Sales Hustle is now Sales Transformation
Oct. 18, 2021

#174 S2 Episode 43 - Transactional Seller to Successful Strategic Seller with Jesse Woodbury

On this episode of the Sales Transformation Podcast with Collin Mitchell, he's joined by Jesse Woodbury, host and creator of The SaaS Sales Players Podcast.

Why is SaaS important in today's sales world and why should you care? It all seems too complicated to understand but Jesse irons out the details and gives it simply as to why it matters. Here about his origin story and more on this episode of Sales Transformation.


02:03 How Jesse started out in his sales journey and his origin story

13:57 How getting a journalism degree helped Jesse up his game in sales

18:25 The skill sets that translate to being a better seller

22:28 Transactional SAAS seller to a Strategic SAAS seller

37:01 How to connect with Jesse and learn more about SAAS


10:10 "So many people are not willing to bet on themselves, like go all in, take a risk, no money in a bank ... there's something to be said about that."

17:58 "Breaking through the noise of all the traditional junk that executives are used to seeing. Like those are skills that people or sellers that need a lot of help in that area."

19:14 "Salesmen are all content creators, and whether we want to be that or not, we're all content creators."

28:36 "You have to surround yourself with people that are doing what you wanna do, and you gotta get close. And what I mean close is literally shoulder-to-shoulder." 

31:46 "Look for an opportunity that has leadership and with somebody with a proven track record."

Learn more about Jesse in the links below:

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[00:00:00] In the world of sales, you either sink or swim or breakthrough to the next level. My name's Colin Mitchell, and this is sales transformation, a new kind of sales show designed to bring you through the epic life-changing moments of elite sellers. So you can experience your own sales transformation.

[00:00:24] All right. Welcome to another episode of sales transformation. And as you know, as always, I've got a fantastic guest for you today. I'm going to be talking. Jesse Woodbury. He is also a podcaster. Uh, he hosts a show called the SAS sales players podcast. I highly recommend that you check it out if you haven't.

[00:00:44] Um, he's got over a decade of experience in the industry and he's closed over one. 5 million in new SAS resident revenue, just in the last year. Um, and so I'm very excited to have Jesse on, uh, we're gonna dig into his [00:00:59] story, his experience, and I know that we're going to pull out tons of learning lessons from that.

[00:01:03] Jesse, welcome to the, thank you. Uh, I'm super excited to be on, uh, as you mentioned, I've got a podcast, so I've been the, the host myself, but, uh, um, I'm still kinda new to being the guest. So I'm, I'm thrilled to be here. Love your show, and can't wait to share some, share some knowledge and anything else that, uh, relates to transforming.

[00:01:24] Yeah, man. Appreciate it. I'm happy to have you on and, and I'll let you know how you do after just kidding. I would love a grade on how I interview as applied as a podcast instead of a podcaster. Yeah. It's, it's, it's funny. A lot of, um, you know, uh, being a, being a host. Definitely can help you be a better guest.

[00:01:48] Um, I found my first couple of podcasts, I went on to like, it'd be painful to, to re-listen to them. Um, but it's, it's definitely a, when you're so used to being the [00:01:58] host all the time, it's, it's kind of a different mind shift, but, uh, I know that it's going to be a lot of fun and, and I'm curious to dig into some of these, you know, things that I read here in your bio and.

[00:02:07] You know, figure out a little bit how the podcast is, is, is going in and kind of the mission behind that as well. So just kinda take us back here for a little bit, uh, where did your sales journey start? What were you doing? How did you get into sales? All that good stuff. Great question. And a great starting point.

[00:02:22] And of course being a sales podcast, or I love just talking about origin stories and how one gets into this crazy business. And, you know, like most other people I kind of fell into. Uh, my journey begins probably earlier than most. Uh, I was recruited at age 17 to do door to door pest control sales, frankly, like in, in, in retrospect, I'm not even sure if it was legal.

[00:02:44] It was a family friend who was starting up a pest control business and he recruited me and three or four of my buddies to go knock doors here in the Phoenix area, which if you've been to Phoenix, it's, it's fricking hot. It's a hundred plus degrees in the summer. Hemi's 120 plus [00:02:57] degrees in the summer. So we were walking door to door in the summer.

[00:03:00] We had a whole sales script, uh, you know, just the more doors you could hit, the better, what I figured out really early on. And I took my brother along with me on this journey was we should just go make some door hangers and we can plant more door hangers faster if we just drive around and place those on as many doors as we can.

[00:03:16] So we covered a lot more ground than my buddies who were going door to door. And I was getting callbacks from people that had found my door hanger. And so I closed a couple of deals that way. And, uh, you know, then I finished out high school and all that, uh, didn't really consider sales as like a profession.

[00:03:32] It was more, just a way to make some more money. And when I finished high school, uh, I actually joined a company called, which is of course now the yellow pages at the time. It wasn't, it was this weird internet startup. This is the early two thousands, by the way. And the whole business was predicated around the fact that they owned the domain and they were trying to sell to the yellow pages.

[00:03:53] And so we were selling these. Frankly [00:03:56] janky little micro-sites. They don't exist anymore. So it can be pretty open forum here. Uh, we were selling these jenky little micro-sites for small businesses and actually I won't get into all of it, but their, their marketing practices. Probably on the border of, of shady.

[00:04:10] And, uh, we would get in their sales practices practices, but it was my first job with commissions. At the time I was making 11 bucks an hour plus commissions at, at, you know, 18, 19, however old I was that absolutely blew my mind that there's people that do this for a living where they make a base salary or an hourly base.

[00:04:28] And then they. Commissions on top of that. And I've kind of been broken ever since, like, I don't think I could go back to doing just some job that didn't have a variable component to the income or some lever I could pull to make more money by, by producing and delivering results. So I really enjoyed that then.

[00:04:45] Um, you know, I took a break from that for a while. Went through school. Uh, and as soon as I finished it, I got, I got a degree in journalism and mass communication. And I, I had no intention [00:04:55] of ever being a practicing journalist or a reporter or anything like that, but I knew I wanted to be really good at writing.

[00:05:02] And I knew I wanted to be a good communicator and presenter, and frankly, I wanted to be an entrepreneur. And I thought, you know, who really gives a shit, what you study in school to become an entrepreneur. I could study, you know, basket weaving and probably figure out a way to do that. Uh, the degree was really just sort of a check box.

[00:05:19] And so when I finished school, my last semester, someone had suggested, you know, Hey, you gotta look into sales. And I was like, no, I'm going to do something in tech and it'll be digital. It'll be really cool. So I went and got a job right out of college as like a digital project manager. And again, no commissions, no reason to really like Excel in the job.

[00:05:35] It was. In the weeds work. And I actually got fired from that job. I don't care to, you know, I'm, I'm cool admitting that now after all these years that, uh, when my boss let me go, it was like the best way to get, let go, because she was like, you really suck at project management at this level and the, in the granular.

[00:05:53] You know, [00:05:54] building code on websites. Cause it was a digital agency. She's like, you're really not good at this. And you just don't seem to be like, you don't have the personality for, for like the down in the weeds. She's like, you're like a 10,000 foot or, or 30,000 foot guy. And you're really good at kissing executive asses.

[00:06:08] So you should get out there and sell. And I was like, oh, okay. It seems like the universe is trying to tell me that sales is where I need to be. And so, uh, she actually, you know, upon letting me go introduce me to a sales. At a fortune 300 company that was her friend and I got a job they're selling me. Uh, so did that first off, sold media know media ads and things like that for awhile.

[00:06:30] And I was sitting at my desk one day and I Google. This is back in 2012. I Google highest paying sales professions. Cause I was like, look, if I'm going to, if the universe is telling me I need to do this and I need to commit to this. What's the, what, what's the most lucrative path in this business. It's probably not selling, you know, print media and, uh, what came up was pharmaceutical sales.

[00:06:51] And I was like, you know, my journalism [00:06:53] degree probably doesn't really qualify me to go out and sell drugs, uh, on that level. And the next thing on the list was enterprise S a S sales I'm like, what is SAS software as a service? I'd never heard the term before. I had been starting to follow some tech trends and I had gotten on Twitter and LinkedIn at that time.

[00:07:12] Uh, but I really didn't understand enterprise software or SAS. And I saw that and I saw that, you know, the, the top reps in the industry make $200,000 a year. And I was like, holy cow, that is more money than I could ever imagine. I got to get into that into. And it became an obsession. I was living in Phoenix at the time and immediately I started, uh, hucking and resumes out to the bay area to Seattle, Boston, and ultimately landed a gig at a software company in Austin, Texas.

[00:07:38] I'd never been to Texas before. I didn't know a single person there. And I literally loaded up all my possessions in a U hall. And in a month's time, drove to Austin, Texas sight unseen, rented a house sight unseen and got into this first, [00:07:52] uh, you know, software role. And honestly, it was not, you know, the most glamorous software company that you could imagine.

[00:08:00] It was very much boiler room. The call requirement was probably a hundred to 150 outbound calls a day. I didn't even have a CRM. I was working out of a spreadsheet with just phone numbers in it. Oh, even worse. It was, here's a spreadsheet of 10,000 domains from like the, who is network, go find out who owns the domains and call that person and sell them an e-commerce site.

[00:08:21] And so they made it like a shopping cart software, very similar to like Shopify today. And it was SMBs transactional. What was great about that role though, was despite the transactional nature to it and just the, you know, frankly, poor operations at that time. Uh, I had a fantastic sales manager and he took me under his wing.

[00:08:44] He had been in, you know, everything from bond trading to media sales, to software sales. So he was just this amazing veteran. [00:08:51] And for whatever reason, we just got along. Well, we both play guitar. In fact, if you, you can see in the background here, I got my Gibson, Les Paul, uh, we both play guitar, so we just hit it off really well.

[00:09:01] And he taught me everything, trial, closing, AB closing, how to, you know, get comfortable asking. I can confess it here. Now that we're years on, on Friday afternoons, he was like, you need to drink a beer and go hit cold calls. You're so nervous on the phone. You need to take the edge off. And so he would, he would feed me a beer under the table.

[00:09:19] I mean, he would, he would hand me a, an open beer bottle under the table and say, just, you know, take the edge off a little. And go make your dials because little liquid courage, courage, and, you know, fortunately, I was able to wean myself off that and now I'm pretty confident with my cold calls. Uh, but it was a major drink all day and hit the phone.

[00:09:37] Not anymore. I, I, for me, I get drunk off the high of getting someone on the phone. Um, but anyway, great managers. And at the time I was really strapped that I want people to know this too. Cause I [00:09:50] hear, I have a lot of people that listen to my show that reach out and say, how did you do it? And what kind of risks did you take?

[00:09:54] Getting into the industry? I moved to Austin sight unseen. I probably had a couple hundred bucks in my checking account. I'm just gonna be honest and. I burned the ship. I burned the ship by saying, look, I'm moving to Austin. I'm leasing a place here. It was more expensive than what I was leasing in the Phoenix area.

[00:10:11] And I have to make my sales career work in software. Otherwise I don't know what I'm going to do moving back in with my parents, which sounds awful. Um, but that's, but that's, that's, that's an important piece in, and we'll go back to some of the earlier things, but I want to touch on this just a little bit because.

[00:10:26] So many people are not willing to bet on themselves, right? Like go all in, take a risk, move, no money in the bank. Like for me, I perform well under pressure. And when my back is against the wall and I have to perform, or I have to produce, um, And so there's something to be said about that. Some people crack under pressure or get stressed out.

[00:10:48] [00:10:49] Um, I Excel under it, um, and that's just kind of who I am. And it sounds like you're, you maybe are the same way where you're like, you're willing to bet on yourself. Um, that level of like conviction and confidence in like, I'm going to do this, I'm going to make it work. Um, that can really be the difference between, you know, excelling in a role at not, and look.

[00:11:09] Putting some skin in the game to forces you to find a path to success. And that's what I ultimately had to do is I was so new at sales, but again, just leverage this manager started closing a lot of deals actually broke some records in this role. I closed six deals in one day in this company, again, transactional, these weren't enterprise deals or anything, but it was still just such a rush to get six people in one day to give me their credit card number and, and get that going.

[00:11:35] And, um, Then from there being an Austin, I started sort of networking and, and Austin, you know, 10 years ago. And today is a great place to be a software tech seller and just [00:11:48] started networking and found new opportunities. And a lot of my, my network and mentors were like, look, you got to get into more strategic selling.

[00:11:54] The bigger commissions are going to be in selling larger brands. And I was really fortunate that, you know, I moved around a couple of different startups in Austin. Got to see, you know, everything from being in the first sales hire. I was the first sales hire at a startup, uh, you know, to helping to build out a new organization for a large unicorn company in the bay area.

[00:12:11] So just have a really diverse experience, mostly all closing. I also did a brief stint as an SDR manager, which was very rewarding, uh, and helped open my perspective to what it feels like to actually buy technology and manage people and manage a process. So I feel like I got a really REL well-rounded career, uh, and just enjoyed being in this.

[00:12:30] Tech startup ecosystem in Austin. And just recently moved back to Phoenix after, you know, 10 years in Austin. Uh, now that I'm sort of taking on remote enterprise selling roles and it, it doesn't matter as much that I'd be in Austin proper to, to do those roles, uh, the family. And I decided to move back [00:12:47] to Phoenix to be closer to my folks.

[00:12:49] And, uh, you know, I've been enjoying that so far, so that's kind of, uh, you know, my career in a very tight niche. Uh, with some details around, uh, you know, some of those early boiler room type experiences that I had that were formative, frankly, formative and fun. And I look back fondly on those experience.

[00:13:06] Yeah. Yeah. Uh, so I want to go back to some of your earlier experiences, and then I have a question about kind of your own sales transformation, which is like going from that kind of highly transactional, like six sales a day to more strategic. Right. So I want to dig into that, but first I want to go back and just kind of touch early.

[00:13:23] Right. So I always have a, I always have a ton of respect for, for people that started out knocking on doors. Um, I love how clever you got with the, with the door knockers. Like you were already. Putting your marketing cap on as an early seller. Um, and then I'm curious, just to know, like you're at your, you know, um, you took a stint to, to kind of go back to school and you got you, you got your [00:13:46] degree in like communication and stuff.

[00:13:47] And I'm curious how that has helped you in say, I really love that question because I get teased a lot for being a journalism major. I used to, I used to anyway, I think it's becoming more of a, an interesting major as time goes on. Uh, but I've had family members say. Well, we were in journalism degree, you know, and, and I get, yeah, I've taken some, some shit for that.

[00:14:07] I actually think it was a really great degree to go get as a, as a now, you know, enterprise strategic seller, working with executives at large companies. Here's why. In that program. First of all, I went to ASU journalism school, which, you know, ASU has a certain reputation, but their journalism school is actually very rigorous.

[00:14:27] And w part of the capstone courses there, one of the courses I took was called digital entrepreneurship. And the final project in that class was we literally pitched real VCs in the Silicon valley because the professor had this connection to, he had worked for the San Jose mercury. So he literally [00:14:45] flew in his VC friends from the bay area to listen to our pitches at the end of the semester for these different businesses that we created, nothing.

[00:14:52] Like, I don't think there's very many other college experiences that will put you through the ringer like that. That was huge because if you can get the confidence in your final year of college to stand in front of Silicon valley, VCs and pitch something. You're going to be just fine. Uh, so that was one aspect of my studies as digital business and digital journalism was sort of my focus and studying.

[00:15:14] The other thing about it was I took a course where we had to get published in newspapers. Like it was a writing, you know, print journalism course, but to pass the class, you had to go get yourself published. That was an early exercise in strategic selling. Cause I had to go out and tell, you know, different newspapers here locally.

[00:15:32] Like, Hey, look, I wrote this piece. I want you to publish. I'm a journalism student, but you should publish it. And they're like, why the hell would we publish something that a journalism student put together you're new? And so you had to first write a good enough piece that the publication [00:15:44] would actually run it.

[00:15:45] And then you had to go sell it. We did that six times over the course of the semester and that exercise, that persistence muscle that, you know, being out of your comfort zone and reaching out and talking to somebody who's scary, like, you know, a newspaper editors tend to be pretty old school hard-ass type people.

[00:16:00] And so it was, it was a really cool exercise. And then lastly, I took a lot of writing courses and what I've found, especially selling to, again, senior level executives, people that have no time, but you need to stand out from all the noise and prospecting is if you can write a very concise. Very, you know, grammatically sound message, whether that's a cold email or a LinkedIn message or a briefing or a PowerPoint.

[00:16:24] So that art of being able to present, which I honed in on, in school, in journalism school, but also the ability to write really well, but also write things that are persuasive and compelling because that's really, the art of journalism is storytelling too. So, you know, in addition to writing. Learning how to structure a story in a way that you can pull someone's [00:16:43] interest in those have been absolutely critical in my career.

[00:16:46] And I didn't know at the time that those were going to be something that I look back on and say, wow, I can pick up the phone or I can present to a C-level executive to. All because I learned how to write and college all because I learned how to present or tell a really good story and be persuasive. So, you know, that's not to say past performance, doesn't always guarantee future successes.

[00:17:06] I'm not saying everyone who goes to journalism school ends up killing it in, in this business. But I do think if you look at it from that lens and say, look there's, and this could apply to a lot of different majors, especially ones that are heavy on writing, presenting, uh, going back, I probably would have done more technical.

[00:17:22] Um, and I actually did. And when I lived in Austin, I audited some courses at UT the university of Texas on programming. So I tried to get familiar with JavaScript and HTML and some of those things. Cause I figured if I'm going to sell software, I should at least have. Some level of knowledge on how technology and code comes together.

[00:17:41] And so [00:17:42] I'm a big, like self educator. I've, I've obviously expanded on my college degree for the, for the last 10, 11 years. But I do think that I was surprised, you know, I am surprised at some of those outcomes again, that like writing ability and. Yeah. Yeah. I love that. I mean, there's so many valuable things there that you took from that education that definitely are relevant and, and apply to your sales roles because communicating, writing, storytelling, standing out, persuasion, catching people's attention, breaking through the noise of all the traditional junk that executives are used to seeing, like, those are skills that.

[00:18:23] People there's a lot of sellers that could still use a lot of help in that area. Um, and you know, you gotta get started somewhere, um, and you know, creating a writing practice to become better in sales or even like, I can't even tell you like how beneficial it is to being a [00:18:41] podcast host to becoming that translates, that skills that you acquire there.

[00:18:46] It also can translate to being a better seller. Um, you listen better. You're more curious. You ask better questions. And then a lot of people say, oh, you want to understand your clients? Like go read their blogs, subscribe to the podcast that they listen to. What about just having your own show, having them on.

[00:19:03] You can ask them any question that you want and all of that knowledge transfers over to every sales conversation that you have thereafter. That's a really good point. So one of the why my podcast is kind of a passion project is precisely because I'm, I. Communicating and, you know, obviously that's what I studied in school.

[00:19:23] Uh, but I also think, so I recently had Brandon foolhardy on my show. I know you've had Brandon on before and he said something that I just can't get out of my head, which is in sales. We're all content creators, whether we want to meet that or not. And whether we want to like lean into that or not. Uh, we're all content creators.

[00:19:39] Yeah. So [00:19:40] if you can give yourself a leg up and look, a lot of you listening are probably already done with school. You don't really have an opportunity to go back and study journalism or writing or English or whatever, but there are no short of, you know, tens of thousands of books on the topic of copywriting, uh, persuasive writing.

[00:19:55] There's great sales writing books. I highly recommend, you know, like Ogilvy on advertising. There's, you know, just scores of different. The skill of copywriting is one. I've studied just in my spare time, because it helps me improve my cold emails to your point earlier. You know, if you're creating content, whether that's a podcast or video content for prospecting or LinkedIn or whatever that is honing in on that stat writing ability and the presenting ability are both skills that are worthwhile and pursuing.

[00:20:23] Even if you're long gone from college, you should still pursue courses. There's tons of those out there, books and ways to, to hone that you kind of build that much. Yeah. Yeah. I think, you know what, even if it's just writing, you know, [00:20:39] social posts and like taking conversations, uh, from prospects and like turning that into like value, bull information, you know, in a digestible format.

[00:20:49] LinkedIn, like that's a great, comfortable place to start. And like, maybe from there it's, you know, starting a blog practice, maybe it's once a week, twice a week. And I'll eventually, maybe you get to the point where you write a book, like all of those skills of like communicating and writing, um, are things that you can always work on and improve.

[00:21:08] Um, absolutely. All right. So I want to, so. So I'm curious. Now I want to go back, um, uh, to, I want to go back to sort of, kind of where we left off in your story. Right. Which is, which is, you know, you're in Austin. Um, you know, you got your first, I'm just visioning you like out at, you know, maybe drinks with a friend and they're like, Hey Jesse, what are you doing?

[00:21:29] You're like, I do S a S sales

[00:21:37] Um, [00:21:38] but I love how you just like, you know, like, Hey, okay, I clearly need to be in sales. Uh, if I'm going to be in sales, like, what is the best possible job for sales, figuring that out. And then like, you know, going on the hunt of getting your job. You know, betting on yourself, packing everything up, getting your first SAS sales job.

[00:21:57] Um, your experience there with no CRM in the, in, in the, in the Excel file is very similar to my own and separate. We didn't even have that. It was like we have a CRM, but it doesn't work. Here's a list of names and there's the phone in the script. And like, that was my training. And so we used to use. Yeah, man.

[00:22:14] We used to use little like a, I dunno, three by six index cards with like our leads, name and phone number and notes. And then like put them in like each day you'd have like a stack of cards to call and it's not that the technology didn't exist. It's just that the CEO of the company, like didn't want to invest in it for whatever reason.

[00:22:33] Um, but Hey, I mean, you, you, you make it work, but right. [00:22:37] So then you got to a point where, you know, you, you, you were getting some wins, were getting sales, like things were good. Um, but then you had your own kind of next, like transformation of like, okay, how do I go from like transactional SAS seller to like strategic SAS seller and kind of walk me through, like, what skills did you need to have.

[00:22:56] To be able to do that. How did you find your first like strategic selling role? Walk me through, because I think there's a lot of people that are maybe in that place of like a transactional sell or maybe they're not in SAS, they're trying to get in. So I'm curious if you know, how you got into a role like that and, uh, what skills you needed to, you know, level up.

[00:23:13] Yeah. This, this is a, this is a big one. Uh, very good question. And one that I know is top of mind for a lot of sellers out there who are selling something that's more transactional and there's no. One path either, by the way, my story could different from, from someone else out there who might've landed their first role at, at Oracle selling into enterprise out of college, it does happen.[00:23:36] 

[00:23:36] Um, but yeah, let me just, just kind of share a few things that I did once I identified that that was the direction I wanted to go in my career and I can certainly. Share a few tips and tricks and, and I don't want to call them hacks, but things that are going to give you a leg up in getting into an enterprise strategic sales role.

[00:23:54] So one of the big things, and I've, I've blown this trumpet for a long time, which is it's different now than the pandemic too. So this one's a little bit more nuanced, but I was really, you know, I, I put myself in Austin, Texas in a time when. Tons of tech companies were moving their, their sales operations into Austin.

[00:24:12] And I, in a lot of ways, I was just in a great market at the right time. It's getting easier in some ways now, because now companies that do, do you know that do enterprise solutions. Finding sellers all over the country. So like, I have people in my network that are living in Detroit or Indianapolis, or, you know, salt lake city or somewhere else.

[00:24:32] That's not, you know, Silicon valley, Austin, Seattle, [00:24:35] Boston. Right. Or, you know, New York. Yeah. So, um, one of the things I think I just did was I, I put, I put myself in the. To make that happen. And everyone who's listening, he's asked themselves, like, if I really want to sell to fortune 500 brands, let's say and do executive level selling, what is my version of that environment?

[00:24:55] And for not, not for everybody, it's not going to be pack up your stuff in a U haul and move to a place you've never been before. For a lot of people. It may be that. Uh, but for some people it's going to be, look, how do I start networking with people that are already doing it? And that brings me to my next point, which was, I started just heavily networking, you know, again, it was easier and pre COVID times when I could go out to a bar, you can go out to bars now, but, uh, it's a little bit different.

[00:25:20] You could go to different meetups in Austin and meet people. And so how I sort of transitioned into that role, I had a recruiter call me, uh, she's still a very close friend of mine. She's been a mentor of mine for many years. She is [00:25:34] know an absolute beast. She knows Elon Musk, uh, from her college days.

[00:25:38] It's, it's absolutely crazy story. This lady is a Silicon valley veteran, but she was living in Austin and she called me on the phone one day and said, Hey. I've been recruited. I've been retained by this, uh, B series startup. Uh, they sell to, you know, enterprise retail brands. They're small. They don't have a lot of money.

[00:25:54] They just raised the money, but they're, you know, they're not a big company and your profile came across our desk on LinkedIn. And I think we want to have you come in and interview. So what do you think? And the key was you. It's going to be scrappy. It's going to be ugly, but you're going to get a chance to cut your teeth on selling into, you know, Macy's and Dillard's and Lula, I don't think lumen existed at the time, but tailored brands, some of these like legacy retail companies, because that's what the solution was.

[00:26:21] But they, you know, I don't know where my name had come from. I think. Searching LinkedIn for people in Austin that were doing sales. I was obviously doing more transactional selling at that time. And that role [00:26:33] proved to be pivotal for me for a couple of reasons. So again, call it luck, call it right place, right time.

[00:26:38] But also just being in that ecosystem and Austin tech sales at the time, even though I wasn't selling an enterprise product, someone was like, look, we're a startup. We're probably not going to find someone with 15 or 20 years of experience selling Oracle. That's going to be willing to come and get paid, you know, pennies on the dollar to work at a startup.

[00:26:54] I mean, paper, money, like ultimately I knew I was under Compton that role because they told me, but I had a lot of paper in the company, a lot of stock stock options or equity options. And that was the trade-off was look, I'll take a lower salary, um, good comp plan and a, you know, a good equity pool and those kinds of things.

[00:27:12] Here's where this role really like dumped fuel on my career, uh, on the career fire that I was starting. Right? So one, my manager in that role is Lindsay bogs. A lot of people know her. She's a very prominent social seller. She wrote one of the first articles about how to use LinkedIn for social selling.

[00:27:29] This is back in like 20 14, 20 15. [00:27:32] And so she was my direct manager and she's still my really close friend and mentor. I still reach out to her and ask for advice. She taught me so much about how to present myself to executive buyers from a prospecting standpoint, from a presentation standpoint. So that was just kind of lucky.

[00:27:48] I got to work for Lindsey box and then. The CEO of that company was the former CRO of a company called Bazaarvoice. How to Austin, which was one of Austin's big IPO success stories. This guy had grown the sales team from essentially zero revenue to like, uh, four or 500 million or whatever it was. I don't remember.

[00:28:07] Figures, but he had grown the team from zero to IPO. So this guy, his brain, his name is Michael Osborne, by the way. So you can look him up on LinkedIn. He was ju I mean, he's, he's like the Michael Jordan of enterprise sales. He grew as our voices enterprise sales team. He was our CEO, but he was absolutely amazing at strategic selling negotiating pitching.

[00:28:29] And I sat next [00:28:31] to him for. Over two years, because we were all in this tiny office in Austin and my desk, my desk was right next to his. So I listened to him, raise funding from our investors. I listened to him pitch some of the largest companies in the world. We ended up doing a deal with Sam's club Walmart there.

[00:28:46] I sat next to him and watched him do that whole thing. This guy had been doing this for a long time. He'd grown teams. He closed massive deals. So the moral of the story is. You have to surround yourself with people that are doing what you want to do. And you've got to get close. And when, I mean close shoulder to shoulder, I was literally shoulder to shoulder from Michael Osborne, the former CRO of bizarre voice and the CEO of the company I had the startup I worked for.

[00:29:09] And there is no better bootcamp. You can't pay for that kind of education. And he's a mentor of mine. He still is a close friend. Someone I talked to, he's a reference on my resume. Uh, and I, I learned so much from those two individuals about how to sell enterprise. There's a lot of other players in that role, too, that, uh, you know, I won't get into all the names, but a lot of other very [00:29:30] experienced enterprise sellers at that company, uh, on the leadership level.

[00:29:33] And then they, they did manage to snag a couple of more experience, you know, 10 plus year sellers. Uh, Jack Kuser is one of them. I'm gonna give him a quick shout out. Barry Clark as well, who is our sales leader? Just some very, very decorated and, and, and, you know, well-known industry Titans, if you will, in the enterprise selling space.

[00:29:51] So working literally next to some of those people, Helped me gain the skills. I mean, really helped me accelerate my learning and get to a point where I was very confident getting on the phone with executives because of the coaching that I received and, and they would sit with me and help me so that in a lot of ways is what it's gonna do.

[00:30:09] Uh, at least if you want to be wildly successful in this business is you've got to surround yourself with people that are doing it. And it's harder to do today over zoom. Um, but you need to find people in your city. Uh, there's there's people out there that you can buy coffee for. That'll help provide that coaching for you find a company that has managers that have done successful, things like that, and have [00:30:29] sold to big brands and sit next to them.

[00:30:30] If you can, if you can't sit next, sit next to them, open up a zoom and. Pop in and out throughout the day. I just want your input on this email I'm writing or this proposal I'm putting together. So that was really a huge turning point. Like when we talk about transformations in my career, that was it. And then from there, you know, I was fortunate to get recruited out of that company into Medea.

[00:30:51] Uh, which is, you know, again, big unicorn SAS, SAS company in the bay area with an amazing formal training program for enterprise sellers that I went through. Uh, so that was just, you know, part of that was because of the network I built at the first company. The first startup, uh, helped me get the role at Medallia.

[00:31:08] And again, went through some pretty intensive like sales training, boot camps for the enterprise and got some more formalized sales training behind it. And then that only broadened my network even more. Once I worked at Medallia. And networked with literally hundreds of other enterprise sellers around the country.

[00:31:23] Uh, I now have this like huge network of, of connections in the industry, which is one of the [00:31:28] reasons I started the podcast was I realized I have a massive network and there's a lot of people out there that are crushing it, that don't really have a platform or an audience to talk about their success, but they're literally killing it there.

[00:31:38] Many of them have do multiple seven figures on their W2's, but nobody ever hears about them. Cause they're just a random field sales person at XYZ software company. So I'll stop there. I'm curious if you have any followups. So I, I, so I just want to touch back on like that first sort of transition to like enterprise started to strategic selling.

[00:32:00] Right? So the huge takeaway there that I see is like, look for an opportunity that has leadership. With somebody with a proven track record, right. Like, you know, might be sexy and like, oh, employee number five or one, or, you know, first sales hire, like say I get to build this from the ground up. And that all sounds cool.

[00:32:21] Um, but like really look at like, who are the leaders? Like, have they done something like this before? Like what are you [00:32:27] signing up for? You know, is this going to. Catapult your career or is it gonna, you know, sabotage it, you know? Um, and so, so like being really strategic and thoughtful about like who those people are on that leadership team, and really look for an opportunity if you're like, Hey, I'm trying to get from train away from transactional into more strategic or into enterprise.

[00:32:48] Look for opportunities that are going to provide you like adequate, adequate experience and all that. So I'll now kind of take it more tactical. The big sweeping thing that you can do today. If you're, if you're really serious about breaking an enterprise sales, you know, the first thing to do is get yourself in an environment where you're surrounded by people that are already doing it preferably already successful at it.

[00:33:11] And it's going to put you in this arena where you can keep getting roles. In that category and keep up in your skillset, right? On a more tactical level, we could spend probably the rest of today talking about, you know, being more prepared. So, so there's a huge mental [00:33:26] shift. When you do go from trans, transactional selling to more strategic selling because the skillset goes from.

[00:33:32] You know, energy and aggressiveness and being able to pick up the phone 150 times a day and, you know, spraying and praying to how do I maximize the chance that I'm going to get that next step from this prospect, this executive prospect and my skill set has completely changed over from, you know, smiling and dialing, even though that was the foundation for what I do now.

[00:33:53] Now it's more. How can I tell a great story via a slide deck? Or how can I put together a demo that resonates? How do I go now do research on big companies via their 10 K reports or their shareholder letters, and how can I really dredge up what their pain points are without asking them, Hey, what are your pain points?

[00:34:10] Because you can't do that with an executive. You have to go in and sound educated and intelligent on their business and their industry. And you have to uncover, uh, Compelling events. And what, you know, you'll hear in skip Miller training. If you're familiar with skip Miller is like the [00:34:25] trains, right? All these executives have these certain deadlines.

[00:34:28] Something has to happen before this can happen. And if this doesn't happen, our share price is going to go down and I'm going to get fired, right? So you need to like work backwards and, and you know, another great advice is from seven habits of highly effective people begin with the end in mind. With strategic selling, you have to sort of visualize what the finished state looks like and who might need to be involved and what steps might need to be taken.

[00:34:49] I've been very fortunate, you know, since that first role I've worked with a lot of great managers who had good close plan processes, who've had, uh, you know, who've taught me how to make an org chart in a, in a, you know, mutual milestone plan so that you can be really strategic at the enterprise level.

[00:35:06] You are still selling, but a lot of it's about managing expectations and managing the project because enterprise companies are, they're intentional about their buying and it's a project and a lot of stakeholders are going to be involved. So the skillset turns from, you know, hard closing or persuasive writing or communicating to [00:35:24] Maura.

[00:35:24] How do we get as many people marching in the right direction as possible? And how do I be the hub in this project? And one other big shift that I want to make sure to call out is at a certain point around 20 15, 20 16, my mindset shifted from I'm a sales person. To Ima consultant. And I think this is really huge.

[00:35:44] If you want to get into enterprise and strategic selling is you have to start thinking about yourself as a partner and not as a sales person. And really this at any level of sales is an important skillset, because if you're approaching your prospects from a weakened position of, I'm trying to get your time, I'm trying to get your money.

[00:36:01] They can smell that on you. When you start to approach them as look, I'm a business consultant. Look, I read your last shareholder letter. And I read your quarterly earnings report. And now I know that you guys are working on X, Y, and Z. I just need to know how we can get more specific so I can help you guys solve for X, Y, and Z.

[00:36:18] Then you can take that back to your shareholders next quarter and look like heroes, right? So those are [00:36:23] all the skillsets, but positioning yourself as look, I'm a consultant. I'm not a salesperson. This is a project. I'm a project consultant. Part of it is going to be the commercial aspect to it. We are going to do some paperwork.

[00:36:34] I'm going to ask you to, to, you know, select us as a vendor, but it is it's very strategic and, you know, it does help to kind of begin with the end in mind and plan the whole process. Yeah. Yeah, those are some great tactical things there. I mean, um, just even, you know, approaching your prospects in these business relationships as, as more of an equal, rather than like, I mean, without being cocky, but like, Hey, you need my help more than I need your business, you know?

[00:37:01] Um, and, and so I think those, there's a lot of value in that, but just. Really enjoyed learning more about your story. Tons of great things in here, tons of learning lessons for, for our listeners. Um, any final thoughts, where can people connect? You learn more, all that. Yeah. In terms of final thoughts, some advice that was given to me a few [00:37:22] years ago, when I was starting out in enterprise selling a mentor of mine, another mentor of mine who had done, you know, multiple seven figure W2's said, look, once upon a time I was in your spot.

[00:37:32] The key is just, don't blink. Don't give up, just keep putting one foot in front of the other. And eventually you're going to have a year like that. You know, like some of the years I've had where, you know, you close a massive four or $5 million annual deal, right. Just stick with it. So anyone out there who's listening.

[00:37:46] Who's wondering how to get into that enterprise selling suite. Just keep sticking at it. You know, keep, keep on keeping. Stick with it. And eventually you're going to find yourself an opportunity to, to break in, uh, where can folks find me. So again, I'm the host of the SAS sales players, podcast, whatever platform you're listening to this on right now, you can find me on iTunes, Spotify, audible, all of the major podcasting platforms.

[00:38:09] Uh, and yeah, I hope you'll check out the show it's full of, you know, very tactical and kind of granular tips and tricks for succeeding in your own sales pro. Awesome. Thanks again, [00:38:21] Jessie really appreciate it. If you enjoy today's episode, please write us a review, share the show with your friends. It really does help us out.

[00:38:27] And as always, we're listening for your feedback. Hey, you stuck around that tells me you're serious about your own sales transformation. If you're tired of doing things the old way and want to get started in your journey with other people on the same page. Head over to sales, and crush your numbers on your local.

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