Episode 10: Be Comfortable Being Uncomfortable | Kelly Dostal

Episode 10: Be Comfortable Being Uncomfortable | Kelly Dostal

From the field to the sales floor, the journey of a former field hockey player turned sales professional is a testament to the power of teamwork, perseverance, and adaptability. In a recent conversation, we had the privilege of delving into the experiences and insights of an individual who seamlessly transitioned from the world of sports to the realm of sales.

Beginning with a reflection on her field hockey career, our conversation partner reminisced about the camaraderie and memories forged on the field. From exhilarating victories to heart-wrenching losses, it was the bond with teammates that left an indelible mark. As she aptly put it, “the games, the wins and losses, those come and go, but the teammates are the ones that stick with you for the rest of your life.”

Transitioning from the field to the sales arena, our discussion uncovered parallels between sportsmanship and salesmanship. Just as in sports, success in sales requires dedication, resilience, and a commitment to continuous improvement. Reflecting on her early days in sales, she emphasized the importance of building a solid foundation and embracing the journey of skill development.

One key aspect that emerged from our conversation was the value of mentorship and guidance, both on the field and in the sales industry. Just as seasoned athletes mentor younger players, experienced sales professionals play a pivotal role in nurturing talent and fostering growth within the sales team.

Moreover, the transition from coaching to sales underscored the transferability of skills honed in the sports arena. Attributes like leadership, communication, and the ability to motivate and educate others are as relevant in sales as they are in coaching. In essence, the journey from athlete to sales professional is a testament to the multifaceted nature of skill acquisition and career development.

When it comes to advising aspiring sales professionals, our conversation partner emphasized the importance of selecting the right company and cultivating a growth-oriented mindset. From prioritizing training and development opportunities to evaluating compensation structures and career progression pathways, thoughtful consideration of these factors can set the stage for a fulfilling and successful career in sales.

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Episode 9: Be A Master | Mike Davis

Episode 9: Be A Master | Mike Davis

The journey from dream to reality often takes unexpected twists and turns, leading us to places we never imagined. Mike’s story is a testament to this truth, as he reflects on his aspirations of playing in the NFL and the winding path that led him to a successful career in pharmaceutical sales.

As a young boy, Mike’s dream was to play college football and ultimately make it to the NFL. However, upon arriving at college, he realized that the leap to the professional level might be more daunting than he had anticipated. Instead, he found himself at West Virginia Wesleyan College, a Division two school nestled in the hills of West Virginia.

Initially expecting to be a big fish in a small pond, Mike quickly realized the caliber of talent around him when NFL scouts showed up for the team’s practices. Despite the challenges and the realization that his NFL dreams might not come to fruition, Mike embraced the camaraderie of the team, the thrill of game day, and the lifelong friendships forged in the locker room.

Reflecting on his college football career, Mike acknowledges the importance of tenacity and perseverance. Despite spending years on the bench, he stuck with it, honing his skills, building relationships, and eventually becoming a team captain in his fifth year. His proudest accomplishment wasn’t the wins or the accolades, but rather the resilience and dedication he displayed throughout his journey.

After college, Mike found himself at a crossroads, unsure of his next steps. It was his brother-in-law’s advice that steered him towards a career in sales. Starting at Enterprise Rent-A-Car, Mike quickly rose through the ranks, demonstrating the same work ethic and determination that defined his football career. He eventually transitioned into pharmaceutical sales, where he found a perfect fit for his skills and passion for making a difference.

In pharmaceutical sales, Mike saw parallels to his football days. Just as in sports, success in sales requires relentless preparation, continuous learning, and a commitment to excellence. Elite athletes, like Mike, bring a unique set of skills to the table—traits such as grit, resilience, and a drive for continuous improvement—that translate seamlessly into the world of sales.

Today, Mike is a seasoned veteran in the pharmaceutical industry, impacting countless lives through his work. His journey—from aspiring NFL player to successful sales leader—is a testament to the power of resilience, adaptability, and seizing opportunities wherever they may lead. As he continues to inspire others with his story, Mike reminds us that the path to success is rarely a straight line but rather a winding road full of unexpected twists and turns.

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Episode 8: Being Legitimate & Legitimately Caring | Mark Smith

Episode 8: Being Legitimate & Legitimately Caring | Mark Smith

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Episode 7: Dressed, Taped, and Ready | Chris Bobel

Episode 7: Dressed, Taped, and Ready | Chris Bobel

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Episode 6: Building a Winning Culture | Sean Hurd

Episode 6: Building a Winning Culture | Sean Hurd

Shift Group has executed a shift of its own and recently expanded our service offerings. As we continue to support elite athletes in their transition to tech sales, we now also offer unique support to veterans looking to transition from military service. For us, supporting this new market made perfect sense—it leverages our expertise to help a new market segment. This is our first podcast focusing on this new vertical, so tune in to hear why this shift makes sense and to learn about ways in which Shift Group can help veterans find new opportunities and help companies tap into this fantastic candidate pool.

First things first, to all veterans and those currently serving:

Thank you.

I’m humbled by and in awe of your selflessness and your sacrifice.

And to Sean, thank you for your 22 years with the US Army, 22 years of dedication and commitment in service to our country.

Thank you. Truly.

When I founded Shift Group, my goal was straightforward—to help elite athletes transition to careers in tech sales. We’ve been very successful in that regard—in our first year of operations we secured over $10M in base salaries for over 180 candidates that we placed with over 85 hiring companies.  But like most elite athletes, I’m always learning from what I’m doing, always learning how to do more, how to get an edge…and since there’s a lot of similarity between elite athletes and veterans, moving into this adjacent space is a logical step for Shift Group.

Creating services for veterans isn’t just a strong play for Shift Group. It’s also a good move for our candidates and for the companies who hire them, and I’m beyond excited to welcome Sean to the team. As someone who understands the unique circumstances veterans face as they transition to civilian life, Sean will help Shift Group develop and deliver programs that fully support and prepare these candidates for careers in tech sales. Additionally, Sean will help hiring companies understand how they can shift some of their standard hiring practices and scripts to accommodate the valuable but non-traditional experiences that veterans bring to the table.

Veterans and elite athletes share many of the same core qualities that lend themselves to successful tech sales careers. In general, both are mission-focused, determined, high-performing, and constantly adjusting to achieve better results. This overlap isn’t a huge surprise, and Sean confirms that many veterans are in fact elite athletes. Here at Shift Group we know how to leverage these core characteristics to help those who possess them to land a role and thrive in tech sales.

There also are some notable differences that we know we need to accommodate to successfully support this group. We need to help veterans translate their unique experiences into compelling stories. We need to help hiring companies adapt their job requirements. And we need to help people get over the stereotypes and preconceived notions about veterans that are so prevalent—for example, the assumption that all military experience is the same when there are hundreds of job roles that require different skills, experience, and personal qualities.

The bottom line is this: the shared core characteristic of these two groups makes Shift Group’s support for placing veterans into tech sales jobs a very logical next step.

At Shift Group, we will work with veterans to help create a strong personal narrative.We’ll help prep for interviews and to anticipate standard questions that can be tricky for someone with “non-standard” experience. We’ll help you evaluate offers to increase the likelihood that once you accept a role, you’ll be happy with your decision and you’ll be able to progress with that hiring company. And we’ll provide ongoing support and training to facilitate your transition once you’ve been hired.When you work with Shift Group, you’ll have the resources you need to be successful, to grow your career, and ultimately to become a true sales professional. There’s an old quote attributed to Julie Andres’ old music teacher of all people, but it’s appropriate here: “An amateur practices until he can do a thing right; a professional until he can’t do it wrong.” We’ll work with you to develop an approach, process, and structure that ultimately will decrease the chances of you getting it wrong.

In this podcast, I follow my “standard” approach. But Sean comes at my questions from a completely different perspective than a “typical” guest on Merchants of Change. Tune in to for more #requiredlistening that’s sure to be eye opening for veterans, athletes, and hiring companies alike. If you’re an athlete, a veteran, or a company looking to hire fantastic candidates, reach out so we can talk about how Shift Group can help.

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Episode 5: Strengths in Fundamentals | Rocky Paap

Episode 5: Strengths in Fundamentals | Rocky Paap

Tune in to this week’s episode of Merchants of Change to hear a seasoned sales executive’s take on what makes someone a true sales pro. Rocky’s measured and systematic approach can teach us all something. Read on to get JR’s takeaways on the convo. The podcast is #recommendedlistening. And the blog is #recommendedreading.

After we record a podcast, I come away so energized. There’s always a new great line, a new take, a new perspective.

In this case it was when I asked Rocky about his favorite sports memory and he reported that it was when his Colt baseball team was one out away from the league World Series and lost the game in classic “bottom of the 9th” breakdown fashion. He admits it’s not a “great” memory, but the lessons he took away from it are invaluable. It made me think about the word “favorite” differently. I can ask one person what their favorite sports memory is and maybe they’ll talk of a big comeback, a big play, a perfect season, or off-the-charts team chemistry. Rocky talking about a loss was not what I was expecting. A “favorite” sports memory doesn’t have to involve an amazing victory, a realization that highlights one of the great connections between sports and tech sales—sports teaches you to learn to lose, to be resilient. Tech sales is the same.

Rocky answered several questions differently than I was expecting which got me to thinking about how differences play out when someone is shifting to sales. Because everyone is different, the system that works for one person might be a total disaster for someone else.

I’m here to tell you that’s ok, and that Shift Group is here to help.

Despite these differences, there’s a similarity in approach that benefits everyone, and I think if you’re starting out in tech sales you need to do two things:

  1. Find someone you respect/admire/want to be like and emulate them
  2. Find your unique voice so you become an authentic partner to your colleagues and customers

#2 above is going to be really difficult if you don’t find a role that’s the right fit for you. In general, when you’re assessing a role, things we encourage you to consider are the technology you’ll be selling, the total market size, the company culture, your manager, and career progression, to name a few. When you have multiple opportunities in front of you, evaluating them can be tricky and it’s important to assess them relative to the parameters that are important to you.

In general, we—and our MoC guests—advise that no opportunity be summarily dismissed and that every opportunity be given due consideration. Other considerations when weighing offers beyond what I just mentioned are compensation and one that’s recently become part of the conversation—whether the role is remote, hybrid, or in-person. I know many of you think you want a remote role. But as someone who derived tons of value from working on a sales floor, I’m a big fan of in-person roles. I get that everyone’s different and times change, but I also think that being in an office in the same space as the rest of your team when you’re starting out provides three huge advantages:

  1. In-person training/engagement. When everyone’s together, it’s easy for everyone to collaborate. Discussions and problem solving tend to evolve more organically. Not to mention it’s easier for people to see you hustling.
  2. Learning by osmosis. When you are around people doing what you’re doing or doing what you want to be doing, the value you get from watching them in action is immeasurable and likely will accelerate you finding your voice.
  3. Easy access to resources. It’s so easy to ask questions when someone’s right in front of you. The more questions you can ask, the more you can learn, quicker. This also will help you accelerate finding your voice.

Everyone is different but I’m here encouraging you not to be short-sighted on this single parameter and to consider it in totality when you’ve got multiple offers. Do not rule an opportunity in or out simply because they let you work wherever you want to. In sales, you’ll typically earn this right over time. Starting in an office might help you get there faster. Maybe it won’t. I’m asking you to consider it. All factors should be considered because if you are working from home trying to sell a product you don’t fully understand to a really niche market and you have a bad manager and no team to collaborate with, how happy will you be?

Tune in to the podcast to get Rocky’s tips on starting and sustaining an impressive tech sales career. Reach out to me if you want to talk about my thoughts here or how Shift Group can help you.

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Episode 4: Long Term Vision, Short Term Focus | Billy Lynch

Episode 4: Long Term Vision, Short Term Focus | Billy Lynch

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Episode 3: Be Learning or Earning | JT Ibe

Episode 3: Be Learning or Earning | JT Ibe

In this week’s episode of MoC JR and John have a great conversation with JT Ibe, former college football player at Rice University then the University of South Carolina before a stint with the NFL’s Carolina Panthers. After breaking in to sales at HashiCorp he’s currently working as an Enterprise Account Executive at StrongDM, helping companies secure their valuable resources.  JT blew us away with his thoughtfulness and mindfulness. Tune into the podcast to hear what makes JT a true sales pro and read on for JR’s insights on this very thoughtful conversation.

You hear “elite football player” and you may think you have some sense of what that person might be like. If that’s the case, all it take