Software Sales Tips by Matt Wolach

Scale Your SaaS

How to Hire and Manage an Amazing Sales Team – with Will Yarbrough


In this episode, Will Yarbrough, the Vice President of Sales at Fleetio, shares his experiences as a leader in managing an amazing sales team with SaaS-Story In The Making podcast host, Matt Wolach. 

He particularly offers his best advice on how technology sales leaders can manage their team to outstanding results, and how to transition from individual contributor to manager. He also shares some of his insights and tips on the hiring process, management process, company best strategies, and advice to other sales leaders who just became leaders.


Podcast: SaaS-Story in the Making

Episode: 168, How to Hire and Manage an Amazing Sales Team

Host: Matt Wolach, a B2B SaaS sales coach, Entrepreneur, and Investor.

Guest: Will Yarbrough, Vice President of Sales at Fleetio


Best Practices on Hiring a Sales Team

Hiring salespeople is tough, says Matt, a long-time Sales leader, noting that some salespeople had great history and experience but would not perform as expected. Will gives pieces of advice around the hiring process, and one of the most important steps is to recognize that hiring is time-consuming and leaders need to take their time. 

The number one thing Will recommends is to standardize a scorecard. Grade people on the same things, ask people the same things so you can compare candidates. He also considers screening people that are not qualified. While this is also time-consuming, Will notes that doing this enables him to know where a candidate fits potentially. 

Next, Will asks managers to pay attention to details, and lastly, do an assessment or ask the candidates for a mock pitch. From there, you can rate the candidates in terms of their confidence and conversational skills.

Having a Scorecard is Crucial

Matt points out that having a scorecard amongst the team is crucial, and this entails letting everybody know where they stand and what they need to do to go towards the top. “I’ve always been a big believer that it’s super critical to make sure people are trying to get ahead and continue to do better and better,” he adds. Will agrees, saying he and his team also keep score using sticky notes instead of digital scorecards, which is practical and more visual. “The more that we motivate through that, the better off we’re going to be.” 

Motivating the Right Way 

When asked about other ways to motivate his team, Will says he encourages people depending on what they feel most inspired about. “We have all different types of personas and archetypes that we’re hiring for. They’re all going to be motivated by this, by different things,” he remarks. “They want the recognition. They want flexibility. So I think you always have to stay in touch with the folks on your team to understand what motivates them because it’s not going to be one-size-fits-all.”

Have Courage and Take the Risk

For sales managers who are starting, Will gives a piece of advice: find a question you don’t know the answer to every day. It’s okay to feel uncomfortable. Take risks. Find ways to put yourself in positions you’ve never been in before. Most importantly, Will urges sales managers to go network and talk to people that know the answers, so you can understand it better the next time it comes around. “Do those things that will shoot you to the moon,” Matt adds. “You’re going to achieve fantastic stuff because that’s a blueprint for how you can get better. Get your product out there and get yourself improved.”


Using Technology in Fleet Management

When the pandemic happened, many companies and businesses had to transition to working online. Founders, business owners, managers, and leaders had to utilize technology to keep their businesses functioning when most employees had to work remotely. Will admitted that in the past seven months, he and his team were trying to figure out what to do during and post COVID, coming out of that. His company went through a fast-paced growth he called “hyper-growth mode.” 

With all the abrupt and unprecedented changes, Will used Fleetio’s technology to allow customers to leverage other technologies better. An example of that is Fleetio can integrate with a fuel card that people use to gas up their lawnmowers. Moreover, Will worked to give Fleetio better visibility and insights.

Growing as a Company in a New World

As companies had to adjust to the new world amid the current global situation, Will had to educate leaders multifaceted. “Inertia wins more often than anything else in sales,” he states. “The education component is critical to our success.” Will continues to share that he and his team did that starting at the top of the funnel with their marketing team, trying to get their brand out there, leveraging SEO and keyword search, and trying to drive as much traffic to their website. 

From there, he educates their customers through a demo, an overview of their platform, or through a free trial. As he notes, “SaaS is not only about the initial sale, but it’s about expansion, revenue, and retention after the sale.”

Transitioning from a Contributor to Manager

Before becoming Fleetio’s vice president of sales, Will started as an enterprise salesperson with the same company, working his way up to becoming a sales manager, sales director, and ultimately, to the top. When asked about how he transitioned from an individual contributor to a manager, Will shares a piece of great career advice: don’t be high maintenance to your manager. 

Take things off your manager’s plate rather than being something that creates work for your manager. As a salesperson, Will looked for things that his CEO was spending a lot of time on, and he tried to take those things off his checklist. By doing so, it gave him opportunities to be more involved and gain more responsibilities. 

What Makes a Great Leader

A great leader inspires others to become leaders themselves, and this is what Will lives by. It’s not the closed contract that he likes most about managing salespeople, but it sees his team move up the career ladder and attain success and how excited they are to experience that success. “The other thing that’s neat about moving into sales management is architecting a process, architecting a career path,” he says. “When you move into management, it becomes much less about you and much more about the team around you.”


Will Yarbrough

[04:47] “SaaS is not only about the initial sale, but it’s about expansion, revenue, and retention after the sale.”

[07:01] “You’re never going to move up the ladder without taking a risk and getting uncomfortable.”

Matt Wolach

[7:50] “Find out what your boss, your director, your manager hates doing that they have to do and take it off their plate.”

[24:12] “Do those things that will shoot you to the moon.”


To learn more about Will Yarbrough and Fleetio, visit  

You can also find Will Yarbrough on LinkedIn at

For more information about how host Matt Wolach helps software companies achieve maximum growth, visit

As part of the founding team in his first SaaS product, Matt owned the sales & marketing processes. But he struggled to sell and gain traction for the company. It took years of learning and tweaking before Matt created The Perfect DEAL Process, an innovative yet easy-to-implement method for closing more software deals. To find out more, visit

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