Come face-to-face with the dark side of sales. These are 10 confessions from a quota-carrying President's Club member at a publicly-traded SaaS company. 

A colleague of our office is an experienced sales representative for a major company. He lives in a beautiful East Coast city and, at age 27, is already making in excess of six-figures at his job. And yet, he absolutely cannot stand his current position. 

In Predictable Revenue and many other sales management books, experts discuss the importance of motivating sales reps beyond mere compensation. My colleague is ready to leave his job the second he has a better offer, despite making great money, because of the toxic culture in which he works.

Welcome To The Machine

The following is a chronicling of confessions taken from my colleague. To protect both the innocent and the guilty, the names and some other minor details of the following accounts have been omitted or altered. 

Confession 1. Our Approach to Sales Cycles Destroys Deals


"It was the only sweet thing in my life."

Before I start, don't get me wrong, I take full, ultimate responsibility for whether I succeed or fail at my job. But I've been in this wheat thresher of a company for five-years, longer than 99 percent of the people that come through can make it. I just have a lot to get off my chest.

Now, let’s talk about sales cycles. We have a very specific sales cycle we have to follow, which takes tons of time and involves tons of analysis, communication, getting and giving feedback, meetings, etc.

So the goal is to follow the specific sales process every time, but the harsh reality is that a lot of the deals you’re working on can get thrown off the path. So we constantly examine how to attack that problem when it happens.

And we meet with our managers, who have, say 12 or more sales reps working on 4 deals a week. That manager has 48 potential deals, he isn’t worried about churning and burning through those. Well I have 4 deals and that’s it, so yeah I’m very worried about not churning and burning.

But then these guys always tell me, call the CFO, call the CEO, go over the head of the person you are meeting with. They want these radical aggressive approaches that oftentimes can kill the deal, especially when the person I am working with is on my side and wants me to get the deal just as bad as I do.

I can’t tell you how many times I’ve worked to develop a relationship with my point of contact in a company I’m trying to sell to, am forced to go over his head to the C-Level, and then have the P.O.C. call me, furious, and tell me never to call his office again.

We’re talking countless times. I think a lot of times managers give bad advice about how to speed up a sales process because they’re not as worried about the churn and burn as the sales reps, they are worried about hitting their number.

Confession 2. Our Company Sets Unrealistic Expectations.

"The Matrix is a system, Neo."

From a management standpoint, I’m blessed in that I do not have a micro-manager. But here’s how our quota works: they purposefully make the quota unrealistic so you’re pretty much always gonna be under it, so if you’re not performing well, they have a reason to write you up and eventually fire you.

Like, we’re supposed to have at least 8-12 meetings a week, which is a very high number. So think about it this way, I’m supposed to have 8 meetings a week, and I have 80 companies in my CRM. If I met that quota every week, I would be out of companies in 3 months.

Which frequently leads to this awesome scenario: So I might have 4 meetings on the board that I have made throughout the week for the future. On Friday afternoon, my manager comes up to me and sternly goes, “D.S.R., I see that you only have 4 meetings on the board [pause] -- you’re supposed to have 8."

And then you have to be careful with how you respond, because you have to protect company culture and be positive. So when the manager asks me that -- and I’m out in the public, out in the open--I literally have to basically hang my head and humbly respond, “I guess I have to work harder.”

Which is a hilarious idea in itself. [Sarcastically] “I guess I have to spend more than 16 hours next week cold calling companies.”  I have days where I cold call for six hours and I will never get anybody on the phone, I will only get voicemails. And there will be days where I send out 150 prospective emails trying to get meetings, and I’ll maybe get one meeting. And it’s a numbers game, but sometimes they just don’t answer. I can only control my effort and what happens when I get someone on the phone.

So the hilarious thing will be, in a week like this, that I’ll go meet with my manager behind closed doors and tell him all this, you know, about the impossibility of the math behind the quota, and how I just couldn’t get through to anybody, and he will totally understand and agree with me. “I know, I know D.S.R.”

But then out in the bullpen, it’s “D.S.R., you’re under expectations, if this happens again next week you’re going to get written up.” And it’s just this 180 degree difference from what he says to me when no one else is watching. It’s this completely artificial persona not just from him, but from me, too.

We are literally having this totally Orwellian experience on a semi-regular basis, which I guess could be funny, except that it’s involving potential discipline and my subsequent termination from my job.

There’s a big difference between being optimistic and unrealistic, and I just think that that so many of the expectations set out for us are unrealistic. And it’s not that I’m negative, I’m just a realist. And realistically, if I meet my goals every single week, I’m out of companies. But it’s set up for you to fail.

Even better, I am in a small market but we have the same expectations as the rest of the country. We have offices in bigger markets and they have the same freaking quotas that we do. So this means I have 80 companies in my target market and another rep in another office has 180. Yet, we are judged by the exact same metrics. How fair is that? On the surface level you have to support it, but on the back end everyone knows that it’s b.s.

Confession 3. Most of My Clients Hate Me, But I Hate Them More


"I have to fill out a form."

By my estimates, in one out of every three meetings that I have, I really dislike most of the people that I’m meeting with, and they dislike me. All day long people tell me, "look we’re not interested in meeting with you." And I try to get the first meeting, where I get as much information from them about their company, and then give as little info as I can about my company. Then, I level set and show that I’m an expert in their field. Then I get the second interview.

So I’m surrounded by these East Coast Ivy-League CFO-types with this good ol' boy network, and there’s this aluminum company CFO who would always would tell me in this big dumb New Yawk accent, "well just give me the proposal and we’ll go from there." In the very first meeting and every time I would talk to him afterwards.

And you never give them the proposal until right up just before they’re about to sign the deal. And I’m very used to that, but  this jabroni was very rude, wasting my time, and essentially he was like, "look, either get me a proposal or you’re never coming back."

So I’ve got to do a very deep analysis in order to create the proposal, but this dude wouldn’t give me the information I needed to make it. So I drew one up and I literally had no clue, essentially had to guess all the critical metrics that would’ve gone into it. What I gave him could have been perfectly accurate or complete BS. I had no clue.

I send it to him out of my better judgement and then he doesn’t even call me, but emails me the most over-the-top, rude thing ever. This guy was furious that the information I had put in the poposal was wrong. Well, "hey idiot, it’s wrong bcause you wouldn’t give it to me!" And he sent it to me at 8:30 on Friday night, which I’m pretty sure he did on purpose, just to try to ruin my evening. I didn't get a deal and wasted hours and hours of my time. That email ruined my weekend.

Confession 4. Our Alleged Company Culture is a Cruel Joke

"You think you're really pretty?"

In the office, when we’re all in there together, there’s this fake idea that we’re all on the same page. But then you go to lunch with 2 or 3 reps, and they’re all sittin’ there bitching.

The most tenured sales rep is this woman who is a badass, but is also the most selfish person in the whole entire office. She’s all about her, she doesn’t care about anyone else, but she kills it at what she does.

So her mindset is--"is this gonna be good for me?" Nope? Then I’m not going to give a damn about it. Excellent sales rep, terrible team player. And she sets the tone for the rest of the office. It's like being back in the day, and you're on a baseball or football team where Barry Bonds or T.O. is your best player.

There's a trickle-down effect of selfishness and pettiness.

Confession 5. Our Sales Team Environment: The Hunger Games


"May the odds be ever in your favor." 

In our company, they basically give you 10 months to prove yourself when you first come onboard. If 10 months pass and you haven’t done something significant yet, you’re fired.

Of the 35 people we lost from my initial team, I think 30 were gone in the first 10 months. That’s kind of how it works, we hire a huge new sales force once a quarter, and only 1 or 2 of them usually last. So it’s kind of hard to build team culture when your entire office feels like they’re participants in the Hunger Games.

This applies even to someone like me, who has been at the company for years. I just had a great past few months, but I still know that I am only two bad months away from going from the top of the roller coaster to the bottom. So when they release all these new trainees into the company and expect us to just welcome them all in with open arms--it's kind of hard to be too enthusiastic.

It's like getting attached to a goldfish your mom buys you from a fair--what's the point? You're going to be flushing that thing down the toilet before you know it.

Confession 6. We Hire People Who Are the Easiest to Brainwash

"A little bit of the old ultra-violence." 

We typically hire people that don’t have a lot of experience because they are substantially easier to mold and brainwash. They come in believing that every sales force is like this.

I’ve had reps in my office that have gotten fired by my company but are killing it now that they've joined one of our competitors--which is actually illegal because we have a non-compete, so a lot of them are in the process of being sued. 

Rueful laughter.

But yeah, does my company cut reps who go on to be successful at other companies? 100 percent. I came to work here straight out of college, but I’m in a web of other sales people, and everyone says the same thing about my company and how we operate: It’s cutthroat to the point that it’s detrimental to the success of the reps, rather than beneficial.

And yet, here comes this steady stream of new hires. They’ll be drinking the kool-aid, being fed this crazy optimism about the company and how many cash they're about to make, and they're super excited. And I support them. I was very hesitant to drink the kool-aid at first, but, you know, welcome to the machine. And I’ve found out that if you’re not going to drink the kool-aid when you first get there, you might as well just quit right now, especially in sales.

The new guys get extremely fired up during their training, but then it’s like clockwork dude. Like a month after the training, they’ve gone from the top of the roller coaster to being like, I’m about to get fired.

Confession 7. I Love Watching Our New Reps Fail

"There are a million people in Hollywood right now--who are all gonna make it."

And here’s how jaded the last four years at this place have made me, I love watching it now. I hate that I like it.

Wait. I don’t hate that I like it, I think it’s great.

Here’s one reason. I’ve spent five years here and really been crushing it in getting new business--like, last month, I closed a $180k deal. And there’s this brand new sales rep who just started two months ago and already just closed his first deal, which would be impressive except the company is below our target market and the deal is worth pennies.

But this guy is all jacked up over a $12k ddeal and still high off the kool-aid from the training. So he’s walking around the office with his chest puffed. The morning that he was going to pick up the deal, he--no exagerration--mentioned that he was going to go pick it up fifteen times.

I know this because my buddy and I made a bet to see how many times he would mention it, with an over-under of twelve. I hit the over so I won $10 bucks, BUT, this is insane! He sold one, tiny deal!

And then, that same afternoon, I’m in a meeting with my manager and this guy walks in, interrupts the meeting and starts asking my manager some dumb, pointless question.

At this point, I’d had it. So eventually I said to him, “Hey, aren’t you supposed to be picking up your deal?” And he snaps at me, “Yeah, I’ve got a new deal I’m picking up this afternoon. How about you? I’ve been here a month and I haven’t seen you pick up one deal!”

I mean, the audacity. So I told him, look, congratulations on the $12k deal, but I just closed one 10 times that size the month before you got here. And I’ve been generating tons of revenue for this company now for going on five years, so go do 9 more of those deals you just did and then come talk to me.

Of course, after he left, my manager was upset that I talked to him that way. But like, that persona that guy has--that’s the epitome of the fresh-out-of-training, still drinking the Kool-Aid, "I’m such a badass because I closed a minor deal" phenomenon that I see everytime we bring on new people.

Don’t get me wrong: You have every right to be proud of yourself in that situation. But don’t spend the entire morning being obnoxious about it, interrupt a co-worker’s sales meeting, and then try to call out a more senior sales rep who has made hundreds the times of revenue that you have for not closing a deal in the one-month period that you’ve been at the company.

So, in concluding, I hope this dude fails.

Confession 8. 85% of Our New Hires Will Be Fired Within 12 Months

Conversation destined to occur with 8.5 out of 10 new hires.

Now, on the other hand, there’s this guy who started the same day as this other rep, but he hasn’t closed a single deal, and it’s because he’s too nice and he doesn’t know what he’s doing. So he’s got no deals, nothing in his pipeline, and [hushed tone] he’s probably not going to work out.

So it will just be the two of us in the office, and he’ll look at me and go, “D.S.R., I’m nervous that I’m going to lose my job. Should I be worried?” And when reps ask that question (shocker: it happens a lot), most other senior reps are like, “No you shouldn’t be worried at all! You’re fine.” [pause]

Well, I just straight up tell him: “look, you should have a little bit of concern and develop a little better sense of urgency.”

And to give you some insight on why I told him that, it’s because, when I was hired five years ago, I came onboard with 30 new reps. One year later, there were only 3 of us remaining. Everybody else didn’t make it. It’s dangerous out there man. The expectations are so high and so unrealistic that they’re impossible to meet, and then that’s a big shot to your ego when you don’t make it.

And when you lose that ego, and you need to pitch to a CEO, you lose that attitude of -- “I’m going to walk in here and blow this CEO’s mind”  -- that you need to have to be successful. That’s why there are so many people don’t even make it a full year at the company.

Confession 9. Want to Get Fired? Give Honest, Negative Feedback

"You want me on that Wall!"

Another thing that sucks is that my company is really bad about giving feedback--because if you give bad feedback, you’re perceived as negative and harmful to the company culture, and therefore fired. I’ve seen that happen firsthand.

So, the manager that hired me was a total badass, but he was like a diamond in the rough. When I came on, we had a bunch of reps who were poaching deals in other people’s territories, the culture was terrible, everyone was all about themselves, and no one cared about anything else. But my manager, and a few other really solid people hired around the same time, managed to change some of that and turn things around.

Well, none of those people are there anymore. Our office has lost 4 of its most tenured reps in the last 2 months. Prior to that, our company -- on the whole -- had lost 10 tenured reps in 2 years.

So at one point, in an interview with his supervisor, my manager was asked: "Do you have any feedback about the managerial position?" Well, my manager said, "I honestly don’t feel comfortable giving you feedback, because I don’t feel that it will be used in a positive way." And he was having this conversation with his manager, who was insisting, "you can tell me," but my manager opted not to.

Eventually, my manager left to go to a different company. In his exit interview, he gets on a call with our H.R. person. The H.R. person asked him for feedback and he said, "I’m going to give you very honest feedback right now: Everyone’s afraid to give you feedback, everyone’s afraid to try to improve the organization, because everyone’s afraid of the consequences."

It was the only time he felt comfortable giving the company  negative feedback. And guess what, my manager later found out that our company's CEO was covertly listening in on the call.

Confession 10. Our CEO is a Sociopathic Despot

Committing nuclear war on company culture.

Our CEO - dear lord. One story says it all.

Not making any of this up. A new hire once got into a taxi with him in Philadelphia, rode with him for 8 blocks. The new hire got out of the taxi, and the CEO proceeded to call my boss and tell him that: when this new hire gets back to the office today, you need to fire him. And they fired him that same afternoon.

Why? Our CEO doesn’t like people riding in taxis with him.

Another crazy thing is--our CEO set up a process for interviewing new hires that's designed to be an intimidation tactic towards current reps. Our company is always interviewing tons of people, and if you’re potentially on the chopping block, it really messes with your head. Because each week, they march 10 interviewees straight through the heart of your office to be interviewed as your potential replacement.

I'll end with this: Everything I’m telling you -- and this is so frustrating -- imagine how much better it would be if I could openly speak about it to my company. It would improve the culture. Imagine the improvement that would happen in my office's enviroment. And that cultural improvement would flow over into sales improvement.

It’s just scary that the organization I’m working for is not allowing me to do that.

Ambition: The Data-Driven Sales Management Platform

Ambition is a sales management platform that syncs every department, data source, and performance metric in your organization on one system.

Sales organizations use Ambition to enhance sales performance visibility. Ambition's drag-and-drop interface lets non-technical sales leaders create custom sales scorecards, contests, reports, and TVs with live data. 

Ambition is endorsed by Harvard Business Review, AA-ISP (the Global Inside Sales Organization), and USA Today as a proven solution for managing activity-driven sales teams. Visit our AppExchange page and hear from our clients below.

Watch Testimonials:

  1. FiveStars: Adam Wall. Sr. Manager of Sales Operations . 
  2. Filemaker: Brad Freitag. Vice-President of Worldwide Sales.
  3. Outreach: Mark Kosoglow. Vice-President of Sales.
  4. Cell Marque: Lauren Hopson. Director of Sales & Marketing.
  5. Access America Transport: Ted Alling. Chief Executive Officer.

Watch Product Walkthroughs:

  1. ChowNow. Led by Vice-President of Sales, Drew Woodcock.
  2. Outreach. Led by Sales Development Manager, Alex Lynn.
  3. AMX Logistics. Led by Executive Vice-President ,Jared Moore.

Read Case Studies:

  1. Clayton HomesHBR finds triple-digit growth in 3 sales efficiency metrics. 
  2. Coyote Logistics: Monthly revenue per broker grew $525 in 6 months.
  3. Peek: Monthly sales activity volume grew 142% in 6 months.
  4. Vorsight: Monthly sales conversations grew 300% in 6 months.

Contact us to learn how Ambition can impact your sales organization today.

Popular Content