How To Succeed In Sales: Tips From A Softchoice Sales Rep And Manager


Most new grads have a tough time picturing themselves in sales, even though there is the opportunity to work with some of Canada’s top employers and make way more money than in a non-sales job (even upwards of six figures in certain industries).

And who can blame you? There’s no such thing as a degree in sales – how do you know if you can be successful in business-to-business (B2B) sales?

Before you apply

Sales rep perspective

Ben Udashkin graduated with a Bachelor of Arts in History from the University of King’s College in June 2010 and, like a lot of new grads, he had no idea what he wanted to do.

He started browsing for jobs online and found a sales position at Softchoice, a leading North American reseller of IT products and services. It seemed like a great place to work, but – like many students – he worried that his education and experience weren’t enough: he’d spent his summers working as a waiter, at summer camps, and in various other jobs.

Ben visited the career office at his university to ask for help. “They said, ‘Let’s take a look at what you’ve done and how it applies to these requirements.’ When I matched all those things up it seemed like it wasn’t so ridiculous to apply after all.”

He asked around about Softchoice and heard they have a great training program. “Perfect for someone like me with no experience,” he says.

Sales manager perspective

Sales Manager Heidi Nisker (Ben’s Manager) has worked in sales at Softchoice for 10 years and as a manager for the last three. She’s interviewed, hired and trained countless new grad sales reps over the years, and she says you don’t necessarily need sales experience – it’s enthusiasm for sales (and Softchoice) that’s she’s looking for.

Heidi says this list of attributes is common among the most successful salespeople:

  • You’re outgoing
  • You love to connect with and relate to people, either in a group or one-on-one
  • You can build relationships easily
  • You work well in teams and you actually enjoy working in a team environment
  • You’re competitive
  • You can stay positive and motivated even when you’re having a bad day


The interview process

Sales rep perspective

A phone interview, an aptitude test, and two in-person interviews later, Ben was hired as a Territory Sales Representative (TSR) at Softchoice’s Toronto office, which was recently featured in the Globe and Mail.

“I was pretty honest about my skill set right off the bat,” Ben says of his interviews. “I didn’t come in here pretending that I had tons of experience because I didn’t. I emphasized how my skill set related to what I believed was important for the role.”

Sales manager perspective

That’s just the kind of attitude that Heidi looks for during the interview process. “It’s really about how someone speaks to their own experience in the interview. If I can see their enthusiasm come through, then I get excited,” she says.

That experience can come in a number of different forms, such as working in retail or food service, doing door-to-door sales, call centers or participating in entrepreneurship programs at school.

Typical interview questions:

  • Why do you want to work at Softchoice? In the IT industry? In sales?
  • What excites you about sales and drives you to succeed?
  • Tell me about a specific situation where you’ve pushed yourself to complete a goal.

Questions you should ask Sales Managers like Heidi in the interview:

  • What does a typical day look like in this role?
  • How are sales reps measured?
  • What inspires you about working here?
  • What are some of the biggest challenges I would face in this role?


Succeeding on the job

Sales rep perspective

Ben says a typical day in the life of a TSR at Softchoice looks something like this: Reaching out to prospective and current clients on the phone. Working on quotes. Preparing proposals for clients. Processing orders. Attending product training. Leveraging the technical team that the company provides for you.

“I’ve had success just cold calling people, being high energy here every day, and building a territory up from nothing as a result,” he says.

“Softchoice is great at recognizing success. They’ll recognize you with the highest people in the company coming up to you, even Senior VPs coming to you, congratulating you for hitting plan when you’ve only been working there for six months. It’s really exciting!”

Sales manager perspective

The two key components to success in sales at Softchoice, Heidi says, are training and motivation. The company takes care of the training, providing new sales reps with three or more months of training around Softchoice’s culture, its systems, and the basics of software licensing and hardware.

Sales reps in training
New TSRs meet with vendors, such as IBM, HP and Microsoft, to learn about their products and how to sell them. “These vendors talk about the best way to make the largest amount of money when selling their products, so people are ready to get on the phone and speak to customers about why one product has more of an advantage over another.”

Once training is complete, Heidi says her most successful reps are the ones who connect and build relationships with as many customers as possible right away. “I want people to pound the phones, call people, get in front of the customers.”

They also have the opportunity to speak to existing small business customers who don’t have Account Managers and, from there, they might move on to a list of small businesses to practice their cold calling with Heidi on the line. Softchoice calls this a “y-connect.” After each call, she’ll tell them where they did well and where they can improve.

“They also have the opportunity to y-connect with everyone on the sales floor,” she says. “The new rep listens in and actually watch how more experienced reps move through our internal systems, set up calls, access our internal resources, and speak to customers.”

Once training is complete
Heidi says her most successful reps are the ones who connect and build relationships with as many customers as possible right away. “I want people to pound the phones, call people, get in front of the customers.”

Success also comes from staying positive, being competitive, and supporting the team. “We have very clear boundaries as to who has which account, so people are just trying to help one another,” she says. “My team is trying to be the best team in Territory Sales Division this year, so every week we celebrate wins and top performers, and we share best practices so people can learn from each other. It’s a lot of fun. It just makes coming to work so much more enjoyable.”


Softchoice is now hiring entry-level Territory Sales Representatives in Toronto and Montreal. Click here to view Softchoice’s career opportunities.


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About the author

Cassandra Jowett is TalentEgg's Content Manager. She joined the team as a student intern in the summer of 2008, and since then her heart has never really left the Egg Carton. Cassandra is a recent graduate of the Ryerson University School of Journalism, where she earned a Bachelor of Journalism with a focus in writing and editing for newspapers. She has also written and edited for The Globe and Mail, The National Post, t.o.night newspaper and other publications.