Behind the cold call | The cult of sales organizations
Why Reps have the toughest job and how managers can ease stress by helping their team close more deals (instead of pulling Salesforce reports and cracking the whip).
It’s a Wednesday morning and a Sales Rep in London is cycling to work because he can work from home only 2 days a week. He picks Monday and Friday, usually. This is a regular week for him.
Charlie (just made up a name) cycles fast to the office in Hackney, where his employer (a *ahem* SaaS company active in the E-commerce industry called SalesCap) recently set up shop.
“Hey look who’s there!”
“Hey Charlie, ready for the Sprint day?”
“Looking good mate - nice shirt!”
After the round of “Hi”s “Hello”s and “Yes, it’s a sprint day today”s Charlie reaches his desk and fires up his laptop. He plugs the headphone jack in the computer and fills half a dozen of Salesforce entries that he “could not get around to the other day because of an important in-person meeting”. It’s 8:13 and his day has already started.
“Hey, hey, hey - look at our stars!” cheers the Sales Manager as he bombs the team with his energy, “It’s a sprint day everybody! Are you ready to smash your targets?”
Everybody looks excited for the day. Some fake it. Others are new.
“OK, let’s get started!” and the sprint begins.
Charlie sits at his desk, his eyes glued to the Salesforce dashboard. He goes through his Close Lost list and desperately looks for a quick win to get his name on the leader-board before the others.
“Hey Charlie, we expect some big numbers from you today mate!” grins the sales manager, as he slaps Charlie’s back and walks off to get his coffee.
“Hey, yeah! I am already eyeing this deal for the day that…” he goes back to his list after noticing Clarke is on his way to the kitchen.
5 minutes later an alert pings on his dashboard, he cannot believe it: it’s an old prospect for whom Charlie had set a reminder months before. “This guy needed SalesCap - he was just busy with something else at the time. I’m gonna straight-up call him now” , he thinks.
The phone rings, Charlie is sweating.
“Hello.”
The toughest corporate job
I’ll tell you how the story ends later. And it will be cool, trust me. It will be an interesting cold call.
But now, let’s discuss who are the people behind the phone. When do these people call you? What do you think? Do you hate them? Do you feel sorry for them?
I used to be one of them. In some ways, I still am. It’s a habit that it’s hard to get rid of.
Cold calling and cold emailing are two skills that, to this day, I couldn't live without. They have opened doors beyond my wildest dreams in such a short time it felt like magic.
One day, I realized that my job consisted in speaking to the CEOs and CFOs of some of the most important European companies, and very few people had the ability to do what I did.
But the allure of sales is matched by its fast pace, ridiculous expectations and a generally toxic environment. This is not because sales is a bad profession, quite the contrary, in fact. I think it’s the most valuable profession in a company, when the machine works well as a whole.
When times are good, being in sales feels like you are a rock star. You close deals, engage conversations with important people, others may literally look for your guidance just because you are doing well. And when the hard data is on your side, it’s hard to push you around. If you sell, everybody loves you.
Unfortunately, companies have ever increasing targets AND internal politics. The two rarely come in the way of helping employees, especially salespeople.
Pressure can build up quickly, in sales. A bad month can happen to anyone. Two bad months in a row and you will start to get strange meeting invitations.
Hey don’t get me wrong. I get it. A salesperson is useful as long as they bring in sales.
All I’m saying is - have you ever wondered why cold callers sometimes sound robotic?
Cold Calling and Sprints
What is cold calling?
Cold calling is the sales practice of calling phone numbers not contacted before to pitch them a product opportunity.
Sales Gurus will shout at me for saying this. But I am not trying to teach sales here. It’s just a definition. Chill…ok? I get it - cold calling is much more than that. I know…I know…
Anyway, a successful cold call is always cause for celebration. It’s the most direct type of approach that you can have and it’s the one that exposes you to the highest number of assholes.
A sales sprint is a lot of cold calls and cold emails (A cold email is like a cold call but with an email address instead of a phone number) crammed in a single day.
Sales sprints are incredible events where everybody gets stressed. Sales Managers are desperate to deliver results to their bosses in the form of metrics (pipeline moves, closed wons, new prospects etc.) and salespeople need to go above and beyond to show they are actually making something useful.
Truth is, in my experience, sales sprints exist because sales is an extremely demanding job. You are squeezed to the bone and pulled left and right to do something that nobody, in their sound mind, would do for free. So it’s best to cram the efforts in one day every week to make sure nobody is slacking away.
During sales sprints, managers check how many calls/emails you make/send or how many prospects you take forward towards a Closed Won (oh btw, sales is a lot like a cult. We have our own Newspeak. A successful sale is called a “Closed Won”, a non-sale is called a “Close Lost”) - this is usually reported on a public leader-board to *sighs* foster internal competition.
A simple framework for managers
Sales, as we have discussed, is a tough profession. The expectations are high and the job is generally very demanding. The customers come first and the sales manager is a close second.
But there are ways to make your sales team happy. A happy salesperson comes to work relaxed, they always manage their pipeline in advance and do not rush to meet their quota (more Newspeak, how exciting!).
Salespeople can be happy, if you let them. How do we achieve happiness for our team then?
Make calls with them. Get down in the trenches. Show your team you can work their job (or at least, that you are not afraid of trying). Managers that pull Salesforce reports and crack the whip are going to be hated by their team regardless of the team’s performance.
Objectives come first, but you can only reach them if your team respects you and works with you. If you get frustrated at them, they will fear you. But they won’t respect you. A sales team is not a Program Management team. You need to be understanding without being too “friendly”. A friendly sales manager can make an employee feel “betrayed” when the times get tough and a change of attitude is needed.
Cultivate the image of an “enabler” rather than a “dictator”. At the end of the day, you want your team to succeed. It is your responsibility to make sure they are able to do so.
Give your team time and space to “let off some steam”. They absorb all the negativity of your customers and it is not an easy position to be in. If your team always feels they need to be ready for an audit of their pipeline, they will find ingenious ways to fake work. And this will create another problem for you.
Do not directly pass your stress to the team. Buck passing is only going to grow resentment towards you - this will eventually come in the way of reaching objectives.
Foster competition among team members but don’t make it “toxic”. Some level of competition can increase performance but a “free-for-all” environment will exert the opposite effect.
Do not shame team members in front of the rest of the team. You may think this will foster competition, but in truth, it will likely cause trust issues in your persona. Other Team members may start to think “Will it happen to me if I miss my quota?”. This is absolutely a no-go. If you need to fire somebody, just do it. Be professional.
Do not rush to make changes to the compensation plan. Sales is the toughest job in an organization. It attracts people primarily because of its earning potential. Changing the comp plan will push A-players away.
Drinking the Kool-Aid
“Drinking the Kool-aid” is an expression that comes from an event that occurred in Jonestown, Guyana, on November 18, 1978. 900 people drank a poisoned Flavor-Aid concoction and died as a result.
They did so willingly, because the People Temple’s cult had ensnared their minds so effectively they couldn’t help but believe the BS they had been fed.

Working in sales closely resembles being in a cult.
It’s a rewarding job that is capable of teaching incredible skills. But I have noticed some harrowing patterns that seem to affect most sales orgs:
The job comes first, the customer comes first, the employee is always expendable. And this is never seen as a bad thing.
From the beginning, the organization will attempt to make its mission your constant focus.
Unique terminology is applied to describe standardized functions (a customer becomes a “partner”, a sales manager is “a leader” etc. etc.) - this is Newspeak. Be very wary of Newspeak at work. A word of advice for managers: try to be “real”. Newspeak can backfire when people experience “sales fatigue”. Salespeople are not stupid.
There is a general tendency to classify other colleagues as “non-salespeople”.
Delusions of grandeur become a coping mechanism for addressing tough times that do not fit the narrative the salesperson builds for themselves. As the mental game of sales wears you down, you try to find clever ways of justifying why things are not going the right way. Failure to do so will result in a state of depression and lack of motivation. This is typical cult-like behavior, where followers gave up their sense of purpose in favor of the organization's.
So yeah. I think that good sales managers keep it real and tell their employees that sales is a job, not their ticket to heaven (Thank you S.R.! You were a really good manager!). Always look up your next sales manager before taking on a job and try to get an interview with them.
Charlie’s Cold Call
“Hey David, can you hear me?”
“Yes, I can, who is this?”
“Hello, this is Charlie, remember me? We had a brief exchange a few months ago!”
“Oh yeah I remember you. You’re that bloke that moved to London! How’s the job?”
“Ah! It’s good. Sales is tough, but you come from this environment so you get me.”
“Ahaha, yea I sure do. It’s tough. I guess you are calling me to sell me that product.”
“Hey David, no use lying here. We have a sprint day today and I need to make a sale. I remembered you were interested in the solution. So I called you. But if it’s not the right time, tell me and we’ll talk again next year.”
“Charlie, actually this is a pretty good time. I still have the trial account credentials. Let me log in for a sec…”
“Sure!”
Seconds feel like an eternity for Charlie, as the prospect is re-exploring the platform he feels like his stomach could explode at any time.
“Look Charlie, I really like your product.”
“OK, here comes the catch…”
‘But…yeah, yeah. Sorry but it’s too expensive. 300 £ a month is something I do not want to spend on this.”
“Hmmm, OK. But is the price the only problem here? It’s a sales tool so it could fetch you more earnings as you use it.”
“That is true, but still 300£ just feels too high for me at the moment.”
“Ok, hold on, are you telling me that if I dropped the price significantly you would buy it?”
“If you drop the price and payments are made monthly, yes.”
“David, give me one second, I think I can make this happen for you.”
‘Sure.”
Charlie runs to the kitchen to find Clarke chatting to a bunch of eggheads from engineering.
“Hey Clarke!”
“Hey look at our star! How’s it going?”
“Look I have a prospect that’s ready to pay but the price is too high for the Standard Package.”
“Can you steer him to the Lite Package?”
“I don’t think so, he is ready to buy, we just need to drop the price a little.”
“OK, but then he needs to pay for the full year.’
“He said he is not available for paying the year in full - this is why he is asking for a price drop.
“So he wants to keep the monthly payments and a price drop?”
“Yes, but this guy can be helpful to us. He could make a video for the product and perhaps even an interview that we could use as a testimonial.”
‘OK, OK - ask him to commit to making the video and I will give you a special one-time code.”
Charlie runs back to his desk.
“David, I need to ask you something. We can drop the price. We can even keep the monthly payment plan. But could you help us get known by participating in one of our videos?”
“I can, sure, if the product works well and I am satisfied I can do that for you.”
Charlie gives a thumbs up from the other side of the room to Clarke, who sends him the code right away.
“OK here’s the code.”
“Ah nice, it is now 150 £ a month. Much better. Let’s do this.”
Charlie is ecstatic. The sale was reached. The day is saved. He could go and grab some real breakfast now.
“Hey wait a minute. It says I need to pay the year in full.”
“What? Wait a second.”
Charlie rushes to Clarke’s desk.
“Clarke the prospect was ready but the platform is forcing a full year payment.”
“Oh really? Hold on, let me call finance, go back to your desk and I’ll be there in a sec.”
‘OK, thank you Clarke.”
Charlie walks back to his desk and apologizes to David. He starts to talk about how these things never happen and that there must have been a mistake because the code provided is something they do not just grant any customer.
“Hay Charlie” shouts Clarke, from his desk.
“Yes? Can we proceed?”
Clarke nods.
“OK David, let’s try again.”
“Ah, perfect! Now it’s asking for a monthly payment. Great stuff. I am buying it”
Charlie is happy. His manager is happy and the customer seems satisfied. He looks at the leader-board. He’s already there. It’s 9:05 AM and he’s already there. Time to celebrate. Charlie hits a Pret’s downstairs and grabs a bacon roll. On his way up, people are cheering loudly. As he enters the room, he notices something. He is now 4th on the leader-board.
It’s 9:15 - another 3 sales were made.
Charlie walks back to his desk and starts the search again.
The beauty of sales
Sales is the corporate job that most closely resembles being an entrepreneur. It is not for the faint of heart. It attracts a lot (an awful lot) of toxic people and it can be detrimental to one’s health (been there, trust me).
Nevertheless, if you don’t “drink the Kool-Aid”, it is the profession that will teach you the most about how to run an organization, meet deadlines, talk to stakeholders of all types and much more.
Because sales is where the value created by a company gets transferred to the customer, and no company can exist without generating sales. Some companies require salespeople, some don’t.
What is certain is that if you work in sales, you will eventually understand the customer, and this is the most prized capability that you can learn in this thrilling position.
And please, please, please. Do not treat salespeople that sound like robots as if they were not humans. They are human beings and they are having a bad day. The fact that they want to sell you something is only due to their job. Sales is a real job. It is tough, and it can be very rewarding.
My advice is to have at least one professional experience as a salesperson. Worst case scenario, you’ll become a lot more polite when you receive a cold call (speaking from experience here) 😀.
Happy Wednesday!