Building a Healthier Sales Environment with Ashleigh Early

Episode Summary

Today’s guest works in a world that Corey “got the hell out of” after a brief tenure when he realized he just wasn’t very good at it. That’s why The Duckbill Group hired on Ashleigh Early as their Head of Sales. Ashleigh joined the team about six months ago and since then has only assuaged Corey’s and Co.’s sales needs. Ashleigh breaks down the nuance in enterprise sale, and shares some secret on how does one actually make money in the space. She shares some pet peeves with some of the sales culture, and she addresses some much needed changes within sales culture at large. This includes the need to connect with people, do your research going in, the role of databases, and more! If you want some insight check in on Ashleigh’s take!

Episode Show Notes & Transcript

About Ashleigh
Ashleigh Early is a passionate advocate for sales people and through her consulting, coaching, and The Other Side of Sales, she is devoted to making B2B sales culture more inclusive so anyone can thrive. Over the past ten years Ashleigh has led, built, re-built, and consulted for 2 unicorns, 3 acquisitions, 1 abject failure and every step in between.  She is also the Head of Sales at the Duckbill Group! You can find Ashleigh on Twitter @AshleighatWork and more about the Other Side of Sales at


Announcer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at The Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.

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Corey: Welcome to Screaming in the Cloud. I’m Corey Quinn. My guest today does something that I, sort of, dabbled around the fringes of once upon a time, but then realized I wasn’t particularly good at it and got the hell out of it and went screaming into clouds instead. Ashleigh Early is the Head of Sales here at The Duckbill Group. Ashleigh, thank you for joining me.

Ashleigh: Thanks for coming on and running, screaming from my chosen profession [laugh]. You’re definitely not the only one.

Corey: Well, let’s be clear here; there are two ways that can go because sure, I used to dabble around in sales when I was, basically, trying to figure how to not starve to death. But I also used to run things; it’s basically a smart team. I was managing people and realized I was bad at that, too. So, really, that’s, sort of, an open-ended direction. We can go either side and…

But, let’s go with sales. That seems like a more interesting way for this to play out. So, you’ve been here for—what is it now—it feels like ages, but my awareness for the passing of time in the middle of a global panini is relatively not great.

Ashleigh: Yeah. I think we’re at day—what is it—1,053 of March 2020? So, time is irrelevant; it’s a construct; I don’t know. But, technically, by the Gregorian Calendar, I think I’m at six months.

Corey: It’s very odd to me, at least the way that I contextualized doing this. Back when I started what became The Duckbill Group, I was an independent consultant. It was, more or less, working people I knew through my network who had a very specific, very expensive problem: The AWS bill is too high. And I figured, this is genius. It is the easiest possible sale in the world and one of the only scenarios where I can provably demonstrate ROI to a point where, “Bring me in; you will inherently save money.”

And all of that is true, but one of things I learned very quickly was that, even with the easiest sale of, “Hi. I’d like to sell you this bag of money,” there is no such thing as an easy enterprise sale. There is nuance to it. There is a lot of difficulty to it. And I was left with the, I guess, driving question—after my first few months of playing this game—of, “How on earth does anyone make money in this space?”

The reason I persisted was, basically, a bunch of people did favors for me, but they didn’t owe me at all. It was, “Oh, great. I’ll give them the price quote.” And they’re, like, “Oh, yeah.” So cool, they turned around and quoted that to their boss at triple the rate because, “Don’t slit your own throat on this.” They were right. And not for nothing, it turns out when you’re selling advice, charging more for it makes it likelier to succeed as a project.

But, I had no idea what I was doing. And, like most engineers on Twitter, I look at something I don’t understand deeply myself, and figure, “Oh. Well, it’s not engineering, therefore, it’s easy.” Yeah, it turns out that running a business is humbling across a whole bunch of different axes.

Ashleigh: I wouldn’t even say, it’s not running a business; it’s working with humans. Working with humans is humbling. If you’re working with a machine or even something as simple as, like, you know, you’re making a product. It’s follow a recipe; it’s okay. Follow the instructions. I do A, then B, then C, then D, unless you don’t enjoy using the instructions because you don’t enjoy using instructions. But you still follow a set general process; you build a thing that comes out correctly.

The moment that process is, talk to this person, and then Person A, then Person B, then Person C, then Person D, then Back to Person A, then Person D, and then finally to Person E, everything goes to heck in a handbasket. That’s what really makes it interesting. And for those of us who are of a certain disposition, we find that fascinating and enthralling. If you’re of another disposition, that’s hell on earth [laugh]. So, it’s a very—yeah, it’s a very interesting thing.

Corey: Back when I was independent, and people tried to sell me things—and yeah, sometimes it worked. It was always interesting going through various intake funnels and the rest. And, like, “Well, what role do you hold in the organization? Do you influence the decision? Do you make the decision? How many people need to be involved in the rest?”

And I was looking around going, “How many people do you think fit in my home office here? Let’s be serious.” I mean, there are times I escalated to the Chihuahua because she’s unpleasant and annoying and basically, sometimes so are people. But that’s a separate topic for later. But it became a very different story back as the organizational distance between the people that needed to sign off on a sale increased.

Ashleigh: Mm-hm. Absolutely. And you might have felt me squirm when you described those questions because one of my biggest pet peeves is when people take sales terminology and directly use that with clients. Just like if you’re an engineer and you’re describing what you do, you’re not going to go home and explain to your dad in technical jargon what exactly; you’re going to tell him broad strokes. And if they’re interested, go deeper and deeper; technical, more technical.

I hate when salespeople use sales jargon, like, “What’s your role in the organization? Are you the decision-maker?” Don’t—mmm. There are better ways to deal with that. So, that’s just a sign of poor training. It’s not the sales rep’s fault; it’s his company’s fault—their company’s fault. But that’s a different thing.

It’s fascinating to me, kind of, watching this—what you said spoke of two things there. One is poor training, and two, of a lack of awareness of the situation and a lack of just doing a little bit of pre-work. Like, you do five seconds of research on Corey Quinn, you can realize that the company is ten to 15 people tops. So, it makes sense to ask a question around, “Hey, do you need anyone else to sign off before we can move forward with this project?”

That tells me if I need to get someone for technical, for budget, for whatever, but asking if you’re a decision-maker, or if you’re influencing, or if you’re doing initial research, like, that’s using sales terminology, not actually getting to the root of the problem and immediately making it very clear, you didn’t do any actual research in advance, which is not—in modern selling—not okay.

Corey: My business partner, Mike, has a CEO job title, and he’ll get a whole bunch of cold outreach constantly all day, every day. I conducted a two-week experiment where in front of my Chief Cloud Economist job title, I put ‘CTO/’ just to see what would happen, and sure enough, I started getting outreach left, right, up, down, and sideways. Not just for things that a CTO figure might theoretically wind up needing to buy, but also, job opportunities for a skill set that I haven’t dusted off in a decade.

So, okay. Once people can have something that hits their filters when you’re searching for very specific titles, then you wind up getting a lot more outreach. But if you create a job title that no one sensible would ever pick for themselves, suddenly a lot of that tends to go by the wayside. It shined a light on how frustratingly dreary a lot of the sales prospecting work really can be from—

Ashleigh: Oh, yeah.

Corey: —just from the side of someone who gets it. Now, I’m not exaggerating when I say that I did work in sales once upon a time. Not great at it, but one of the first white-collar-style jobs that I had was telemarketing, of all things. And I was spectacular at it because I was fortunate enough to be working on a co-branded affinity credit card that was great, and I had the opportunity to position it as a benefit of an existing membership or something else people already had. I was consistently top-ten out of 400 people on a shift, and it was great.

But it was also something that was very time-limited, and if you’re having an off day, everything winds up crumbling. And, eventually, I drifted off and started doing different things. But I’ve never forgotten those days. And that’s why it just grinds my gears both to see crappy sales stuff happening, and two, watching people on Twitter—particularly—taking various sales-prospect outreach for a drag. And it’s—

Ashleigh: Oh, God. Yeah.

Corey: —you know, not everyone is swimming in the ocean of privilege that some of the rest of us are. And understand that you’re just making yourself look like a jerk when you’re talking to someone who is relatively early-career and didn’t happen to google you deeply enough before sending you an email that you find insulting. That bugs me a fair bit.

Ashleigh: And I think part of that is just a lack of humanity and understanding. Like, there’s—I mean, I get it; I’m the first person to be jumping on Twitter and [unintelligible 00:08:41] when something goes down, or something’s not working, and saying, you know—I’m the first one to get angry and start complaining. Don’t get me wrong. However, what I think a lot of people—it’s really easy to dehumanize something you don’t see very often, or you’re not involved in directly. And I find it real interesting you mentioned you worked in, you know, doing telemarketing.

I lasted literally two weeks in telemarketing. I full-on rage-quit. It was a college job. I worked in my college donations center. I lasted two weeks, and I fully walked out on a shift. I was, like, “Screw this; I’m never doing anything like that ever again. I hate this.”

But what I hated about it was I hated the lack of connection. I was, like, I’m not just going to read some scripts and get yelled at for having too much banter. Like, I’m getting money; what do you care? I’m getting more money than other people. Maybe they’re not making as many calls, but I’m getting just as much, so why do you care how I do this?

But what really gets me is you have to remember—and I think a lot of people don’t understand how, kind of, most large, modern sales organizations work. And just really quickly giving you a very, very generic explanation, the way a lot of organizations work is they employ something called SDRs or Sales Development Reps. That title can be permeated in a million different ways. There’s ADRs, MDRs, BDRs, whatever. But basically, it’s their job to do nothing but scour the internet using, sometimes, actual, like, scripts.

Sometimes they use LinkedIn; sometimes they have—they purchase databases. So, for example, like, you might change your title on LinkedIn, but it’s not changing in the database. Just trust me Corey, they have you flagged as a CTO. Sorry. What [crosstalk 00:10:16].

Corey: My personal favorite is when I get cold outreach asking me on the phone call about whether we have any needs for whatever it is they happen to be selling at—and then they name a company that I left in 2012. I don’t know how often that database has been sold and resold and sold onwards, yet again. And it’s just, I work in tech. What do you think the odds are that I’m still in the same job I was ten years ago? And I get that it happens, but at some point, it just becomes almost laughable.

Ashleigh: Yeah. If you work in a company—that when in doubt—I tell every sales, kind of, every company team that I work with—do not use those vendors. Ninety percent of them are not very good; they’re using old databases; they don’t update. You’re better off paying for a database that is subscription-based because then, literally, you’ve got an SLA on data quality, and you can flag and get things fixed. The number one sales-data provider, I happen to know for a fact, I actually earned, I think, almost $10,000 in donations to a charity in—what was this—this was 2015 because I went through and did a scrub of are RCRM versus I think, LinkedIn or something else, and I flagged everything that wasn’t accurate and sent it back to them.

And they happened to have a promotion where for every—where you could do a flag that wasn’t accurate because they were no longer at the company. They would donate a buck to charity, and I think I sent them, like, 10,000 or something. [unintelligible 00:11:36] I was like, “None of these are accurate.” And they’re, like, you know? And they sent me this great email, like, “Thank you for telling us; we really appreciate it.”

I didn’t even know they were doing this promotion. They thought I’d be saving up for it. And I was, like, “No, I just happened to run this analysis and thought you’d want to know.” So, subscriptions—

Corey: You know, it turns out computers are really fast at things.

Ashleigh: Yeah, and I was very proud I figured out how to run a script. I was, like, “Yay. Look at me; I wrote a macro.” This was very exciting for—the first—God, the first five or so years of my sales career, I’ve consistently called myself a dumb salesperson because I was working in really super-technical products. I worked for Arista Networks, FireEye, Bromium, you know, PernixData. I was working in some pretty reasonably hard tech, and I’d always, kind of, introduced myself, I definitely talked about my technical aptitude because I have a degree in political science and opera. These are not technical fields, and yet here I am every day, talking about, you know, tech [crosstalk 00:12:25].

Corey: Well, if the election doesn’t pan out the way you want, why don’t you sing about it? Why not? You can tie all these things together.

Ashleigh: You can. And, honestly, there have several points—I’ve done a whole other shows on, like, how those two, seemingly, completely disparate things have actually been some of the greatest gifts to my career. And most notably, I think, is the fact that I have my degree in political science as a Bachelor of Science, which means I have a BS in BS, which is incredibly relevant to my career in a lot of different ways.

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Ashleigh: Yeah, so wrapping up, kind of, how modern-skills organizations work, most companies’ employees can be called BDRs, and they’re typically people who have less than five years of sales experience. They, rightly or wrongly, tend to be people in their early-20s who have very little training. Most people get SDRs on phones within a week, which means—

Corey: These are the people that are doing the cold outreach?

Ashleigh: —they’ve gotten maybe five or six hours of product training. Hmm? Sorry.

Corey: These are the people who are doing the cold outreach?

Ashleigh: These are the people who are doing the cold outreach. So, their whole job is just to get appointments for account execs. Account execs make it—again; tons of different names, but these are the closers. They’ll run you through the sales cycle. They typically have between five and thirty years of experience.

But they’re the ones depending on how big your company is. [unintelligible 00:13:35] the bigger your company, typically the more experience your sales rep’s going to have in terms of managing most separate deal cycles. But what ends up happening is you end up with this SDR organization—this is where I’ve spent most of my career is helping people build healthy sales-development organizations. In terms of this churn-and-burn culture where you’ve got people coming in and basically flaming out because they go on Twitter or—heaven forbid—Reddit and get sales advice from these loud-mouthed, terrible people, who are telling them to do things that didn’t work ten years ago, but they then go try it; they send it out, and then their prospects suddenly blasting them on Twitter.

It’s not that rep’s fault that they got no training in the first place, they got no support, they just had to figure it out because that’s the culture. It’s the company’s fault. And a lot of times, people don’t—there was a big push against this last year, I think, within the sales community against other sales leaders doing it, but now, it’s starting to spread out. Like, I have no problem dragging someone for a really terrible email. Anonymize the company; anonymize the email. And, if you want to give feedback, give it to them directly. And you can also say, “I’m going to post this, but it’s not coming back to you.” And tell them, like—

Corey: Whenever I get outreach from—

Ashleigh: “Get out of that terrible company.”

Corey: Yeah. Whenever I get outreach from AWS for a sales motion or for recruiting or whatnot. I always anonymize the heck out of the rep. It’s funny to me because it’s, “Don’t you know who I am?” It is humorous, on some level. And it’s clear that is a numbers game, and they’re trying to do a bunch of different things, but a cursory google of my name would show it. It’s just amusing.

I want to be clear that whenever I do that, I don’t think the rep has done anything wrong. They’re doing exactly what they should. I just find it very funny that, “Wait, me? Work at an AWS? The bookstore?” It seems like it would be a—yeah. Yeah, the juxtaposition is just hilarious to me. They’ve done nothing wrong, and that’s okay. It’s a hard racket.

I remember—at least they have the benefit over my first enterprise sales job where I was selling tape drives into the AS/400 market, competing against IBM on price. That was in the days of “No one ever gets fired for buying IBMs.” So, yeah. The place you want to save money on is definitely the backup system that’s going to save all of your systems. I made one sale in my time there—and apparently set a company record because it wasn’t specifically aimed at the AS/400—and I did the math on that and realized, “Huh, I’d have to do two of these a month in order to beat the draw against commission structure that they had.”

So, I said, “To hell with this,” and I quit. The CEO was very much a sales pro, and, “Well, you need to figure out whether you’re a salesperson or not.” Even back then, I had an attitude problem, but it was, “Yeah, I think that—oh, I know that I am. It’s just a question is am I going to be a salesperson here?” And the answer is, “No.” It [laugh]—

Ashleigh: Yeah.

Corey: It’s a two-way street.

Ashleigh: It is. And I say this all the time to people who—I work with a lot of salespeople now who are, like, “I don’t think sales is for me. I don’t know, I need [unintelligible 00:16:24]. The past three companies didn’t work.” The answer isn’t, “Is sales for you?”

The answer is, “Are you selling the right thing at the right place?” And one of the things we’ve learned from the ‘Great Recession’ and the ‘Great Reshuffling’ in everything is there’s no reason to stay at a terrible company, and there’s no reason to stay at a company where you’re not really passionate and understand what you’re selling. I joked about, you know, I talked down about myself for the first bit of my career. Doesn’t mean I didn’t—like, I might not understand exactly how heuristics work, but I understand what heuristics are. Just don’t ask me to design any of them.

You know, like, you have to understand and you have to be really excited about it. And that’s what modern sales is. And so, yes, you’re going to get a ton of the outreach because that’s how people—it still works. That’s why we all still get Nigerian prince emails. Somebody, somewhere, still clicks those things, sadly. And that gets me really angry.

Corey: It’s a pure numbers game.

Ashleigh: Exactly. Ninety percent if enterprise B2B sales is not that anymore. Even the companies that are using BDRs—which is most of them—are now moving to what’s called ‘account-based selling’. We’re using hyper-personalized messaging. You’re probably noticing videos are popping up more.

I’m a huge fan of video. I think it’s a great way to force personalization. It’s, like, “Hi. Corey, I see you. I’m talking to you. I’ve done my research. I know what you’re doing at The Duckbill Group and here’s how I think we can help. If that’s not the case, no worries. Let me know; I’ll leave you alone.” That’s what selling should be.

Corey: I have yet to receive one of those, but I’m sure it’ll happen now that I’ve mentioned that and put that out into the universe.

Ashleigh: Probably.

Corey: What always drove me nuts—and maybe this is unfair—but when I’m trying to use a product, probably something SaaS-based—and I see this a lot—where, first, if you aren’t letting me self-serve and get off with the free tier and just start testing something, well, that’s already a ding against you because usually I’m figuring this out at 2 o’clock in the morning when I can’t sleep, and I want to work on something. I don’t want to wait for a sales cycle, and I have to slow things down. Cool. But at some point, for sophisticated customers, you absolutely need to have a sales conversation. But, okay, great. Usually, I encounter this more with lead magnets or other things designed to get my contact info.

But what drives me up a wall, when they start demanding information that is very clearly trying to classify me in their sales funnel, on some level. I’ll give you my name, my company, and my work email address—although I would think that from my work email address, you could probably figure out where I work and the rest—but then there are other questions. How big is your company? What is your functional role within the company? And where are you geographically?

Well, that’s an interesting question. Why does that matter in 2022? Well, very often leads get circulated out to people based upon geography. And I get it, but it also frustrates me, just because I don’t want to have to deal with classifying and sorting myself out for what is going to be a very brief conversation [laugh] with a salesperson. Because if the product works, great, I’m going to buy. If it doesn’t work, I’m going to get frustrated and not want to hear from you forever.

Which gets to my big question for you—and please don’t take the question as anything other than the joking spirit in which it’s intended—but why are so many salespeople profoundly annoying?

Ashleigh: I would—uh, hmm.

Corey: Sales processes is probably the better way to frame it because—

Ashleigh: I was going to say, “Yeah, it’s not the people; it’s the process.” So—

Corey: —it’s not the individual’s fault, as we’ve talked about it.

Ashleigh: —yeah, I was going to say, I was, like, “Okay, I think it’s less the people; more of the processes.” And processes that will make [crosstalk 00:19:37]—

Corey: Yeah. It expresses itself as the same person showing up again and again. But that is not—

Ashleigh: Totally.

Corey: —their fault. That is the process by which they are being measured at as a part of their job. And it’s unfair to blame them for that. But the expression is, “This person’s annoying the hell out of me, what gives?”

Ashleigh: “Oh, my gosh. Why does she keep [unintelligible 00:19:51] my inbox? Leave me alone. Just let me freaking test it.” I said, “I needed two weeks. Just let me have the two weeks to freaking test the thing. I will get back to you.” [unintelligible 00:19:58] yeah, no, I know.

And even since moving into leadership several years ago, same thing. I’m like, “Okay, no.” I’ve gotten to the point where I’ve had several conversations with salespeople. I’m like, “I know the game. I know what you’re trying to do. I respect it. Leave me alone. I promise I will get back to you, just lea”—I have literally said this to people. And the weird thing is most salespeople respect that. We really respect the transparency on that.

Now, the trick is what you’re talking about with lead capture and stuff like this, again, it comes down to company’s design and it comes down to companies who value the buyer experience and customer journey, and companies who don’t. And this, I think, is actually more driven by—in my humble opinion—our slightly over-reliance on venture capital, which is all about for a gathering of as much data as possible, figuring out how to monetize it, and move from there. In their mind, personal experience and emotion doesn’t really factor into that equation very much, so you end up with these buyer journeys that are less about the buyer and more about getting them from click to purchase as efficiently as possible in terms of company resources, which includes salespeople time. So, as to why you have to fill out all those things, that just to me reeks of a company that maybe doesn’t really understand the client experience and probably is going to have a pretty, mmm, support program as well, which means the product had better be really freaking good for me to buy it.

Corey: To be clear, at The Duckbill Group, we do not have a two-in-the-morning click here and get you onboarded. Turns out that we have yet to really see the value in building a shopping cart system, where you can buy, “One consulting please,” and call it good. We’re not quite at the level of productizing our offering yet and having conversations is a necessary part of what we do. But that also aligns with our customer expectation where there is not a general expectation in this industry that you can buy a full-on bespoke consulting engagement without talking to a human being. That, honestly, if someone trying to sell someone such a thing, I would be terrified.

Ashleigh: Yeah, run screaming. Good Lord. No, exactly. And that’s one of the reasons I love working with this team and I love this problem is because this isn’t a quick, you know, download, install, and save, you know, save ten percent on your AWS bill by installing Duckbill Group. It ain’t that simple. If it were that simple, like, AWS wouldn’t have the market cap it does.

So, that’s one of the things I love. I love really meaty problems that don’t have clean answers, and specifically have answers that look slightly different for everybody. I love those sort of problems. I’ve done the highly prioritized stuff: Click here, buy, get it on the free tier, and then it’s all about up-sale, cross-sale as needed. Been there, done that; that’s fun, and that’s a whole different bucket of challenges, but what we’re dealing with every single day on the consulting’s of The Duckbill Group is far more nuanced and far more exciting because we’re also seeing some truly incredible architecture designs. Like, companies who are really on the bleeding edge of what they’re doing. And it’s just really fun—

Corey: Cost and architecture are the same thing in the Cloud.

Ashleigh: —[crosstalk 00:22:59] that little—

Corey: It’s a blast to see it.

Ashleigh: It’s so much fun. It’s, it’s, it’s… the world’s best jigsaw puzzle because it covers, like, every single continent and all these different nuances, and you got to think about a ‘ephemerality,’ which is my new favorite word. So…

Corey: It’s fun because you are building a sales team here, which opens up a few interesting avenues for me. For one, I don’t have to manage and yell at individual salespeople in the same way. For example, we talk about it being a process and not a person thing. We’re launching some outbound sales work and basically, having the person to talk to about that process—namely you—means that I don’t need to be hovering over people’s shoulders the way I felt that I once did, as far as what are we sending people? These passive-aggressive drip campaigns of, “Clearly, you don’t mind lighting money on fire. If that changes, please let me know.”

It’s email eight in a sequence. It’s no. This stuff has an implicit ‘Love, Mike and Corey’ at the bottom of everything that comes out of this company, and it represents us on some respect. And let’s be clear, we have a savvy, sophisticated, and more-attractive-than-the-average audience listening to all of these shows. And they’ll eat me alive if we start doing stuff like that—

Ashleigh: Oh, yeah.

Corey: —not to mention that I find it not particularly respectful of their time and who they are. It doesn’t work, so we have to be very conscious of that. The fact that I never had to explain that concept in any depth to you made bringing you in one of the easiest decisions we’ve ever made.

Ashleigh: Well, I think it helped—I think in one of my interviews I went off on the ‘alligator email,’ which is this infamous email we’ve all gotten, which is basically, like, you know, “Hi. I haven’t heard from you yet, so I want to know which one of these three scenarios has happened to you. One, you’re not interested in my product but didn’t have the balls to email me and say that you’re not interested. Two, you’re no longer in this position, in which case, you’re not going to read this email anyway. Or three, you’re being chased by an alligator, and I should call animal control because you need help.” This email was—

Corey: He, he, he, hilarious.

Ashleigh: Ugh. And there’s variations of it. And I’ve seen variations of it that are very well done and are on brand and work with the company. I’ve seen variations that could be legitimately, I think, great humor. And that’s great.

Humor in emails and humor in sales is fantastic. I have to shout out my friend, Jon Selig up in Canada, who actually, literally, does workshops on how sales teams can integrate humor into their prospecting. It’s freaking brilliant. But—

Corey: Near and dear to my heart.

Ashleigh: —if you’re not actually trained in that stuff, don’t do it. Don’t do the alligator email. But I think I went off on that during one of our interviews just because I was just sick of seeing these things. And what kills me, again, it comes back to the beginning, is people who have no training, no experience coming in—I mean, it really kills me, too, because there’s a real concerted effort in the sales community to get more diverse people into sales to, kind of, kill the sales bro just by washing them out, basically. And so, we’re recruiting hard with veterans, with black and other racial minority groups, LGBTQ communities, all sorts of things, and indigenous peoples.

And so, we’re bringing people that also are maybe a little bit more mature, a little bit older, have families they’re supporting, and we’re throwing them in a role with no support and very little training. And then they wash out, and we wonder why. It’s, like, well, maybe because you didn’t—it’s, like, when I explain this to other people who aren’t in sales, like, “Really, imagine coming in to being hired for a coding job, being told you’re going to be trained on, you know, Ruby on Rails or C# or whatever it is we’re currently using”—my reference is probably super outdated—but then, being given a book, and that’s it. And told, “Learn it. And by the way, your first project is due in a month.” That’s what we’re doing in sales—

Corey: For a lot of folks, that’s how we learned in the engineering spaces, but let’s be clear, the people who do well in that, generally have tailwinds of privilege at their back. They don’t have headwinds of, “You suck at this.” It was, you’re-born-on-third-you-didn’t-hit-a-triple school-of-thought. It’s—

Ashleigh: Yeah.

Corey: —the idea of building an onboarding pipeline, of making this stuff more accessible to people earlier on is incredibly important. One of my, I guess, awakening moments as we were building this company was it turns out that if you manage salespeople as if they were engineers, it doesn’t go super well. Whereas, if you manage engineers like they’re salespeople, they quit—rage quit—cry, and call you out as being an abusive manager.

One of the best descriptions I ever heard from an advisor was that salespeople are sharks. But that’s not intended to be unkind. It is simply a facet of their nature. They enjoy the hunt; they enjoy chasing things down, and they like playing games. Whereas, as soon as you start playing games with your engineers on how much money they’re going to make this week, that turns out to be a very negative thing. It’s a different mindset. It’s about motivating people as whatever befits what it is that they want to be doing.

Ashleigh: It is. And the other thing is it’s a cultural conditioning. So, it’s really interesting to say, you know, “People,” you know, “Playing games.” We do enjoy—there’s definitely some enjoyment of the competition; there’s the thrill of the hunt, absolutely, but at the same time, you want your salespeople to quit? Screw with their money.

You screw with their money; we will bail so fast it’ll make your head spin. So, it’s like, people think, “Oh, we love this.” No, it’s really more—think of it as we are gamblers.

Corey: Yeah. To be clear when I say, “Playing games with money,” I’m talking about the idea of, “Sell to a company in this profile this quarter, and we’ll throw a $5,000 bonus your way,” or something like that. It is if the business wants to see something, great, make it worth the sales team’s while to pursue it, or don’t be surprised when no one really cares that much about those things—

Ashleigh: Exactly.

Corey: It’s all upside. It is not about, “He, he. And if you don’t sell to this weird thing that I can’t really describe effectively to you, we’re going to cut your bet—” Yeah, that goes over like a lead balloon. As it should. My belief is that compensation should always go up, not down.

Ashleigh: Yeah. No, it should. Aside from that, here’s a fun stat—I believe this came out of Forrester, it might’ve been out of [Topel 00:28:54]; I apologize, I don’t remember exactly who said this, but a recent study found that less than 68 percent of sales reps make their quota every month. So, imagine that where if you’re—we have this thing called OTE, which is On Target Earnings. So, if you have this number you’re supposed to take home every month, only 68 percent of sales reps actually do that every month.

So, that means we live with this number as our target, but we’re living and budgeting anywhere from 30 to 50 percent below that. And then hoping and doing the work that goes in there. That’s what we’ve been conditioned to accept, and that’s why you end up with sales reps that use terms like ‘shark’ and are aggressive and are in your face and can get—[unintelligible 00:29:30]—

Corey: I didn’t realize it was pejorative.

Ashleigh: I know. No. But here’s the thing too, but somebody called it ‘commission breath,’ which I love. It’s, like, you can smell commission breath coming off us when we’re desperate. You totally can. It’s because of this antiquated way of building commissions.

And this is something that I—this was really obvious to me, and apparently, I was a little bit ahead of the curve. When I started designing comp plans, everyone told me, “You want to design a comp plan? Tie it to what you want them to do very specifically.” So, if you want them to move a pen, design a comp plan that they get a buck when they put the pen from the heel of your hand to the tips of your fingers. Then they get a buck. And then they can do that repeatedly. That’s literally how I was taught design comp plans.

In my head, that meant that I need to design it in such a way that it’s doable for my team because I don’t want my team worrying about how they’re going to put food on the table while they’re talking to a client because they’re going get commission breath and it’ll piss off the client. That’s not a good client experience; that’s not going to lead to good performance. Apparently—

Corey: Yeah. My concern as a business owner has nothing to do with salespeople making too much money. In fact, I am never happier than I am than paying out commissions. The concern, then, therefore has to become the, “Okay, great. How do I keep the salespeople from being inadvertently incentivized to sell something for $10 that costs me $12 to fulfill?”

It’s a question of what behaviors do you incentivize that align what they’re motivated by with what the company needs. And very often getting that wrong—which happens from time to time—is not viewed as a learning experience that it should be. But instead, “They’re just out to screw us.” And I’ve seen so many company owners get so annoyed whenever their salespeople outperform. But what did you expect? That is the positive outcome. As opposed to what? The underperforming sales rep that can’t close a deal? Please.

Ashleigh: Well, no. And let’s think about this too, especially if it’s tied to commission and you’re paying out commission. It’s, like, okay, commission is always some, sort of, percentage—depending on a lot of things—but some sort of percent of what they’re bringing in. If you design a comp plan that has you paying out more in commission than the sales that were earned to bring it in, that’s on you; you screwed up. And you need to either be honest and say, “I screwed up; I can’t pay this,” and know that you’re going to lose some sales reps, but you won’t lose as many as if you just refuse to pay it.

But, honestly, and I’m not even kidding, I know people. I’ve worked at a company that I happen to know did this. That literally fired people because they didn’t have the money to pay out the commission. And because they fired them before the commission was due to be paid out, then that person no longer had a legal claim to it. That’s common. So, the commission goes both ways.

Corey: To be clear, we’ve never done that, but I also would say that if we had, that’s a screaming red flag for our consultancy, given the nature of what it is that we do here. It turns out that when we’re building out comp plans, we model out various scenarios. Like, what is the worst way that this could wind up unfolding? And, okay, some of our early drafts it’s, yeah, it turns out that we would not be able to pay salaries because we wound up giving all of that in commission to people with uncapped upside. Okay, great.

But we’re also not going to cap people’s commissions because that winds up being a freaking problem, so how do we wind up motivating in a way that continues to grow and continues to incentivize the behaviors we want? And it turns out it’s super complicated which why we brought you in. It’s easier.

Ashleigh: Yeah, it’s a pain. But the other side of this too, I think, is there is another force at play here, which is finance. A lot of traditional finance modeling is built around that 50 to 70 percent of people hit commission. So, if all of the sudden, you design a comp plan such of a way that a hundred percent of the team is hitting commission, finance loses their shit. So, you have to make sure that when you’re designing these things, one of the things I learned, I learned the hard way—this is how I learned that not everyone does it this way—I built my first comp plan; my team’s hitting it.

My team’s overperforming, not a ton, but we’re doing really well. All of the sudden, I’m getting called to Finance and getting raked over the coals. And they’re like, “What did you do?” I’m like, “What do you mean what did I do? I designed a comp plan; we’re hitting goal. Why are you mad?” “Well, we only had this much budgeted for commission.”

And I was, like, “That’s not my fault.” “Well, that’s what historic performance was.” “Okay, well that’s not what we’re going to do going forward. We’re going to do this.” And they’re like, “Oh, well, you need to notify us if you’re going to change it like that.” And I was, like, “Wait a minute. You modeled so that my team would not hit OTE?” “Yes.” “That’s how you’ve always done this?” “Yes.” “Okay. Well, that’s not what we’re going to do going forward, and if that’s a problem, I’ll go find a door.” Because, no.

Especially when we’re talking about people who are living in extremely expensive areas. I spent most of my career living and working in San Francisco, managing teams of people who made less than six figures. And that’s rough when you’re paying two grand in rent every month. And 60 percent of your pay is commission. Like, no. You need to know that money’s coming.

So, I talk about modern sales a lot because that’s what I’m trying to use because there’s Glengarry Glen Ross, kind of, Wolf of Wall Street school, which is not how anyone behaves anymore, and if you’re in an environment that’s like that or treats your salespeople like that? Please leave. And then you’ve got modern sales, which is all about, “Okay, let’s figure out how we can set up our salespeople to be the best people they can be to give our clients the best experience they can.” That’s where you get top performance out of, and that’s where you never run into the terrible emails with the alligators, and the, “Clearly you like lighting piles of money on fire.” That’s where you don’t get emails to Corey Quinn asking him if he’s interested in coming to work for AWS, the book company.

It’s by incentivizing the people and creating good humans where they can really thrive as salespeople and as people in general. The rest comes with time. But, it’s this whole, new way of looking at things. And it’s big, and it’s scary, and it costs more upfront, but you get more on the back end every single time.

Corey: Not that you care about this an awful lot, but you have your own podcast that talks about this, The Other Side of Sales. What inspired you to decide, not just to build sales teams through a different lens, but also to, “You know what? I’m going to go out and talk into microphones through the internet from time to time.” Which, let’s be clear, it takes a little bit of a certain warped perspective. I say this myself, having done this far too often.

Ashleigh: Yeah. No, it’s a fun little origin story. So, I’m a huge Star Trek geek; obsessive. And I was listening to a Star Trek podcast run by a couple of guys who are a little bit embarrassed to run a Star Trek podcast, called The Greatest Generation. Definitely not safe for work, but a really good podcast if you’re into Star Trek at all.

And they always do, kind of, letters at the end of the shows. And one of the letters at the end of the show one day was, “Hey, I was really inspired by you guys and I started my own podcast on this random thing that I am super excited about.” And I’m literally driving in the car with my husband, and I’m, like, “Huh. I don’t know why I’m not listening to sales podcasts. I listen to enough of these other random ones.” Jumped online, pulled up a list of sales podcasts, and I think I went through three or four articles of, like, every sales podcast that was big. And this was, like, January of 2019.

Corey: “By Broseph McBrowerson, but Everyone Calls Him ‘Browie.’” Yeah.

Ashleigh: Literally, there was, Conversations with Women in Sales with the late, great—with the amazing Lori Richardson, who’s now with it, but she took over for a mentor of mine who passed in 2020, sadly. But there was that, and then there was one other that was hosted by a husband-and-wife team. And that was it out of, like, 30 podcasts. And [laugh] so it was this moment of, like, epiphany of, like, “I can start my own podcast,” and, “Oh, I probably need to,” because, literally, no one looks or sounds like someone who I would actually want to hang out with ever, or do business with, in a lot of cases. And that’s really changed. I’m so grateful.

But really, what it came down to was I didn’t feel there was a podcast for me. There wasn’t a podcast I could listen to about sales that could help me, that I felt like I identified with. So, I was, like, “All right, fine. I’ll start my own.” I called up a friend, and she was, literally, going through the same thing at the same time, so we said, “Screw it. We’ll do our own.”

We went full Bender from Futurama. We’re like, “Just screw it; we’ll have our own podcast… with liquor… and heels… and honest conversations that happens to us every day,” and random stuff. It’s a lot of fun. And we’ve gone through a few iterations and it’s been a long journey. We’re about to hit our hundredth episode, which is really exciting.

But yeah, we’re—The Other Side of Sales is on a mission to make B2B sales culture truly inclusive so everyone can thrive, so, our conversations are all interviews with amazing sales pros who are trying to do amazing things and who are 90—I think are over 90 percent—are from a minority background, which is really exciting to, kind of, try and shift that conversation from Broseph McBrowerson. Our original tagline was the ‘anti-sales bro’ podcast, but we thought that was a little too antagonistic. So…

Corey: Yeah, being a little too antagonistic is, generally, my failure mode, so I hear you on that. I really want to thank you for taking so much time out of your day to speak with me. Because—well, not that I should thank you. It’s one of those, I should really turn around and say, “Wait a minute. Why aren’t you selling things? Why are you still talking to me?” But no—

Ashleigh: No, I’m waiting for you to say, “Back to work.”

Corey: Do appreciate your—exactly. I think that’s a different podcast. Thank you so much for your time. If people want to learn more, where’s the best place to find you?

Ashleigh: Well, definitely please go check out We would love to talk to with you about anything to do with your AWS bill. Got a ton of resources on there around how to get that managed and sorted.

If you’re interested in connecting with me you can always hit me up at—I’m on Twitter @ashleighatwork, which is another deep-cut Star Trek reference, or you can hit me up at LinkedIn. Just search Ashleigh Early. My name is spelled a little weird because I’m a little weird. It’s A-S-H-L-E-I-G-H, and then Early, like ‘early in the morning.’

Corey: And links to all of that will wind up in the [show notes 00:39:11]. Thanks so much for your time. It’s appreciated.

Ashleigh: This has been fun; we’ll do it again soon.

AndIf your AWS bill keeps rising and your blood pressure is doing the same, then you need The Duckbill Group. We help companies fix their AWS bill by making it smaller and less horrifying. The Duckbill Group works for you, not AWS. We tailor recommendations to your business and we get to the point. Visit to get started.

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