Coaching the Winner of the Great Canadian Sales Competition

Rich Dang
10 min readMar 14, 2017

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Out of the 2,187 applicants across Canada and 400 selected semi-finalist, we chose 1 person to represent our company at the Great Canadian Sales Competition this year.

This post will discuss our journey in selecting Carter Grant and coaching him on his way to beating 21 other finalists. Before I get into the strategy behind the selection process and the techniques used for coaching — I want to emphasize how incredibly talented Carter was.

A number of people approached me after winner was announced to congratulate us, but I wanted them to know that Carter was the biggest reason for the win — not me, nor the company.

I was happy I was able to share the moment with him but without his preparation and determination to win, we would surely have had more challenges in our first year in the contest.

The Selection Process

Scott Clugston (Director of Sales), Carter and I on the day of the competition

First and foremost, kudos to the Great Canadian Sales Competition for providing us a very strong pool of candidates to choose from. Having to sift through 2,187 applicants would be daunting but their ability to provide 32 exceptional applicants made this a lot easier on our company to prepare for.

To pick the perfect candidate we employed the divide and conquer technique and then we made it into our own little (shorter) competition.

Internally as a company we wanted to be sure we gave every student a fair and equal opportunity to impress us. Each student put a lot of effort in their 2 minute presentations and I wanted to be sure I had no applicant fatigue when reviewing each person.

Between the 32 applicants, I split the group into 2 and shared the responsibility with a colleague of mine. From there, we shortlisted the top 2 from each group and pitched those applicants to our Director on why we should choose them.

For future students thinking about applying for the GCSC next year, the features we were looking for when scoring our semi-finalist:

  1. Understanding our value proposition: In two minutes, demonstrate the value our product provides, and why our customers love us. The key to a successful pitch is preparation and confidence.
  2. Presentation: As I mentioned above, your presentation will be a reflection of how well you’ve prepared and how confident you are. Memorize your script, look directly into the camera, dress to impress and let your personality shine through. We’re looking for humans, not robots, so show us that charisma.
  3. Professional Brand: Never had a sales job? No sweat. FreshBooks is hiring :) There are a number of things you can to do elevate your personal brand and make your application stand out. For example, candidates that were highly engaged on LinkedIn stood out above their competition.

Among this group — Carter had all the qualities we could ask for. His presentation for us shined head over shoulders above everyone else. On top of that his experience being the President of DECA, sales internship at Indeed and involvement as a Campus Ambassador for GCSC really showed us he’s an A-player that’s committed to winning it and not just being a part of the show.

Preparing for the Competition

10 Days

After we chose Carter, we only had 10 days to get him ready to pitch our product in front of our peers in the industry; leaders from multi-million/billion dollar firms.

Those who follow my blog know I’m a big believer in empowering my team and putting the onus on them in building their career. Normally my 80/20 rule applies here but I was fortunate to have Carter who pretty much did 90/10.

I knew from his video presentation that he could pitch the value proposition but did he really understand it?

Additionally, he’s never worked a sales job so could he really guide a sales meeting from (1) Rapport Building to (2) Value Proposition to (3) Discovery Questions, to (4) Objection Handling and then finally go for (5) Next Steps/Close?

The Initial Meeting

My first phone call with Carter gave me a feel for where he was professionally and where there was room to improve. The great news was that Carter was prepared and understood the sales cycle very well. What he needed was more exposure to our company value proposition, our tools and our common objections.

To solve for this: I gave him homework.

As a recent graduate myself I connected with Carter and understood he’s still living the world of exams and assignments. I told him by the time we meet the following week, I wanted him to:

  1. Create an account with FreshBooks (www.freshbooks.com)
  2. Timetrack and send me an invoice for the time he spent with me that day and bill me for his time at $15 / hour on both the web app and mobile app.
  3. Add me on his team as a Contractor so we could collaborate easier.

The great thing about Carter’s drive: within the next day I got that invoice and the rest of his assignment.

It really taught him how simple and easy to use FreshBooks was and solidified my confidence in his ability to know the tool. He knew it so well another contestant at the day of the competition told me Carter was selling him on using FreshBooks for his business.

In addition to the homework, I shared some marketing materials with him, getting him well-versed in not just our fit in the accounting software space, but also expose him to common objections, and how to overcome them. Carter is a student, so I did what professors do: over-supply information. He then had to decide what to absorb, and use as arsenal in the competition (more on this below!).

For those students applying next year, some tips:

  1. Communication: Help your coach by communicating what you’re hungry to learn, or where you think you can improve the most.
  2. Sales Process: pick up a few books before the contest like Spin Selling or the Challenger Sale to understand the sales cycle better if this is a gap for you
  3. Understand the Product: try to put yourself in the buyer’s shoes and identify ways with your coach on how you can learn the product as quickly as possible

The First Face to Face Meeting

Beyond myself, I wanted Carter to meet the WHOLE team

Already impressed with Carter’s first phone call, I set up an agenda for our first and only face-to-face meeting before the event. We carved out 3 hours after his class to do the following:

  1. Show him a tour of the office
  2. Introduce him to important leaders to show their department’s impact on the company (more on this later)
  3. Go through the PowerPoint presentation I created for him
  4. Roleplay, roleplay, roleplay! Build a couple scenarios and stories that will compel and engage the audience.
  5. Call shadow our sales team (we ended up skipping this due to his ability to understand the sales cycle)

This was invaluable because it gave us a chance to build a dynamic chemistry that we carried into the big day.

For the semi-finalist next year:

  1. Come with your own agenda on what you want to work on
  2. Take this opportunity to learn more about the company and the culture that you may not get from the website
  3. End the day with takeaways on what you need to work on and truly practice them. Do it in front of a mirror, in front of friends, in front of your parents, etc. etc. etc.

The Day of the Competition

The 80/20 rule pays off here. Coaches support your student by being on call for them through the whole 10 days. If you’ve done a great job preparing them then everything else will hopefully run smoothly.

If this is your first event like it was mine, it may feel overwhelming at first but the GCSC staff are wonderful and well organized. Just follow their direction.

Remember that you are there supporting your student. It is their day: not yours, nor the company’s.

During the two presentations have them lead you with open-ended questions and answer in a way that positively favours and shines their personality and guides you as the buyer to the close. When Carter was on stage I wanted all the spotlight to be on him but I also wanted to match his energy and charisma so that it made a compelling show.

The judges will think of you as an extension of them. If you’re not genuinely engaging or asking objections that they would ask — they won’t believe your story and your feedback from them will reflect that.

I wish I could give more advice here for future students but all I can do is gush about Carter and his presence during the event. He had a confidence and calming demeanour that the other students gravitated around. He came ready and we ran through the various scenarios one more time before he would spend his own time preparing mentally for the big moments.

Tying the Value Proposition to ROI

In 10 minutes, your presentation should have strong ties between what the Seller’s company value proposition is to the Return-On-Investment for the buyer. If at the end of your buyer journey you are unable to give a definitive dollar figure that compels the buyer to action — then you should reinvent your story.

For Carter and FreshBooks as an example, he built a compelling story for three of our main verticals. They all had similar pain points which revolved over the main features of FreshBooks: (1) invoicing, (2) time tracking, (3) expenses and (4) reporting.

During our presentation we focused on the Management Consultant who had issues getting paid through invoicing and tracking their time. Consultants are notorious for being in the industry where “time is money”.

Through the proper open-ended questions, Carter was able to quantify how much time FreshBooks could save the buyer and tie that into how much they bill out. At the end of the presentation, he asked these key questions:

  1. “If we’re saving you 16 hours a month, what would you do with those hours?”
    Possible answers: Bill back out to other existing clients or spend time with family
  2. “How much do you bill your clients now?”
    Answer: $100 / hour (to keep it easy for calculating)

With this he went for the close masterfully:

“Considering you’re saving 16 hours a month at $100/hour, we’re potentially giving you $1,600 back for your business. FreshBooks is $50 / month, don’t you think it’s worth it for your business to invest in this product?”

The Hook

The Top 5 Finalist

All 5 finalists had incredible presentations and I have a feeling it was a very tight race. Aside from Carter’s outstanding charisma and presentation skills — we wanted to tie in a “hook” or a “climax” to the buyer’s journey that really showed the value proposition of FreshBooks being the #1 cloud accounting software for small businesses and also handle the majority of objections that our company had.

Our hook was FreshBooks’ award winning customer service. So good that if you call our Support line (1–866–303–6061) you’ll get a live agent within 2–3 rings. This is just one way we put customers first at FreshBooks.

Carter, after being able to meet our Director of Support during his onsite visit and see our award winning team at work, decided to super-charge his presentation by testing our 3-ring policy live.

So while we could have played it safe and depended on his presence and knowledge of the sales process alone, we went all-in with a live phone call in front of all the judges, people in the audience and live national TV recordings.

With everyone on the edge of the seats: on the 3rd and final ring it paid off and the gasp of relief came across the crowd.

The feedback and perspective from the judges:

Julian Brass, CEO from Notable.ca: “That was the climax of the presentation…”

Amanda Lang from Bloomberg North, commented: “If every salesperson could orchestrate that, that would be fantastic and that was great on FreshBooks [to be able to do that]”.

At night they announced the winner

The Importance of Developing Future Sales Leaders

There’s a big misconception with today’s students on what type of career “sales” can be. When people see sales they think “Wolf of Wall Street” or “Boiler Room” and think they’ll be that used cars salesman that everyone hates.

They think it’s an unfulfilled and short-lived life of stress with no accolades and this has had a stark effect on the economy’s recent shortage of sales talent.

Why this competition is so important is that it fights against these misconceptions and exposes students to the great start-ups and established corporations that are out there to help develop their promising careers.

We want to expose these students early on to the opportunities in sales careers, and offer guidance as they start out. With post-secondary institutions now developing new courses on sales, we’ll be experiencing the evolution of the sales professional as new graduates close the gap on learning and executing complicated sales cycles.

Carter Grant is a model of that future.

As managers and mentors, we will have to evolve our skill set. The next generation of sales leaders isn’t born, it’s developed. GCSC has given Canada’s top companies the chance to educate the country’s brightest students on the opportunity presented in sales. Now, we have to rise to the challenge of keeping this talent hungry for more.

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Rich Dang

Sales Strategy and Operations @ Uber Eats, MBA/CPA/CMA.