Episode TwoHundredFortySeven

Don’t Rush Your Leadership Career (The Grass Isn’t Greener)

Guest: Rory Stern, VP, Northern Europe at CybelAngel

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About This Episode

You’re an IC right now, but you want to be in leadership.

You hear about an opportunity outside your current company… What should you do?

Recently on the Sales Engagement podcast, we had a chance to chat with Rory Stern, VP, Northern Europe at CybelAngel, about what it takes to plunge into leadership — and the best route to get there.

Rory said he got into sales because of serious debt. With his father as an amazing sales role model, he could envision building a better life for himself through sales.

He credits his leadership at a prior company for building an amazing community and caring about him personally: “When I got into Yext after college, I could literally not deposit my payslips. So [Brian] Rikowski walked me over to Bank of America and cosigned for me on my very first checking account,” Rory said.

That’s what it takes to be a great leader.

Let’s dive in!

Leadership in sales

Rory said it’s good to have a variety of leadership styles as role models when you are starting out in sales. 

You might realize you’re heading for the leadership track if you start to see an interest in team wins, not individual wins.

Rory was a very contented individual contributor until he had the chance to move to Europe in a leadership role. He was so excited by the prospect of learning more about different cultures and solving problems in an all-new venue that he made the leap.

“There are some very serious questions you have to ask yourself when you are stepping down from an IC,” Rory said.

  • Are you ready to make less money for a short period of time?
  • Are you ready to stop thinking about yourself first?
  • Are you ready for your satisfaction, to not come out of monstrous paychecks, but to come from building an organization? 
  • Are you ready to watch people’s careers grow (not necessarily yours)?
  • Are you ready to give up your freedom?
  • Are you ready to start a whole new challenge?

If you aren’t ready, then don’t go. Being an individual contributor for the rest of your career can be an amazing and fruitful decision.

Another caveat: Don’t go into leadership thinking you can get away from hitting your number. The number in leadership is just way, way bigger.

What does it take to be a successful IC?

“If you’re in an IC role today, you need to focus on doing your job,” Rory said.

  1. Dedication. Maybe that’s a cliche, but if you haven’t put in the time driving pipeline, you aren’t going to understand the funnel for your specific business.
  2. Resilience. Don’t be afraid to pick up the phone and cold call. Ask for feedback, and then implement it.
  3. Curiosity. “Take the time, learn your product, okay?” Rory said. Big hint: Your manager wants to work with someone who is hungry to learn.

Those 3 intangibles — dedication to the job, resilience, and curiosity — will set you apart from the pack.

In terms of your career path, Rory advises you be considered about your decisions. “Don’t rush into the very first recruiting call that you get to be a leader somewhere else. If you’re in an IC at a good company, and you like the leadership, you like the product? Well, that’s probably the best place for you to take your first step in leadership,” he said.

“Those intangibles are those qualities that will serve you for the rest of your life — things like that curiosity, that energy, and the hunger to be the best,” Rory said.

What does it take to be a successful leader?

All of the above and then some.

Knowing how to recruit great talent is a big part of successful sales leadership. 

Flexibility is another one. “Not all sales methodologies are one size fits all, but I think it’s helpful to at least have some general understanding and at least be an expert in one,” Rory said.

Know your motivation, as well. “Motivation is a hell of a drug,” said Rory.

At the end of the day, what motivates you?

  • ICs: Get financial stability & win all the competitions.
  • Leaders: Grow people’s careers & build the business.

“That has to be something that really, really gets you excited. If that doesn’t, it’s probably not the role for you,” Rory said.

Rory told us that those original intangibles constantly get fed in leadership, too. He loves representing the notion of American sales in Europe (even working against stereotypes if necessary). His dedication is to team success now, not just his own.

“What really excites me on a day to day basis is interacting with people all over the world. There’s a lot to learn,” he said.

Rory’s parting wisdom

Rory: “Don’t rush your career path. The grass isn’t greener.” View your time as an IC as a highlight in your professional career — and seek leadership where you are first before rushing off to the first outside opportunity you find.

Get in touch with Rory at his LinkedIn.

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

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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