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The Definitive Guide To Sales Part 2: Life As A Salesman

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In part 1 of this four part series we outlined the entire industry from top to bottom. Now that you have an idea of what sales jobs are available to you, we’re going to get into what you need to know before taking a job, how to interview, the key workplace strategies you need to survive and exactly what to expect from life as a salesman.

Like I told you in part 1, I’m not your manager and I’m not a sales trainer so I don’t have to lie to you. This post will show you the day-to-day reality of what to expect from life in sales. I definitely don’t recommend a career in sales but selling and servicing your customers is the most marketable skill you can learn in business. And a sales job is the quickest way for a young guy to make money without selling drugs.

Sales was my path to business ownership and financial freedom, it can be yours too, if you want it.

So here’s what you need to know:

Know Exactly What You’re Looking For In A Job

Before you start your research you need to know exactly what you’re looking for and the criteria you won’t accept eg. you want a job located downtown with a base pay of $40,000 and a company car. Your expectations should be dependent on your skill set, the more marketable you are the more you can demand.

The good thing about sales is that there are always tons of jobs available (because no one wants to sell) which gives you the power of choice. Stick to your guns on what you want and don’t let the recruiter try and sell you a job that doesn’t match your criteria, remember they are salesmen too and all they care about is getting you to sign a contract.

How To Research Jobs

Treat your job research as a full time job, if you do this you can easily have a new job within a month. You should be able to send out at least twenty resumes a day. The best site for finding jobs is indeed.com, it’s an aggregator of all other job sites.

You should also sign up with a few recruiting agencies, ideally ones that specialize in filling sales positions. Many of them will just spam blast your resume but the more options you have the better.

What You Need To Know Before Interviewing

Most of this information you can get online but some of it you’ll need a recruiter to get for you. If you’re not using a recruiter then get as much as you can online. Many times the recruiter won’t know all this stuff (because they’re not very good) so get them to ask for you and call you back when they have all the details.

Remember, when dealing with a recruiter you’re the client in the relationship so you have the power. Once you get past the introductory meeting, never meet a recruiter until you have all the details you need, many times they deliberately hold off/manipulate information to get you in the office so they can sell you in person.

First you need to find what the company is like, what the average age is, how aggressive the culture is etc. A company that sells itself as young and aggressive almost always means high pressure and unethical. The recruiter will usually give you a rundown but the website is a great place to look as well.

You want to find out what kind of guy your boss is, what his interests are, what his style is, what he likes to see in the guys he manages. Linkedin and Facebook are your friends here. Ideally you also want to know what’s required of you in terms of call time, call volume and travel time.

The most important aspect is what your OTE is (On Track Earnings) but take it with a grain of salt, unethical companies will inflate this by as much as 30%-40% in an effort to get you through the door.

Your OTE should be minimum 60k for your first year, ideally 70k or more. Glassdoor the fuck out of the job first though, this should get you an idea of salary, commission and culture. If you can’t find your job on Glassdoor then search the company’s competitors to get an approximate idea of the industry.

Find out what the top guys make, you want to hear over $200k. If you hear the top guys are only making $100k that means the company average is probably only about $50k, not good. Find what the turnover rate is, if it’s high they might not flat out tell you so listen carefully to any hesitation from the recruiter when they answer this question. If it’s a company that promotes itself as young and aggressive then I can guarantee you they will have a high turnover rate. You should try and avoid these companies if you can.

What Kind Of Job You Should Aim For

My advice is to apply for outside sales jobs at big companies. SMEs sell dreams on mobility but that’s usually bullshit. The pay is worse, the benefits are worse, they’re always at risk of going under and they will breath down your neck on targets. You also can’t hide at small companies like you can in big corporations.

Aim to stay out of phone sales if you can, phone sales is shit and once you’re in it’s harder to get out as company’s look for experience in outside sales. They don’t want 35 year old phone monkeys.

The only time large companies take inexperienced salesmen is coming straight out of university. If you’re a nice looking white kid who presents well then aim for an outside sales job with a large company straight out of school. It’s cushier, pays better and you don’t have to work as hard.

How To Interview

You want to present a well dressed, confident, aggressive alpha male, this is what every sales manager is looking for. You should always come correct in a tailored suit and tie, this doesn’t have to be expensive though, a nice suit from Zara and tailoring will only cost you about $350. I’ve been hired on site twice and at least 50% of that was from how I look. In a properly tailored suit you will look better than 100% of guys.

When you walk in the room remember to keep that chest out, back straight, speak from the diaphragm, and give solid eye contact combined with a nice firm handshake. You can be scared shitless on the inside and feel like a little boy in your dad’s clothes but on the outside you need to be cool as a fan, that’s what sales is.

Expect to be asked about your job history, your previous salary, what your targets were and what challenges you overcame. If you have no sales background you should have a story as to why you think you would be great at the job.

When he asks you why you want to be in sales the answer he’s looking for is money, he wants guys who are hungry for money. You should also mention sports or other competitions where you’ve excelled and how that will translate to excelling at sales.

If you’ve been fired or quit your last job you should have a good story for that, even if you have to lie and get a friend to act as your reference. Getting fired is a tough position to sell yourself from. Ideally you want to be coming straight out of school or be already employed at another company.

If you’re interviewing for an SME you can lie your fucking ass off because they never do proper background checks, I guarantee they won’t call your university to see if you graduated. Barb the lazy office manager would rather go for her fifth smoke break then do the necessary due diligence.

My last 3 jobs have been built on lies, I lied about graduating university, my sales experience and the amount of money I made. For my first sales job I even invented a company and got my friend to play my ex boss. For another I convinced my ex manager to extend the amount of time I worked for the company and the amount I made. Lying also might be necessary if you have a criminal record, this is the last thing employers want to see.

Worst case scenario you get caught and don’t get the job, even then, you’re a fucking salesman, it’s your job to lie. Your resume is not a legal document so they have no grounds, plus a company wouldn’t waste their time, they would just move on. If they catch you down the road years later you’ll get fired but you shouldn’t be working a job 5 years from now, you should be working on your mission.

When it comes to large companies, unfortunately they will do a criminal background check, call your university and thoroughly check your references. They have a whole team of HR girls for that kind of busywork. Almost all of them will need to see a degree and a clean record. I’ve known many guys confined to small and mid-tier companies for these reasons alone.

When it comes to my survival I do what it takes. If lying on your resume goes against your ethics, I respect that. But the way I viewed it was that I was going to go in and give 110% and make money for that company, which in all cases I did. The fact that I had to lie to get in the door hurt no one in the long run.

You should also be prepared to sell something, a lot of sales managers will use the old school method of asking you to sell them a pen, it’s dumb but you should have at least five features and benefits of buying a pen.

When you’re interviewing, try to get an idea if you can work for this guy. Many sales managers are not nice guys so if he rubs you the wrong way off the bat that’s a really bad sign since this is him on his best behavior. Only take the job if you find the guy tolerable.

What To Expect

1) You Probably Won’t Like Your Manager

I’ve come across some really bad guys in my sales career, not Jordan Belfort bad but only because they didn’t have his intelligence or organizational abilities. The truth is, many sales managers are low empathy kind of guys if not outright sociopaths.

I’ve had exactly one good manager, he’s a friend to this day but 9 times out of 10 your manager will lie to your face and sell you a dream that doesn’t exist and insult your intelligence by selling you the same way you sell your clients all day long.

To see what many managers really think of you, watch Alec Baldwin’s phenomenal speech in Glengarry Glen Ross. A must watch movie for any aspiring salesman.

2) You Won’t Like Many Of Your Clients

Your clients won’t treat you as badly as your boss but they won’t treat you much better. You’re expendable to them and since you’re always calling from a position of weakness many won’t have a problem ordering you around like an Applebee’s waitress.

With your own business you can afford to fire your problem clients, but in someone else’s business you can’t because you have targets to meet. The last thing your manager wants to hear is you turning away business.

3) You Live And Die By Your Targets

Sales pays well because it’s hard, and not just because you have to make 100 cold calls a day. Compared to the pressure of meeting your monthly target, cold calling is a breeze. You think about your target in the shower, on the weekends, when you’re at family dinners, it never stops.

You’re only as good as the number you put up on the board that month. Last month means nothing, last year is a lifetime a way. You are one bad quarter away from being fired at all times, in some companies one bad month away.

4) Lying Is Built Into Your Targets

All salesmen lie, no exceptions, anyone who says otherwise is selling you. Lying is built in to your targets. Many sales managers will insist on you pitching clients using exagerrated features and benefits. Many companies only exist because of deceptive practices.

To consistently hit 100% of plan, many times you have to lie or at least stretch the truth. You have to get some clients who aren’t a great fit for your product to buy. If not you won’t hit 100% of your target every month.

Whether it’s outright lying or manipulating the truth it’s all the same thing. The only time you can sell without lying is when you control the targets and the product. At RLD I’m in charge which means I can be completely honest with you guys. In fact I built my whole site around being honest and I love not having to compromise myself.

Do you think I could ever write an article like this if I was working in Corporate America? Not a chance.

Every day in sales is an ethical challenge. My advice to you is try and keep as much of your integrity as you can. At the end of the day you have to look yourself in the mirror and be able to sleep at night. I would try to keep my exaggerations small and outwork the rest of the team to make my numbers. Sometimes I would quietly kill deals when I knew it wasn’t a good fit for the guy, especially if he was a small business owner.

But when it came down to it and I was behind on my target I would do what I had to do to hit it.  I’m not proud of it but when it comes down to my survival I will always do what I have to do. With that said I’m an angel compared to some of the guys I worked with who were more than happy to rip their clients faces off, it was funny to them how dumb their clients were.

5) Sales Is Uncomfortable 

Sales is the hardest white collar job. Most guys can’t deal with the discomfort of having to constantly break rapport and harass people for money. Fear of provoking a negative reaction in someone is normal. That’s why your entire training is based around overcoming this fear.

6) Failure Is Built Into Your Targets

Failure, like lying is built into your targets. You’re either supposed to get fired, quit or move up. You’re supposed to burn out, that’s built into your targets. Your targets go up every year like clockwork and eventually you won’t be able to hit them, that’s by design. I know guys who had to do $200,000 a month in revenue just to keep their jobs.

Most companies have no problem firing salesmen. Because when you fire a salesman you get to keep his book of business and release a monthly salary and commision payout.  hen they can bring in a new, younger, hungrier guy for cheaper and let him build up another book of business.

This is especially true in some industries like ad sales where commissions are booked in advance. Firing salesmen means you can keep years worth of future commissions. When I left ad sales I left with at least $100,000 in revenue that I’d booked but hadn’t been paid on.

7) You’ll Burn Out

After Dealing with all this bullshit you will burn out. Most guys either quit or get fired within three years.

The standard arc is guy gets hired, buys into the company dream but over time slowly starts to sour on the company, his manager and his coworkers. By year three he’s burnt out, negative and on his way to getting canned or quitting. Then he finds another company and repeats the same process. Some guys power through and move up into management but this is rare.

Some older guys are just permanently burnt out, but they have a mortgage, kids, car payments and no way out. Most of these guys use food, cigarettes or alcohol to cope with the stress. Still being a salesman into your 50’s is not the right move for your life.

8) Sales Will Toughen You Up

Before I started in sales I didn’t even like calling the pizza man. I was not only raised to be extremely polite but I’m also Canadian which means that harassing random people on the phone was literally the last thing I wanted to do.

But after working close to a decade in the meat grinder I can pitch a CEO of a multi billion dollar company on advertising to a venture capitalist on investing in my tech startup without flinching. I can pitch them in the boardroom, on their way to the washroom at a conference or at their company Christmas party. After that kind of training picking up a girl off the street is a joke.

Workplace Strategies

1) Make Your Boss Like You

The most important strategy in the workplace is having your boss like you. It’s very easy to fire a salesman and if your boss doesn’t like you it’s just a matter of time. Forget about being an alpha male, the best way to make your boss like you is to kiss his ass. Show him you have the same interests, same sense of humor, whatever you have to do. It’s a matter of your survival because your resources are at his command.

As a wise man once said: know your role and shut your mouth. When you sign that contract your role is slave, the contract might as well be written in blood. Acting defiant means nothing, you’re still a slave, it will only make things harder for you. This goes for any job, sales or otherwise.

With that said there is a right way to kiss ass and that’s to become his friend or as close as you can. Show him you’re a cool guy but still defer to him, kissing too much ass makes you look like a bitch. You still need the guy to respect you and other salesmen will hate you if they see you kissing your boss’s ass all day.

Dressing well and asserting yourself is important, you want to present the image of a winner. Many sales managers are functional sociopaths and will ride weaker salesmen with no mercy because they know they’ll take it. Don’t let yourself become the office whipping boy. Every sales floor has one, usually they have families or demanding girlfriends and can’t leave no matter how badly they’re treated.

You want to establish yourself quickly as a winner and a producer, someone your manager is afraid to lose. Everything is always great, that’s what you present, the company is great, your weekend was great, your boss is great, you’re happy, you’re going to make more next month, you see a great future at the company, etc. It will get you leverage in asking for more money as well as taking time off and having on the job freedom.

2) Hit Your Targets

The fastest way to make your boss hate you is to consistently miss your targets. That means he’s going to get shit on about your performance and then he’s going to shit on you. Shit rolls down hill. Hitting your targets is also the fastest way to get your boss to like you, see point number 1.

The best way to hit your targets is to keep your head down and work hard. For the first few months don’t socialize too much at work and outwork every guy on the floor. Show them you have a strong middle-class work ethic, this is exactly what they’re looking for. Even if you miss your targets off the bat your work ethic will buy you a lot of breathing room.

3) Make The Guys Like You

If you’re a confident well dressed guy, other salesmen will hate you for at least the first month. They will see you as competition and rightfully so, until they get to know and like you.

The guys will test you to see how weak you are, just like on the playground, most of your coworkers will be primitive retards so assert yourself early and often. With that said you should also be super friendly and nice to offset all the confidence you have, it’s really hard not to like a cool guy who is nice.

Sales culture is white, middle class and masculine. Guys who work in sales are culturally white, middle class and ex jocks. Many guys come from smaller cities or towns and move to the big city to find work in sales. So to get these guys to like you, present yourself as a culturally white, middle class, ex-jock. Even if you’re not white, show them you’re still part of their culture.

Pretend you like sports, the more you know the better. If you’re a follower of this blog you know I don’t waste time worshipping 20 year old employees who can put things in nets but the guys you’ll work with do. These guys talk sports non-stop and it’s important to pretend you know what’s going on, also your guy clients will usually want to talk sports. I used to watch highlights to get an idea what’s up. Middle class guys won’t trust you unless they think you like sports.

4) Act Like You Have Money

If you don’t have money in the bank, it’s important to hide that from your boss and colleagues. If your boss knows you need money he can leverage that by leaning on you harder because he knows you can’t afford to quit.

If you’re fresh out of school, make it seem like you come from money and if you’ve had jobs before let people know you’ve saved a lot. Never ever talk about money problems or wish out loud for payday. Guys do this all the time and it makes them easy targets. If they find out you’re poor, that means they own you.

5) Don’t Buy Dreams

Your manager is not your friend, don’t believe a thing he tells you. He didn’t get to that spot by telling the truth, he got there by selling dreams. He will sell you on all kinds of dreams for your future at the company, don’t believe a word, those talks are just designed to keep you running fast on the treadmill.

The new client incentives, the team meetings, the cash bonuses are there to squeeze more juice out of you. You’re only there out of necessity. If you could be replaced by a machine or a phone monkey in the Philippines you would be without a second’s hesitation. The dream is not yours because you have no equity, it’s the company owner’s dream.

6) Save Your Money

Save your money so you don’t have to live like a slave for the rest of your life. Unfortunately most salesmen blow their money on expensive toys and live paycheck to paycheck. Build a safety net for yourself that you can invest in your business and pay for your runway.

7) Learn How To Sell And Service Clients

Selling is the most marketable and important skill I have. From picking up women to writing a sales page there is no aspect of my life that my sales training hasn’t helped me with. Despite how tough life in sales was, it has been a massive advantage to me in my business and personal life. If you’re going to be stuck doing what you hate you might as well soak up as much knowledge as you can.

8) Use Phenibut

Taking Phenibut twice a week will make selling a lot easier and for a few minutes a day even enjoyable. Add a caffeine pill in the morning and you’ll be flying. Phenibut releases GABA which relaxes you and raises your mood making it easier to sell.

My sales figures would double on Phenibut. When you watch Wolf Of Wall Street you’ll see these guys taking Qualuudes to sell better. Qualuudes like Phenibut and alcohol are GABA agonists. But instead of coke and qualuudes use caffeine and phenibut and preserve your health.

9) Get Off The Phone

Get out of phone sales as quick as you can. You’ll always be capped earnings wise, always be monitored heavily and always have to be in the office. Get into outside sales early. You make more money, you get a car and you get to work from home. I knew a guy who made six figures a year and only booked two days of meetings a week. The rest of the week he spent smoking weed and playing Xbox.

10) Plan Your Exit

Let me paint the picture, you’re a 45 year old guy bouncing from job to job every 3 years and your coworkers and manager are 10 to 15 years younger than you. Every three years you start from scratch building a new book then get fired when you burn out. You also have a mortgage, a car and a family to pay for. Eventually you develop problems with alcohol, food, cigarettes or all three.

I worked with a guy in his sixties who ended up having a stroke from all the stress. He was an overweight alcoholic who talked constantly about the glory days of his youth. All his money went to his greedy wife and kids. When he recovered after a year in and out of the hospital he was brought back on board only to be demoted to cold caller. A position that usually goes to guys in their early twenties.

He couldn’t leave because he didn’t have any savings and eventually he was fired by a manager half his age because he wasn’t even competent to be a cold caller any more. Don’t let this happen to you. If you want to see the reality of a guy getting old in sales, watch this scene of Jack Lemmon’s brilliant performance in Glengarry Glen Ross. The sadness and desperation is palpable.

Guys rarely last at companies for more than 5 years unless they move up into management. Every salesman wants to get off the floor but only a few move up.  Every salesman talks about starting his own business but most never do. Most guys get a family, a car and a mortgage and become slaves for life.

Outside of myself and my business partner no one I worked with started their own business. They all got hooked on the paycheck, on the toys. Don’t sell your life away for a big screen TV. Don’t still be in sales by your late 30’s. Plan your exit, know how much you need, get your business running and set a hard timeline for getting out.

Check Out Part 3 On How To Sell


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8 Comments

  1. Jackie
    April 12, 2015 at 12:43 pm

    Just started a job in sales at a tech firm. It’s a growing company that’s set to go public in the next two years. Before I joined I felt like I was giving up my dreams, but it’s just a means to an end. This series has been extraordinarily useful. Waiting for the next chapter…

  2. April 12, 2015 at 8:13 pm

    This article is eye opening is so many ways. Much of your advice is applicable in many other aspects of life, not just sales.
    Can’t wait for part 3.

  3. Andrew Miles
    April 13, 2015 at 10:23 am

    Great follow up to part 1, Will. One of my best friends is in sales and so much of this is like his experience – so I know it’s the truth and that guys need to listen up.

  4. April 13, 2015 at 11:40 am

    Thank you, that means a lot, you are the guy this series is written for. If I just reached one guy that makes this whole series worth it. Hold on to that dream, don’t buy into theirs and use it as a means to an ends, just like you’re doing.

  5. April 13, 2015 at 11:40 am

    Thank you, I really appreciate it.

  6. April 13, 2015 at 11:41 am

    Thanks Andrew, that’s exactly it.

  7. JungHan
    April 27, 2015 at 3:57 am

    Incredible series Will. I’ve read your other quality posts, but the sales series have been eye opening. I’m interested in tech sales like SAP and Oracle, so should I be concerned about my Asian name? I’m pretty much Americanized except I couldn’t give a shit about sports. I heard the tech sales culture, especially Oracle, is fratty.

    Anyways, thank you for your honesty, involvement, and knowledge Will. I’ll be purchasing your products when I wake up.

    -JungHan

  8. April 27, 2015 at 8:29 am

    Hey JungHan, thank you, this post is written exactly for guys like you. Your name and ethnicity won’t be a problem, with that said if you have an english name that you go by, like some asian guys do that would be easier. I’ve seen guys from all races succeed you’ve just got to show them you’re one of the boys. I think watching sports is retarded but everyone around you will be into it so again its about being one of the boys, I would check out the highlights to see what was going on, I looked at it as just being a part of the job. Literally the last interview question I got at my last job was if I was a leafs (toronto hockey team) fan. If I had answered no I might not have got the job, not joking.

    All sales culture is fratty, at least in jobs where there is money to be made. The guys who excelled at sports and social competition (frats) are the same guys who go into sales to make dough. You also get the guys who sold drugs in high school who straightened themselves out. It’s an alpha male culture, one of the only acceptable places for alpha males in corporate america.

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