Episode TwoHundredThirtyNine

Owning Your Career Progression

Guest: Ryann Leonard, Director of Global Restaurant Operations & Enablement at Slice

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About This Episode

Most people want to go somewhere with their careers. They’re usually not comfortable staying in one spot for too long.

Sure there are some folks who get into a role and they want to do that role for their entire careers, but most people aren’t like that. Most folks want to use a role to learn, grow, and help them move into the next role. 

But how do you do that, particularly in a sales role? What does an entry level cold-calling sales rep have to do to put themselves in a position for the next role, and then once they get there, how do they keep setting themselves up for success? 

On this episode of the Sales Engagement podcast, we talked with Ryann Leonard. Ryann is the Director of Global Restaurant Operations & Enablement at Slice. She’s had an amazing career run, and spent over 2 years as a cold-calling sales rep, all while setting herself up for the next thing. 

Prioritize Your Main Job

What is it that gave Ryann the ability to spend that long in the trenches as a sales rep? To take rejection and turn it into an opportunity? 

Simply put, she made the role more than what it was, but she never sacrificed her primary role. 

If you’re in an IC role, it can be tempting to look around at all the cool things happening and want to get a foot in the door. To show your worth by volunteering for projects, figuring out what needs to be done to improve, and really trying to add value in any way possible. 

But be careful that it doesn’t come at the cost of your primary role. Far too often, especially with the younger generation, they’re so gung-ho set on getting into management that they don’t hit their sales goals. They forget about what they’re actually being paid to do because they’re so excited about what they COULD be paid to do. 

Your goal should always be to do the best that you possibly can in whatever role you’re given. That way you’ll be the no-brainer when it comes time for a promotion, or the next big thing. 

Never Assume

It happens all the time. You are killing your sales numbers, and there’s a big promotion that comes open, and so you make sure that your work is impeccable.

And then someone else gets the promotion. 

So what do you need to focus on in order to make sure that you stand out? Because oftentimes it’s not enough to simply be good at your job. Your leaders  can’t read your mind. They may not even know that you’re wanting a promotion. They may just think you’re really good at your current job. 

Sit down with your manager and ask, “What do I need to be doing in order to put myself into position for the job that I want?” and be able to articulate exactly what that job is. Be direct, and honest, but also open to feedback and helpful criticism.  

Remember, if you don’t ask, the answer is always going to be no.

Making Your Role More Than it Is

As an individual contributor, one of the most crucial things that you can be doing in order to set yourself up for success is to always be the vocal one on your team. The one who is coming up with the ideas and bringing them to the team.

It’s simple things like “I sent this email and it got a lot of traction, maybe this would be a good idea to try.” 

You also want to make sure that you’re always working on the problem and doing more than just what you’re told to do. But in doing more, remember not to ignore your primary role. 

As a manager, it’s a lot easier to execute on what the next level of people are telling you to do. But at some point, you may realize that you’re simply an executor. And there isn’t anything wrong with being an executor, but if you want to come  u p with new ideas and be strategic, don’t be afraid to think crazy. 

Instead of simply executing, think about  what crazy idea you could implement? How could you improve the sales process? What’s the completely off-the-wall thing that just might be crazy enough to actually work. 

Three Main Things

If you take just three things away from this episode, what would they be? Ryann was asked that question and had these three points to consider

  1. Always put yourself in the best position to be the no-brainer decision for the next big thing.
  2. If you don’t ask, the answer is always no
  3. Take ownership and treat whatever your job is like it’s your own business. 

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