Sales Hustle is now Sales Transformation
Jan. 10, 2022

#225 S2 Episode 94 - A Revenue Leader That Writes Code & Books with Jeremey Donovan

In this episode of Sales Transformation, Collin talks to Jeremey Donovan, Senior Vice President of Revenue for Salesloft, coder, and author of five books that include the immensely successful How to deliver a TED talk and Predictable Prospecting.

Jeremey talks about his sales journey and professes his true love for data crunching and analysis, and wanted to apply analytics to domains that aren't traditionally analytical, and this shows in his journey from semiconductor engineering to marketing and then to sales.

Jeremey's love for learning ultimately led to him authoring a series of business books. Jeremey says that you should write for yourself and enjoy the process first, and don't worry about if it's going to be successful or not. Your book might not be the next Harry Potter, but you should write it anyway.

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  • From semiconductor engineer to serial salesperson
  • Rolling up the sleeves: Moving from Fortune 1000 to smaller companies
  • Smaller companies don't have red tape 
  • Coding on the side and forecasting quotas 
  • You can be a coder and a leader, but it may take some convincing
  • Writing a book is not usually lucrative, but do it anyway


Jeremy: “A cog in the wheel is the wrong way to put it but I felt that way sometimes that I had to stay in my lane very tightly. And then when I got into leadership at those bigger companies, I felt like my whole day was just meetings, this is long before the 'Zoom' world.” 

Jeremy: “One can delegate and code. You can be both. But a lot of companies I've worked in, you're sort of branded and it's hard for people to maintain in their heads that you can both be a great leader and a high impact contributor. It's really hard for people to manage those simultaneous brands.” 

Jeremy: “Know that if you want to be a wicked coder, or hacker, I should say, that may, in weird ways, limit your career opportunities. What's important is to understand what's possible -- that you need to know. And if you're not gonna code, you need to find somebody who can code.” 

Jeremy: "I can't remember the exact statistics but basically you just go in expecting you're gonna lose time and money writing books. I believe the reason you should write, particularly, business non-fiction books is because you're trying to figure something out and you're trying to structure those thoughts and learn and understand and then great if someone else picks it up."

Learn more about Jeremy in the links below:

Also, you can join our community by checking out If you're a sales professional looking to take your career to greater heights, please visit us at and set a call with Collin and Chris.

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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. Very excited today. I've got Jeremy Donovan. He is the SVP of revenue and strategy over at sales loft in his spare time, he has. Five books, including how to deliver a Ted talk and predictable prospecting. Wow. Five books in your spare time.

[00:00:44] That's crazy. Uh, we're going to dig into his story and pull some learning lessons out of there today. Jeremy, how the heck are you doing of doing a reasonably well. The rest of the United States, I'm at the tail end of a very mild case of Cron, but I can't claim people have it much worse than I do. Yeah.

[00:01:02] Yeah, man. Uh, bummer. Um, but I'm glad to hear that. It's not, it's not too bad. That's come across a people have had it and I've heard the same thing. So that's super, super, super mild. Can't again, can't complain. Yeah. Yeah. So take us back a little bit. Where did your. We're going to get into a lot of things, especially like who the heck has, uh, you know, who the heck writes five books in their spare time.

[00:01:25] Right. Um, and you're, you know, you mentioned before we hit record that you really love to dig into data. So we're going to touch on that. Um, but before we do all that, Just take us back a little bit. Where did your sales journey start? Yeah, I guess everyone's a special snowflake. Uh, I have my own special snowflake.

[00:01:43] I actually started my life out as a semiconductor engineer ages and ages ago. Uh, now what is it over? Uh, almost 30 years ago. Um, and I was, it was an engineer for a while semiconductor industry analyst for awhile. And then I, you know, people talk about. The careers kind of changing that they used to careers used to be a ladder or many careers.

[00:02:06] Maybe they still are a ladder is like, you start as an SDR, you become an, a, you become a manager, you become, you know, ultimately an RVP or a CRO, then you rule the world. Right. So I, I didn't, I did not have that progression that was sort of bouncing around. Uh, jungle gym, someone. I, I heard that that metaphor used recently.

[00:02:24] It was jungle gym. So I moved through a lot of product functions, product development, product marketing, product management, some M and a work. And I found what I was chasing was the application of analytics to domains that weren't analytical because I thought that was where I could add value. So I did that first in marketing with marketing made that transformation and I was a COO of a fortune 1000 company.

[00:02:46] And then I decided. I love sales. So I juggled Jim my way, you know, and it wasn't like I could step from fortune 1000 CMO and, uh, you know, fortune 1000 head of revenue strategy and operations just wasn't, wasn't the thing. So I, I needed to build that skill up and I moved out of the fortune 1000 world into much smaller companies and, uh, uh, you know, ultimately found my way over to sales loft, where I've been for the last four years.

[00:03:15] Yeah. So tell me about the, how did you jungle gym, your way from marketing to sales and then even furthermore, like from working from, you know, fortune 1000 to, you know, smaller, you know, kind of more, I guess, maybe startup and, and what was that transition like for you? Yeah. Um, well, all, you know, it's been it's.

[00:03:37] Uh, Rocky at times. Awesome. At times. So from marketing to sales was really, again, this weird thing, which is I went from being a CMO to being a CRO and a smaller company. So I picked up revenue responsibility without ever selling really anything other than mangoes and baseball cards when I was a little kid.

[00:03:57] So I considered myself a bit of like a sales fraud in that respect, but I, I. You know, I, I make up for it by, by, uh, I re I referred to it as out trying to outlearn everybody. Right. I mean, I don't know that I'm going to be successful, but, uh, you know, I don't have my zoom filter on, in the background, but you can sort of see the, you know, see the bookshelf cluttered behind me with a lot of books.

[00:04:20] Um, and I've stopped actually reading paper books. So my Kindle, if Kendall's could be thick, you know, I'm, I'm reading constantly, I'm listening to podcasts, I'm talking to people one-on-one to get deep insights. So yeah, I mean, Th that journey of being able to jump around is really learning, learning, motivated.

[00:04:42] And then to the other part of your question about moving from, you know, fortune 1000 to smaller companies, that's the awesome part, right? Is fortune 1000 companies, right? Like what? I was an individual contributor you're you're, I mean, a cog in the wheel is the wrong way to put it, but I, I felt that way sometimes that I had to stay in my lane very tightly.

[00:05:01] And then when I got into leadership at, at, you know, at those bigger companies, I felt like my whole day was just meetings even before it was this, this is long before the zoom world. Right. As I just sort of sat in meetings all the time and you know, that's okay. I can't complain. Right. I mean, it's a high class problem to have making decisions.

[00:05:19] Um, but what I, what I, I really do love to roll my sleeves up. That's that's like when I enter a flow it's because, um, you know, and I it's, it's a blessing and a curse, like when I enter flow it's because I'm, I'm staring at data, I'm in a spreadsheet. I'm writing code. Like just before this podcast, I was, I was coding in Python.

[00:05:39] So, uh, that sort of thing brings me into a, into a total state of flow. So I love the fact that in these smaller companies, You see a problem, you go fix it, right. And you don't need, you don't have all this red tape people, you know, leadership in smaller companies loves, loves people who get, who roll their sleeves up and get things done.

[00:06:03] So, yeah, that's, that's been. Wow. That was a nice surprise. You're coding in Python as well. Yeah. Well, I've been coding since I was a teenager back before Python probably even exist. So, you know, to me, all these languages are basically are basically the same, but I started in. You know, on Ms. Dawson basic now 35 plus years ago.

[00:06:27] And, uh, th there's, there are very few languages that I haven't touched and I'm a hacker, not a programmer. And the difference as I understand it is I couldn't produce production code. Right. But I could have together most. Most things pretty quickly. What's the use case there? Like what, what is that something you're, you're doing in your free time while you're, you know, maybe writing your next book or is this something that is useful in your role?

[00:06:59] Yeah, I should comment on the free time thing, by the way. And the free time thing, um, just comes from a, like a, I think it's two things. One is, I'm a big fan of this author, Cal Newport. He writes he's actually a computer scientist, but he writes a lot about. Work. And, and he wrote a book called deep work. He wrote a few other books just about, um, sort of how you stay focused and in an era of constant distractions.

[00:07:25] And, uh, so I think, you know, I adhere to some of those principles. I like to refer to my. My like secret weapon is that I, I don't watch television, which makes me a little boring, I guess, in some respects I do like movies. So it's not like I don't like media at all, but, but since I don't watch television, I don't really, you know, like I'm not distracted.

[00:07:45] By media. I limit my social media consumption as well. Someone asked me yesterday if I was on Facebook or Instagram. And I said, no, uh, I'm on LinkedIn, a decent amount. But anyway, so, so yeah, the, the, the coding use case, as you asked, is really around. I mean, it's usually sales related stuff. The stuff I was just working on right now is, is, um, forecasting algorithms.

[00:08:09] So, um, about a year or two ago, I CA like I created the, the forecasting algorithm we use at SalesLoft. Uh, to this day and, and my goal there, or goal there is, is we want to be able to call the quarter within plus or minus 5% while we compare day 15 today, 90. So, um, the reason for, for the day 15 thing, There's like most companies, right?

[00:08:36] The first two weeks of the quarter, we have QPRs and a lot of garbage gets cleaned up during that time. So I don't think it's fair to compare day one to day 90, but I think day 15 to day 90 is a good comparison. So I'm sort of constantly tuning a little bit of how we, of how we execute that algorithm.

[00:08:55] Wow. That's a pretty, that's a pretty bold mission, right? Considering. We've all heard the numbers of how many people are not, not hitting quota. Right. So how do you get forecasting that accurate? Uh, yeah, I mean, that's our goal and we're consistently at the goal, like usually within plus or minus 3%, actually, even when our target, this is a good, like this quarter is a great example we had in the quarter, January 31st, you know, we're recording this in early January and you know, we've been calling a number that is about 44, 0 40% higher than our target.

[00:09:31] And our target was already significantly higher than that last year. So. You know, our, our, our leadership team was sort of look at the number. I was G you know, we were generating with the algorithm early in the quarter, over there saying no way, no way. And then of course, right now we're approaching that in January.

[00:09:48] And it's looking like that call was, was, will end up being like within plus or minus 3%. So the way we do it is, is, uh, there's a few pieces, right? As, as we're triangulating across a few times, Uh, approaches, but that, I would say that the, the two biggest things, one, our w one is we're S we're either stage we're stage waiting in the SMB segment, and then we're forecast category waiting in enterprise.

[00:10:15] And that's really important, right? Because stage stages had to be more accurate when you got a large volume of more transactional deals and yeah. That human forecast category is, is much more valuable, much more useful the enterprise where you've got war more deals, right? So I'm sorry, you got fewer deals, but larger, larger numbers.

[00:10:34] So that tells us the piece, that, of the deals that are already in the pipeline. But the thing is right, as in every, in every business, there's a ton of deals that get created enclosed are pulled forward in the quarter. And I think that's where people miss is that they they're not estimating that accurately.

[00:10:51] And, um, so even at the enterprise, right, where you've got large, long sales cycle deals, um, you also have upgrades that happen faster. So part of the secret sauce in our internal algorithm is that we do, uh, a really wicked job of estimating that we call it run rate. So we do a wicked job of estimating how much business will get created and closed in the quarter in every segment, both new, new business and upgrades.

[00:11:19] Wow. Okay. And how many, I mean, how many companies are, are, are not waiting it in this way? I mean, do you know if anybody else is doing this way? I've talked to, I've talked to like a very, I talked to a lot of rev ops peers. It's one of those, one of the things I love to do, um, so much. So actually I created a, uh, there's not like a selling from the stage because it's completely free, but I created this thing called true peer T R U E P E R a true

[00:11:49] But true peer is it's just like. Um, a way for people to get one-on-one meetings once a month, it's like lunch club, but for, for, you know, sales and revenue professionals totally free. Um, and in fact, that's a money losing endeavor for me because I I'm licensing this platform called orbit. That, uh, I just used to do it and, um, it's my, it's a give back basically, but anyway, I'm talking to Ralph's people all the time and yeah, it's, it's, uh, it's an overwhelming minority.

[00:12:17] I mean, I can only think of one or two or three people I've run across that are that this degree of sophistication that they're applying to their forecasting, plenty of people are stage one. Um, I don't know many that are splitting, like the approach for SMB and enterprise, which I think is critical to accuracy.

[00:12:37] And then I don't know many that, that have this degree of sophistication on, on the run rate estimation. Yeah. Or how many do you know that are writing? Yeah. Not, not, well, you know, the people like, again, I think it's a blessing and a curse, like people ask me, should I learn to code? And my answer is actually I've, uh, there's a, uh, uh, another SalesLoft employee that has become a fast friend.

[00:13:03] And, um, you know, he's probably 20 years, 20 years my junior. And so we're, you know, I'll call it co mentorship, but, but he asked me recently, should I learn to code? And I said, Only learned to code if it's something that you really, that you really want to do, because it actually can be career limiting, right.

[00:13:22] Is, is if you're perceived for better or worse, like if you're perceived as someone who, who, um, one can delegate and code, right? Like you can do both, but a lot of the companies I've worked in the you're sort of branded and it's hard for people to maintain in their heads that you can both be a great leader and be.

[00:13:46] You know, hyper, hyper high impact kind of contributor it's as you know, I think that it's really hard to manage this like simultaneous brands. And I don't even know if it's possible. So anyway, what I, I was giving them this advice. It's like, depends on what you want to do, you know, like know that if you become a wicked coder hacker, I should say then.

[00:14:07] Yeah. Like that, that may, and in weird ways limit your career opportunities. I said, it's, what's important. To understand what's possible that you need to know. And then, um, and then you need to, if, if you're not going to code, you need to find somebody who can code. And I said, you know, for him, he's got me.

[00:14:29] Like he can delegate sort of upwards, I guess, to me, he comes up with brilliant ideas. His name is David Lee bell. Uh, he comes out he's an in. Customer success part of our world. So he like comes up with these brilliant ideas in the customer success world. And, and then I'm like his, I joke, I, his code monkey because I turn his vision into reality.

[00:14:51] I said like, you can continue to operate that way. Right. You know, whether you've got me or you've got contractors or whatever, you just know that need to know the art of the possible. And then go ask someone else to. To go hack. So yeah, there's no, it's really fascinating to me, which is why we've obviously spent a lot of time here because it's very rare that you find a revenue leader that codes and for a SAS company who has coders.

[00:15:15] Right. I mean, like it, yeah. It's very interesting. So, um, what, I'm, what I'm really curious about, um, Uh, and I appreciate that perspective right. Of like, you know, do you want to be, you know, what do you want to be pinned for? It's like the coder or the revenue leader. Right. Um, so I'm, I'm curious about the books you've written, you know, five books over what period of time.

[00:15:40] Um, you know, I don't know if we'll have time to talk about all the books, but maybe the one most recent book or the one you're most passionate about. Just walk us through the journey a little bit. So, um, The I'll start with saying yeah. Over what period of time the, I wrote probably five, five in like five or six years.

[00:15:59] It's probably been a couple of years since I, since I wrote one, although I badly want to write another one on revenue strategy. And a couple of days ago, I was actually trying to bang out the first, the first chapter. Um, I started out by writing a really it's what on reflection is like a terrible book, but I'm very proud of, cause it was the first, the first one.

[00:16:20] And that was basically just, I was, I had moved into, I started to move into leadership and strategy roles and I was learning so fast and I couldn't keep it in my head. So I wrote it down on PowerPoints. What was PowerPoint slides? And I wish I shared it with a few of my colleagues. One of my friends, his name was Matt French, uh, said, Hey, you should really like turn this into book form because not everyone consumes, you know, in PowerPoint form.

[00:16:47] So on his, on his suggestion, I sat down and, you know, Kind of crappy crappy book, but what I'm very proud of because it was something that was like a leave behind for me. And I lost my father when I was a teenager. And I always felt I had this chip on my shoulder that like, I wish I could have had the knowledge, right.

[00:17:08] That, that he had wisdom that he would have imparted on me. So, you know, at the time, like I think I had my, we had our first child and, um, To have a legacy for him just in case it's very morbid, but just in case something happened to me, uh, now we have two, they both refuse to read any of the books because they're too, they're sorta too tactical and boring.

[00:17:29] So yeah, that was the, that was the thing. And then I I'd say that like all the books, um, they are there. I, I wrote like, When they go to write a book, they have this, I think a lot of people have this dream that it's going to be the next Harry Potter, right. That they're going to make money while they sleep.

[00:17:44] And it's passive income and whatever. Um, I can't remember the exact statistics, but basically you should just go in expecting you're going to lose time and money. Right. Um, writing, writing, writing books, the reason you should, I believe the reason you should write particularly non-fiction business nonfiction books is because you're trying to figure for me, it's, you're trying to figure it out.

[00:18:09] And you're trying to structure those, you know, you're trying to structure those thoughts and learn and understand, and then great. If, if like someone else picks it up. Great. And that really was the Genesis of it for me. I mean the most, the most successful of the books was definitely the how to deliver a Ted talk book.

[00:18:26] I was super geeked out about public speaking at the time. And I was watching Ted talks to understand, yes, the messages that were in them, but much more the construction. And the delivery, right. I was much more after that kind of stuff. And because I was deconstructing them for myself, I just said, huh, I recognize a formula in here and I'm going to write that up.

[00:18:50] So that was, um, that one. And then it just happened to be like right at the right time. And, and like, that was the most successful of them, the other ones. So, you know, the more recent, other than the first one, the other ones I've done. Okay. I mean, I'd say the one, um, I don't know. I'm proud of all you asked me, like, what am I most proud of?

[00:19:09] I'm proud of all of them. The, the, my two favorites, I suppose, are a book I wrote with, uh, Aliyah Harbison called leading sales development. And at the same thing, like she's a super expert, um, on that. And I have a decent amount of expertise and I just wanted to synthesize and figure and figure out. So I'm super proud of that.

[00:19:34] And then another one is actually not even under my own name, it's under a pseudonym. Um, it's called strategic storytelling and the pseudonym is Dave McKinsey. And the reason I'm proud of that one is because it's, it's again like a relatively, super tactical thing. But what I find is that there's a lot of books on storytelling that I find to be not so useful.

[00:19:55] And the reason I find them not useful is because they're storytelling books, but they're not business stories. And I wanted, uh, I couldn't find anything on business storytelling, and I really want to do something that was more practical. Um, and particularly like when you get into a meeting with an executive and you're trying to convince them to make a decision, that's a story.

[00:20:16] And that's what that book is about. It's about. Exactly. It's about persuading executives to, to green light ideas. Wow. So it sounds like that what's interesting is that you've not only written all these books, but you know, each of them. A little bit different, right? Like typically when you, you know, maybe say have a revenue leader or sales person that's, you know, written books, they're kind of all sales books.

[00:20:43] Right. But each one has a, is a little bit different. It has a little bit different reason. Um, why do you think the, you know, how to deliver a Ted talk, you know, did so well, what made that book sort of stand out outside of, you know, and then you mentioned the timing a little bit. Um, but why do you think that one was a little bit more successful than say the others.

[00:21:00] Um, you know, I, I reflect a lot on, on, um, you know, how success is traditionally defined and I, I really strongly believe. It's it's timing, which is luck effectively. Uh, there's hard work skill. Yes. Um, and then they help help, help from other people. Right. I mean, but I think those other factors, like luck and help from other people are underestimated by things that, that work out.

[00:21:29] So if I reflect on that particular book, one, people do judge a book by its cover. Right. So that's. Perfect. The cover was perfect as it could be, you know? Um, it was actually the, the original version of it was super short. It was like a hundred pages. And it was at a time when people like wanted to consume much shorter things.

[00:21:52] Um, so that was that inflection, Ted had just taken off right. As I wrote that book. So that was another timing aspect. And then, um, you know, I think the content was. Was not derivative. Like it was really something that didn't didn't exist. So there was some, some meat, uh, underneath and then the help from others.

[00:22:14] Um, Uh, this, this, uh, this, this person who, I mean, I don't think listeners listening to his name, his name is Michael Margolis. He's a, like, he's a storytelling expert. He got ahold of the book and he, he really, he liked it. And I, I didn't know him at the time. And he said, Hey, I have a group of friends. We all get together periodically and sort of, you know, geek out on stuff.

[00:22:39] So, so he says, why don't you come in? And w you know, we'll, we'll like spend half a day or a day going through the stuff. And I look, I look up his group of friends and like the group of friends I'll, I'll maintain their anonymity, but they're basically like mega authors and speakers. And, um, you know, these are people who charge $50,000, a hundred thousand dollars for speaking engagements.

[00:23:07] And. I was, he invited me and I was terrified when I looked at the invite because I figured these people could run circles around me, which they, they, you know, they, they can and did, but like they wanted to go through the, the ideas of the book with a fine tooth comb and then, you know, help of others. So, right.

[00:23:25] So Michael got these people together and then they told their friends. So it was kind of like these things where you, you know, you work so hard to get your, you know, your, your one Z on the baby of the, of the celebrity. And, uh, I just locked, you know, luck. I lucked into that. Um, something you couldn't plan as part of the strategy.

[00:23:49] No way, no way. So that was, yeah. So that was kind of what a lot of factors, but again, like, I almost don't like to tell the story because I want people to know. Just just for themselves. Cause I think that's, that's, it's, it is a labor of love. And if you don't have that mindset, you're going to have a, not as great, not as, you know, positive of an experience before and afterwards, like you'll be disappointed, but I don't think you should be like, I'm I'm as proud of that first book that does not sell as I am with the other books that do.

[00:24:24] Yeah. Yeah. Awesome. Jeremy, this has been incredible learning. Uh, so many interesting things about you and your story and your journey, any final thoughts and kind of just, you know, anything else you want to let folks know and how they can get in touch. Yeah. Um, I mean, I, I'll just summarize final thoughts here.

[00:24:46] You know, one is, is certainly the, you know, right for yourself is, is one another one is, is, think about your career and whether you do the ladder thing or the jungle gym thing. And I think there really is. No, no right here. Um, and then yeah, in terms of like, uh, ways to get in touch with me, LinkedIn is the best way to do it.

[00:25:08] Um, go check out true peer it's free, and it's just a way to connect one-on-one to learn from other. No, no hidden agenda, no hidden agenda there. So yeah, it was, it was a blast chatting. I wish we had more time because we would get into like the other piece of, of what I do, which is a lot of data-driven stuff around yeah.

[00:25:27] Everything to do with sales and revenue. So with more time, we're going to have to, I think we're going to have to have you back for a part two for that. Sweet, sweet. Yeah. I just, I've got some fresh off the presses data on. Unlike whether or not biographical data can predict whether or not an enterprise sales person will be successful.

[00:25:45] So bio data is things like, you know, where they go to school and what degree did they get and how long did they work in their prior job? Do they have winter circle, you know, in their resume, all those kinds of things like sports. Did those things actually matter. And a lot of people have beliefs about that, but data trumps, you know, it data I trust.

[00:26:04] So we could, we can do that next time. Yeah. I love how you gave him a little sneak peek of what, what to expect. You guys are gonna have to stay tuned for part two with Jeremy. Uh, thanks so much for coming on again. Really appreciate it. We're going to drop your LinkedIn in, in the show notes there. Um, and the link for true peer is, well, if you enjoy today's episode, please write us a review.

[00:26:26] Share the show with your friends really does help us out. And we're also listening for your feedback. You can go to sales,, drop me a voice DM, and I will get back to you. Hey, you stopped. 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 path, head over to sales,, and crush your numbers on your leaderboard.

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