Kevin Micalizzi: Welcome to the Quotable Podcast. This is Kevin Micalizzi. Today we’re going to be talking with Tom Alaimo from TechTarget. Tom is an AEE and one of the hosts of the TR Talk Podcast. They’re focused on finding ways for millennials to be better at selling. So let’s see what Tom has learned and how he’s applying it to his own career. Tom, thank you so much for joining us.
Tom Alaimo: Yeah, thanks for having me on.
Micalizzi: We’ve got Justin [Royal] joining us, co-hosting today. Justin is on the Sales Cloud product marketing team here at Salesforce. Welcome.
Justin Royal: Yeah. Hey, Tom. Nice to meet you.
Alaimo: Hey, nice to meet both of you guys. Excited to be here.
Micalizzi: Tom, I’ve been dying to get you in the studio. We talked first a couple months ago. I think you and Ryan are in a unique position because you guys are not only out there selling, but you’re also running your own podcast, you’re working really hard to uncover the best ways to approach a lot of these things. I think you’re bringing a very unique perspective. Where I’d love to start is just give us a quick overview of what you do and a little bit more about your podcast as well.
Alaimo: Yeah. Yeah, my full-time job is an account executive. I work over at TechTarget, also in San Francisco, and I’m an outside AE there. I’ve been there for about three years now, first starting in our office in Boston and then moved out to San Francisco about two years ago.
As you mentioned, I also co-host a podcast called TR Talk with Ryan Warner. We started that about six months ago in the middle of 2017. Our whole philosophy is that we want to interview leaders, people that we think are doing inspiring things on how millennials can follow suit and fast track their personal development. We’ve been doing that. It’s been a blast and we’ve learned so much in six months. It’s kind of turned into a big passion project for us.
Micalizzi: I’m most interested in what you’ve learned from it and how you’re applying it.
Alaimo: Yeah. I think it’s interesting. When you think about podcasting and when you do it, it’s actually almost a direct correlation to how a sales cycle works. Right? You’re prospecting. You’re trying to figure out who your next guest should be. Cold emails, cold calls, Instagram direct messages, whatever it takes.
Then you’re doing a bunch of research for that call, for that meeting. And then when you’re in the meeting, you want to ask really specific questions, try to drive as much value. And then afterwards, the goal is to build the relationship with that person and build a network with them.
So it really relates to sales a lot. Where I think if I had to choose one thing that it’s really helped me in my sales career is about really being present and asking specific questions and really working on my language. We, Ryan and I, did a number of podcasts before we put any of them out. We were stuttering everywhere. We’re asking terrible questions. It sounded terrible.
I think over time, little by little we’ve started to take out some of our crutch words and we’ve been able to ask better questions. That relates directly to sales and being able to ask specific questions and have better conversations with your customers.
Micalizzi: Right. [There’s a] certain amount of practice and almost desensitizing yourself to it. Yeah, you put a microphone in front of your face and you get a little nervous, just like folks do when getting on the phone, especially with a prospect.
Alaimo: Yeah, and I think there’s always that shellshock at the beginning when you first hear your own voice. Actually about a month before we did the podcast, our boss had us do an exercise where everyone had to listen to one of their own calls and critique it and then share what they learned with a partner and then with the whole team. I’ll tell you, that was probably the most painful 30 minutes, that and first listening to our podcast, was just atrocious, cringeworthy. But little by little I think it really helps you to become a better [conversationalist] and be able to have conversations in a more clear manner with your customers or your prospects.
Royal: Tom, I have a question for you. Was there any particular inspiration for you actually wanting to start your own podcast? Were there any particular podcasts that inspired you? What motivated you to take that additional step beyond your day job?
Alaimo: Yeah, that’s a great question. There’s a few reasons for it. First and foremost, Ryan and I are really hungry as reps, but just as people. We’re always striving to learn more and dip our toes into new water. We’ve been listening to podcasts for a long time, whether it’s Tim Ferriss or Joe Rogan or the Quotable Podcast. There’s probably a dozen that I listen to pretty consistently. And then the second piece is that I saw a lot of people my age or older that I considered to have really good networks.
I didn’t think six months ago that I had a very strong network. There were some people that I knew. But I just knew there were so many successful, talented people that were probably willing to share their knowledge with someone young like myself, but I just didn’t have a great excuse for it. People are a lot more likely to have a conversation with you if you say, “Hey, this is for my upcoming podcast” versus “Hey, can we just grab coffee for 15 minutes?”
It started out as kind of an experiment where we each had our bosses on to start off, and then we started reaching out to people who we saw as sales leaders in the space — thought leaders like someone like a Gabe Larsen or an Anthony Iannarino.
Then we were like, “Hey, we’re interested in some other things, too. We’re interested in sports and we’re interested in health and fitness and other types of entrepreneurship.” So we’ve been able to have CEOs on and U.S. Olympic gold medalists on, and just really disperse the types of people we’ve been able to have conversations with.
Micalizzi: Yeah, and not only have you had a diverse collection of folks, but your topic areas have been pretty diverse. You’re not just focused on sales skills, which I love. What’s your favorite non-selling skill conversation that you’ve had so far?
Alaimo: That’s a great question. One of the best conversations that I think we had personally was with Michael Gervais. He is a high performance sports psychologist. He works with the Seattle Seahawks. He works with the U.S. Olympic teams. He’s worked with other entrepreneurs and musicians and just high-caliber types of professionals. He talked to us a lot about mindset and how that controls your actions.
And so trying to put yourself in a place where you have a confident mindset where you’re staying present in the moment, that you’re focusing in the here and the now. And giving small mental tips for — these people are doing it in really extreme circumstances — the Super Bowl at the fourth quarter or the gold medal is on the line — that you can easily put into a sales call or you can easily put into your relationship with your family or your friends, and just trying to use those little tips that I think can really help in everyday life.
Micalizzi: That’s excellent.
Royal: Yeah, so I guess based off of the different sales related podcasts that you’ve had, are there any specific lessons or tips that you purposely remind yourself of every day just to help you sell better at work?
Alaimo: A podcast that I listen to, or just like tips and reminders that I should focus on?
Royal: Sure. Either a podcast that you’ve listened to or guest that you’ve had that have really transformed the way that you do your daily routine at work.
Alaimo: Yeah, a lot of what we’ve talked about, sticking on the thought of mindset, too, is the way that people have overcome hardships whether it was a tough upbringing in their life or their business crashed and they had to rebound. Anyone that’s been in sales for any amount of time knows that it’s an up-and-down game. There’s days where you close the million-dollar deal, and there’s days where you get hung up on a hundred times in a row and it seems like you’re the worst salesperson in the world.
I think really trying to keep that mindset the right way and focus on the bigger picture, which it seems like all of these successful people that we’ve been able to talk to, they always have their eye on the bigger picture and are able to not get too high when they have a great day, not to get too low when they have a bad day. So I think that’s one thing that I’ve tried to take into my sales tactics.
Micalizzi: And kind of bring that resilience, you know? It can be incredibly rewarding, but at the same time it’s not a very forgiving career at certain times.
Alaimo: Yeah, it’s funny — I was talking to someone that I knew from where I grew up earlier today. He’s in college and he saw I was in sales and was just asking me about it as a career. I told him that I love it, there’s no other job that I would want to have, hands down, but it’s certainly not for everyone. If you can’t handle the ups and the downs, if you can’t handle getting told “no” a hundred times and maybe not hitting your quota and having a lot of pressure, then it’s something that you either need to mentally work on to get there or maybe go down a different path.
Micalizzi: Any advice you’ve received on the podcast that you haven’t used? No need to mention names or anything. I was just curious. Everyone’s perspective on selling is different. Some advice that I hear I don’t necessarily hang onto and keep and apply.
Micalizzi: So I was just curious if there were any topic areas where you’ve —
Alaimo: Yeah, I’m trying to think because that’s actually a really good question.
Royal: I guess in addition to that question, have there been any examples of getting conflicting advice from different people that you’ve interviewed and you’ve had to figure out which route you wanted to take?
Alaimo: Yeah, that’s definitely true. If you have three sales experts on a podcast and you ask them all the same question, you’re likely to all get different answers. Should you do social selling? Should you only cold call? Is cold calling dead? It’s hard to tell. A lot of the focus of where the sales conversations are are the vehicle in which you’re prospecting — like I was mentioning, if it’s through social media, if it’s through cold calling, if it’s only sticking behind email.
And so we’ve had people on that have really expressed one way or the other that they’re all gung-ho on, “Hey, you need to be on the phone all day long,” or all gung-ho on, “Hey, no one answers calls. Stick to email.” And so one thing that I kind of disagree with is either approach, and just really use them as just an incremental way to try to start a conversation. So try to use them all at various points and test and see which one works best in a given scenario.
Micalizzi: How would you say your approach to selling has changed since you started this journey?
Alaimo: I think one thing is the time management process and being able to really stick to deadlines. Just as a side tangent, we’ve been doing this obviously as a side hustle. We have interviews at 5:00 or 6:00 a.m. if it’s there on the East Coast, or late at night if we’re on the West Coast or Saturday mornings. We’re doing a lot of that stuff. So when it’s selling time, it’s selling time. There’s no time to be on Facebook. There’s no time to be checking out ESPN.com.
I’ve really started to more structure my day into 30-minute increments or 15 or an hour depending on the task and help prioritize. If there’s a customer that needs something, if there’s a follow-up due, if there’s a proposal due, let’s get that done, let’s get that out the door immediately, and then backtrack into things that are less urgent like going about the prospecting or doing mundane administrative tasks and maybe save that for the end.
It’s more of a philosophy that I’ve started to gather more is that you got to take the big rocks out first and try to really have that focus when you start off the day.
Micalizzi: I like that, because it’s almost like the podcast became a forcing function for you.
Micalizzi: So with that added pressure, you’re like, “I really got to get this organized and hit the right things.”
Alaimo: Yeah, it’s funny. I know there’s a sales expert, Grant Cardone. I know that he says whenever his team feels overwhelmed, he adds on one more task and just tries to get them a little bit busier, and then somehow they’re able to function. Just being able to maybe add a few more tasks and not go from zero to a hundred, but like every week just a little bit more and you can be surprised with how much you can get done.
Micalizzi: Are you an end-of-the-day plan your next-day kind of guy?
Alaimo: I have to.
Micalizzi: Have to, okay.
Alaimo: I have to. Yeah, I never can leave the office until I have everything sorted out for the next day. That’s knowing when am I going to be setting up my prospecting or my meetings, prep for the next day. When am I going to — ? If I’m going to work out that day, is it going to be in the morning, is it going to be at night, any other outstanding things that need to be done, and is that on the calendar¿
Because for me if I start the day and I get into the office in the morning and it’s like, “I have all these emails. I’m not sure exactly what I’m supposed to be doing,” all of a sudden two hours pass by and I’ve done one thing, I haven’t done anything. So for me, I have to get it all set in stone. Then as things change throughout the day, as they always do, you can adapt. But at least to have that baseline is really important, at least for me.
Micalizzi: You start with that framework.
Alaimo: I need to, yeah.
Micalizzi: You can move as you go. I like that. Yeah. No, that makes sense.
Royal: Tom, for other millennials or for other young people that are early on in their career, what advice would you give for starting not necessarily your own podcast, but your own side project that really compliments your career, or maybe it doesn’t compliment your career but just having a side project? I feel like that’s really awesome work that you’re doing in terms of dedicating a lot of time outside of your normal job. How did you make that a part of your already business schedule and what advice would you give to people that want to do it but aren’t sure how to take the first step?
Alaimo: Yeah. I mentioned that Ryan and I did several episodes of the podcast before we put one out. We’ve started to write, too. I’ve probably wrote 20 blog posts before I ever put one out. Because there’s that fear of letting the public world know what you’re thinking and what you’re passionate about. I don’t know why we’re naturally afraid of that, but it’s true.
People come up to me all the time and say, “Hey, I’ve been thinking about starting this blog about the recipes that I cook or about something around sales or marketing or my weight loss journey,” or whatever it is. I think just taking action and being able to put yourself out there is huge.
Once you take the first step, like once we put the first episode out, we’re like, “I guess we’re doing this,” then you just go forward from there. People are a lot more likely to be receptive of what you have to say and just getting over that fear of putting yourself out there, I think has done a lot of favors for both Ryan and I, but it’s really hard.
Micalizzi: Yeah, and I would say that same fear is the one that holds people back from picking up the phone and making that call or trying to book that meeting.
Alaimo: Right, and it’s the same fear that if you know there’s a customer that they’re having a bad day or there needs to be a difficult conversation for whatever reason. If you used to having the difficult conversation, doing the difficult task, I just think you’re more comfortable in those situations, too. When it’s a tough situation, you have a clear head; you can stay calm. I think that’s, again — a big piece of sales, too, is being able to defuse those tough situations.
Micalizzi: Yeah, part of it I would say is it’s desensitizing yourself to it, similar to what you were saying about the podcast itself. It’s forcing you to ask better questions and be more present in it.
I think there’s also the aspect of it where you have to practice just like you would with any sport. You have the concept of having the right mental attitude for, let’s say, playing a particular sport. That’s not going to buy you anything if you haven’t practiced the skills to play that sport. I think the same thing applies to selling and pretty much anything professionally.
Alaimo: Yeah. Yeah. There was one episode that we had early on with one of the VPs that’s at TechTarget, Annie Matthews, who talked about her first six months, I think it was, at TechTarget coming from college, where every single day she would leave a voicemail to the CEO of our company with her elevator pitch every day on her drive to work. It’s just that type of repetition.
Doing it to the CEO obviously takes some guts and that’s awesome. But just practicing your pitch or being able to practice having conversations like this, whether it’s through a podcast or whether it’s through some other form of activity outside of your regular job that can directly apply, I just think that’s so important. It’s only got set you up for more success for whatever you’re interested in.
Royal: Tom, sales isn’t necessarily something that you get a degree in or that you learn in school. You always hear about salespeople talking about the value of mentorship in their careers. Can you speak on that?
Alaimo: Almost all the guests that we’ve talked to have talked about mentorship at some point. I think through sale — probably through anywhere — but millennials, I think, really crave mentorships and it’s something that’s really a hot topic. I’ve seen it break down into a few different levels. James Alticher broke it down in a way that he calls it a “plus, minus, equal.”
You find pluses who are people that you deem are more successful than you, that are higher up, that you can either learn from virtually. Like I haven’t been able to meet Grant Cardone or Warren Buffett or whomever else, but there’s a lot that they’re writing. There’s a lot of speaking engagements that they have. I’m trying to learn from them virtually.
On the other side, it’s finding people that, again, you deem are more successful but being able to have a conversation, whether that’s your boss’s boss or someone at a different company that you admire or that inspires you in some way and being able to learn from them.
The equal being collaborating with your colleagues and sharing ideas and saying, “Hey, this email template that I’ve been using has really been working. What’s been working for you?” or, “Hey, I had this call and I tried doing XYZ, and the customer, it didn’t go over very well. They didn’t buy” or, “This cold-call technique, they’ve been hanging up on me all day long. Can you give me some help?” Being likely to share ideas with your colleagues.
And then the minus being paying it forward to others that may be below you in age or in experience. If there’s the intern at the company or if there’s someone in college, or anyone that reaches out to you, being able to say, “Hey, I’m no expert by no means.” And I’m definitely no expert, but being able to say, “Hey, here’s one or two things that I’ve picked up from someone else and maybe this will be helpful for you.”
And so I think, no matter where you look, and especially in a sport like sales, it’s really important to be able to have it as a team game and be able to learn from others and help others and really push forward all together, even if it is a competitive environment.
Micalizzi: How has the blog and even the writing you’ve been doing, how has that shifted your thinking in terms of the concept of adding value?
Alaimo: It’s interesting because that’s really what I think is the most important thing in sales or really in any form of relationship that you have. We’re at a point where a customer, not only do they not want an email that says, “Hey, just checking in” or, “Hey, bubbling this up.” That’s an instant delete. If anything, that’ll probably just lower their perception of what you are as a sales rep. So it’s being able to find some reason to engage.
People always ask how do you add value or how do you find a reason to engage. It’s almost impossible not to with LinkedIn or with Twitter or a press release or anything. People are so open about what their interests are either professionally or personally.
Being able to just tie something really small and say, “Hey, Mrs. Customer, I saw that you guys had a press release about your earnings report in Q3. That was great. Love to see the growth.” And then oftentimes you don’t even ask for anything. You don’t ask for a call. You don’t ask for a contract. You just say, “Hey, I took the time. I took the 15 minutes to read that report today. I sent you an email. That’s all.”
And just being able to do that on a consistent basis so that you’re making a deposit, and you make another deposit, and then you make another deposit. So when you do ask for something, when you ask for a call, or you ask for the deal, or whatever you’re asking for, you’ve already added so much value that it’s an easy conversation and they’re more than willing to help you out with that and to go that next step.
Micalizzi: Right, but now when you’re approaching sharing it and trying to add value, let’s say, on your social network, you can curate content or you can create content. Curating meaning you’re just finding good resources and sharing those out. Creating meaning you are taking the advice you got from Mark Cuban and writing a great article for Quotable.
Alaimo: Yeah. Thank [you].
Micalizzi: Yeah, no problem. I’ll put the link to it in the show notes. When you’re looking at it, I think it’s obviously much easier to curate content. Now that you’ve been creating content for a while, how has that changed not only your selling game but also the professional image that you’re putting out there?
Alaimo: Yeah, that’s a great question, too. You guys can see in the room, and maybe there’s a picture aligned on the podcast, but I’m 24 years old and I probably look like I’m 17. I often get mistaken for someone that may be in high school.
Stepping into a meeting with someone new that’s been in the industry maybe for 20 or 30 years that is a prospect of yours, that can be a frightening task. They often don’t necessarily trust someone that’s this young that can add value to them and that can help them with the actual problems that they’re having. “What can this person add that’s going to possibly be valuable to me?”
I think there’s an aspect of being able to tell that someone actually cares about the work that they’re doing, they care about your business and your problems, and the fact that they’re putting time and effort into both of them, that I think if you’re actually creating content and putting in the work that that helps with.
I have conversations with customers all the time, because I’m pretty active on LinkedIn and on Twitter promoting some of this. They’ll see it, they’ll like it, and they’ll comment. They’ll say, “Hey, I listened to the episode with whomever and thought it was great,” or, “I saw that you mentioned the Mark Cuban article.”
That’s been one that a lot of people have mentioned seeing on the Quotable blog and saying, “Wow, that’s so crazy. You emailed Mark Cuban and you got a response.” It’s obviously a great way to have a conversation. But I think it’s just another way to help differentiate yourself from the thousands of people that end up in their inbox that want to sell them something. You’re someone that actually is providing value to the marketplace.
Micalizzi: Right. So you’re upping your game here.
Alaimo: Trying to, little by little.
Micalizzi: Give yourself some credit. Come on, Tom.
Royal: Tom, you’ve touched on interacting with different generations of prospects and with different generations of co-workers. We have several generations of sellers in the workplace right now. Do you find that you’re learning from other generations or maybe teaching other generations concepts that are unique to your generation? How does that generational difference actually play out in your role?
Alaimo: Yeah. It’s a good point because I think millennials that are in sales treat the craft much differently than folks that may have been doing it for 10, 20, 30 years just in the sense that everything is different now. It’s easier to get information. Social selling is a huge piece of everything. Email has become probably a lot more relevant than phone calls for a lot of industries.
And so I think the millennials have a tendency to hide behind their device, whether that’s their email or whether it’s through social. They’re not as apt to just pick up the phone and call someone. Whereas when you talk to someone that’s been doing it for 10, 20, 30 years, when they were first starting they had to go door-to-door and they had to be a lot more resourceful and be a lot bolder, I think, to get that first meeting.
I’ve learned a lot from any time that we have an executive at TechTarget that comes out and we go on the road and maybe we talk about their old selling days at EMC or wherever it was back in the ’90s. They say that they had to make however many cold calls or they had to go door-to-door. I think that can kind of inspire you to say, “Hey, I can pick up the phone and make a cold call if these guys did 50 door-to-door sales in a day.”
On the flipside, I think that folks that have more experience and are not as in tune with some of the digital side of sales as someone like myself or another millennial, I think they’re becoming more and more apt to use it as well to help shape their brand. Someone that may not have had a Twitter a year ago or three years ago, I think that millennial salespeople have helped them to say, hey, it’s not just for show. It’s not just because you have an ego. There’s actually an ROI benefit to it.
That you’re building your brand so that when people go to check you out, you’re not just the person with the gray face that doesn’t have any real face to it. Like you have your picture. You have some descriptions about you. You have a person, because people want to be able to connect with you. So I think that’s important and both sides being able to learn from each other.
Micalizzi: You often hear that whole ride along mentality somebody is talking about back in their day when they were doing it. It comes across like, “Back in my day, we walked eight miles to school uphill both ways,” that kind of thing.
I really like your approach and your attitude towards it because I think you’re absolutely right, there is something you can take away from it, even if the tools have changed and the landscape has changed. A lot of the grit, the determination, the work that goes into it and even the relationship building side of it, those really haven’t changed. There’s still somebody on the other end of the other device.
Alaimo: Yeah, it’s so simple. The recipe has not changed. The vehicles to find that success have changed. There’s more ways that you can go about it and get your research. But the fact of the matter, it’s still the same sale. You need to prospect, you need to add value, you need to build relationships, you need to believe in what you’re selling, and you need to always think about what the customer needs and how you can help to transform their business and earn the right to do that.
And so whether that’s through texting them or through calling them, or going door-to-door, that part shouldn’t even matter because it’s all doing the basics and having those mental skills that you talked about — the grit, the resiliency, the perseverance — to get the job done. That’ll last the test of time. You always need to have those types of skills.
Micalizzi: Right. We’re not at the point where machines are selling to machines. Not yet.
Micalizzi: Not yet.
Alaimo: I don’t know if that — I hope that doesn’t happen, but I don’t think it will.
Micalizzi: I am totally joking on that one, totally joking.
Alaimo: My job security is on the line.
Micalizzi: Yeah. I am completely joking on that one because I do believe that the more transactional selling — and I think a lot of folks are saying this — the more transactional sales where you as a sales rep really aren’t adding value. You’re just pushing an order form. Those obviously can be automated.
Micalizzi: I think the technology frees you up as a sales rep to add more value and really focus on what the customer needs as opposed to just, “Okay, let me check off. You need quantity of three and you need this item and here’s your total.” if it’s that kind of approach, then yeah, obviously. I’m totally with you, Tom.
So Tom, let me ask you our lightning-round question. If you could take all the knowledge and experience you have know and go back to the beginning of your career and give yourself one piece of advice, what would you tell yourself?
Alaimo: I would say the one piece of advice that I would give myself for the early on in my career would be to just go for it. Everything as I look back that has shaped me positively in both sales and in the podcast, and just professionally as a whole, has always been made from a bold decision.
And so if I can elaborate on that a bit, my sales career actually started when I was in college. I started selling Cutco knives, and that was made on a whim. My mom was like, “No, don’t be one of those Cutco sales reps.” I had a shoulder surgery. So I was an 18-year-old that looked like he was 14 wearing a suit in a sling with a bag of knives going door-to-door for the whole summer and ended up doing really well there. That’s what brought me on the sales path.
And then when I was a few months into my sales career in Boston, I always wanted to move out to San Francisco and I heard that there was an opening one day. That night I called the VP of sales that was sitting in San Francisco, and it was probably 9:00 p.m. out in Boston. I called him. I said, “Hey Bill, I heard there’s an opening. I want the job. I’ll move out for you right now.”
Same with the podcast, going out there and finally getting over that fear and putting it out, and it’s been one of the best things I’ve ever done. I think the same goes for just having the courage to walk to someone at a tradeshow floor, or make the cold call, or send the email, or have the important conversation with your boss. I think it’s all based on just being bold and go with your gut and just go for it.
Micalizzi: I love it. We’ll share a link in the show notes to the TR Talk Podcast.
Alaimo: Thank you. I appreciate that.
Micalizzi: That way people can definitely check it out.
Alaimo: Awesome. Thanks so much for having me on.
Micalizzi: I was going to say, thank you for joining us.
Royal: Yeah, thanks Tom. Great to meet with you today.
Alaimo: Yeah, thanks guys. I had a blast.
Micalizzi: Yeah, and Justin, thank you for jumping in again.
Royal: Yeah, thanks Kevin.