Episode TwoHundredSeventyFour

3-Part Framework for Career Growth

Guest: Kyle Norton, Head of Revenue, Canada at Shopify

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About This Episode

Growth is the only thing that matters.

Given that, we need to be more intentional about what and how we’re trying to grow.

Recently on Sales Engagement, I had a fantastic conversation about career growth with Kyle Norton, Head of Revenue, Canada at Shopify.

Kyle cut his teeth on sales for a company with a negative brand reputation when emailing was still soft — so an uphill selling experience for sure.

“I’m hoping more universities can teach the business of sales more and hopefully find ways to give people exposure to it to help them figure out if this is actually for them,” Kyle said. He’s all about self-development, growth, and voracious learning.

Quick aside: Kyle’s discussion was peppered with about 10 excellent book recommendations. Definitely give the whole episode a listen.

Let’s get right into the conversation!

Hard work

There’s no sugar coating the fact that the sales profession is very hard work.

In sales and in sales leadership, you grow your career by proving that you’re willing to go above and beyond, to work harder, and to invest in your skills more intently. That’s how you get noticed and how you gain opportunities.

Kyle was 22 when he got his first team of people in their late 20s and 30s. His youth was a big risk, but he was already making his numbers and sharing his learnings with the team.

A 3-part framework for career growth

Here’s the framework that Kyle gives his team.

The three drivers to career growth are…

  1. Skills development
  2. Impact
  3. Luck

We’ll discuss each one in turn.

Skills development

Skills here refers to both career skills and personal skills. If you’re getting better at your job and your craft beyond just closing more deals, then you’ve begun to grasp deep learning.

Here’s a fantastic system that Kyle implemented to help his team go deep on one skill for 4-6 weeks until they’ve achieved organizational momentum around getting better at that one thing.

The system comes from mixed martial arts:

  • Introduce. In the first week, give your team a topic and allow them to intellectually explore it with podcasts, books, reviews of calls, and other pre-work tasks prior to the live learning environment.
  • Isolation. In the second and third weeks, construct environments where the team will perform deliberate practice of the topic. Aim to make the challenge just hard enough for a 60-80% success rate.
  • Integrate. In the fourth through sixth weeks, the team will incorporate the skill into the real world environment with specific metrics and feedback.

So if you were focusing on discovery, you’d assign a little bit of research and then bring the team into breakout groups to explore the topic. Then you’d spend a couple of weeks practicing discovery over and over, analyzing the process and trying to improve. Finally, you’d run a contest about how many times team members elicited the response “That’s a really good question” as an integrated live feedback mechanism.

And the coaching for that whole period would be about discovery.


Growth is really the foundation of impact. The growth and skills development phase lays solid roots for the impact phase, which is measured by the fruit or yield.

It means being great at your job. Being at the top of the leaderboard. Showing your growth by doing outstanding work.

Are you driving results and impact within your organization and within your teams?


“If we look at the luck component of the model, you can make your own luck by increasing your visibility,” Kyle said.

It’s great that the framework incorporates luck, because that’s just how real life is. But growth and impact can inform and improve your luck by giving you a goal of building the skills you need for the next job you think you want.

Reading leadership books, building a mentorship relationship, taking on a project — these can help build the skills you need to be a good sales manager, if that’s your next step.

While you’re waiting on your luck, focus on skills development and impact.

“You can make your own luck by being in the right places at the right time,” Kyle said. Examples would be a high growth environment or an environment with a really well defined career track or an environment with a specific leader for you to learn from.

That last one is partly why Kyle landed at Shopify: values alignment and someone he felt offered valuable learnings for him.

Kyle’s 3 takeaways

Kyle: Growth is the only thing that matters, so own your own development. Two is: extraordinary career results do not come with ordinary effort or ordinary work ethic. Three is: try to make your own luck. Find ways to find ways to stack the deck in your favor, but always know that it’s still a game of probabilities even if you do all the right things. Never get dissuaded from your process and things will turn out really well in the long run.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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