Finding your dream job

Action shot of the Clearbit sales team and I at Base CRM’s annual conference.

Action shot of the Clearbit sales team and I at Base CRM’s annual conference.

Needless to say, the college environment and the work environment are drastically different. They both have their pros and cons — for the former, I have a lot of free time, a predictable schedule, and I’m surrounded by people at a similar stage of life as me. The latter has its perks too — the work is more engaging, I have a consistent source of income, and there are a ton of people to learn from.

Chatting with friends who are also wrapping up their final year, the conversation varies. Most people fall into one of the following buckets:

  • Signed a full-time offer / committed to grad school, enjoying the year

  • Know what they want to do, but still looking for full-time work / applying to schools

  • Not sure what they want to do, aren’t sure where to start

I’ve written a fair amount about finding internships and succeeding in the workplace, but the tl;dr is that it all comes down to finding what you’re both interested in and good at (usually correlated). In this post, I want to dive into how I found my passion for technology and marketing, what questions I needed to answer along the way, and what role I think is the best for new grads.

Dazed and confused

First year was a bit of a mess. Trying to adjust to school work and a new social environment is hard enough, without everyone stressing about finding jobs and being the best at whatever you’re interested in. My older brother had just graduated from Western, and the friends he introduced me to, who had done the business program (Ivey), were committed to paths in finance. You get to wear a suit, make lots of money, and work in ‘capital markets’, so that had to be pretty sick, right?

The first piece of advice I received and still stick to today, is that you need to dive deep into whatever you’re interested in. It’s not enough for me to say “yeah I think finance is cool”, without having ever spoken to anyone working in the industry, learned any of the material, or discovered whether I’m good at it. The sad reality is that a lot of people never make it past the ‘interest’ stage; I could have gone through all 4 years of college being ‘interested’ in a variety of roles, but when it comes to getting a job, I would have been unqualified for them, and more importantly, would be unsure which path I wanted to commit to.

So following this logic, I started to dive into finance. I read Mergers & Inquisitions to learn about the work and lifestyle, talked to older friends who had worked in finance, and started the (in)famous Breaking Into Wall Street prep course for future financiers. After months of digging and figuring out…

Well actually, scratch that. It didn’t take long at all. In about 3 weeks, I realized some key points:

  • Finance was cool, but I wasn’t really interested in how the markets worked

  • The work (at an early stage of your career) was dry and repetitive

  • The lifestyle involved gruelling hours and being constantly on-the-clock

Keep in mind, this is my personal view of finance careers. I have a ton of friends going down that path, many of whom are genuinely interested in finance, and I commend them for it. It’s an amazing career for many people. Just not for me.

Tech? But I can’t code…

Back to square one, I had to do some deep thinking to figure out what I was really interested in. A lot of my friends told me about management consulting; a job where you get to solve problems, work in different industries, and travel! It sounded glamorous, and a pretty great fit for me. Most importantly, it would ‘help me figure out what I wanted to do’.

There were two small issues with this: first, if I was in first year, I had at least 3-4 years to figure out what I wanted to do, by trying different roles and diving into my interests. It didn’t make sense to commit (that early) to a job path that would eventually help me answer those questions. Second, they typically only hired 3rd year business students for summer internships, so I had to do something in the meantime, right?

Hitting the career fair at Western, I met a recruiter from a large telecommunications company. I was bright-eyed and eager to learn, so I asked them about their internship program. Their response:

“Love your enthusiasm, but we only hire 3rd Year students in the Ivey HBA program”

Great, well that wasn’t helpful. I had plans for Ivey but still had a ways to go. After talking to a variety of firms at the fair, I didn’t have too many leads to run with. Returning back to residence, I realized I signed up for London Tech Fest — a night of free food and informational booths from tech companies. I couldn’t find anyone to go with, so I hopped on the bus solo to get to the venue.

At the fair, there was a green booth with a familiar name: Shopify Plus. I had heard about Shopify before, and though it was a pretty cool place to work. Unfortunately, I wasn’t in engineering (or even business), and didn’t think I had much of a shot. So I walked up to the recruiter, and tried to think of a way to impress him. The conversation went something like this:

Me: “Hey I’d love to work for Shopify, but I’m only in first year and I’m not in business”

Him: “Why would that be an issue?”

Me: “Well I went to a career fair today, and (telecommunications company) said they would only hire 3rd year business students”

Him: “Screw (telecommunications company), we do things differently here”

In a matter of minutes, I was already a big fan of Shopify — they didn’t abide by the status quo. During our short chat, I kept telling him how I wanted a role where I could hustle hard and do work that mattered. He gave me his card, and said to reach out about a sales internship.

Naturally, I was still a little shocked that my limited education wasn’t a barrier. So I asked if I should learn how to code. He told me that ‘tech’ companies don’t just hire engineers — they need salespeople, marketers, customer success experts, and a ton of other non-technical roles to grow and succeed. These people should know about the product, but they don’t need to know how to code. So I ran with it.

Sales: the ultimate launchpad

Fast forward a few weeks of interviewing, I got the offer to join the Shopify Plus team for Summer 2016 as a sales intern. Keep in mind, during this process I was never asked for my transcripts or GPA. I learned later on that those things are a filter for ability, but don’t predict how you will perform in the workplace. Most small to mid-sized tech companies don’t care about your major or grades, they just want to know if you can do the job well.

The interview process was challenging, in that I didn’t really know what to expect. I read up a ton about Shopify as a company and their various products, along with reading up on sales and what it entailed. I reached out to people working there to see what they had to say about a career in sales — here are some of the key points:

You’re a consultant, not a salesperson.

Wow, that got me excited. I was planning on doing consulting anyways, so imagine what this could do for me! In all seriousness, every rep I talked to stressed how important it was to understand the needs of the person you’re selling to (a lead), what their hesitations are, and how your solution might be a fit for them. Shoving products down someone’s throat doesn’t get you anywhere — in fact, it actually costs the company more if they leave (churn) soon after becoming a customer. The best salespeople help leads figure out what they want, and the leads sell themselves.

It takes perseverance, hustle, and creativity.

Sales is not a cushy job. You don’t have vague deliverables or layers of promotions before you actually get to do the job. From day 1, you’re learning to sell and getting direct contact with leads, soon after getting a quota that you need to hit. If you don’t hit the quota, you’ll be placed on an improvement plan and eventually fired. It’s the only job where there is no cap on the amount of effort you can put in — the more you sell, the more money you make and the better for the company. It’ll teach you how to hustle, get creative with your outreach, and hit your goals (your quota).

You’ll become an expert at controlling conversation.

My initial reaction to sales, like many people, was that it’s a sleazy profession that doesn’t involve many ‘hard’ skills — you basically just need to be good at persuading people. The reality is that it’s not that simple, especially when you have to convince the 50 year-old executive of a multi-million dollar enterprise that your product is worth their time of day. Most of my sales colleagues at Shopify Plus were under the age of 25, many of them fresh new grads. They sold to Drake, Tesla, Big Baller Brand, and Kylie Jenner. I can’t think of anywhere else where you’re the main point of contact to such incredible companies, let alone where you’re solely responsible for bringing them on as a customer. Knowing how to drive conservation, set deliverables, and get someone from “I don’t care” to “Take my money” is a magical process — and it’s called sales.

You’re working up from ground zero.

The best part about careers in sales is that there is really no ‘ideal path’ into it. Some of the best salespeople were psychology majors and never sold a day in their life. All entry-level sales positions, whether it’s at Google or a 10-person startup, will teach you how to sell and eventually turn you into a confident salesperson. There is NO pre-requisite, except an ability to think quickly and a willingness to learn fast and hustle hard.

The world is your oyster.

After learning how to sell, you can stay in sales and move up the chain to be a killer account executive, or move to management and run a full sales team. You can also make other transitions — people I know who started in sales have gone on to become successful entrepreneurs, marketers, product managers, and much more. Sales is the ultimate toolkit / skillset that will enable you to succeed in a number of career paths.

Okay — Where do I start?

There are hundreds of tech companies that are hiring new grads as salespeople. All it takes is preparation to learn the sales basics and an open ear from the hiring manager. I saw this gap over my time in tech, both in Toronto and in San Francisco.

That’s why I’m starting a program to get more new grads into tech sales. It involves a 3-week bootcamp on learning how to sell, written by current sales professionals, and then we refer you to a variety of companies — everything from 10-person startups to UberEats — to interview and get a sales job.

If you’re graduating in April 2019 and are still looking for full-time work / aren’t sure where to start, or know someone who is, shoot me a message so I can get you involved in the next cohort.