Episode 10: Jim McInerny

Episode 10: Jim McInerny

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.

Post Tags :

Share :

Episode 9: Colin McDonald

Episode 9: Colin McDonald

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.


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.

Post Tags :

Share :

Episode 8: Hayley Skarupa

Episode 8: Hayley Skarupa

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.

Post Tags :

Share :

Episode 7: Zeke Testa

Episode 7: Zeke Testa

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.

Post Tags :

Share :

Episode 6: Chris Ward

Episode 6: Chris Ward

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 builtin 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.

Post Tags :

Share :

Episode 5: Maura Sweeney

Episode 5: Maura Sweeney

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.

Post Tags :

Share :