Many of us dream of joining the world of Big Tech one day, but it’s not easy! Whether you’re a student with no experience or a mid-career professional who wants to make the switch, you’ll find some tangible tips in today’s blog.

Since joining Microsoft Canada as an Aspire (new grad), I’ve been lucky to meet Sales Director, Sean Laughlin, who is an avid advocate of the early-in-career community. When I expressed my interest in pursuing a sales career during the pandemic, Sean gave me opportunities to shadow his team and learn what it was like to work with one of our most strategic retail partners in the country!

When it comes to the topic of breaking into big tech, I thought it would be a great opportunity for all of us to learn from a supportive and committed leader like Sean, who has been leading successful sales teams for over a decade at companies like Microsoft, Oracle, and SAP. Before joining Big Tech, Sean was a marketing student at McGill University who didn’t really know what to do after graduating. It just so happened that one of his dorm leads was working at a small software company that automated processes for dental offices. They told him about an IT Support & Training role where he would have to drive around the U.S. training staff on the software and providing technical support. Little did he know that this gig paying $26,000 a year would be the launch of his career into the tech industry! Today, Sean leads an enterprise sales team for Microsoft Canada that looks after some of the most strategic customers in the country.

Tip #1: Gain industry expertise

Hiring managers are often looking for sales professionals with relevant industry experience. The best way to build this industry expertise is through on-the-job exposure — aka working in that industry. For example, if you’re interested in public sector sales then it is a good idea to work in the healthcare or government industries and gain real industry experience. This way, you have an understanding of how decisions are made and how the businesses are run. This unique knowledge helps you become a better sales person because you can empathize with your customers.

Tip #2: Develop a strong WHY

As a hiring manager, Sean is always interested in understanding a candidates interests and purpose:

• Why do you want to work for this company?
• What do you really see in this opportunity?
• Do you understand the company mission?
• How can you add value?
• Do you have a plan for helping the company with its mission?

There are no right answers, but it’s important to do the research and articulate your thought process and intentions to help the hiring manager with their mandate.

Tip #3: Get your foot in the door

If you’re looking to transition into a new role or career path, actively seek opportunities to build relevant skills and experiences. This could mean going back to school and taking some courses, looking for stretch projects in your current role, or volunteering for projects outside of work to get exposure and experience. The key is to develop transferable skills that demonstrate your ability to get the job done, even if you lack on-the-job experience.

If you can’t get into your dream company right away, don’t worry! Experience from other companies is really valuable. Consider starting somewhere, like a start-up or mid-size company, where you can gain initial experience. Once you’re in the ecosystem, you’ll have many opportunities to gain relevant skills and experiences and expand your network in the right places.

Tip #4: Watch how much time you spend in a single job or company

Sometimes, early-in-careers can get impatient and move on too quickly from a role. Doing this can hinder your growth and impact in a role — even if it’s not your dream job — which is what ultimately propels you into your next role. You can still learn a lot and build transferrable skills even when you’re in a role that you know isn’t a long-term fit.

For instance, Sean realized on the second day of one of his jobs that it wasn’t a long-term fit. Since he had already made a commitment, he stuck around for 3 years, built a team, and earned a promotion. This demonstrates that you can still make good things happen with the right mindset!

On the other hand, staying in one place for too long can skew your understanding of the industry and market. Immersing yourself in one team or company can lead to tunnel vision and blindspots. You can combat this complacency by constantly questioning if you are still learning and growing. Moving to new functions or companies can help you see things through a different lens. Ultimately, it’s a delicate balance.

Tip #5: Your grit and attitude trump everything else

When you’re early-in-career or even embarking on a new path in your career, having a positive attitude will get you very far. You can’t always control the outcomes, like whether a customer will sign your deal, but you can always control the effort. Sales is hard work. Don’t let rejection get in the way of your goals because there are many paths to get to where you want to be. If you can demonstrate your ability to learn swiftly, persevere through challenges, and consistently show up, then you will find people who are willing to take a bet on you. 

While thinking about your career, think about what else is important to you. Looking back, Sean shared that because he was so focused on getting a job, he missed out on an opportunity to travel with friends after university. Although he regretted that, he made up for it several years later by taking a leave of absence to travel for a few months.

More likely than not, you will have a long successful career. Remember that life is short, and it’s OK to take breaks to pursue other goals and passions!

Thanks for reading!

Thank you so much to Sean for taking the time to share his advice with early-in-careers and those who are looking to transition into Big Tech. I’d also like to personally say thank you to Sean for investing in the Aspire Canada community and being a leader who really cares about our growth and development.