customers.

How'd you make that transformation from transactional, they either buy or they don't buy, To that kind of transformation where there's no one call where the decision's being made. You're, you know, you're talking to different people about different things, and a lot of people don't get that. That's, it's hard.

Well, I mean, the— I guess there's 2 things that I, I think about when you ask that. One is like, you know, I started my software career kind of doing an SDR type role where I was like appointment setting and stuff, and, and, you know, you— and use that to kind of build myself into an enterprise software person or salesperson. And, you know, so that helped me kind of learn the business, I guess, from the inside out. But yeah, it's the way I think about it is there's a series of battles, you know, that you're fighting to win the war.

Yeah.

For people that haven't had a lot of success with major enterprise software selling, it can be very unnerving, all the eggs that you end up putting in a handful of baskets. I've been lucky enough to just crush it in a lot of years. And those years when I've done the best, the amount of transactions I've closed is usually like 2 or 3 or maybe 4 transactions, right? the course of a year. And it's when you're winning, when it takes winning 60 battles over the course of a year or 2 to win a war, yeah, it can be very frustrating to manage that anxiety, really.

And how do you define that, or how do you describe that ability? Because that's not only the opposite, it's the other end of the spectrum of a transaction, because you have to have the confidence that this can close and will close.

Yeah. Well, I was thinking about, I don't know, for me, I think one of the things is just my philosophy around how I manage my time and stuff like that and make decisions on where I'm going to invest my time. Because I think as sales people, you know, even if you're in a transactional selling model or doing something like I do, you know, we all start with the same amount of time each day, you know. And so time management is everything, you know. And so for me, you know, it's kind of like, you know, the things that I think about when I'm thinking about, you know, where I'm gonna invest my time is Is, you know, from an account perspective is I'm constantly qualifying, you know, and thinking about, you know, 2 things usually. What gives me the best opportunity to close like an 8 or 9-figure transaction, you know?

Yeah.

And then, which— so that's the first thing, that's what I'm prioritizing. And then the second thing is like, where can I get a deal Right now. And maybe that initial deal is a stepping stone for this transformational vision that I'm trying to sell, right? And I don't know, for me, I think one of my kind of shticks or my strategies, like I was listening to one of your other podcasts, somebody was talking about this, but it's really about trust, especially with this type of transaction that I'm aiming for, is the way that I start going after an account and investing time is you got to become an expert, expert in their business, expert in their business, understand what it is that they're trying to do and what problems they're trying to solve. And then it's my responsibility to make it very easy for them to understand you know, how my product or solution is gonna help them solve their problems. I need to translate it into their language, you know, and be able to be very concise and make it understandable for them and give them value. And if I do that long enough, you know, and effectively enough, eventually that's gonna lead to a sale, you know, and that's kind of how I try to think about it.

And did it take a while to develop this judgment skill of what to work on in what order?

I think one thing that I, you know, God's just blessed me with or something is like being able to prioritize, you know, even when I was in a trend in the transactional world. I think it's been pretty easy for me, luckily, you know, to be able to see the writing on the wall and place my bets in the right places. You know, even if I was selling, you know, 5 deals a month, it was, you know, still a similar thing. But I think what was hard to make the transition for me was this, you know, quantity over quality, right? And I've had a lot of conversations even this week with some people that are in an SDR role Yeah. You know, in today's world, it's like, look, we're all dealing in a pandemic world, right? And when you're selling software like this and everybody obsesses over kind of getting these executive, you know, senior C-level meetings and all that stuff and like, you know, I want those meetings too. You know, you want to meet with the decision maker, the buyer as soon as possible. But I try to have empathy. I try to encourage people to have empathy with like what those people are going through right now, you know, and the fact that there's like 500 other people like us trying to get on their calendar, right? And so if you're taking this, you know, marketing content that's on your website and you're just regurgitating that, you know, and setting up a you know, a sequence in outreach and there's like 10 emails that, you know, are standard and it looks like a robot sent it, you know, you're not gonna have success. It's not working. Yeah, you're not gonna have success. You have to, it's your job, you know, to translate. You're the translator, right? And it's no disrespect to marketing folks, you know, our marketing content is awesome. I love it. You know, but, you know, that is satisfying a different need, you know, than what your job is when you're pursuing a specific account, right? And so it's your job to translate, you know.

And do you see a lot of other reps kind of working on too many deals, not deep enough?

I do, yeah. I think, I think, you know, when you're This is something that I've learned the hard way. When you're— in my last job, I'd have maybe like 30 accounts on my list, right? And these are big companies like Intel, AMD, Applied Materials. These are large— Google. These are big companies. to run a sales cycle and sell a transformation with like 30 of those, like that's impossible, you know, like you have to pick like 3 or 5, right? With the level of depth that you need to go into with these accounts, right? And so, yeah, I think that the hard thing I wish I would have learned earlier, I guess, in my career is just being honest with myself and, where to put time and being realistic about, you know, there's only so much you can do, you know, in a given day and just, you know, pick the top 3 and make bets there, you know, and be opportunistic outside of that. But like, if you had to bet, what is the one deal that if you close, it's gonna hit your quota? You should probably be spending, you know, 50% of your time on that thing. Right. And so that's how I've approached it. And whenever I've done that, you know, that's when I've really crushed it, you know, from a performance perspective.

Because I see so many reps getting into the, you know, I've got to spend enough time on the other 29. Well, if you know 3 are going to close, yeah, you use that Sophie's Choice brutal judgment. of which 3 are you putting your money, which you are, your time is your money, on.

Yes, right.

And if it changes, it changes.

Yeah, I think the other thing that we as sellers sometimes can forget, and I remember even in that first sales job when I'm selling door-to-door internet service, one of my, one of my bosses, um, I remember I, I was talking to these people in the back office and it was their responsibility to you know, set up the customer, right? And like get their stuff turned on. And I was getting really frustrated, you know, about something stupid that they were doing. My boss overheard me and he like brought me into his office and he goes, hey man, don't leave your selling shoes at the door. And that really stuck with me, right? Is that, you know, we have a responsibility as salespeople to translate not just externally, internally. but internally. Right. And you need to— sometimes I would say, arguably, I do a lot more selling inside the company than I do outside the company, right, to get people aligned with whatever narrative or vision I'm trying to create for this deal, right? And that, that is, that's an important part of our, of our job, you know, as sellers.

And when you're talking to an account, how do you know it's one of those 3? You must look very quickly because some of them are too big and it's going to take 2 or 3 years. You're looking for the ones that are within the scope of your comp plan or your window, whatever it is.

Yeah, I think there's a combination of things that you should be able to measure, and then there's some of it is just like gut feel. So in terms of the things that you can measure, I'll give you an example from my last company. You know, we sold supply chain planning solutions and the best prospective customers were typically discrete manufacturers and the ones that were the most mature buyers were like high-tech companies, right? Because they had already started outsourcing their manufacturing process overseas and they had the most complexity and we were solving complexity. Right? And so like if I had a list and I had like, you know, Applied Materials on there and I also had Ford, right? I'm gonna pick Applied Materials because, you know, they're— the attributes that they have are more likely to be fitting into, you know, the wheelhouse of what it is that we do. So I think you need to, you know, if you're coming into a new job as a seller, like look at the case studies, right? What are the— where have you been successful before? And I would tend to kind of over-rotate into those areas. So there's things like that. It's, you know, size of the company. And again, some of my advice is like based off of how I run my business. I'm trying to hit grand slams, right? Not singles. I'm not trying to do 500 singles. I'm trying to do like 2 grand slams, right? So, you know, it's the biggest— who has the biggest revenue in my patch, right? If they— whoever makes the most money can afford giving me the most money, you know, that's the reality, right? So those are the things that you can measure. And then there's kind of the gut feel stuff too, right? Where it's like, you know, if I'm coming in, I'm taking over an account that another salesperson has been banging their head up against the door of this account. You know, try to find out as much as I can about why they were unsuccessful, and then gut feel, like, was it the person, you know, or, or is this just a bad time investment? Yeah, is it approach, you know, stuff like that.

And is your style top-down, bottom-up?

I'd say it's, it's both. Yeah, it's both. I mean, I, I think the reality is when you're selling transformations like I am You know, these are deals that have to be built from the ground up. You know, it's, you know, I haven't won many RFPs in my day unless I wrote them, right? You know, if I'm getting brought into an RFP, chances are that somebody wrote that.

Somebody wrote it.

And so you're playing by somebody else's rules. Right? So the— I usually try to ask myself 3 questions, like when I'm engaging, whether it's bottoms up or tops down. The first question is like, what does this person want to buy? You know, and in today's world with the internet at our disposal, and if you're selling to big public companies, you should be able to have a good perspective going into a meeting, whether it's with a senior person or a junior person. Right, of what is it that this person wants to buy, right? So that's one question that I'm asking. And then, you know, the other question, the next 2 questions is like, can we win? Can we win based on what they want to buy, based on what I have to sell them? And if we win, how much? You know, how much do we get, right? And those, those kind of 3 things I'm thinking about when I'm trying to You know, make time investments. But yeah, to answer your question, it's— I'd say it's mostly bottoms up. You gotta, you know, build these transformational visions, get the people that are gonna execute it bought in, and then be able to go to a CEO, a CFO, right, to be able to get them on board with it.

Yeah.

Yeah.

And what lessons have you learned along the way? Because I'm sure, have you got it 6, 9 months into it and it dies or it gets delayed or it's a false positive?

Yeah, I mean, I think one of the, one of the lessons that I've learned the hard way is, um, one thing that I try to think about is like when you're, when it takes when you're closing 2 or 3 deals a year, it's so hard to get to the table, the negotiation table, right? At the end, the crucible of the deal. And so when you get there, my philosophy is get as much as you can in the deal and protect your upside, right? And whenever I have deviated from that thought process and been defensive about how much this should be worth, let's say, because I've worked with a Bain and I have this great ROI and business case that everybody said yes to. If I get defensive and people are being emotional because people make emotional decisions and I try to protect my price, you know, like that's always led me into bad places, right? So just recognizing how hard it is, you know, to get to the table when you're doing this major enterprise software selling. Don't be greedy. Just take the deal that you can get and then move forward.

I'm sure when this type of money is being spent, they're looking at alternatives internally, externally, whatever. How do you block out those alternatives?

Well, that's why I think What I'm— why I love what I'm selling and what I sold at my last company too is it's transformation, it's vision creation. And that's why you usually have to start in maybe not the bottom, but the middle layers of the organization. And so what your job is, if you're selling a transformation, is like what I try to do from the beginning is create a vision. The first thing I'm selling actually is a vision. of a solution, right? And then, and I try to define the vision of the solution to something only I can satisfy, you know, with my product, right? Knowing that—

Selfish.

Oh yeah, well, yeah, but if you have a product that you believe in that is differentiated, then it, maybe it doesn't feel so selfish. It's just like being realistic about, you know, swimming in the right pool, you know, or something like that. But yeah.

And I gotta also imagine that you're running or competing against when to do it.

Yes.

You want it now, they want it, or they could push it off forever. They haven't done it.

Yes. Yeah, I think timing You know, with these, with when you're selling like a transformation, like whenever possible, you want to try to align it to something that they're already trying to solve. I, one of my colleagues in the past life, he called it globbing on, you know, like, is there already a big, you know, are they already spending $200 million with Accenture on something? You know, can you attach yourself to that? You know, it's a lot easier to do that.

Infrastructure.

Right. Yeah, it's a lot easier to do that than, you know, building something completely from scratch. But yeah, I mean, you know, creating an impending event, creating the reason for change, you know, the why now? reason. That's a big part of what you got to be thinking about, you know, in terms of how you invest your time in different accounts too. Because, you know, if you're spending a bunch of time— we all have quotas, you know— if you're spending a bunch of time for something that's going to close in 2 years, you know, and you're not spending time finding something that you can close in the next 3 to 6 months or this year, Maybe you need to rethink your time investment process.

And have you found it a challenge to sell your manager on deals, that why you picked this one versus others, or had a manager go, well, you got 29 others?

Yeah. I think it's once you get a track record, it's easier. But before, if you don't have that, Kind of the trust and confidence of your boss, you know, then it's harder. But I would say that's part of the time management thing and part of like not leaving your selling shoes at the door, you know, is that, you know, you got to convince people and you have to be protective of your time, right? Even with your boss, you have to be willing to say no to a bad deal or a bad time investment. You know, and only you, you know, like we're all running our own businesses, we're all entrepreneurs, right? Like only you know, like, and so sometimes it's like even just like your own personal passion and that gut feel, like, do you, are you gonna be excited to wake up in the morning and work on this particular thing? You know, like do you feel in your heart, right, that you can close this thing? And if you feel like the answer is no, you know, then run for the hills, you know, go, go do something else. So, yeah.

And what's your why? What keeps you motivated, keeps you excited?

Yeah.

In the morning?

Yeah. So, I mean, I went through the process, um, you know, when, when I, um, I remember just being in, in like high school and just talking with friends and trying to decide like, what do you want to be when we get older? You know, things like that. And at that time, I just knew that I wanted to make a lot of money. That's what I— that if somebody asked me that, that's what I would've said. And that's probably why I was thinking I wanted to be an attorney because that's— I thought they made a lot of money. And so that used to be a lot of my focus. And, you know, now having been in this game for a while and having made a lot of money and built a dream house and been able to provide for my family the way that I have, a couple years ago, I went through this process of trying to redefine my purpose. What is it? Because I've done that now. I've already done that. And I read the book Find Your Why by Simon Sinek and went through the exercises with that. to be able to find my purpose, my why. And mine is to challenge myself and others so that we're inspired to do good. You know, and for me, doing good is, you know, kind of living by the golden rule. I'm a man of faith. I believe that everything that I have has been given to me by my Lord and Savior Jesus Christ who died for me. And so, you know, that's why I wanted to join this podcast too and be able to just share lessons learned in an effort to give and share and challenge others so that they're inspired to do good.

Excellent.

Hey, appreciate your time today, Tim. Where can people go to connect and follow you?

Yeah. Check me out on LinkedIn. You can find me there. That's really the only social media I'm really investing in these days.

Not on fans only or whatever?

Yeah. Not on fans only. But, uh, yeah, I mean, I, I love talking about deals with fellow salespeople and just, you know, um, sharing advice. And like, we're all in this together, man. We're all people. And, um, you know, if I can help, uh, any of your other listeners in any way, you know, I would love to do that. And I really enjoyed speaking with you.

There's something about teaching, uh, winning the complex sale that's so rewarding.

Is that you get to teach people how companies buy, how deals get done, and how to prevent them from getting stuck. The default is for them to get stuck. And this— these skills, the part of it's knowledge, but most of it is hard-earned lessons from a career of trying to win and winning large complex deals with no brand name, with no account ownership, just from scratch competing against bigger companies. And I got to tell you, I talk to a lot of sales leaders. I read pretty much every sales leadership book that comes out, everything that's on the complex sale. And nobody else teaches this because so many people who have been successful, it's because there's a demand for their product. There's a brand behind it. But what if you're in a new space? What if your company isn't that established? What if you don't have time for all that? You've got to learn how to win the complex sale and how to not get stuck in the traps that we're all going to face. It's that time of year. This is the time to really double down on your skills. And how do you do that? You got to hear other people talking about deals. You got to talk about particular situations, traps that you're either in Or you're concerned about falling into. And from the comments that I see from very senior people on LinkedIn, ah, they don't know. They have— they don't understand. They listen to the platitudes. I'm a trusted advisor. Yeah, okay, where's the deal? If they trusted you and your advice so much, where's the deal? Well, they don't know how to get it done. You gotta learn this and apply it and get it out of your head so that you can anticipate it and not fall into those classic traps. But what if you have the other problem? My pipeline, it's kind of skinny and no leads coming in, Brian. Where are all the good leads? Where are the Glengarry leads? They don't come in anymore. Sorry. Unless you're in the tornado or you're a unicorn or you lucked out, you have to go get your own leads. And that's changed. People don't want to hear your cold calls, your pitches, your spam, but they do want to talk about themselves. So how do you build up that conversation? How do you develop a system to do that? Start the Conversation, Get the Meeting helps people in the course fill up their calendar With great conversations that turn into business discussions. Today we can tell before we even contact somebody, can they afford it? Are they most likely to have the problem that we solve? It's not blind anymore. We're not opening up phone books and calling off a list or bingo cards. We have the internet and we should be able to leverage that to prioritize who is most likely going to need the product that we have to solve the problem that they have. Winning the Complex Sale solves that. And with both courses, I include the Questions That Sell course with it. So once you sign up, just send me a note. I'll send you the coupon code and you'll be able to get that as well. The Questions That Sell course builds up the exact questions to build The conversation into a business urgency. Instead of pitching, it uses questions, the only mind control that we have, to focus the client on what we want them focused on. It's infinitely better than spin. It's not crap selling. It's real questions from somebody who sold his whole life, starting where the other person is and getting them to where you want them to be. So go sign up today. Don't waste your time. Don't keep losing deals. It's costing you every day. You can pay per month. It is a monthly payment plan, or you can pay all at once. The payment plan— it's not a membership, it's a payment plan. So, but it does give you the ability to stretch it out over 12 months, your access time to the course, so that it doesn't cost a lot. Up front, you get access for a year. You get unlimited one-on-ones, which is a 30-minute Zoom call with me. We have office hours every other Friday. Everything is recorded and put in the course. Office hours is an hour-long discussion about what you care about, not what I care about, what you care about. So bring your issues, case studies, problems, situations, questions, and we cover them all. We record it. Everything's put back in the course. You never miss anything in case the times don't work out for you. And guess what? There's 3 years of them in there. There's, there's more content that you could probably consume in a year, but you need to get good at sales. It is a performance profession. It only matters how well you do it today. Now, much like a musician, much like an athlete, much like any other performance profession. It's not a quiz, it's a performance. It's how well you do it. Now sign up today.