How to Develop and Hire Salespeople with a Winning Mindset

It’s unclear when the trend started, but it’s become a prerequisite for all startup / technology / sales jobs to include a provision for “culture fit.”

Aside from the product a company builds, or service it offers, organizations go to great lengths to define themselves by the corporate culture they try to instill.

Asking for candidates and, ultimately, new team members to fit a particular company culture is the easy part, however. Building, and growing, that inclusive environment is a bit more tricky.

At best, shepherding company culture is a tightrope walk, with countless important factors constantly at play – empowering your staff, avoiding prescriptive top-down approaches to work, and providing some semblance of work-life balance, just to name a few.

Underpinning all of these different considerations, however, is leadership. It’s the tie that binds culture together. It’s the north star that gives team members the template for how to fit, and enhance, the company they work for.

But, how do leaders learn to set the right example for their team? How do they ensure the right blueprint is being put in place?

“I interview a lot of people, and this is a question I get a lot. I used to try and put an answer together on the fly, but one night I figured I’d really start thinking about this,” says Matt Millen, Senior Vice President of Revenue at Outreach, on a recent edition of The Predictable Revenue Podcast.

“And I decided to think about the leader I want to work for.”


Matt’s three-part leadership philosophy

The leadership template that Millen ended up drafting, and putting into practice, is comprised of three core planks:

  • Giving everyone permission to just have fun. “It’s about recognizing how hard people work – and understanding the need to have fun while doing it. I mean, I want to have fun. So, I think people should be able to get a release at work. You just have to do this, and provide space for it to happen.”
  • Empathy for the team. “This is an understanding and appreciation for how hard people work in customer-facing roles. This is a hard job. I carried a bag myself during my 31-year career, and I remember what it was like. I never want to have amnesia about my experience and where I came from, so this is an important plank for how you relate to your team.”
  • Do the right thing. “This applies to both your team and the customer. When your team knows you have their back, they will perform for you. Not everything is perfect – so you have to step and make sure you do the right thing. And, it’s also about entering every deal with the mindset that we are going to make ‘yes’ happen.”

The S.A.M. model

Once a proactive and inclusive leadership style is in place, it can then be applied to, and expanded upon, by any number of company disciplines.

For Millen, of course, that application was developing high-producing, positive, and engaged salespeople. To do so, he’s developed a sales philosophy he calls the S.A.M. model (Story, Activity, Mindset).

“I used to drive a race car in the late 80s, and I learned something really quick on the race track: the best car and the best driver doesn’t always win. A lot of things have to go right for you to win on a race track, including having a good car and being a good driver,” says Millen.

“There were, however, three things I could control:

  • How much I trained and practiced
  • How much I invested in my car
  • How much preparation I put in for each race

“In sales, I started learning the same lessons (except there are no medals for second and third place, of course). I could control these elements in sales:

  • What comes out of my mouth, or my story
  • What I do all day, or my activity
  • How I approach the day, the opportunity, and the things that happen, or my mindset

Millen’s S.A.M. model, broken down:

  • Story: “Whether you are an SDR, AE, manager, or customer success professional – we tell stories all day long at work. So, tell your story with compassion. If you can do that, the better chance you have of moving someone, and helping them.”
  • Activity: “We understand the activity levels necessary to win today. That’s a discussion we’ve been having for years. And those activities have a quality conversion tied to them. In sales, there is no replacement for daily activity. You have to do the work. And it’s great.”
  • Mindset: “Mindset is where you win or lose the game. It’s your desire, hunger, and commitment to your goals. It’s your internal motivation, your drive. It’s what gets you in the office earlier than everyone else, and keeps you there later than everyone else. And, it’s the accountability you put on yourself. It’s owning your job and everything that comes with it.”

“It’s a success system. When you put these principles to work in your job, think of the zeal you take on tasks with,” says Millen.

“You have the right story, the right activity with the right metrics behind it, and the right mindset – you’re unstoppable. It’s basic, but this works for anyone in a customer facing role.”

Finding people with a winning mindset

So, how does this proactive leadership – and it’s granular applications – inform on hiring practices?

According to Millen, the two processes can mirror each other: candidates should be able to discuss their story, illustrate they understand the principles and activity levels necessary for the job, and how important a positive mindset is to success.

“Hiring is so critical. But what I have found with salespeople, is that they can sometimes sell themselves better than your product. So I go through their resumes and ask them if they have done all the stuff on their resume. Then, I ask them to give me a pitch,” says Millen.

“We need to test for selling when hiring salespeople. If they can pitch me, than they can sell my company’s product. But, if they can’t pitch me, there is no need to move on.”

From there, adds Millen, he looks for resiliency because it’s a great indication of whether the candidate can maintain the mindset needed to excel in sales, and juggle what can often be a challenging workload.

If you’ve determined that your candidate has sales skills, than you must also determine of they have personality to slug it out each and every day.

“We ask our candidates what they think is the most important attribute for an Account Executive is. They often say grit. I agree with them, but then I say, ‘well I haven’t seen grit.’ And I wait to see how they respond,” says Millen.

“If they don’t respond, they don’t have it. If they defend themselves, they have resiliency.”

Finally, as a candidate moves through the interview process, Mllen says he, and other sales leaders, make sure to paint an accurate picture of what the daily expectations of the job are. They even make each new hire write a promise note to themselves saying they commit to handling everything that’s throw their way.

“it becomes clear what the minimum activity level is for the job throughout the interview process. The emails, calls, hours – what’s expected of you, at a minimum, is shared,” says Millen.

“So, we have the candidate send a promise note saying they promise to do all of that. So, on their first day, you can print it off, and have it as a great reminder of what you promised.”

Matt is now the Chief Revenue Officer for FLEXE, the leader in on-demand warehousing and fulfillment.

For more Matt’s thoughts about leadership and hiring successful salespeople, check out the rest of his interview on a recent edition of The Predictable Revenue Podcast.




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