Episode 4: Rob Flynn

Episode 4: Rob Flynn

Rob was an elite hockey player who grew up playing in Massachusetts, earning him the opportunity to play at Harvard University. Although it is confirmed he graduated, his GPA remains a mystery.

Prior to entering the real world and his journey into technology sales, Rob played a few years of minor pro hockey, making stops in some legendary minor league cities like Wheeling, West Virginia, Danbury, Connecticut (Yes the same Danbury from the legendary Netflix documentary on the Danbury Trashers) and beautiful San Diego, California.

Of all the stories and good times playing in the minors, one skill stuck with Rob and continues to be one he can hang his hat on. If you guessed Karaoke, congrats, you’re right, Rob has a legendary Karaoke routine to the song…you’ll have to listen to the pod to hear the song actually.

Like most hockey players and athletes in general Rob experienced some pains in the transition out of hockey and into the real world. The locker room, the camaraderie, and being part of something bigger than yourself that you were working towards every day with your peers. JR asks him “what he misses most” and Rob answers quickly how much he misses the ability to release your aggression by trying to body check someone through the boards, a fair point and another thing on the long list of things that athletes miss about their sport when they enter the real world.

After moving to New York and trying to find a job in the financial crisis of 2007, bouncing around from job to job, managing databases, and doing mundane tasks for companies and products he didn’t care about though it did allow him to figure out what he liked. What he likes is building things. Teams. Processes. Etc. Sometimes finding what you like and getting to spend time on it is very sexy. Sometimes we forget about what it took to get ourselves into that privileged seat. Rob started at EMC and then spent years as an IC wearing a headset and pounding the phone for very demanding leaders and mentors.

This experience and exposure coupled with a natural curiosity allowed him to keep his eyes open and pay attention to what he was interested in. Working for people who had been in before him and built teams and processes made him interested in that pursuit. It’s also one of the playbooks for making big lumpy checks. If you can get in early and build a team and be valuable, you set yourself up for financial returns. Commission checks but also equity that becomes more valuable every day that you are building.

To end the episode John asks Rob what unpopular sales opinions he holds, and immediately JR knows where it’s headed. Rob explains how his team at LinkSquares is in the office 5 days a week, which in 2022 is rather uncommon. You might think that’s archaic in today’s business world but I dare you to listen to his explanation as to why and I guarantee you’ll see things differently. And if you still aren’t convinced, take a look into the companies Rob has built and the current growth and success of LinkSquares. The numbers don’t lie.

Rob is another perfect example of why we do what we do at Shift Group and further reinforces what we already know and believe in. Athletes make the best salespeople. You’ve been learning the skills of an elite seller your entire life and you didn’t even know it. We’ll teach you how to use those skills to catapult yourself into a career where you can make $100k in your first year AND love doing it because it’s in your DNA to compete, be resilient and push yourself to be the best you can be.

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Episode 3: Andrew Thomas

Episode 3: Andrew Thomas

Andrew Thomas was a standout hockey player and leader from his teen years all the way through his professional career. He was a member of a University of Denver team that won an NCAA title. His peers and coaching staff elected him to be a captain during his final two seasons for the Pioneers.

Towards the end of Andy’s episode on Merchants of Change, he talked about the idea of starting over. This theme comes up every day with the work that we do at Shift Group. Athletes dedicate decades of their lives to becoming excellent at their sport. When your athletic career ends, you’re left with invaluable memories and experiences and lifelong friends. But, there can also be a deep sense of loss. Sadness and even grief can linger as one career ends and you stand on the brink of the next chapter in your life.

During the transition from sports to entering the workforce as a professional salesperson, all of the status that you attained over the years depreciates to the point where you become just another butt in a seat as Andrew puts it.

We hear from our podcast guests constantly about how tough but necessary it is to be able to detach from your ego to “carry the water bottles again”. No one skips from BDR to VP of sales just like no one goes from pee-wee hockey to the NHL. You have to find the courage and resolve to become the next version of yourself. To plod along the path that others have laid out.

The good news is, that all of the skills, habits, and behaviors that you developed playing competitive team sports are directly transferable to selling technology. You need to adjust and redirect your focus. Instead of being the first one in the pool and the last one to get out, you’ll need to be the first in the office and the last to leave. Instead of spending hours in the film room instead of frat parties, you’ll need to watch Gong calls instead of late nights at the bar.

Andy talks about “not skipping any steps” and “getting the foundation right.” Everyone is in a rush to be promoted into a closing role, but the BDR days are critical. This is your time to incubate and marinate in the skills and habits that will serve you well when it’s time for you to close deals on your own.

“If you were coaching someone through this transition period, Andy, how would you guide them?” asks JR Butler.

“The biggest thing I was missing was community. A group of humans to share wins and frustrations and sadness with. The feelings of leaving your sport behind don’t fade after a week or two. It takes years.”

This is one of the things that has been so rewarding about running Shift Group. Every day, we get together virtually or in person to spend time together going through the transition together. We spend a lot of time on AMA calls without any agenda so that candidates can listen to and respond to questions and challenges presented by their peers.

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Episode 2: Jacob Karp

Episode 2: Jacob Karp

Jacob Karp is no stranger to cold outreach. An early experience with “putting himself out there” that paid off was back in his baseball days. His parents were moving to a new area that was home to a solid Junior College program. Instead of showing up as an unknown commodity and trying to walk on, he got a head start in the process by setting himself apart. He sent an email to the coach with his stats and a highlight reel in order to pave the way for his arrival. It helped him get a tryout which he converted into a spot on the team.

He leveraged it successfully again during a career shift from hardware sales to software sales. Jacob was sharp enough to see the potential of the software sales market. He used LinkedIn to find companies that he wanted to work for and to highlight people that he’d need to get in front of in order to get at-bats. He was making connection requests, sending InMail, tracking down email addresses, and hitting people there as well. He was able to find a spot at Xactly and hasn’t looked back since.

Cold outreach can be an uncomfortable concept for college kids and for new sellers. Picking up the phone to ask a stranger for something is not a natural thing for most people, however, your success as a salesperson relies on it. Jacob has a stack of tactical advice to help us with outreach. It starts with detailed account research.

In Jacob’s episode, we hear about the distinction between blindly emailing people and doing deeper research work to make your outreach personal.

Here’s a story from earlier in his career.

Jacob was trying to find a way into a top account. During his research, he noticed that one of the decision makers was a University of Texas graduate who was active on Twitter. After wading through a bunch of old tweets, Jacob found one that he could work with. The prospect had been tweeting regularly about his passion for the 2006 Rose Bowl where UT faced off against USC for the national championship. Jacob put together an email where he listed off a few of his favorite moments from this game and sent it off. The prospect and Jacob exchanged a few more notes about the game and Jacob eventually got a meeting and eventually a deal. The key was working hard to find an authentic moment to connect. There was no ask, just the intention of starting a conversation about a common interest point.

One from JR:

JR recalled a time when he noticed that a CIO from a target account was on the board of a non-profit that he regularly wrote about on LinkedIn. JR took an opportunity to donate to the non-profit and send the receipt and a note to the contact about how the cause was important to him. He was able to start a conversation and eventually land a meeting.

One from co-host John Davis:

John recounted a time when he played matchmaker. He had become close with a CIO that he had done business in the past. The CIO was starting to look for a new job. A target account that JD wanted to crack had a vacancy at CIO and was actively recruiting. JD took the opportunity to put the two parties together. The target account eventually hired the CIO and JD was able to get in front of all of the stakeholders at the company where he previously had struggled to find a foothold.

For sellers trying to break into an account, here are some guidelines for research and outreach. Before you ever hit send on an email you should know:

  1. A company’s short and long-term business objectives
  2. The strategy that they will use to achieve them
  3. The people who will be responsible for generating these results
  4. Some detail about these people and what they care about most

Ask yourself if you can connect what your company does to the answers you uncover through research.

Jacob Karp is here on LinkedIn (https://www.linkedin.com/in/jacobkarp/). Do yourself a favor and follow or connect with him. Using his background as a journalism major, he publishes daily posts that will be helpful to any seller at any stage of their career.

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Episode 1: Origin Story

Episode 1: Origin Story

The year is 2019 and JR Butler is posted up at one of his favorite spots in Scottsdale, AZ, Fox Cigar Bar. I can picture the scene clearly in my mind as if I were there. JR has a fat cigar sticking out the corner of his mouth and is having a hard time keeping it from falling out because he’s grinning like the cheshire cat. Backward hat, stylish eyeglass frames, small dark clouds wafting into the rafters. He’s clacking away at a laptop that sits on his high-top table. He pumps in his AMEX number from memory into the checkout screen for GoDaddy.com. He’s just locked down shiftgroup.io for the next ten years.

JR and his co-founder and partner, John Davis were serious athletes and eventually crossed paths high up on the hill at Holy Cross. JR played hockey and JD football. Athletics were a giant part of their formative years. It seeped into their identity, as it does with most young people who are serious about it.

“I’m a softball player.”

“I’m a hockey player.”

Everyone ultimately faces the end of their athletic career. It happens at different times for different athletes. Some people are able to be compensated handsomely for their skills while others hang up their swim cap after their last college meet. What are you supposed to do when something that becomes part of the fabric of who you are ends?

After his hockey career ended in college, JR was in a bar in his hometown in 2008, where he bumped into an entrepreneur who owned a technology business.

“JR, what’s next for you?” He asked.

“I’m planning to take the LSATs and go to law school,” JR responded.

“Why? You don’t want to be a lawyer. You’re great with people and you had to be a competitive guy to play college hockey, you should think about tech sales?

“Dude. I don’t own a computer,” JR chuckled back.

“I’m looking for entry-level sales people. You should come and give it a shot. All the habits you developed in hockey will make you a good salesperson. If you stick with it, you’ll make 250k within three years.”

John’s playing days ended at Holy Cross also. His path was different. He packed his bags and headed off to Wall street. He was peddling his resume to all of the big banks in 2008, in the middle of one of the worst financial corrections in world history. Unable to land a spot in New York, he found himself at a bank in Boston where he hunkered down and spent 10 hours a day using Microsoft Excel. After five years in banking, he’s struck with a realization.

“I want to spend time with people. How come we’re not talking to humans?”

He started talking to some friends and his old pal JR. It took him three or four rounds of interviews before he got his story dialed in. Eventually, he ended up at an entry-level sales job at a Fortune 500 company selling software.

Both men attribute their starts to a mix of luck and mentorship. Starting the Shift Group allows them to spend their days working with former athletes looking for a little luck and guidance themselves. Over the years, JR and John have helped countless friends and strangers land sales jobs for free. John literally wrote the book “How to Get a Sales Job.”

You can buy it here: Buy John’s Book

JR and John’s path naturally led to the lightbulb moment where they thought, “ maybe we can get paid for this.” JR secured the domain name and John set up the LLC. They gave themselves a few months to see if they could hit a placement target. They got the model wrong initially until they realized that companies are willing to pay agencies like the Shift Group for access to their pool of candidates.

The Shift Group was off and running.

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