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Episode 4: Versatility | Jessie Bryant

Bhupendra Rathod on December 15, 2022

Episode 4: Versatility | Jessie Bryant

December 15, 2022

Jessie Bryant, longtime friend of JR and the Butlers, three-sport high school athlete, softball standout (and captain) at Providence College, college coach, and sales professional extraordinaire talks to JR about her road from playing to coaching to selling.

Born into a family of athletes, Jessie was destined to be an athlete. She likes to say that growing up around me and my brothers and instilled a competitive spirit in her from a very young age—can’t deny it. We both valued our friendship as time went on, though I’m not sure I noticed the extent to which Jessie was quietly observing everything and taking it all in. When she decided to transition from college coaching, the story she tells is that she thought of me. She knew I was in tech sales, and she saw me as successful. I traveled. I had a nice house. She saw in me what her life could be, so she went for it, and took the leap. I’m flattered by this, but that’s not why I mention it. I mention it because it illustrates one important piece of transitioning from sports to sales—find people you want to be like and model yourself after them.

Here’s why the transition from coaching to selling was a relatively easy one for her.

  • It takes versatility. Being a multi-sport athlete gives Jessie a leg up. She clearly has the core mindset of an athlete but is aware that different sports require different mindsets. This enables Jessie to be flexible, to see important nuances and details that other people simply wouldn’t see, or they might incorrectly dismiss as not important. Jessie can find critical details hidden in the shadows. She’s always listening, looking, and taking it all in to inform her next move.
  • It takes a good team. Jessie has strong relationships with many former teammates that have stood the test of time, and the impact of having good teammates isn’t lost on her. When evaluating a professional opportunity, make an in-person visit to the company. (Jessie paid for this herself—it is that important!) Get to know the people you’ll be working with, pay attention to what’s going on in the office, tune in to body language and other non-verbal clues. Make sure you interview them as much as they do you—you’re going to be working with these people and you’ll be depending on each other for your paychecks, so you need to feel comfortable that you’re joining the right team for you. As things evolve, maintain important connections—you will build the network you will inevitably need to help you make a career move, get questions answered, or just talk things through.
  • It takes persistence. Love it or hate it, you gotta do it. When you go into sales, everything is new. You’ll get the same training as everyone else, but that’s hardly where you’ll develop your key skills. For Jessie, role-playing was the part of training that was hardest for her but going along with it is what ultimately led her to find her sales style, to find her voice.

When you’re a competitive athlete working as a BDR, you’ll likely have your eyes on the prize and will be looking to get promoted, to win at tech sales. But the only way to get experience is to do the thing, and it takes time. As you’re learning, don’t underestimate the role that the AEs you work for and with can play in your success. If you view each other as partners, you’ll be bought into each other’s success. If you become an AE, don’t forget that you were a BDR once. Make them feel part of your team and make time to help them—something that takes you two minutes to explain might save them six hours.

Jessie obviously has what it takes to be successful. She shared her secret for becoming elite, and it’s such an important and overlooked thing: utilize technology to help you do your job.

In Jessie’s case, it started with becoming an expert at LinkedIn Sales Navigator. Spending a few hours on the front end, doing research, building reports, and working smart is what saved her countless hours making hundreds of cold calls—allowing her to focus time and effort on her highest-value, highest-impact activities.

At this point in her career, what does Jessie think makes her a true sales pro? Transparency. Be honest with your customers. If your product isn’t the best fit at the right price for them, tell them that. When their circumstances change and they’re looking for a new solution—they will remember you, they’ll remember your product, and they will come to find you. I can’t overstate the importance of trust here—as it relates to reputation and networking and so many other critical components of tech sales success.

Tune in to get all the details and to hear Jessie’s story in her own words.

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Episode 3: Act with Intent | Dwight Henderson

Bhupendra Rathod on December 8, 2022

Episode 3: Act with Intent | Dwight Henderson

December 8, 2022

This week JR and John sit down with one of JR’s former colleagues at Turbonomic to talk about what put Dwight on a path to sales and to dig in on all the work that he puts in to influence where his path leads.

Dwight Henderson, former Dickinson College lacrosse player and current Commercial Sales Manager at Workato, is a thinker. He approaches his life and his work in a very deliberate and measured way, which reminds us that no single type of person or personality is a requirement to be successful in sales.

You Have to Like It

As a kid, Dwight was a baseball guy. That’s what his dad played, that’s what he played. But Dwight couldn’t stand it and did what very few 7th graders would dare do—he told his dad the truth and asked to try something new. Enter lacrosse, which took Dwight through high school and on to a prolific career at Dickinson College. About four or five games into his college career, his coach and mentor asked Dwight to switch positions, for the greater good of the team. Dwight did, and Dickinson had some extremely impressive win-loss records during his time on the team. He was a team player, driven, steady, and hardworking. As we hear from most former college athletes, the relationships with his teammates are among the more valuable relationships in his life to this day.

Finding Your Career

Finding your career means finding yourself. When it came time to think about life beyond college Dwight brainstormed about what he liked, what skills he had, where he might use them, and how they might translate in different ways. Knowing a bit more about what he did and didn’t want was particularly helpful in a conversation that led to an internship before his senior year. He spent the summer doing research on LinkedIn, identifying prospects, and populating spreadsheets. He could see and feel the excitement all around him—he was hooked.

Inform Your Choices

When you’re first starting out, it’s hard to know what to do. Dwight advises that you get yourself well-prepared, particularly to understand how your skills translate to the role, to turn that relationship into a strong story, and to have good examples to illustrate your points. Once your story is written, cast a wide net at all kinds of tech companies with all degrees of trajectory, and then tell that story to as many people as you can. Keep telling it until you find something that feels well-aligned with who you are and what you want.

Specifically, Dwight suggests evaluating three things when considering a company:

  1. Who you will be working for—do you feel they are bought-into your success and will offer you the teaching/coaching/mentoring you need?
  2. The product—do you understand why customers and consumers buy and use it, and do you think you could sell it?
  3. Your objectives—do you see how the company/team/opportunity will help you get to your next goal, whatever that is? It’s going to be really, really hard work no matter what, so you might as well set yourself up for success.

20/20 Hindsight

When Dwight looks back, here’s what he wants you to know:

  1. Start early, evaluate your skills, and dig down from there.
  2. Use your network, which includes things like teammates’ parents.
  3. Don’t close an option or opportunity off until you’ve fully explored it. See it through—you never know.

As far as what he wishes he’d done differently, while he’s happy now he does wish he had prioritized his college studies a bit more. He has clarity now that he didn’t have then.

Dwight learned as much as he could along the way, and he has learned a lot. But he’s humble, so talking about what makes him special is clearly uncomfortable for him. But we got him to identify for us what he thinks makes him elite, what makes him a sales pro—and it comes from a) being able to relate to people on a personal level, no matter what role he or they are in, and b) having process and meaning behind his actions.

This points to something important—the power of reflection.  You might feel like you always should be moving, hunting, and making a deal. But stop and take time to reflect. If you’re honest with yourself, self-reflection might be the highest form of learning you can undertake.

Tune in to the podcast to hear details on all of this and more, including how to sell yourself, how to build strong relationships with the AEs you work with, leading a team, and how asking questions might help you find a mentor without even trying. There’s something special that comes through in how Dwight speaks and the words he chooses.

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Episode 2: Shoot Your Shot | Porchia Jenkins

Bhupendra Rathod on November 23, 2022

Episode 2: Shoot Your Shot | Porchia Jenkins

November 23, 2022

Home Resources November 23, 2022 Home Resources November 23, 2022 Home Blog November 23, 2022 Home Blog November 23, 2022 Home Blog November 23, 2022 Home Blog November 23, 2022 Home Blog April 11, 2024 Pellentesque et tempor ante, sit amet consectetur ipsum. Mauris ex turpis, fringilla ac lectus a, luctus accumsan tellus. Curabitur consequat …

“The Power of No”
In this episode, Porchia Jenkins, a high school three-sport athlete, collegiate volleyball player, and Manager of Commercial Sales Development for TripActions gives a master class in transitioning from sports to sales to sales leadership with a mix of grit and grace. Tune in to hear Porchia talk about how she does it and learn about the importance of taking ownership of your path and being accountable for your success—which sometimes means making big, bold moves and taking chances.

Shoot Your Shot

I was expecting to have a great conversation with Porchia—but I was blown away by how it went. She was full of energy, enthusiasm, advice, and insights. I had such a great time talking to her.

Happy Accidents

A huge smile crosses Porchia’s face when she talks about the bonds she still has with her former teammates, but behind the smile lies unflappable determination. When she joined the cross-country team because her basketball coach required participation in a Fall sport, Porchia signed up for cross-country. And when she stepped in a gopher hole and sprained her ankle, she committed to gutting it out and finishing the race.

“You’re not a runner. And that’s OK.” 

This acceptance turned her cross-country spill into a happy accident. She switched to the volleyball team. Volleyball became her main sport and introduced her to her best friend, the one Porchia refers to as her “equalizer.” She’s the friend who to this day keeps her in check—and Porchia knows she needs the balance.

Steady, She Goes

When I asked Porchia how people would describe her in her playing days, she didn’t hesitate. As a player, they’d say she was tough, wanted to win, and never let up. Off the court, they’d tell you she was all about unity. She was a vocal advocate of respect and inclusion for all, knowing that kindness feeds growth.

Porchia takes a consistent approach to things today. She possesses a unique combination of tenderness and toughness, allowing her to provide gentle guidance while putting ownership of others for their success. Balance and consistency are foundational to Porchia as an authentic, inspiring, and credible leader.

The Road (Back) To Sales

The COVID pandemic compelled Porchia to leave her teaching role, and when she thought about when she was happiest, she kept coming back to her time working in sales at Sprint, fresh out of college. She knew that transitioning back to a sales career would take preparation and practice, found a 10-week virtual bootcamp geared toward candidates with non-traditional backgrounds, and committed to completing the program while wrapping up her teaching career.

Know (and Sell) Your Value

The connection between your background and what you’re applying to do isn’t always obvious. Understand your value outside of the sales world. Be explicit about how your experience aligns with the new role and talk about it in a compelling way. Practice telling that story. Be prepared.

Some companies are shying away from hiring candidates with no prior experience as a BDR, but Porchia has her own balanced take on this trend. She sees value in experience, but she also finds value in other places and is open to bringing that value into her organization. New mindsets, new ideas, and new synergies are often required to drive new growth.

Know (and Receive) Your Worth

After transitioning from teaching, Porchia was all about compensation and benefits, but now enablement and growth are the two most important characteristics in an employer and a role. When it comes to choosing an employer, Porchia offers some advice.

  • Check the alignment. The job will take a lot of your time so you need to be sure that it aligns with who you are as a person; no amount of money will ever make you happy if it doesn’t.
  • Trust your gut. If the vibe feels off, stop the journey. When company values align with yours, you’ll be proud to say you work there.
  • Size matters. Make sure the company has a sizable addressable market. This is important for both opportunity and personal development.

Forge Your Own Path

As you look to progress, have clear and reasonable expectations. Hold yourself accountable for results. The best BDRs are curious, coachable, and competitive, three tools that put your growth in your hands.

It’s important to look at career paths both inside and outside of sales. Porchia took a chance on herself—she wanted to get back to coaching, to lead people, and to help them grow, and now she’s in a leadership role where it’s important to be clear, direct, transparent, and realistic.

Shoot Your Shot

Females make up a high percentage of the student-athlete population, but tech sales have historically not been as diverse. Porchia offers some great advice for women (and everyone!), and this one really gets the adrenaline going: Shoot your shot. When someone tells you “No,” take that opportunity to learn, to grow, and to figure out what’s right for you. Don’t go through life wondering “what if?”

Listen to the pod to hear details on all this and more, like the importance of mentoring and being mentored, to learn the secret sauce that makes Porchia elite, and how shooting her shot landed her here with us.

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Episode 1: The Excuse Department is Closed | John Kaplan

Bhupendra Rathod on November 17, 2022

Episode 1: The Excuse Department is Closed | John Kaplan

November 17, 2022

“Nobody cares, Work Harder!”

Fundamentals:

How It Started

John heads to Boise State with a history of athletic success built on size and pure strength. It’s the first day of D1 football practice and on the first play of the first drill he finds himself—for the first time ever—flat on his back, driven to the turf. Not the memorable firsts you tend to think of when you think of success stories. At that moment, John learned two things:

  1. Size and strength alone aren’t enough.

  2. Pro football was out—time to hit the books.

How It’s Going

After successful stints at Xerox and PTC, John is the President and Managing Partner of Force Management, an organization he co-founded to help companies build elite sales teams through custom programs based on goals, customers, products, and people. Force Management also has an online platform, Ascender, that motivates, empowers, and inspires users through a unique combination of content, curriculum, and community.

How He Got Here

Listen to the episode to get a 360° sense of John—dynamic, engaging, enthusiastic, funny, driven, and humble. John shares stories and insights on why athletes are suited to and successful in sales careers. He also cautions that being a good athlete doesn’t mean you’ll be a good salesperson—it takes hard work.

When John talks about his college football days (at Boise State then at Bowling Green), he doesn’t talk about achievements or accolades. He talks about his teammates. And when he tells you proudly that he’s a better teammate today than he was then, you get a sense of just how important personal growth and relationships are to John. He talks about the role that friends, faith, and family play in his life—you can feel how they are fundamental to his success.

On that first day of practice, John learned that size and strength were nothing without the underlying fundamentals to optimize them. And on that same day, he started thinking about what he wanted to do for a living. Since then, John tuned in to the success of others, giving him a taste of what he wanted for himself.

On Why Athletes Should Consider Selling

It’s a smooth transition, given the role that effort plays in sports and sales.

  • Work harder, and get more opportunities—you may not win but you will get more opportunities.

  • Follow a playbook and a system—the map shows you the collaboration and teamwork needed to achieve outcomes.

  • It’s a meritocracy—you’re rewarded for performance.

  • Coaching counts—but whether you have a good one or a bad one, you’ll still need to perform.

The closest professional environment you can get to sports is sales. If you love the planning, prep, hard work, adrenaline rush, and exhilaration that comes from playing sports, a job in sales may be for you.

On the Importance of Fundamentals

There is a joy to be found in the process of learning the fundamentals and how they help. Here are John’s four pillars of strength when it comes to sales success.

  1. Discovery is an art; ask great questions and make it all about the customer.

  2. Identify and attach yourself to the biggest business issue, then talk about what customers are talking about.

  3. Influence decision-making by highlighting the differentiators of the solution you’re selling.

  4. Qualify voraciously; learn qualification skills and criteria and practice regularly.

On What Candidates Should Look For in an Employer

There are some key questions you should ask prospective employers.

  • Do they have a culture of coaching? You need coaching (trust me), so don’t underplay it in the interview. John offers some great specifics in the pod.

  • What is the total addressable market for the product you’ll be selling? How much opportunity really is there?

  • Does the buyer understand what they’re buying? In other words, does the buyer understand what problem your product helps them solve?

  • Does the company have a mission? Does everyone understand it? Will everyone stand behind it when times get tough?

On Being Uncommon

From the lessons learned from the view flat on his back on the field until today, John’s commitment to being uncommon has been consistent over time—this authenticity helps drive his success.

  1. Be a student of the game.

  2. Learn the fundamentals.

  3. Commit to excellence.

  4. Do things the common person chooses not to do.

Tune into the podcast for all the tips John has to help you be uncommon.

Bonus: Book recommendation from John. The Qualified Sales Leader by John McMahon.

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Episode 10: Jim McInerny

Bhupendra Rathod on November 3, 2022

Episode 10: Jim McInerny

November 3, 2022

This week JR sits down with one of his personal sales heroes for a chat and they cover it all from where and when the seeds of “Merchants of Change” were planted to Jim’s current role as the CRO for an exciting startup, Blink, whose app is revolutionizing the way companies and front-line employees communicate and collaborate to create cultures of success.

Our podcast is called Merchants of Change so you can only imagine how excited I was to sit down with Jim McInerny, the man who introduced me to the three words that completely changed the way I think about sales, of my role in the process, and the impact that my efforts have. Our conversation covers the origin of the expression; offers highlights of our shared history; and explains some nuts and bolts about breaking into sales, developing the skills and behaviors needed to sustain success, and how to be happy (most of the time) doing it.

Lesson #1: Be all in. You need to have faith, stick to the process, and good things will follow. But if you’re not all in, forget it.

Lesson #2: Dumb luck might get you started, but hard work keeps you going, and a commitment to learning makes you successful.

Lesson #3: When you’re breaking into sales, you’re only as good as the people you train with. If you’re around strong people, you’ll get stronger. As you progress in your career, you’re only as good as the network you can tap into. Nobody is good enough to do anything on their own. Build a strong network. Surround yourself with good people.

Lesson #4: Find people you want to be like, then emulate them. You’ll learn a lot and your confidence will grow.

Lesson #5: The job will be hard no matter what. Find a place where you can make it fun.

Lesson #6: You can’t be successful without discipline, ambition, and accountability.

Lesson #7: Don’t be disingenuous. Be respectful, thoughtful, prepared, and vulnerable. It starts with trust and these qualities will help you build it.

Lesson #8: Find your voice and have range, because you’re going to be talking to all kinds of people.

Lesson #9: Be a student of your prospect, not of your product. Focus on the customer’s problems and find the right solution.

Lesson #10: Be prepared and purposeful. Use LinkedIn and other research tools to your advantage. This will help you when you’re interviewing for a job and when you have a job. Learn about the person you’ll be interviewing with or selling to—find, make, and explore connections.

Lesson #11: Ask questions. Natural curiosity comes through and can generate critical conversations that lead to high-impact outcomes.

Lesson #12: Non-verbal cues tell an important part of the story. Bring a pen and paper to meetings and use them—it says something about you when something matters enough for you to write it down and remember it.

Lesson #13: When you’re looking for a new role, be prepared to tell your story in a compelling way. Why sales? What can you do? How do you use your time?

Lesson #14: Differentiate yourself. Take advantage of the small opportunities to do things that most other people wouldn’t do. This will set you apart and make you memorable.

Lesson #15: Take ownership and be accountable. Leave nothing to chance.

Lesson #16: Make a good impression on as many people as possible.

Lesson #17: Dare to be different, but always remain professional. Everyone’s hugging the tree trunk so take chances and get out there on the skinny branches.

Lesson #18: Don’t hide behind technology. Get good at the social aspects of selling. Ask questions. Be empathetic. Someone not answering your emails? Pick up the phone.

Lesson #19: You don’t necessarily need to be confident. But you do need to be prepared so you can take advantage of whatever opportunity a given moment presents you with.

Lesson #20: Be aligned with the people you’re working with—culturally, make sure you fit.

Lesson #21: Make sure you understand what problems the hiring company’s product is solving and what makes it unique.

Lesson #22: How big is the hiring company’s addressable market? It’s an indicator of opportunity size.

Lesson #23: Be a good listener, and learn from everyone.

Lesson #24: Want to be considered a Sales Pro? Develop and maintain relationships that create customers for life.

Jim is unbelievable. Listen to the podcast to hear for yourself, and to get his insights on why and how these lessons matter.

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Episode 9: Colin McDonald

Bhupendra Rathod on October 27, 2022

Episode 9: Colin McDonald

October 27, 2022

Bhupendra Rathod

This week on the pod, we have Colin McDonald. Colin played thirteen years of pro hockey before becoming a salesman. Spending thirteen years earning a paycheck by shooting pucks and getting smashed into the boards is rare. Anyone who works hard enough to play professional sports for thirteen years has earned the right to identify as a pro athlete. It gets into your bones, it becomes who you are. A career that long makes reinventing yourself painful, that’s why Colin’s story is so impressive. He’s been selling cybersecurity software for Recorded Future for almost two years now.

Technical Difficulties

We spent a good chunk of time talking about Colin’s transition back into civilian life. In my head, I was imagining that there must have been many dark nights of the soul and an identity crisis to wrestle with. As you’ll see and hear from the show, Colin has a really stoic way of carrying himself. It didn’t seem like he got sucked into the muck of feeling lost.

“What’s been the hardest part of the transition for you?”

Drinking from the fire hose. Trying to learn as much as I can about our products.

And…

All of the kids who I started with were able to hit the ground running. They knew how to build presentations and use google sheets. I took a thirteen-year break from all of that stuff. It’s been like learning how to walk again.

Understanding new technology and how to show it off to prospective customers can be daunting for anyone. I hadn’t considered that taking a break from using basic tools like PowerPoint, email, and google drive could be equally as hard. Colin’s answers sparked a couple of thoughts.

Consideration of what you’ll be selling is a critical piece of being successful in sales. Are you a technical person? Were you the type of kid who took computers apart to analyze their guts? Ever tried to learn a programming language for fun?

If you were thinking, “hell no”, to those questions, you’ll want to pay attention to where you end up. Not every company sells super technical software. Some tools are really straightforward. A company like Scratchpad comes to mind. They sell software that sits in front of Salesforce to make it easier and faster to get your data into SFDC. Recorded Future sells cyber security software making it imperative that you learn how to speak about endpoints and threats, and be able to get into the weeds with IT people. Neither path is better, they are just different. Make sure you know what you are getting into. A super technical sale isn’t a bad place to be, but maybe also ask about what kind of support you’ll have during the selling process. Do you have direct access to your own sales engineer? Will you be mostly on your own?

Who are you? Why you?

What about lack of specific experience? How did you overcome that?

Colin gave a masterclass on the episode of how to use your experience playing sports to overcome the “lack of experience” objection that you’ll be sure to face during the hiring process.

They wanna know if they can rely on you to go out and hunt new businesses. They want to know that you aren’t going to hide.

Athletes DO have experience. Athletes operate under much greater pressure than a quarterly quota, especially if you are in the pros. A string of bad games could limit your ice time or even put you in a suit and tie watching from the stands. A weak season could be the difference between signing a contract to continue playing or packing your bags and looking for other ways to make a living. Can a 20-year-old college student say they’ve felt that pressure?

What about all of the training time? Elite athletes are required to always be looking for little ways to get better. A career in athletics is a long-term commitment to achieving specific goals and milestones along the way. “Do you think that kind of dedication and approach is valuable to your company?”

On Fast Promotion

Colin shared some advice towards the end of the episode for BDRs who want to get into a closing role as fast as possible. You’ve got to find your own motivation for wanting to be promoted quickly. Colin’s got a family to support. His advice?

Be visible. Most companies have a pool of BDRs to select from when an AE role opens up. So, does the AE manager know who you are? Do the HR people know who you are?

How do you be visible?

The same way you did it on the court or on the ice. Be the first one in the office and the last one to leave. Put in the work. When you’ve got questions about different aspects of the business, walk over and schedule a few minutes with someone in marketing. Schedule some time with people in different functions. Be interested. Ask thoughtful questions. Most importantly, get yourself to the top of the leaderboard in the metrics that they care about.

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Episode 8: Hayley Skarupa

Bhupendra Rathod on October 20, 2022

Episode 8: Hayley Skarupa

October 20, 2022

Bhupendra Rathod

Organizational Excellence

If you’re looking for BDRs, pay special attention to where people come from. Playing hockey for Boston College and Team USA is an incredible training ground for operating at the highest level. Maybe not all of your candidates come from such high profile organizations, but it might pay to research where your candidates spent their athletic careers. Reach out to their coaches and ask questions about what it’s like to play for the teams they’ve played for. Athletes like Haley have experience in BIG moments supplemented with conditioning and toughness that will be unmatched by other interviewees. If you’ve spent a decade competing for ice time with some of the best players in the world, you’ll show up with a set of attributes that will directly carry over into your sales career.

Gold Medalist to BDR

Haley describes her transition from winning a gold medal in South Korea to logging into SFDC every day as jarring. This is normal. It’s hard to restart and reinvent yourself. You should expect some tough days as you find your footing. Here are a few ideas to help:

  • Find a mentor who’s done it. People want to help.
  • Acceptance. Just like sports, you can’t really skip the development period. You have to carry the water bottles again.
  • Build your cabinet. A small trusted team of family and friends who will support you.
  • Don’t forget what got you where you are. Continue to train and take care of yourself.
  • Consider extra support like counseling.
  • Be selective about where you land. The people that you’ll go to work with every day are the most important consideration in selecting an employer.
  • If you’re researching potential employers and you feel naturally curious about a company or its product, pay attention to that. If you’re googling for more info in your free time, you might have found your spot.

Haley attributes a large chunk of her early success to “having a motor”. Having a motor is the ability to generate a high volume of quality work over the long haul.

We often forget that one of the simplest (not easiest) ways to succeed as a BDR is to work at a fast pace while maintaining high standards of quality. I’ve never seen someone lead their team in calls and touches and not succeed.

Getting to a Closing Role Fast

If you’re reading this blog, we’re all motivated by money and we all want to go fast. Haley thinks speed to promotion is not the most important metric. Think about readiness over speed. If it takes twenty months instead of sixteen, those four months will feel like the blink of an eye over a career, but investing the time to make sure you’re ready could be the difference between being a decent AE and a top performer.

Being a Great Teammate

A critical aspect of doing the job well is finding a solid operating cadence with your teammates. The BDR to AE relationship is important to nail. When you first start as a BDR, you’ll likely support one to four AEs. Pay attention to the ones who seem most interested in helping you. A good AE will be interested in building a working relationship built on trust. Over time, they will let you go further and further into a sales cycle. A good AE will get you ready to become a good AE. When you do get promoted don’t forget to reach back and take a BDR with you.

We always close an episode by asking our guests what “being a pro” looks like. Here’s what Haley said.

  • Natural curiosity
  • Customer focused
  • Making their team better

It’s obvious that to be a Pro, you’ll need to perform and put up numbers. But what kind of an impact have you had on your teammates? Have people gotten better because they’ve spent time working with you? That’s the ultimate teammate.

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Episode 7: Zeke Testa

Bhupendra Rathod on October 13, 2022

Episode 7: Zeke Testa

October 13, 2022

Bhupendra Rathod

Zeke Testa is a model case study for the experience that we are trying to give our candidates at Shift Group. Zeke was an All-American goaltender for the Babson College Beavers and developed habits and behaviors during his playing days that have served him well as a sales professional. Zeke has had such a strong run that he was able to leverage his sales success to put down roots for his family in his beloved hometown of Wellesley, MA.

Slow down to go fast.

Most people who get into sales enter at the same point, the BDR role. BDR’s are the tip of the spear for sales organizations. The first time a prospect spends any time with someone from your company it is usually a BDR. The role is one of the most challenging roles in all of the business, which is why when most people land the job, they are already thinking about how to get promoted as quickly as possible. Zeke cautions us to slow down.

Being a BDR is the best training ground to become a great AE. The six or twelve months that you spend as a BDR will be an intense boot camp of learning how to sell. If you land at the right company, during this short window, you’ll become an expert in account research, using technology to support your selling, starting conversations, and booking meetings. No sale can happen without a booked meeting. Don’t rush through this period. Sit still and soak up the lessons and the exposure. You’ll supercharge your earning potential when you move into a closing role.

Just like in your sports career where you consumed all of the resources at your disposal (trainers, instructors, specialty coaches, meal plans, extra time on the ice, film room), take the same approach to getting started in sales. A career in sales is a marathon, not a sprint. The people who succeed over the long term are able to put one foot in front of the other for long stretches amidst obstacles.

You work for your team, not the other way around.

After a successful stint as a BDR, you’ll move into a closing role. The AE seat. This is an opportunity for you to use the skills that you developed as a BDR to start making money. After some success as an AE, you’ll start planning where you’d like your career to go. In our experience, your gut will tell you if you want to lead a team or continue being an individual contributor. There are pros and cons to each path and they are highly personal. What matters to you, may not matter to another person. If you decide to become a leader, Zeke tells us that the initial urge is to “spew” everything you learned as a rep. Show your team how good you were as a rep. Teach them to be like you. He got snared into the trap when he first became a sales leader.

Hard-earned lessons for new leaders:

  • Observe and listen to your people
  • Learn how they operate
  • Allow them to do the job their way
  • Figure out what drives them (money? sense of fulfillment? validation?)
  • Take everything you learn from watching and listening to your people and make a custom success plan for each person
  • Lead them in the most effective way for them. It will be different for each person.

Every day you are preparing for your shot/

Zeke’s favorite memory from his sports career at Babson was during his senior year. The team had recruited an incredible freshman goalie (shoutout to Jamie Murray) who took over the starting job two games into the season. Zeke, a senior captain, was now backing up a freshman and the team was rolling. If you’ve ever been in this position, you know how easy it would be to fade into the background and get lost in showing up and going through the motions every day. Zeke decided early that he was not going to alter his approach. He lifted weights after games, took extra shots, he committed to being a great leader and teammate. Later in the season, when Jamie had a tough start, Zeke was ready to take back his job. It’s a lesson in discipline and mental toughness that has served Zeke well long after his hockey career.

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Episode 6: Chris Ward

Bhupendra Rathod on October 6, 2022

Episode 6: Chris Ward

October 6, 2022

Bhupendra Rathod

Chris Ward comes from humble beginnings in small-town Massachusetts. His parents grew up in Dorchester and are the kind of blue-collar, salt-of-the-earth folks that have never heard of the NESCAC.

Chris might have been a teacher, firefighter, or cop, had he not ended up at Bates. His time at Bates expanded his horizons and showed him another world. Instead of heated small-town rivalries with Medway and Medfield, Chris met people from Pakistan. At Bates, he saw his first BMW and got a job at a high-end moving company. He got a chance to move couches and dressers for professional athletes and titans of industry.

For those of us from humble beginnings, how can we improve our trajectory?

Maybe sales.

Chris credits his Mom for his start in technology sales. You’ll have to listen to the episode to hear his impersonation of Mrs. Ward, but she urged him from a young age to focus on “math or computers.”

“And I sucked at math.”

Most people seem to end up in software sales by accident, but not Chris. He followed his Mom’s advice and set out to become a tech salesman. He got started by leveraging his network. If you’re lucky enough to go to college and play on a sports team, you’ve got a built–in family of people who want to help you succeed. Start there. Find people who’ve done what you want to do and then reach out and ask for help. Most people want to reach back into their network and pull people along if they can.

Chris did a shift at Oracle, learning a bit about tech and sales, and business.

Chris remembers spending time with friends who were working at startups like BrightCove and HubSpot back in the mid-2000s. They had their own language and inside jokes and he felt jealous of the fulfillment that they were getting from their jobs. He wasn’t getting that at Oracle.

Chris talks about this triggering a period of self-reflection and coaches the listeners to do the same. A couple of helpful questions that he asks:

  • “Do you have a growth mindset?”
  • “Do you want to make an impact or be one of a few thousand sellers on a well-worn career path?”
  • “Do you want to build teams and fix real problems?
  • These questions can help crystallize your intentions when faced with the decision of joining a well-established company versus jumping into the startup game. To be clear, there’s nothing wrong with joining a large company. Startups are often touted as sexier and more fun, but large companies have advantages of their own. Large companies offer stability and a proven, predictable career path.

The key is to ask questions and listen for the answers. Chris knew that he needed to test out the viability of a career with an early-stage company. This brings Chris into contact with Jimmy Mac (episode 10) and Turbonomic.

Chris could immediately feel the difference in working for an organization of this size (Turbo was smaller than he initially felt comfortable with). He talks about intense, sweaty sessions where he learned to cold call. He talks about a ten-year run at a company that ultimately got acquired by IBM. Here are a couple of lessons that helped Chris thrive.

  • Push yourself out onto the “skinny branches”
  • Work hard to make a real impact
  • Zoom out periodically and figure out where your skillset can be most helpful

This last lesson is an important one that we haven’t heard from any other guests. In order to have longevity at a startup and be around long enough to see your options vest, you need to be an impact player. One way to do this is to reinvent yourself every couple of years. It can be brutally hard to be an individual contributor for a decade, so keep your eyes open for other opportunities to use your skillset to propel the company forward. Chris launched the first formal BDR program and grew it to 45 people. He followed that up by launching the first customer success and the post-sales team at Turbo. Each new position brought the energy of a fresh start but inside a company where he was already highly valued. If you have a chance and the skillset to follow Chris’ path, it’s one worth considering.

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Episode 5: Maura Sweeney

Bhupendra Rathod on September 29, 2022

Episode 5: Maura Sweeney

September 29, 2022

Bhupendra Rathod

On Episode five of Merchants of Change, we listen in as three Crusaders have a chat about work. We spent all of season one, interviewing former athletes who have become high-powered sales execs, but in this episode, we decided to zoom out for a dose of self-reflection.

Maura Sweeney graduated from Holy Cross in 2007 and found herself back on the hill in 2011 after a stint in recruiting. Today she works exclusively with HC alumni who need help with career services and professional development.

Shift Group candidates have already made the decision that they want to pursue a career in sales but we wanted to try an episode for listeners who are higher in the funnel; listeners who might not be sure what’s next. This episode is loaded with actionable insights on how to find meaningful work.

Where should you start?

Maura’s favorite conversations with alumni are when someone comes into her office and opens with “I have no idea what I want to do.” If you watch the show on YouTube, you might notice her physically lean forward in her seat. Maura is an expert at helping her alumni sift through the murk by nudging them to consider the big questions.

  • Who are you?
  • What have you been doing?
  • When do you work hard?
  • Can you think of a time when work felt enjoyable? A time when you got lost in the work in a good way?
  • What motivates you?
  • What are you curious about?
  • What do you need right now?

The answers to these questions will help you find a career that fits who you are, instead of the reverse, where you start with a job and see if you can twist yourself in a pretzel trying to fit in.

Eleven minutes into the episode Maura starts hitting us with great resources for people who want to go deep. The first book that she calls out is “Flow” by Mihaly Csikszentmihalyi (you’ll need to listen to the episode to hear Maura crush this pronunciation).

Humans in Transition

The pandemic has caused a lot of us to reconsider big pieces of our lives. People have decided to relocate to new cities and towns and re-evaluate their relationship with work. Maura’s spent more time recently with teachers and coaches that are now interested in sales. They want to take some of the skills that they’ve developed in the classroom and see if they can find a spot where their communication chops, organizational skills, and work ethic can be leveraged into a different, potentially more fulfilling path.

For these folks and others who might be interested in sales, Maura walks us through some different attributes and some ideas of what to explore. Not everyone should be a quota-carrying account executive. “If you thrive in team settings and love to solve problems but hate the idea of forecasting and being measured against a quota, maybe sales operations or customer success is worth checking out.”

“Nothing is a sure thing except for what you can do for yourself.”

When was the last time you sharpened your skills? Are there courses or books or certifications that you can explore even if you still have a job?

The current climate has taught us (again) that the people you work with are not your family. Employers are forced to make tough decisions every quarter and it’s a good idea to stay sharp in case you need to call an audible. Set aside some time to read job posts and try to imagine yourself in different roles so that if a great opportunity comes along, you’ll be ready to pursue it. Most of the best work opportunities of your life will come while you are gainfully employed somewhere else.

As you work on your job search, Maura tells us that the biggest thing that prevents people from moving forward is this question:

“How do I find the perfect job?”

You don’t need to find the perfect job for the rest of your life. You need to find the perfect job RIGHT NOW. Focus on what you need from work today because it’s going to change in two, four, or six years. We can’t predict where we will be, what we will need, and what the market will look like in the future. Focus on roles that fit your life today.

Pull up your school’s website and find out if they have a career services team. There may be someone like Maura waiting for you to reach out so that they can use their experience to help you find a way forward.

Additional Resources:

“How to Get A Sales Job” – John P. Davis.

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