Episode OneHundredSeventy

How Good Leaders Embrace Challenges

Guest: Rebecca Croucher, VP of Sales and North American Sales Operations at ManpowerGroup

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About This Episode

Sales leadership lessons don’t come cheap.

But they do shape a sales leader who excels in embracing challenges and supporting her team.

In this episode of the Sales Engagement podcast, I talked with Rebecca Croucher, VP of Sales and North American Sales Operations at ManpowerGroup, about finding leadership success in loving challenges.

Rebecca has worked for Verizon and Dun & Bradstreet and has held roles in both sales and marketing. 

“Everything has been for me so tightly wound around the data perspective, which really makes sales and marketing both very efficient,” Rebecca said.

Sales and marketing should be closely aligned to each other — and built on a foundation of data.

Rising to the challenge of a startup

Moving from marketing to sales… and from a mature company to a startup… has given Rebecca deep insights into the mindset of a leader.

She shared her 3-step process to helping a startup get set up with their systems and processes, as well as why she likes the environment of challenge.

1. What data assets does the company have?

Rebecca looks for internal data, client touch points, and billing data. “What are they buying from a third party perspective?” she asks.

2. Is the dataset clean?

Making the dataset as clean and structured as possible means you can quickly execute on the information, especially if you have multiple brands that you’re supporting internally.

3. What’s the value of this data?

In other words, the last step is to monetize the data by learning to treat it as an asset.

Multiple sales reps that are all selling to the same client or sales support teams that all have to access information need to understand how to leverage the data they have. The data needs to be organized, relevant, and valuable.

Rebecca likes startups because, frankly, their processes can be a little bit broken.

“I tend to go to where there’s the biggest challenge and the biggest reward,” Rebecca said. “The last role I would want to step into is a sales organization that is totally optimized, running at high performance.”

Sales leadership truths

In gravitating toward the greatest challenge, Rebecca has to keep an open mind toward failure.

Unsolvable problems

There are none.

“I don’t think I’ve ever come across something that couldn’t be solved,” Rebecca said.

Which isn’t to say that she always solved the problem the right way the first time. But the spirit of persistence kept her from giving up on difficult situations.

Failure is good

“I’m a fixer,” Rebecca said. “If I have a failure, then I think, Okay, what did we do wrong? What do we not want to do again? Is there anything good that came out of it?”

At MCI (now Verizon), Rebecca launched so many campaigns every month that not everything could succeed. “Even though it was a failure, you could learn from and apply it to the next campaign,” she said.

Persistence and the “fixer” mentality have served Rebecca well in sales leadership. She suggests creating an atmosphere in which failure is allowed.

She teaches her team to come with her with solutions to problems (even if the solution doesn’t work the first time around).

“I show by example as a leader that if I fail, I call it out. It doesn’t mean that we’re going to stop doing it. It just means that we’re going to figure out how to do it correctly,” she said.

Positioning your team for success

Besides calling out her own failures and demonstrating tenacity, Rebecca positions her team for success in 2 other ways.

1. Be an encourager

Rebecca’s team of 8 sales reps consists of senior level salespeople — each with a different personality. 

Some still need this encouragement: “Hey, you are really good. Believe in yourself.”

“They have talent, and all they need is a boost of self-esteem,” Rebecca said. She pointed out that knowing someone believes in you can turn you around really quickly.

When you make hiring decisions, look for traits you can encourage.

2. Be a supporter

While encouragement usually means verbal affirmation, support can take different actions, including learning about someone’s optimal environment.

Rebecca will dive into a rep’s history to figure out why someone who has the potential for success isn’t showing it yet. “When someone has those good, time-tested sales skills, then you can definitely figure out the best position to put them in and what needs to change,” she said.

It could be a simple fix. Flip them into a different account structure, industry, or role.

This supportive leadership extends to customers, too.

Rebecca has been spending time during the COVID-19 pandemic connecting companies that are hiring with people who have been furloughed. “There’s no time like right now for our company to do some amazing things for a lot of people in the country,” she said.

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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