Going. Ahead. with Gage: Interview with Jeff Wells, CEO of High Achiever Software Leader

It’s Monday which means it’s time for some #MondayMotivation! My next #GAWG interview features a talented sales leader who was once my boss, and will forever be a friend and mentor (whether he knows it or not ;)).

You’ve started a new company, High Achiever Software Leader. What inspired the creation of this company? 

My three years at Spredfast was an amazing learning journey. After the acquisition by Vista and my leaving the company, I had a decision to make – jump into a head of sales role at another software company or be more intentional about what I was going to do next. I decided to commit to myself and be intentional about my next move.

At this point in my career, I feel like I’m a better leader than ever before, my energy is high, and I’m fired up to make a difference. I said no to opportunities, which I must confess saying no is really hard, but what kept playing through my mind was the idea of making a bigger difference. So my question changed from “what do I want to do” to “how can I make a bigger difference?”

As I sat with that question, what resonated with me was the response I was getting from CEO’s and investors when I asked, “What’s the number one revenue problem in software today?” They consistently said, “The number one problem is the lack of sales leaders who can deliver consistent results.” They also said, “the head of sales role might be the hardest job in software.”

Ironically, when I started pulling on the strings of that statement, there were so many quantitative inputs that validated their perspective. I was convinced! They were right and that it’s not just a perception, it’s reality. One statistic summed it up: the average tenure of a head of sales has declined to between 16 and 19 months. That’s not enough time in a job to do anything other than break shit! And, unfortunately, that’s what a lot of leaders are doing – breaking stuff and moving on.

To be clear, we are all complicit – CEO’s, investors, heads of sales, and everyone else. The reality is that the market is changing so rapidly that it’s almost impossible for a sales leader to keep up. As a result, they keep doing what they have always done and it’s simply not working.

This brings me to High Achiever Software Leader (HASL). I am consumed with the thought that “making a big difference” means helping leaders solve this BIG problem and that’s what we aim to do! It’s WHY we exist – to literally “re-engineer the way sales leaders lead for the sake of their companies, their people, and their own sanity.”

For me, it’s driven out of my highest personal value that “people matter most,” and I am 100% certain that “poor leaders hurt people and great leaders change lives.” Sales leaders of the future won’t look like most do today.

Much of your career has been in Sales – What enticed you to the world of Sales and what made you continue to stay in it? 

Ironically, I never wanted to be in sales. Early in my career I would often say, “If I could ever get out of sales and get a real job I would be thrilled!” What I realized was that being in sales had little to do with my desire, but my destiny. It’s what I was made to do. However, there is a paradox with that statement, which I have shared in multiple settings with teams and executives: “Never one day in my life have I gotten out of bed because I was fired up about selling software.”

Try saying that out loud while leading a sales team that was proud to be referred to as “coin operated carnivores” (LOL)! That was back in the day and it still makes me laugh that it was a noble description of a sales team. The bottom line for me is this: I’m good at it and have never viewed it as anything other than a God given platform to build into the lives of people in a positive way. It’s more of calling than a career for me, so here I am! J 

What are some predictions you have for 2019?

From a sales perspective, I could literally speak for hours about emerging trends and workforce, so let’s focus on one.

For the first time in history, we have five generations in the workforce which is awesome! I believe that companies who learn to connect the strengths of each of those generations and leverage them to work together will create a massive competitive advantage in the market. All you have to do is spend a day on social media and listen to the generational dialogue, and you will quickly see how far away we actually are from being able to this. Boomers are down on “entitled Millennials”. Millennials are not valuing experience and think that Boomers are no longer relevant. Generation X is watching quietly and just doing their jobs.

It’s incredibility important to not under estimate how hard working together is. It’s not easy, but it’s worth it. Companies without a thoughtful people strategy will struggle in 2019 and beyond. But, the beauty is that they are not just generations, they are people first! Instead of trying to change their tendencies, we need to fan the flame of each of their strengths.

Think of it this way: I’m a Boomer and my DI (digital intelligence) will never be as good as your (Gage) DI and I am okay with that. I love that you (Gage) help me by leveraging your strengths. On the other hand, my EI (emotional intelligence) is better than most at this point. Why? It’s not because I’m better, but because I have “seen the movie.” I have the benefit of wisdom that comes from time. That’s the foundation of EI. It allows me to help you (Gage) navigate the world of business, dial into relational nuances of the workplace, learn from proven best practices, etc. Simply put, “Gentelligence” is the competitive currency of the future.

What do you think leaders need to be doing in the workplace to keep Millennials and Generation Z at companies longer?

There has never been more of a need for deep training, coaching, and enablement, both structured and unstructured, than there is today. If Millennials are not growing, developing, and contributing in measurable and intentional ways then they’re leaving. A lot of people think that “leaving” is evidence of entitlement. I don’t. I think it’s a poor people strategy at the company level. Millennials will take responsibility for doing the work of developing. What they need is guidance, framework, exposure, and clear expectations. You may think I am wrong, but here is the harsh reality – Keep doing what you are doing and let me know how it works out for you. I promise it won’t. We need to change and in changing we will learn that the opportunity before us is to get the most of out what might be the brightest generation in history. Do it right and business results will follow.

What’s the best advice you’ve ever received and from who?

First, let me say that I am unbelievably grateful because I have been given so much great advice from so many mentors that this list could be really long. Not sure why I was so lucky, but my encouragement to you is to constantly be on the search for great mentors. “When the student is ready the teacher will appear.”

Three things come to mind:

  • My grandfather always told me to “get the first punch in” LOL! I hate that in my early days that comment served me well, but it really did.
  • “You will be rewarded in direct proportion to the value you deliver in the market place” — Jim Rohn
  • “You will get all you want in life, if you help enough other people get what they want.” — Zig Zigler

A lot of people think quotes like this are cliché. Not me. I have lived my entire career hanging onto these quotes and found them to be 100% true! But here is the secret sauce – The minute your motivation in driven out of your own desire instead of the essence the quotes are found in, the idea of serving others first, the power of the principal is diminished. Great leaders are willing to subordinate their own desires and progression for the sake of others. The beauty is that you can’t out give the universe, which was exactly Jim and Zigs point.

How do you encourage innovative and creative thinking on the teams you lead and work with?

You have to not only give people the freedom to be innovative, but great leaders are even more intentional. They don’t just grant people the freedom, they run a process within their operating engine that enables people to be thoughtful about where they should be solving big problems in innovative ways. One of the biggest barriers to this is that leaders are generally unrealistic about time and rarely carve out enough space for people to be thoughtful.

Great leaders set the expectation and the team will solve the problems. The worst thing on the planet is when the leader thinks they are the smartest person in the room and that they have to come up with the next innovation.

It all comes back to what we talked about earlier, know your people and fan the flame of their gifts, skills, and passions.

What advice do you have for junior level employees wanting to make it to the C-Suite one day?

“A willingness to do what other won’t so I can have what others don’t”

WORK! There are no short cuts. The smartest person in the world in the absence of work ethic is no better than your father’s old encyclopedia that sits on the shelf. 

I would be really intentional about framing my personal point of view on “work/life balance” – High achievers always struggle in this area. A little secret… the answer is rarely founded in a 40-hour work week! That might sound contrary to the popular trends like the “4-hour work week” which I am a fan of, but not as it relates to your desire to be an executive.

The harsh reality is that the pursuit of the C-Suite is a competitive one and like it or not, the advantage comes from a mindset and a willingness to do “whatever it takes” which often means an investment of time. Saturday work is a great competitive differentiator. Even God only rested on Sundays.

But, isn’t there always a but, not at the expense of family. The C-suite is the emptiest place on the planet if you don’t have family (inclusive of your work peeps) and friends around you. As you frame your POV around work/life balance, make sure there are accountability triggers in place to reign you back in when you are out of balance. Need help? Don’t call me! I am BAD at this one 🙂

What is one of the most difficult decisions you’ve made in your career and what did you learn from it?

Frankly, I think I am in the middle of it. To choose to launch HASL instead of defaulting back into the “known” of taking a job is big. Especially at a time when my earning power is greater than it’s ever been. The theme for the day is trust. I am learning to trust that doing the right thing and living every day with a deeper and deeper desire and conviction to make a difference in the lives of people is enough, and that the rest will take care of itself.

WOW! Now I get why everyone keeps saying I am crazy!

I love book recommendations to help me grow in my career and challenge my thinking – What books would you recommend as a must-read for career growth and just for fictional fun?

I literally have a list of hundreds but these come to mind quickly:

Thanks for reading and stay tuned for the next #GAWG next month!

— Gage Grammer

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