Merchants of Change

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Speaker 1
This week on Merchants of Change, we talked to one of Marlborough, Massachusetts, finest, Jesse Bryant. Jesse was a force sport high school athlete before playing college softball at Providence for the Friars and becoming a captain his senior year. And then going on to a great coaching career at the United States Military Academy at West Point in Cal State Northridge.

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Speaker 1
She's coming off a very successful five years, shifted HubSpot, which she started as a BTR and finished as a team lead principal, partner, specialist. Here she is, Jesse Bryant. I'm J.R. Butler, co-founder of the Chef Group. And you're listening to Merchants of Change. Oh, this is a podcast about transferring the skills and behaviors we acquire as athletes into being a professional technology salesperson.

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Speaker 1
Each week, we'll introduce you to a top performer who will help us understand how they became professional merchants of change.

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Speaker 1
What's up, kid? How are we doing?

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Speaker 2
Oh, we're doing great down here in Florida. You still up in the good old Marlboro?

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Speaker 1
You know, I'm actually in Brookline, but I get out there a lot.

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Speaker 2
Yeah, jazz from time to. Yeah, the Butler household sendoff.

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Speaker 1
Yeah, yeah. There was a lot of too diplomacy.

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Speaker 2
Yeah, we were only a week. I wasn't. I was in a mall over the weekend before, though.

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Speaker 1
Well, in working for all our for all our listeners, we got Jesse Bryan today. I've known Jesse basically, literally since he was in diapers. So I think Jesse, you know, I would love for you. I actually get to hear you answer this question, but can you can you just tell the listeners what it was like growing up around the The Butler family?

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Speaker 2
Yeah, I can definitely do that. Gosh, where do you start? So my my family, we lived about probably a mile up the road from you guys. Yeah. So we lived a very mile off the road. I've known J.R. since I can remember, because literally. Right. My mom and your dad were already coaching together at the time I was born, and luckily they are a little older than me.

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Speaker 2
But his mom decided that, you know, I needed to have a buddy for the rest of my life. So Al and I were hockey partners probably from before we were even born. It was probably somewhere I'm sure our parents signed a contract. I'm sure they did. But it was a lot of fun. I mean, it was street hockey in the cul de sac, you know, chasing Mikey O'Brien with ping pong paddle the whole nine yards.

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Speaker 2
But it was always a good time. We were always outside playing and definitely never short of laughs.

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Speaker 1
Absolutely. The good old days.

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Speaker 2
So I.

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Speaker 1
Jesse, you like me? You kind of grew up predestined, predestined to be an athlete. Your mom was a phenomenal athlete. You had an unbelievable athletic career. Can you just talk about like I'd love to hear like, what are some of your most like fondest memories of playing sports?

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Speaker 2
They're all the best ones, right? Oh, God, I could that list could go on and on for days. But I mean, honestly, it's you know, it is the second family you make, the family you have. And just like you think about I think about, you know, back in Cape Cod, like doing belly flops into the pool. You know, every family vacation was a was a different tournament.

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Speaker 2
So, like, that was my my life from the day I was born, as you know. But, you know, you're around a lot of the same people. You're all traveling together. You're building your family together, but competing at the same time. And we were competing at a pretty high level pretty early on, both both you and I. So it was a it was a fun balance, though, for sure.

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Speaker 1
Absolutely. How would you describe yourself as an athlete, Jesse?

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Speaker 2
Right. Can I just ask you that, J.R.? You probably watch more games of me than I have maybe grown up. And it's funny because I think I'm a little bit of a different athlete mindset wise, because I've played so many different sports and I think honestly, I feel like what we're probably get into, like in terms of your professional career and working in tech sales, like because I played so many different sports and each one has its own mindset, like softball is a very different game than hockey, very different game.

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Speaker 2
So I think like just like that versatility of the model like multi-sport athlete, you know, definitely would be probably what? Scott Yeah, kind of.

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Speaker 1
I think.

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Speaker 2
You know, I always get so uncomfortable talking about myself.

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Speaker 1
I know, I know.

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Speaker 2
I usually have big out just pop archetypes.

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Speaker 1
I, I was, I was literally going to say like versatile and dynamic I think are good words because you were such a I mean, you literally played everything. Jesse, and you made the point of like your fondest memories really being about like, you know, your fear, the fame, the family you choose, right? Your teammates. Do you have any any favorite teammates from your playing days like, you know, college, etc. that and like why were they your favorite?

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Speaker 2
I got a few favorites. I can't pick one out. Like, obviously me and your brother's still super close. He's definitely my longest friend, right? We've be partners from the day we were born, and I could go on about four days, but they're, I think, like the more impactful one, because we all make friends, right? We have our favorite friends, but my favorite teammates actually, when I was a sophomore, there was one Justine and she was a junior.

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Speaker 2
I was a senior that you're actually and I had had a tough freshman year and it's like she kind of just took me under her wing, was like, You're too athletic not to be starting, so let's go. And you don't forget those like to them they just see maybe another couple. WS If they can get this athlete to figure out a more technically skilled game and softball like the detail wise.

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Speaker 2
But you know I just that's a good one. And then another one be Dan Abrams also from my college days. And then the last one will be actually she's still my best friend today. To Melissa Tolbert. We played just one year of travel softball together and she actually she's a hawk, J.R. Hudson Hawk.

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Speaker 1
Nobody's perfect rival. High school, so exact. Yeah.

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Speaker 2
We played against each other on high school, but just from that year we played we've gone through a lot of life together too. That summer, going into my sophomore year or college like she was before I was driving the ice cream truck over to the Butler house for Bobby's called her Cup party. I was at the softball field in Baltimore.

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Speaker 2
So you remember that?

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Speaker 1
I so I know what you're talking about. And it's not that I it's not that I forget that. It's that I mean, you know.

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Speaker 2
I'll have to send you the picture that I think Wendy took of me pulling the ice cream truck up to that party. And it's all the kids. And we were able to cover my entire day, see, that day. So I didn't have to work. It was great and unreal.

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Speaker 1
Yeah, that's I mean, that that was Ira member it being a phenomenal day. I do remember I have a slight memory of the ice cream truck.

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Speaker 2
That was my great job.

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Speaker 1
I love it. That's right. That's right. My favorite. My favorite part of that day is when we and hopefully nobody from the NHL is listening to this. But we lost the we lost the Calder Cup for like 7 hours and then realized that it was literally sitting at the bottom of our pool the entire time. So if anybody, if anybody's getting their day with the call to cup, you know, we're sorry about the wood.

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Speaker 1
It wasn't our fault. It was it was it was just ferry's lickers. Jesse, I'm like, you know, you went away to went away to school. You know, I was working, you know, I loved it. Like, hear from your perspective, like, what do you think? You're your Providence teammates. How would they describe you? Like, you grew up very versatile and dynamic, but like when you got focused on softball and you kind of got into those like higher classes junior senior year, like how would those teammates describe you think?

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Speaker 2
I think they would describe. I mean, I always had a chip like kind of like a chip on my shoulder type of kid. It's like it made me work hard, you know, I played with the boys. So being the only girl and that chip was there for a long time, not be, like, had nothing to do with you know, being a freshman and college or anything like that.

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Speaker 2
But like the coach, I think told my dad at dinner when I graduated, like her chip never went away. I was like, Oh, she's a little punk freshman. We just it's, you know, generally quiet at first. You find that to be shocking. But I like to just like I'm really observant, you know? But I work hard in silence.

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Speaker 2
Yeah, probably the other one. And definitely, probably one you'll want at your wedding someday. Or you're. I'd say wedding, but most of them would probably say planning the bachelorette party. That's that's probably how you know.

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Speaker 1
That is awesome. That is great. So, so Jesse kind of you know obviously, you know what what chef group does, you know, I remember having some conversations with you, you after your your playing career, you went on and coach did some like really kind of special institutions West Point which which I did an official visit at Imagine me at West Point, by the way, you know, Cal State, Northridge, Northridge.

00:10:46:12 - 00:11:02:09
Speaker 1
And then you you became a BTR. So one day you're you're hanging out on the field, the next day you're you're sitting in a cubicle wearing a headset. How how tough was that change for you, Jesse.

00:11:04:04 - 00:11:27:07
Speaker 2
I think maybe one of the differences and and probably a benefit really is like, sure, I'm an anti person. I always stand whenever I do a call. I'm one of those people. But you're so used to hours and hours of film and that stuff that it wasn't that big of a change, right? There wasn't the cubicle like we're all used to just doing the job.

00:11:27:07 - 00:11:52:15
Speaker 2
We all had to go to study hall. So it wasn't that that different like you've already been taught those skills how to kind of like sit down and do your work. I just realized I needed to work out at lunch because at some energy levels, but we are all very college athletes. If you played a, you know, a high level in college, I considered doing a one, two or three, all high level.

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Speaker 2
You just you learn those skills that actually translate pretty well. The tech sales, if you really sit back and listen, I remember I called you and I was getting out of coaching. I was like, how do I just my only experience is teaching people how to hit top all day are like, what? How do I translate this? But at the end of day, it all kind of translated.

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Speaker 2
There wasn't much of a difference competitive at the task to focus on. You know, I get really detailed with which I think is, you know, something that differentiates athletes is we're used to doing the work on our own. Every one of us probably did work on our own. So it wasn't that big of a difference, not as much as I thought it would be.

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Speaker 1
That that's really actually good to hear and that I remember that conversation. One of the many conversations that led me to starting the starting shift grew. I guess like, you know, Jesse, you have a like you have an awesome network, right? You know, a ton of people want like, why did you choose sales and how did you end up specifically at HubSpot?

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Speaker 1
Because, you know, when you join HubSpot, you know, they're obviously huge and they were big back then, but not as big as they are now. Like the how how did that whole thing play out for you?

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Speaker 2
Right. I mean, it all comes down to a sports connection. So I actually I played softball with there all through high school, my travel softball team, her name is they're called the Cold Argento from Ashland. She actually also coached with me. We had our first college coaching games together at West Point. She was there for a year and then she got the job at Harvard, went back home.

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Speaker 2
You know, I stayed at West Point for a couple of years in California and then, you know, some family circumstance kind of was needed to bring me back home. I had already been thinking about it a little bit, and I knew she had just got done coaching and that her brother owned a VC firm. Like what I knew about ABC at that time, nothing like my dad's a cop.

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Speaker 2
My mom's a, you know, a teacher. Like, I don't think I ever heard those were like those letters put together. I was like, vice captain. I don't know what to think now.

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Speaker 1
We heard we heard PC not the easy.

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Speaker 2
Easy, easy. And she he had referred to HubSpot. He's like good scaling company coming up. She's like, I just started as a PR last week, like, you want me to refer you in? And I was like, Yeah, definitely. And then I think the next thing I did was call you J.R. and those like, Can you help me do my resume?

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Speaker 2
And from there, like, obviously you don't put all your eggs in one basket. And I just kind of went to LinkedIn and found similar Boston companies that fit a similar profile and apply to like, you know, four or five of them.

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Speaker 1
That's awesome. Jesse It's it's I'm like really fortunate. And now I get to like, I get to work with a lot of Jesse Bryant's back then, like girls that are just coming out of playing in coaching. We actually just, just work with a girl who's on the, the Great Britain national softball team. They just won some like.

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Speaker 2
I might know her. She plays their bass.

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Speaker 1
No, our name is Kendall. Okay. She's awesome. Yeah. But, you know, like, obviously we try to relate to him. I try to relate to him as former athletes and put myself in their position. But like I always think, you know, men and men and women are different. And, you know, it's always good for them to hear from from their peers.

00:15:31:01 - 00:15:47:23
Speaker 1
So, like, I guess I would love to know, like what kind of what kind of guidance, what kind of advice would you give to two women who are about to go from playing sports to starting a career in sales? Is there anything that you would have done differently?

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Speaker 2
You know, and maybe this is a lot of playing sports with Boys Yong playing with I was always on Boys and Girls teams. I'd say my advice is to be just look at them as like your teammates. Like I think girls are often just too I mean, even I mean, I don't know if it's just because I didn't have experience, but even like in our house, I was super quiet, like, you know, you look to your left and right and even five years ago is still primarily male dominated.

00:16:19:20 - 00:16:42:00
Speaker 2
Thankfully, I had my, you know, locker room days of helmets and gloves, you know, that I could rub some elbows with them, but or talk hockey with them because, you know, it's kind of a common ground. But I think it's just like literally look at them, like your teammates. I should have done that earlier because that's really all they are.

00:16:42:00 - 00:16:58:07
Speaker 2
They're they're going to be your biggest asset, the person sitting to your left and right. Or they could, you know, really be a detriment. Getting in a sales is scary. Like I, I don't like to talk on the phone as it is like take up and dial my parents. Like my dad texted, are you alive? Can we chat this week?

00:16:58:15 - 00:17:11:23
Speaker 2
Like, so it's intimidating. And if you don't, you know, lean on people to get, like a right or like, you know, really make sure you're in a good environment that you're comfortable in. That job is just very, very difficult to do.

00:17:13:06 - 00:17:13:14
Speaker 1
Yeah.

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Speaker 2
Yeah. And I definitely I definitely was intimidated slightly at first, even with my my background, but there's no need to be.

00:17:23:16 - 00:17:50:16
Speaker 1
Yeah. And I think you had like a, like a little bit of a leg up kind of because you did a, you did a few years in coaching and recruit recruiting at like phenomenal, like I said, like West Point, California Northridge, like unbelievable programs. Like do you think do you think those those years between playing and then sales, those years coaching and recruiting, do you think those helped also prepare you for a career in sales?

00:17:51:08 - 00:18:18:13
Speaker 2
Yeah, well, how I describe it, tears like like my playing days gave me like the worth that worth work ethic, right. And like the ability to take some, the natural ability to let something roll off your shoulder or roll up your sleeves a little bit more it more towards work ethic. But I think the coaching years actually made me super successful beyond the BTR role, you know, a lot quicker.

00:18:18:23 - 00:18:42:22
Speaker 2
I mean, I was 24 years old coaching at West Point. I was going to 22 year olds like you had to have an authoritative position, but like also very much as an assistant, it's like two years on, I'll get on the same side of the table and get a lot of respect and trust upfront. I think what made me actually super successful more than I playing was probably my coaching, my coaching years.

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Speaker 1
Absolutely. A lot of immaturity comes with that too. I think that you maybe don't have while you're a player, right?

00:18:50:22 - 00:19:10:14
Speaker 2
Yeah. I mean, even think I met you like a lot of the players you work with, they are team captains. Like it's the same thing when you can notice someone's shoulders down, like you just notice so much more about body language. I think we forget to like recognize that as athletes, but like, I mean, they want body language is key.

00:19:10:14 - 00:19:17:21
Speaker 2
Like what coaching allow me to do is like really interpret body language or is it just recognizing.

00:19:19:05 - 00:19:21:21
Speaker 1
Yeah, like a little more empathy. That's really cool.

00:19:23:21 - 00:19:49:04
Speaker 1
So this is I'm actually I literally just look these numbers up because I think it's a cool stat. So you joined HubSpot in August 2017 and you might not even know this, but so the stock at an August in August 2017 on this date five years ago it was was trading at $67.35.

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Speaker 2
Obviously they had had it around like I was like, oh, probably 101 hundred bucks.

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Speaker 1
Yeah, yeah. Wow. 67, $67. And obviously everything is down right now, so I'm not going to use this number. But at the height at the height of the market, three months ago, it was it was over $800 or 800, $810. Right. So like that kind of speaks for itself in terms of what what choosing HubSpot did for you and your experience.

00:20:18:03 - 00:20:40:19
Speaker 1
But like we like you, we definitely tell our candidates not to put all their eggs in one basket. We put them in front of multiple companies. And typically our candidates do such a good job, they usually get multiple offers and like when we're talking to them, a lot of them are thinking like, okay, well, base salary, base salary on track earnings benefits.

00:20:41:03 - 00:20:58:19
Speaker 1
You know, hey, this one's in the office. This one's remote. What do you think? Like, what do you think is missing from the list? And like, if you could tell Jesse Bryant when when you were going through that process, how would you advise somebody to evaluate potential employers?

00:20:59:09 - 00:21:20:10
Speaker 2
Yeah. So, I mean, it was it was an interesting one because I was completely changing careers. I was also moving from L.A. to Boston. So it's going across country, you know, multiple like you get through to the second round on all of them. And, you know, I'm like, all right, well, I'm not taking five in-person interviews, but for me, it was really important to go on site, even though A, B, R wasn't getting flown out.

00:21:20:11 - 00:21:41:21
Speaker 2
Cross Country like. So I flew myself out and kind of coordinated all my interviews because I wanted to meet the team like I wanted to meet the team and that was even more important to me. I was already knew I was taking a pay cut. I was coaching a top 50 program at the time. Like I was going to be taking a pay cut.

00:21:41:21 - 00:22:22:00
Speaker 2
But I knew that if the team was right when I got there, like the like, I was going to be fine. I was always going to learn. I was going to, you know, be able to take it. And I obviously knew how successful you were then, you know, in your career, I'll just kind of have like seeing what it could be and not putting what it could be too far out of reach for, you know, the better deal now I think that's super important is like less than benefits and things like really fine like what your comfort is in the process too.

00:22:22:05 - 00:22:27:07
Speaker 2
I always said like you're interviewing them too, so it's really important to remember.

00:22:28:04 - 00:22:36:17
Speaker 1
And is that like, is that like comfort with your potential, like hiring manager, like you feel like you vibe with them and you feel like you're going to learn from them. I was going.

00:22:36:18 - 00:23:02:08
Speaker 2
To say the hiring manager as much because like, you know, they're forward like having coach. Like I think that like I knew that they, you know, have a check point. They have to hit things that they have to ask like they're not don't joke around with you. But they're really you know, they are very much coming into the mindset that oftentimes that they're interviewing you and like there's no back and forth.

00:23:02:08 - 00:23:34:01
Speaker 2
Like, sure. You know, everybody prepares the two questions for the end of it, you know, the end of an interview. But I more like just paying attention to like what's going on, like the nonverbal. Right. What are you seeing going on in the office? I think it's super important the BTR job and thank God I chose comfort because I like the comfort of the team and what I saw over the interview process because like the BTR job can be grueling and that.

00:23:34:11 - 00:23:52:17
Speaker 2
But you know, not many people are ready or you know, not everybody comes out the other end in any role. It can be a grinding, grinding position. So I think, you know, being in your comfort zone is really important. You know, whatever you do to get ready before a game, it's the same thing.

00:23:53:16 - 00:24:08:02
Speaker 1
Yeah, I love that. That's great. And it's almost like you can feel it like and that's why I like going, like you said, going on site. It's like, okay, I can, I could see myself there. I can I, I love that. That's huge.

00:24:08:02 - 00:24:29:17
Speaker 2
You know, you get a little lucky every once in a while. You're trying to find that not right. But like, I think, I mean, you listed off all the things that people are going to actually want to know. But. Right, the decision making process, I don't think that it should come down to those things, especially, you know, as you go into an entry level role.

00:24:30:15 - 00:24:52:15
Speaker 1
Yeah, 100%. 100%. And the other thing that I'm really like, I'm excited to hear you talk about, we we have to kind of like like you said, you took a pay cut, right? We have some candidates we work with that. It's like, you know, we basically have to talk them into why they have to start as a bidder.

00:24:53:11 - 00:25:15:10
Speaker 1
But but everybody, especially as an athlete, I know you went into this career this way. Like they just want to get promoted into a closing role as fast as they can, which they should. Right. That's the right attitude. What do you think, in your opinion? What's the right way to approach the job? And if someone is interested in getting into that closing role quickly, what advice would you give them?

00:25:16:07 - 00:25:40:20
Speaker 2
I would say, and it's interesting because I, you know, was very successful as we are. But I was in our channel program, so we kind of had a promo freeze, as you know, a lot less account managers and ease, if you will, in the channel program versus the direct side of business. But um, so I actually got like a six month hold from my promo, which can be really frustrating.

00:25:40:20 - 00:26:05:00
Speaker 2
It's like you hate all your promos, but there's just not that opening it, you know, there's still a starting senior at shortstop, if you will. So it's like during that time, though, what was interesting is I think I got closing experience the entire time I was doing the exact same job at that point in my career that I knew I'd be ready to hit the E for running.

00:26:05:00 - 00:26:22:15
Speaker 2
So having a good relationship with my years actually like was my saving grace because I started closing deals in those six months, you know, for my ease. And I think that was, you know, 12 to 18 months of trust building with them. And they were like, Yeah, go run that one.

00:26:23:11 - 00:26:25:04
Speaker 1
That's awesome. That's great.

00:26:25:07 - 00:26:26:17
Speaker 2
Gave that to me, which is.

00:26:26:18 - 00:26:38:18
Speaker 1
Nice. So that like solid operating cadence with the ADP in your opinion is a pretty important piece of like finding that path to becoming a yourself, right?

00:26:39:02 - 00:26:57:04
Speaker 2
Yeah, absolutely. Like we all go through a month of sales training like it. That's not where you learn how to do the job and you have to be like, if I wasn't a BTR first, like and I got thrown into a role, I would have had no clue what I was doing.

00:26:58:01 - 00:26:58:09
Speaker 1
Right.

00:26:58:17 - 00:27:22:17
Speaker 2
And I didn't know my selling style. Like, I know, like I know my coaching style or like my playing style, right? But I think the selling style and it can be very different. There's a lot of different selling styles and being a PDR allowed me to see multiple ones. All right, I got to worked with seven reps. I think, you know, that's a lot to handle the reps like.

00:27:23:06 - 00:27:33:13
Speaker 2
But you start to work with the ones that put an investment into into a little bit more and it ends up working out because you kind of find your own style there.

00:27:34:14 - 00:27:51:00
Speaker 1
Yeah, hundred percent. How do you think? Like how do you they're going to be like what's it going to look like in terms of like being helpful to those buyers, like you said, like, well, if one of them was going to lead in and that's going to help, what does that look like to you think?

00:27:51:07 - 00:28:27:14
Speaker 2
Yeah, I got the opportunity mentors, the bidders have a spot after the fact. And then being a team lead to make new hire two days the I think it's make them a part of your like literally make the BTR part of your team like I have they whether they trust me or not they invited me to all of their meetings and partners they you know the ones that were that did that and took, you know, and gosh, what I was doing, I thought they were giving me all this time in the world, some of them over there.

00:28:27:16 - 00:29:05:15
Speaker 2
And really, I mean, it's 30 minutes of four years of knowledge. Like it's easy for them and you don't realize you're like, oh my God, they just like blew my world. They saved me, like, at least 6 hours and prospecting tonight, like, by just showing me, like, take a 2 minutes to show me something, and then I think, you know, it's hard because, you know, we all like to get paid and have a little control, like sales reps, like we like to have control of our own paychecks or, you know, we wouldn't be working so hard.

00:29:05:15 - 00:29:32:20
Speaker 2
But it's tough to trust someone with your paycheck right? Like and I didn't realize that even sitting on the other side how much trust my days had in me. Um, we might have to. I might have to call on and ask them why or if that's normal. But I like on the other side of it, it's the trust component helps a lot that gives you the confidence to go close deals without a manager asking you for your forecast every you know.

00:29:33:12 - 00:29:52:21
Speaker 2
Yeah they weren't asking me for a forecast like they had a few they'd let me run through. Right. If I closed it for them, it was a bonus. It's like getting the Amazon Prime gift cards I keep getting from something that I've signed before. Who knows? It's like they just don't expect it. And it's, it's. It's extra for them.

00:29:53:15 - 00:30:03:02
Speaker 2
Yeah, but I'd say, like, allowing your readers to have some trust on some of those smaller deals is going to help you in the long run to cause them more experience, to close more deals for you.

00:30:03:23 - 00:30:35:00
Speaker 1
Absolutely. We obviously, you know, like what's going on in the job market right now, it's that the interviews are getting more competitive. So what we're doing is we're trying to like add to our training, give give these athletes as much as we can in terms of skills beyond the intangible characteristics, right? Like so they can talk intelligently in, in an interview about how to research an account, write a novel, write a cold email, make a cold call, qualify whatever.

00:30:35:06 - 00:30:57:06
Speaker 1
I'm curious to know, like, what do you think is like a top area of development that athletes can really lean into to to differentiate themselves from all the other people that are going for these these BTR roles that are that are, you know, the number of roles is shrinking. That's just the reality. Like what's what's a good skill to think about for these folks to think about?

00:30:57:06 - 00:31:28:11
Speaker 2
Yeah, maybe I had it just because I worked 100% commission job in high school at some point driving an ice cream truck. But I would say, you know, more so than what you described, it's a how do I put this? It's I'm trying to describe it the right way, but essentially, like, it's I don't know. They're this one's complicated for me.

00:31:28:11 - 00:31:31:05
Speaker 2
Repeat it for me, because I want to answer this one right now.

00:31:31:05 - 00:31:32:10
Speaker 1
Of course, like like.

00:31:32:16 - 00:31:33:20
Speaker 2
You got a good one here for you.

00:31:34:01 - 00:31:48:07
Speaker 1
Yeah, you got you. We're trying to develop they're trying to develop skills and we're wondering, like, what skills should they focus on heavily or the mastery to kind of cheat themselves, role playing.

00:31:49:01 - 00:31:58:11
Speaker 2
I hated that part of training. I absolutely despised it. I probably was the worst. Like ever and role play. But it is part of that interview process. Like.

00:31:58:19 - 00:31:59:03
Speaker 1
You know.

00:31:59:14 - 00:32:21:08
Speaker 2
Like thankfully I think I had some years of experience. My belt, being a coach and talking that I snap myself through, but I hated it. Like even as a, like going to a role, I hated it. It and I don't know, I don't know how you got into textiles there, but like I had no idea of Texas. Like, that was an option in college.

00:32:21:08 - 00:32:39:17
Speaker 2
It's like I was digging holes in Framingham in the summers when I could have been doing a sales internship. Because the only way is if you had that experience of getting up, getting on the phone in a variety different ways, getting in front of people. You know, I think back to coaching, like I would have to give out the practice, right?

00:32:39:17 - 00:32:53:13
Speaker 2
I even when I worked at camps, I had to give a lesson on hitting even just like teaching in any way I think is like anywhere you can get up and speak in front of people, whether that's a sales internship or not in college, I think that's the biggest myth.

00:32:55:01 - 00:33:23:03
Speaker 1
That's so good. I couldn't agree more. You talked a little bit when we were talking about your softball career. Yeah. See, about, like, you know, Justine, Jen and Melissa. Now that you're in the tech world, I'm wondering like, if you come across colleagues or peers like that that have that have become like valuable mentors for you in this new in the new career that you're in.

00:33:23:03 - 00:33:56:00
Speaker 2
Say, I. Right. Just let them start. Right. So is my first time experiencing like how long do these relationships last but and you know, like being at the same company for five years and so this is kind of a little different. Me, HubSpot, it happens all the time. It's a great company to work for, like but then you hear about other stories like, oh, the average is like two and a half years, I think Max like I was like, Oh, but, but definitely like there's just some people that well, you don't talk to them every day, right?

00:33:56:00 - 00:34:24:06
Speaker 2
Like some of your old teammates. Like I just texted Jen Abrams yesterday because a song came on of the nickname she used to call me. Like, just call me Franny. I don't know why, but, like, I'm sure there was other things, like, like small memories like that, but like, if the people used still want to pick up the phone and text or call, you know, six months or six years down the road, just randomly, you know, it makes your day and you text and makes their day.

00:34:24:10 - 00:34:32:08
Speaker 2
You wouldn't do that for, you know, just anybody. And I'm already finding that. And, you know, my career, my second career, I feel.

00:34:33:01 - 00:35:00:02
Speaker 1
Totally, totally. Yeah. And and you're going to build just as strong long term relationships as you did in sports. And you were a leader at the Friars at Providence team. Captain, you led, you know, the future young women of America at the two schools you coached at. But, you know, it's different going from an individual contributor to a leader of people in.

00:35:00:02 - 00:35:10:08
Speaker 1
The workplace is different. Can you talk a little bit about what that transition was like going from I see to to kind of that that leader title.

00:35:10:08 - 00:35:38:11
Speaker 2
Yeah. I mean I'll be honest like a first like it because I mean the leadership positions I held outside was like a team, like I was still an individual contributor at the end of the day. The interesting thing is I had to remind myself that I was still an individual. Individual contributor at the end of the day, because I found myself like really investing in, you know, the mentor, the mentees I had over.

00:35:38:15 - 00:36:00:01
Speaker 2
Yeah. You know what my task at hand, what actually paid my check and what, you know, I wasn't paying enough attention to that and it it's a hard job. Like I think what I'm going to get is like the balance of it is the most important and you don't really realize the balance of it until you're in a leadership position.

00:36:01:22 - 00:36:20:09
Speaker 2
You know, once I was able to figure out that balance, so it made me a way better. E A working with, you know, any mentors they can because you learn different ways to describe things, which gives you different ways to talk to, to describe it to the prospect. You're like challenge there. Again getting in front of people being force.

00:36:20:21 - 00:36:41:16
Speaker 2
One of my least favorite questions is like, Jesse, what you do for work? I'm like, How do I describe that? Like, off the cuff, like, I can't do it. Like the leadership role like really allows you to be able to allow other people to get there faster than hopefully I did. Yeah, I just got to it to them.

00:36:42:00 - 00:36:51:15
Speaker 2
Obsessed with the coaching component, probably missed it a little bit, but I was I never like I didn't have that like manager role. So it's a little bit different as a team leader.

00:36:52:12 - 00:36:58:20
Speaker 1
Totally, totally. Well, now you can tell people you're a merchant of change, Jesse, because that's what that's what we think salespeople are.

00:36:59:13 - 00:37:01:14
Speaker 2
Versions of to describe that one.

00:37:03:07 - 00:37:28:09
Speaker 1
So merchants, obviously, these are, you know, one of the oldest professions. They're they're they, you know, traded people, you know, for for other goods or for, you know, financial, financial backing. So, you know, what I always think of when I think of technology salespeople is you're selling change, right? Someone's doing something a certain way. They have been for a long time.

00:37:28:19 - 00:37:50:22
Speaker 1
You're coming in with a solution to say, hey, have you thought about it? You know, have you thought about the negative consequences of what you're doing today? And have you thought about the potential positive outcomes if you did it this way and this way, is HubSpot seamless or whatever, you know? So that's that's how we kind of, you know, my my old boss had Turbo.

00:37:50:22 - 00:37:56:15
Speaker 1
It was his nickname was Merchant of Change. So that's why we never we name the podcast that Merchants of change.

00:37:57:00 - 00:38:31:23
Speaker 2
I like it yeah I like yeah I like it I think they're like I don't know the sales athletes in the in the sales room definitely brings about change no matter what. Like who you were like it. I mean, naturally, like it's that team component of it. Like it's very and it's not easy even a lot harder in today's world with with COVID and primarily working remotely like how do you make that connection piece?

00:38:33:12 - 00:38:45:11
Speaker 2
And I think athletes have a, you know, a much better ability to do that. They've done it for a lot longer. They're not, you know, ever just playing for themselves or their individual sports. But like even in college, those are all part of team.

00:38:46:09 - 00:39:15:08
Speaker 1
Oh yeah. Hundred percent. Yeah, I think. Are the customers agree with you too? So one last two questions, Jesse. I love asking this one because I'm always curious to know. So we we ask guests always to highlight one sales that they've developed that makes the family like, what do you think your strongest sales skill is?

00:39:15:08 - 00:39:56:13
Speaker 2
You know, my mom said I had the gift of gab since the day I was born, so not that, but I think I got really good, really early at utilizing technology to do my job. I get I essentially was the LinkedIn sales. Now trainer for my eight years when I was a PR like I got really, really good at working smart and I'm not going to pick up the phone and just dial a hundred people just because we have a call blitz like I'm going to take 3 hours the night before, grabbed my list of 20 and get myself five, meaning because I only get I don't get paid on calls I make I get

00:39:56:13 - 00:40:10:06
Speaker 2
paid on meetings. I book deals that close. So like I got very good at utilizing like text technology to do my job and just putting in a little work early. That's amazing.

00:40:11:00 - 00:40:32:08
Speaker 1
I love that that we have never gotten that answer, Jesse But I like that. That is and I'm honestly like, it's a game changer, right? We, we had people like that at Turbo that like just Wizards with, you know, LinkedIn Sales Navigator or building a record Salesforce, right. Like and now you've got like all these other tools that are out there.

00:40:32:08 - 00:41:01:12
Speaker 1
So like, yeah, that, that's a really good one. That was, that was a surprise. I like that you might remember this, Jesse, but my, my dad used to tell me, Bob and I, when we were little like, hey, guys, there's a there's a lot of people that play hockey, but there's not a lot of hockey players. And he kind of instilled in this idea of us of like being a pro and like really like making it part of your identity and like, you know, it's not just about showing up to practice and practicing.

00:41:01:12 - 00:41:20:22
Speaker 1
It's like shooting parks in the driveway, you know, doing sprints on the football field, like, you know, doing everything you can to continue to become better. And we think, like, you know, when I talk about a sales person, I think the highest praise I can give someone is that they're a pro like this. This guy, this girl is a pro.

00:41:21:07 - 00:41:34:12
Speaker 1
What does in this industry and this in this role in sales, software sales, what does being a pro mean to you?

00:41:34:12 - 00:42:02:07
Speaker 2
Definitely transparency's a big one that just popped into my head. They're like, you're not. We real picture what we grew up with, right? That door to door salesman. That's not the case. And in Texas, I was like, there, if there is no sale, there is no sale. Like the transparency and just putting like someone's ability to put like one your own ability to put yourself in their shoes, like am I going to be pissed off?

00:42:02:23 - 00:42:23:03
Speaker 2
And sending a Karen email if I'm them, right. If, if I'm going to sell that, yeah, that person's a great salesperson, but I wouldn't consider them a pro. Right? Right. I think the pros are the ones that are transparent and honest. They're going to be the ones that are most successful. And they're the pros in my eyes.

00:42:24:01 - 00:42:40:14
Speaker 1
I could I couldn't agree more. Like they're just trying to figure out is do you have a problem solve? Is it worth you investing the money to solve it? And can I solve it? If if if that's true, can we solve it? Can we solve it uniquely? Can we solve it better than any any other option you have?

00:42:40:14 - 00:42:44:08
Speaker 1
Right. And the best salespeople operate that way.

00:42:44:11 - 00:43:06:20
Speaker 2
And if we can that I'm going to tell them we can't like. Right. And you know what, though? That person, whether you're at the same company for 20 years or not, like that person will remember at their next company that their next job and maybe your software, whatever you're signing at the time, is a fit. They're going to find you.

00:43:06:20 - 00:43:08:19
Speaker 2
It's just going to happen.

00:43:08:19 - 00:43:09:02
Speaker 1
Yeah.

00:43:10:04 - 00:43:13:21
Speaker 2
Absolutely important to know to someone dirty. They'll come back to buy you.

00:43:14:13 - 00:43:38:07
Speaker 1
Oh, yeah, oh yeah. And people always remember those bad experiences. Jesse I think I'm like, about to cry right now because I have to tell you how proud I am of you. We haven't talked about this, this stuff ever. And I feel like the last, you know, we catch up, we talk. But the last time I talked to you about sales was when you were thinking about getting into it.

00:43:38:07 - 00:44:00:02
Speaker 1
And I'm just so impressed by, you know, the person and the and the professional you've become so I'm first of all, thank you so much for for giving us some of your time. Congratulations on everything you've accomplished since since making the transition. And I'm really, really excited to see they are you.

00:44:00:11 - 00:44:18:18
Speaker 2
I got to thank you too, though, because like you were what I saw in this industry, right? Like just always being yourself. You still got the backwards hat on today. If there are like, what was he doing? Why did he like like what? Why did he go off and travel to and have these this nice house? Like, what is J.R. doing?

00:44:20:04 - 00:44:37:06
Speaker 2
You know, you don't always have that, but, you know, made a scary jump a little bit easier. It's like what it could be and you could still be yourself. Like, we're both very similar people. Like, I was like, okay, I can do that career. I don't have to jeopardize where I am and I can be really good at it.

00:44:38:16 - 00:44:48:01
Speaker 1
You heard it here. You heard it here, folks. You can take the kid out of Marlboro. You can't take Marlboro out of the kid. And he never shared Jesse so much for joining me.

00:44:48:01 - 00:44:56:12
Speaker 2
Talk about a Boston accent for the next 4 hours, thanks to that one.

00:44:56:12 - 00:45:18:18
Speaker 1
This wraps up this episode of Making Some Change. If you enjoyed this episode, the most meaningful way to say thanks is, to submit a review wherever you listen to podcasts. If you're interested in working with us, please come find us at WW Dot Chef Gregorio.