5 things I learned working for 1 year in sales

I remember just over a year ago I was staying in a shitty AirBnB that was essentially just one room, in a relatively rundown building that was pretty far out of downtown Toronto. I was also, unfortunately, sharing a bed with the friend from college I moved over with (this was a low point that I can look back on and laugh about now), listening to the audiobook of “Fanatical Prospecting” by Jeb Blount as I was trying to fall asleep. We had both set this goal to get a condo downtown with a balcony. Not sure why the balcony was such a part of it but anyway, whatever gets you motivated. We had both just accepted jobs working in sales for tech startups, had no idea what we were doing, but we really wanted that balcony.

As I’m writing this, I’ve just completed my first year working in sales, and boy has it been a ride. I moved to Canada with two suitcases and a friend from college with a newfound enthusiasm for getting uncomfortable and pursuing a new challenge in tech. I was coming from a background working in data for a large corporate company and didn’t really know what I wanted to do, but I was sure that it wasn’t what I was doing - so I took a risk and made a change.

Once the novelty of trying out new and obscure Ontario craft beers, my friend and I set to work on getting a job so we could afford to eat, find somewhere to live and not have to go back to Ireland. This meant a lot of time crawling through all the usual job boards you can think of and applying for jobs, except we were doing it from a hot and stuffy basement apartment in uptown Toronto during the heatwave last summer.

After 2 weeks or so I had interviewed for and accepted a job with a 100+ person programmatic marketing company with okay money, decent perks, and a nice office. The problem was that the learning opportunity didn’t seem that huge. This company was already pretty well established, stable and somewhat at the end of their story. The role was pretty analytical and was relatively well suited to my previous experience and I was pretty familiar with programmatic from my last 2 jobs.

I had another interview for an outsourced sales prospecting company that I had zero intention of taking but had already agreed to the interview before I accepted the other job, so out of courtesy I attended the interview wearing a t-shirt and shorts. I was going to at least hear them out but honestly planning to still take the other job rather than take a sales position in this 15 person startup. I’m a classic INTJ who’s strengths are in analytical thinking and problem solving - what business did I have being a sales rep?

But once I got into a room with these folks in a co-working space in downtown Toronto, they completely won me over. These people were passionate, who had drive and wanted to grow fast. So did I, so it seemed like a good fit. It wasn’t so much of an interview as it was a conversation. I had breezed in wearing a t-shirt and shorts as I said and they didn’t even bat an eyelid, whereas for the other interview I wore a suit and I felt like I was on trial for 45 minutes. I immediately felt comfortable being myself and speaking my mind with these startup people. The difference was night and day.

So rather than go the safe, predictable and stable route of joining the 100 person company (in a role that arguably was much more suited to my strengths) to just be another number, I decided to roll the dice and take a very new job in a new industry. The learning opportunity seemed far great and even if I sucked at sales, what's the worst that could happen? I'd just go on the job hunt again or go back to the other company. I had taken a risk by moving country, why not bet big on changing career too? In for a penny in for a pound right? So about an hour after the interview with the sales startup, they sent me an offer to start the next week. I accepted.

I don’t think I could have ever predicted what would happen over the next year, how much I would learn and (not to toot my own horn) how successful I would be in sales. I even remember a conversation with my manager telling me he wasn’t sure if he made the right choice after hiring me after 3 weeks. We can both laugh about that now after what I was able to achieve in the last year.

Based on all the feedback received over the 12 months, I made quite an impact on the company and turned out to be a much better hire than expected. I was managing a team within 6 or so months. And I spend the next 3 months developing a new business line and managing a remote team. These are honestly the five most important things that really propelled me forward and moved the needle the most in my success in sales and start-up land in the last 12 months.

1. Hard Work

There is nothing sexy about this one but it has definitely been the biggest determining factor in my performance. It’s cliché and obvious as fuck to say, but I really feel that hard work is honestly the most important thing you can do to be successful. To quote David Goggins, hard work is the great equalizer.

Everyone wants to find a short cut or workaround to skip this part by looking for the next big secret like micro-dosing LSD Juul pods or transcendental standing desk meditation but this fad type shit is cheap surface level juice cleanse bullshit. Everyone knows what they need to do to be successful, they just don’t want to put in the work.

To me, it seems like a no brainer to just work hard. I don't think I'm particularly special or intelligent, but working hard is something anyone can do. It's completely within your control so I just can't comprehend why you wouldn't work hard at something you're trying to do. The author and founder, Derek Sivers, said that anything you do should be a hell yes or not at all. So if you aren't pumped or excited about what you're doing, you shouldn't have this as your main focus because it will make working hard much harder.

2. Discipline

Some people around me have asked before "How are you so disciplined at X?" or "How do you keep going at Y?". To me, discipline isn't really a choice. It's no longer difficult because I've put the right habits in place to make most of my decisions not require much willpower. Two really good reads on this subject are "Atomic Habits" by James Clear and "The Marshmallow Test" by Walter Mischel. Both are great instruction manuals on how to hack your habits and environment to work for you so that your default decisions (that require no willpower) become easy.

Having the discipline to do the shit that no one wants to do when you don’t want to do it can put you miles ahead of everybody else. It’s really that simple. When I was a BDR I used to work an extra 4 hours on Saturday and again on Sunday morning on top of the normal expected office hours. But if you do an extra 8 hours of work, week over week, this can really add up. You don't need to be doing this all the time, but when you are really sprinting/pushing for progress, it can make a huge difference.

I don’t imagine this is something many people would want to do. But I did it anyway because it produced results to put me ahead. In the long run, it's all about consistency over time, but don't let that fool you into thinking that doing unsustainable sprints now and then can make a huge impact on your progress and results. It also builds a muscle inside you to help you grind when things are tough. It’s not about riding the highs and doing the work when everything is coming up rainbows, it’s about continuing to work hard when you don’t want to.

3. Play To Win

This is especially important to me. And it means exactly what you would think by reading it. If I’m playing a game, I’m playing to win. A casual game of pool with my friends? I’m playing to win. How many pull-ups or bench press reps you and a friend can do? I’m playing to win. Who can run the fastest 10K? I’m playing to win. The number of booked meetings in a month? I’m playing to win. 

While you can't necessarily always control whether you win or not, you can certainly influence the outcome of most things depending on what attitude you take. I hate people who say "I could have/should have/would have XYZ" after the fact about something. Or even worse "I could have done X but I wasn't really trying". If you aren't really trying you're just taking up space and wasting everyone's time. Find something else that makes you want to try.

To me it doesn’t matter what it is that I’m doing, I’m playing to win. Other people don’t always take this that well or understand why I take some things so seriously. And to be honest, either do I. Regardless, I will always play to win. Life is a game, and you should play to win.

4. Prioritization

Ruthless prioritization is the best time management system you can have. Saying no to most things is the best way to stay focused on what matters. By combining these two things, you can achieve unstoppable levels of focus. Everyone has core tasks and responsibilities they should be focusing on to be successful. When people fall behind or aren’t performing well, they often aren’t clear about what they should be prioritizing.

One you ruthlessly prioritize, it makes planning how to spend your time a lot easier. Once you have a main priority or core activity that you know will have the most impact on what you're trying to achieve you should double down and bet big on that. You'll be surprised how much nobody cares how many small unimportant things slip through the cracks if you're producing exponential results in the one area that really matters to your success. Plan your days, focus on the most important priority at the time of day you are most productive. For me, this is usually early in the day right after I work out and have some caffeine in my system.

It doesn’t really matter what goal or milestone you are trying to achieve, everything has its core meat and potatoes activities that will move you closer to success day by day. Greg McKeown talks about this in his book “Essentialism: The Disciplined Pursuit of Less”. Say no to most things, focus on your priorities and you will be successful. The exact same message is found in "The One Thing" by Gary W. Keller and Jay Papasan, by doing one thing that has the most impact really well, you will be successful. It's kinda cliché but true, it's not about doing everything right but doing the right thing and focusing on that.

5. Persistence/Grit

Being persistent, especially in outbound sales, is a game-changer. Even when you do everything in your power to do things right, you will hear no a lot. It can be discouraging. Especially if you are new to sales, it can be really discouraging. But you need to trust the system, follow the data and remain objective so that you can persist.

I remember getting two responses to the same outbound message that was personalized to two individuals doing the same job at different (but similar) companies. One of them said “This is one of the best sales messages I’ve ever received, I love the approach and appreciate the time you spent researching me before reaching out. Let’s hop on a call”. The other one said, “As a CEO, this is the worst approach I had ever received - don’t ever message me again”. You’ve gotta have grit and not let that second message stop you. You can’t please everyone, that out of your control - but persistence is a choice.

Even if you do a lot of things wrong, being persistent can serve you really well. If you're willing to send that extra email, follow up once more and make one more dial - that could be what was needed to push the prospect to at least making a decision. And that's all we're trying to do, push people to a decision so that you can move on to the next person. Maybe is the worst decision in sales.

In conclusion, these are five things that really helped me be successful in sales over the last 12 months. Apply them yourself and see what happens. Happy hunting.