Episode TwoHundredTwo

The Success of Your Sales Team is a Direct Reflection of Your Leadership

Guest: John Healy, Sales Director at Grub Hub

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About This Episode

What is “normal”? Does it even exist? 

After the first half of 2020, it sure seems like nothing is, or ever will be “normal”. 

Pandemics aside, what do you consider a typical successful sales career to look like?

If it starts inside, progresses up through the ranks and winds up in a leadership role, you are absolutely…


Why is that the only way to think about someone having a successful career in sales? 

Leadership isn’t for everyone, either by choice or by nature.

And that’s ok!

John Healy, Sales Director at  Grub Hub joins the show to explore just that. 

He believes in coaching and building sales teams to succeed, whatever that looks like. 

He believes in mentoring and connecting with the individual, and cultivating each reps individual talents. To build the strongest contributions to the overall team. 

If that means leadership roles and upward paths? 

Good things for everyone!

If that means investing in a talented person who will deliver and shine, but head out at 4pm to be with their kids? 

Good things for everyone!

Let’s dive into his approach, by taking a quick tour of how he came up in the ranks.

Developing your leadership style 

You fought the good fight to break free of dialing for dollars, endless CRM entry, flaky appointments and grinding it out. 

Congratulations, you are in a sales leadership role!!!

Ok. Now you have to lead. And mentor. And shape. And teach! And so much more.

It’s all going to be ok. Breathe. We’ve got this.

Your reflex thinking, being the hustler that you are, is to focus on the numbers. 

Make the bottom line so impressive that whatever else is happening won’t matter! 



You are in a leadership role now, and that is very, very different from being in rep mode. 

John’s leadership journey started out just like that. He was looking to just deliver and stack those numbers. 

“It’s very easy to look at that immediate scoreboard and use that as your gauge of, of how you’re performing and how others are going to view your brand performance.”– John Healy

As he eased into the role though, he recognized that leadership wasn’t just a number, and as everyone is fond of saying lately, he pivoted towards a more humanistic approach.

Coaching salespeople: Keyword “people”

Coming into his own, John recognized something about himself. He wasn’t cut out to just throw numbers up. In his personal life, he was drawn to coaching and mentoring.

  • Spend time with them as individuals
  • What motivates them? Advancement? Bonuses? Autonomy? 
  • Where do their innate talents point them?
  • What is the next step? 

Not everyone is cut out for, or interested in leadership! And some are born for it. 

Learn about your team. Get to know them as individuals, and uncover their strengths, weaknesses and dreams. Then guide them accordingly.

Leadership is turning vision into reality

“I think there’s a certain responsibility for companies to make sure that there are multiple career paths out there for people.”-John Healy

Salespeople are unique creatures, with some very specific skills and attributes. Unfortunately, they are usually pushed in one of the following directions:

1. Super rep mode 

2. Leadership

3. Find another career

Don’t  throw away the baby with the bathwater as they say. Invest in your team. Understand them and utilize their skills to grow either your department, someone elses or the overall industry. John considers his team as a reflection of his leadership. If they are winning, he is doing it right. 

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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