Sales Hustle is now Sales Transformation
Sept. 27, 2021

#159 S2 Episode 28 - From Selling Cutco to Growth AE at with Tom Alaimo

On this episode of the Sales Transformation Podcast with Collin Mitchell he's joined by Tom Alaimo, Growth Account Executive at Gong, and a podcast host on Millennial Sales.

Tom gets into a discussion with Collin regarding how he started his career in sales, how to level up your sales game through podcasts, when should you jump to a bigger role, and so much more! Continue listening to find out.

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01:26 How Tom started his sales journey and being an introvert didn't stop him from learning and getting money to mastering the craft of sales

08:00 Things you should consider before jumping into a new role

12:46 Why podcasting is great for levelling up your sales game

17:12 How Tom started podcasting with a friend to running it solo

19:35 Why Tom is passionate about giving back to the sales community and why

22:05 How to connect with Tom and get in his radar


06:57 "When you here that voice kinda like inside you at like 5 in the morning, it wakes you up and you can't get back to sleep. Or you're hanging by yourself in the morning or in the evening and it just something that gets a little too out there ... that's an indicator like 'somethings gotta change.'"

09:07 "As I started to have tons and tons of conversations, it started to become more and more clear of what I didn't want. And that started to lead me to what I was passionate about and what I really did want. So at the end of the day, what I was really looking for was a place that really believed in what I was selling and was very passionate about it."

16:07 "I think people are just a little bit overwhelmed with how to get started so they just do nothing. And the biggest thing I like to tell people is like, because most people don't get started with anything generally, we're talking about podcasting here, is because they're scared they're gonna suck at it. And I tell people, 'you are gonna suck at it and that's totally ok.'"

16:34 "And if you get over that then you will get better over time, you'll interview more people, you'll find a little bit more of your own voice, you'll find your rhythm, and you'll level up personally and professionally through the activity."

20:03 "The reason for the salespeople part is because one because that's what I know to do and that's the community that I'm in. But I distinctly believe getting into sales can change your life, right? And it did for me and it's one of those careers that, you know, there's not that many of them that the success that you have is equally determining how far that you can go."

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[00:00:00] In the world of sales, you either sink or swim or breakthrough to the next level. My name's Colin Mitchell, and this is sales transformation, a new kind of sales show designed to bring you through the epic life-changing moments of elite sellers. So you can experience your own sales transformation.

[00:00:24] All right, what's happening. Welcome to another episode of sales transformation today. Tom Alaimo on, he's a mid-market AAE over at gong and he's also a fellow podcast host. So I'm very excited to have him on, he got his start in Cutco knives and surprisingly enough not knocking on doors. So we'll get into that and pull many learning lessons out of his own sales transformation.

[00:00:46] Tom, welcome to the show. How you doing Colin? Thanks for having me on. I'm excited to be here and re the chat. I'm doing fantastic. Uh, I, uh, look forward to [00:00:59] having people like you on that, or, you know, in the trenches getting shit done, you know, working their way up in companies. So, um, I'd love to just jump into your story, kind of figure out like, why the heck did you pick sales and you have stuck with it and dig into what happened and see what we can learn in the process.

[00:01:18] Let's do it. So, do you want to hear how I, uh, how I got, uh, got into, uh, into the world you want to hear about the customers? Um, Siri curious, I'm super curious of where you got started. I made the assumption, it was in Cutco based on your bio, but maybe, maybe it was before Cutco. I don't know. So just hit us with it.

[00:01:39] Yeah, I'll put a small asterisk. I wrote a sports newspaper back in the day in like fifth grade and did sell subscriptions, uh, annual subscriptions door to door in the neighborhood and to family members. So I guess that was like the first real kind of sales job. But the first one where I was making actual money [00:01:58] was, was Cutco who was in college.

[00:02:00] Um, I was a college athlete. I played tennis and, uh, always had that competitive spirit, but truthfully, I just saw a flyer that said, make money, work your own hours. And it was like neon colored in a grocery store. Parking lots. I said, that sounds good enough to me. Uh, and so, you know, interview without really knowing what.

[00:02:18] Um, you know, I had family advised against, you know, selling for Cutco because naturally, you know, I'm an introvert. I was always very shy kid and, uh, they didn't think that I would take too well to it. And it just, it turned out to be one of the best decisions I've ever made. And, uh, it was a great summer learned a ton, made some good money.

[00:02:35] And, uh, it really just started me on this path of wanting to master the craft of. Awesome. I love that. What great messaging make money, make your own hours neon sign. I mean, what college kid would not be like? Yeah. That's for me. [00:02:57] Exactly. Exactly. Yeah. I mean, whoever did the copywriting, uh, did a hell of a job on that one.

[00:03:03] Yeah. So something you mentioned is that it was, it was a great experience. And I'm curious why, like, what did you learn there? You know, it sounded like you don't really, you didn't really know, you know, what you were signing up for, but you had a great experience. Explain that to me. Yeah. A lot of people, uh, in college can relate to the experience of not knowing what the hell you want to do when you grow up.

[00:03:27] And I remember that feeling distinctly, I was studying marketing and entrepreneurship and there was no talk of, of a sales profession in school. And there's nothing really that I felt like I was sticking to. And so it was the first time that I. Was really developing a skill that I thought that I could start doing as a career.

[00:03:46] That one that I was actually pretty good at too. I was starting to build confidence about it and, and get more confidence in myself. And three, um, [00:03:56] of like, oh, wow. You know, financially, you know, the more I sell, the more money I make, it's, it's a pretty heavily commissioned, uh, job over at Cutco. And so it really just opened the door for me mentally of like, oh, this is something that I think I can actually do.

[00:04:09] I can enjoy. I can be good at coming out of school. Um, took a lot of pressure off the last year or two of college of not having any idea of what I want to do to starting to come up with like a, a path for what that could look like. Okay. And so, so after school, after Cutco, then what was next? Yeah, so I got, I went to a company called tech target, uh, in the media and 10 data centers.

[00:04:38] Um, and, you know, took an entry level sales job there. Um, and, you know, just started cutting my teeth, you know, cold calling and emailing all day long, uh, trying to book meetings just as, you know, most people do that as they started into tech sales. [00:04:55] And, you know, really, I think the, the Cutco background helped because when I was there, I was making cold calls every single morning.

[00:05:02] You know, I was setting goals. Like I learned all the goal setting I learned. You know, tailor a demo and do discovery and get referrals and all these skills that kind of gave me a headstart. I feel when I got my first, you know, quote unquote real job and, um, you know, took to it quickly, you know, earned a promotion, uh, in about nine months and got moved from Boston to San Francisco.

[00:05:23] Uh, and, and from there, the rest was, you know, kind of history of just continuing to rise through the company and, uh, into mid-market to enterprise sales, to being a sales manager and stayed there, uh, for about five years, right before I quit or left there, uh, right as the pandemic was kicking off last year, which people could question the timing of that, but, um, it was a great fight.

[00:05:47] Yeah. Yeah. And you just felt it was time to move on or wanted to learn some new skills. [00:05:54] Yeah. I felt like, you know, um, I was hitting a plateau a little bit in terms of how my skills were developing and I felt like I had a limit for where I could go in the company. Um, and so after five years, you know, I had that pit in my stomach for a good six months.

[00:06:13] And there was something like, you know, the straw that broke the camel's back. That ultimately made me want to, uh, you know, try a new experience. But I felt like there was so much that I learned and when I feel like the learning is decelerating or stagnant to me that that's what I prioritize over.

[00:06:29] Anything else. Like, that's why I do the podcast. That's why I work super hard. That's why I'm reading books and it's just a passion of mine. And so when I feel like that's not being met, I knew in my gut, I had to try something else and move. Yeah. And, and, and that's a, that's an interesting point, right? Is, is once you sort of feel in your role, you've [00:06:53] hit a ceiling as far as like learning or acquiring new skills or progressing, or moving forward on whatever career path you have set as a goal.

[00:07:02] So, I mean, you have one, um, that's a good indicator that it's time to go try something else. Yeah, I agree. For me, it's always been something that when you hear that voice kind of inside you, uh, at like five in the morning, you know, it wakes you up and you can't get back to sleep or, you know, when you're hanging out by yourself in the morning or the evening, and it's just something that kind of like is whispering in your ear.

[00:07:28] Uh, maybe that's getting a little too, like out there, uh, for, for what you, what you're all about or what this podcast is about. But for me, that's always an indicator, like, all right, something's got to change whether that's in your career or something personally. And for me, I was hearing that voice for a long time and it was just one day I was like, man, I got to make a change.

[00:07:46] And I'm glad that I did. Yeah. Yeah. And, [00:07:52] and so what, w when, and, and I'm curious, because there's probably a lot of people that maybe are in a similar place, right. They, uh, are at a place, you know, with the kind of way the economy is and everything going on. And they're like, eh, I don't know if I want to leave.

[00:08:07] Maybe I'll just kind of wait it out till we are out of this situation or whatever. Um, but you just took the plunge and felt like it was the time it was. Uh, what were some priorities in looking for the next place to go for you and what are some things that people should maybe consider, you know, before jumping into a new role at a new organization?

[00:08:28] Yeah, that's a great question because. In those five years, there was only one time that I've really interviewed somewhere. And so I was a novice at the whole interview process and everything that, that entails I was, I was so green. I had no idea what I was doing. So I, you know, I'm someone that's pretty type a, so I built out like a Google sheet spreadsheet.

[00:08:50] Of all [00:08:51] the categories of things that mattered to me, you know, uh, what did the growth look like? What was the, what were, what were they selling? Um, who are the leaders at the company? Um, what was the cup, uh, you know, where were they located? Would I have to move or be remote? Or what does that look like? And so those were a few of the things that I cared about.

[00:09:09] Uh, you know, I, I had companies that were, I would be the first rep in a five person company. And then I had like, you know, publicly traded thousand plus 5,000 plus organization. So I really had no concept for what I wanted, but I felt like as I started to have conversations and a ton ton, ton of conversations, It started to become more and more clear of what I didn't want.

[00:09:33] And as I kind of filter through that, it started to lead me to what I was passionate about, what I really did want. So at the end of the day, what I was looking for was a place that I really believed in what I was selling and was very passionate about. Which for me happens to be sales tech and happens to [00:09:50] be a gong.

[00:09:50] Um, I, I knew that I could learn a lot from the leadership in terms of growing my sales skills, my leadership skills becoming a better person. Like the company had a huge growth mindset. Um, and I just believed in where everything was going in terms of the company, in terms of the market, there's a big opportunity that I felt like we were taking advantage.

[00:10:11] And so those three things were what I was looking for. Um, but man, it took me months and months to figure that out more than more time than I would have. Uh, I mean, Yeah, it's, it's a big decision. And I think that, uh, it sounds like you took it very seriously and you laid out a process for making sure that it was the right fit, because I can't tell you how often people just, you know, sort of.

[00:10:39] Sometimes, you know, it sounds like in your case, you left for the right reasons, whether people are leaving for the right reason or the wrong reason. And they just jump into the next role without [00:10:49] a process, without a process of eliminating things without prioritizing the things that are important to them.

[00:10:55] And, you know, there's even some very cool resources now that you could use, or even reach out to people that you may be know or somehow connected to. That are working there and get their, you know, feedback on what their experience has been like. Um, is there any resources or things that you followed when you know that helped you make a decision before, you know, choosing a place that you felt was right.

[00:11:17] Yeah. I mean, I think you bring up a super great point. I've heard it said that you should treat the interview process, like you would a sales cycle. Right. And so part of that entails, you know, trying to, you're obviously selling yourself in an interview, but you're also, you know, you want them to sell themselves to you, right?

[00:11:37] Like you're, you're evaluating them just as much as they're evaluating you. And so that means you're not afraid to ask tough questions. Right. And maybe that's why. W some of the things that matter to [00:11:48] you, uh, Personal growth, whether it's what the cop is, whether it's what the leadership looks like or whatever it might be.

[00:11:55] Um, not being afraid to ask questions, uh, to really kind of uncover what's going on at a company. Um, and see if there's any red flags. I think the other part of that is trying to meet people that work there. Um, I think you'd be surprised how, how often, if you can string up a relationship with another AAE, say at a company on LinkedIn and tell them you're evaluating.

[00:12:18] Working over there and just see if they have 15 minutes to chat. And, um, there was actually two people at galling that I knew, like only somewhat, we weren't really close friends, but they were willing to chat with me and chat with me through the process and tell me, Hey, what's really going on. What's the good, what's the.

[00:12:35] What's the middle. Um, and every company has positives and negatives. And so I think you got to know what you're getting yourself into when you go anywhere and, and hearing firsthand from someone that's been there for at least [00:12:47] six months, maybe at least a year, uh, can really kind of give you a good picture of that.

[00:12:52] Yeah. And I love, uh, I love something that you said early on is, you know, how you're just really dedicated to the craft of sales and reading books and doing all these things. But my personal favorite obviously is that you have your own podcast. I mean, I believe everybody in sales should have a podcast and you can look at it a couple of different ways, you know, whether it's.

[00:13:15] Actually collaborating and creating content with the people that you want to work with or partner with. That's a great way of using a podcast platform. Um, but in your case, I think in a lot of cases, it's, it's, uh, you know, giving you education, right? I mean, you can ask anybody on your show, you can ask.

[00:13:34] Any question that you want. And there's something about being a host that actually levels up your sales skills too, because it sort of flexes that curiosity, [00:13:46] muscle it, you know, flexes, you know, your active listening skills, your question, you know, your, your ability to ask good questions. Those are all like essential skills to become.

[00:13:59] Better seller and any role, um, not to mention, you know, you can ask anybody on most, most times, most people are going to say yes, some are going to be harder than others, but, um, you know, and you can ask them any question that you want that you're curious about, which is fantastic. So I'm curious to know, uh, just a little bit about, you know, why you started the podcast, what's your experience been and what your thoughts are and, you know, people in sales having a podcast.

[00:14:24] Yeah. I mean, You know, this is good. As, as anyone you mentioned earlier, you've interviewed what 300 plus people, uh, I'm at about two 50 as of this recording, it's the ultimate network hat, right? There's people that, and I won't speak for you, um, because maybe you have a better network and more experience.

[00:14:43] And, but I know for [00:14:45] me, You know of those 250, at least half of them would not have even considered talking to me. You know, when I started this podcast four years ago, right. I was eat cold email and CEOs all the time or VPs of sales, Hey, you want to grab some coffee and I could pick your brain. And I was a 23 year old sales rep with virtually no experience.

[00:15:05] And the answer was either no or, or no response. And so the podcast kind of puts you on a different level, right? Where it's not about. Um, it's not about, you know, what, I'm going to pick your brain about. It's, it's actually flipping it. Right. And it's, it's adding value to whoever that person is because they get to talk about themselves.

[00:15:24] They can talk about their company or the book they wrote or whatever it is that they're trying to, um, to grow. And you've all of a sudden kind of like changed your, uh, your authority level or your position with them. And it gives you so many opportunities. So the best thing, you know, there's the learning piece.

[00:15:41] You can ask any question, like you mentioned, you have access [00:15:44] to people that you wouldn't have access to before, and then if you treat those relationships well, you know, there's people I've met that, you know, become mentors and good friends of mine. That, you know, have had phenomenal sales and leadership success over decades that, um, you know, I, I use the podcast as a way to kind of weasel my way in there to, to meet them in the first place.

[00:16:04] And then, you know, try to help them out in whatever way I can. So, um, I've never thought about every sales person element of podcast. Uh, maybe that would water it down a little bit, but, um, I couldn't agree more that it it's the ultimate network and learning hack that I'm surprised more people don't know.

[00:16:23] Yeah. I mean, I think people are just a little bit overwhelmed with how to get started, so they just do nothing. And the biggest thing that I like to tell people is like, cause most people don't get started with anything generally, but we're talking about podcasting here is cause they're scared. They're going to suck at it.

[00:16:41] And I tell [00:16:43] people you are going to suck at it and that's totally okay. Like you are absolutely 1000% going to suck as a podcast host when you get started. And if you can get over that, then you will get better over time. You'll interview more people you'll find a little bit more of your own voice.

[00:16:57] You'll find your rhythm and, you know, you'll level up personally and professionally through the activity. Um, I mean, most people that I know they get started with it absolutely fall in love with it. I mean, you clearly seem to enjoy it cause you've been doing it for quite some time now. Um, And if you could just kind of get over yourself and realize, yeah, I'm going to suck at it, but it's something that I want to get better at.

[00:17:19] Um, then it's a little bit easier to get started. Totally. I mean, you're building the muscle of doing something hard or scary or challenging. I remember I started a podcast actually with one of my good friends. Uh, I run it solo now, but we, we recorded our first interview is with my boss at the time, you know, uh, and we just went to his apartment and talk shop for an hour and we [00:17:42] held that for about two months before we hit the publish button and every.

[00:17:45] We were roommates. We get home from work and be like, should we do it? Should we do it? No. Or we're scared of what people are gonna say. They're gonna say we suck. They're gonna, uh, you know, make fun of us at the office. No, one's gonna listen. What, you know, whatever. And honestly, call it. All of those things happened.

[00:17:59] People made fun of us. We didn't get a lot of listeners. Uh, people were making jokes. People said we weren't good because we. And then just over time, like, you know, episode seven was better than one and like episode 32 was better than that. And then like, as you get better and more experienced, you know, that your skills grow just like anything else.

[00:18:19] If you're in sales or you're working out or whatever, it might be, whatever skill you're building, you just got to stack up those small wins over time. Yeah. Yeah. Wow. How long did you say, how long did, how long did you say you held on to that before you published it? It was about two full. Oh, that's not bad.

[00:18:40] Um, [00:18:41] I mean, this is what we manage. We, we, that's not bad at all. Um, I talked to people about starting a podcast every day and, uh, the average, well, the average is people typically. Uh, think about it for at least two years before they actually take the plunge of doing it. That is the average answer that I hear.

[00:19:02] Um, so-so, that's better than most in, and I love that you just leaned into it, knowing that like, Hey, all of these things might happen if I do it and they did. And that's okay. Um, and, and I love that about it because. You know, there's a lot of podcasts that don't stick with it either. And it's typically because they don't have, they don't get into it for the right reasons or they don't have sort of a passion that drives it or they don't have like a strategy.

[00:19:27] Um, and that's why there's so many podcasts. And what I like to call the podcast, graveyard, the ones that never make it to eight or 10 episodes, there's a ton of them. Um, But, you know, if you stick with it, [00:19:40] it's a lot of fun and there's, there's many benefits. Um, so tell me a little bit, you know, about you, you kind of mentioned that, you know, you have it, you're pretty passionate about, you know, trying to give back to the sales community.

[00:19:53] Tell me a little bit more about that. What are you doing and why? Yeah, I mean the, the purpose of the podcasts that I have, um, the blog. You know what I'm doing on LinkedIn. Uh, and now with, with working at gong and selling to salespeople and sales teams, everything that I'm doing is all universally focused on helping salespeople succeed.

[00:20:17] And, uh, you know, the reason for the salespeople part is one, because that's what I know to do. And that's the community that I'm in. But I do distinctly believe that getting into sales can change your. Right. Uh, and it did for me. And it's one of those careers that, you know, that there's not that many of them, that what you.[00:20:39] 

[00:20:39] The success that you have is equally determining like how far that you can go. Right? There's a lot of jobs that whether you're the best at it or the worst at it, you all get paid the same. And you're just kind of on this, this eternal, uh, conveyor belt. Right. But if you're in sales or if you're an entrepreneur, or if you're, you know, maybe a, an athlete or a musician or something like that, you know, the, the amount that you get paid, the success that you can have, the opportunities that you have is directly related to how good you are at that point.

[00:21:06] And I think there's so many people, there's millions people that get into sales every year. Uh, oftentimes coming out of college sometimes as a second or third career choice after something else. And that first year is so make or break that, you know, my, my goal is to try to help influence people in that first year so that they can get through all of the obstacles, the adversity.

[00:21:29] The self doubt, all of those different things, uh, succeed through that and then build a great career of we know whatever they want to do with their lives. But, [00:21:38] um, for me, that's incredibly rewarding and fulfilling. And you know, again, I don't know about you, but the podcast, I have a sponsor, uh it's it's not paying my San Francisco rent, uh, or it's not paying for like my wedding next year.

[00:21:51] Right. Uh it's you know, financially not particularly significant. So the reason that I'm doing. One, it helps me out, but two, I get DMS, uh, pretty frequently of, Hey, I listened to this, I tried it. It was super helpful, you know, keep doing what you're doing. And like that's the fuel that keeps me going, you know, every single week for four years.

[00:22:12] Yeah. Yeah, that's awesome. Uh, all right, Tom. Thanks so much for coming on, man. Really appreciate it. Uh, looking forward to going on your show as well, tell people where you know, how they can get into your world and find out more about the podcast and anything else. Yeah. Thanks Scott. Appreciate you having me.

[00:22:30] Um, and shout out to you for continuing to elevate the sales profession as well. Uh, but yeah, folks want to connect, like I [00:22:37] mentioned, the, the best place you can go is wherever you're listening to this podcast, you can check out millennial sales does the name of my show, and it's all focused towards a young salespeople trying to elevate their careers.

[00:22:49] Uh, we've got one or two episodes coming out every single week, uh, from top sales leaders. So make sure to check that out. Um, but otherwise, um, you know, really appreciate you having me on called. Awesome. We will drop the link there so you can check out Tom's podcast. Um, and if you enjoy today's episode, please write us a review, share the show with your friends.

[00:23:09] It really does help us out. And as always, we're listening for your feedback. Hey, you stuck around that tells me you're serious about your own sales transformation. If you're tired of doing things the old way and want to get started in your journey with other people on the same page. Head over to sales, and crush your numbers on your leaderboard.

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