Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on July 6th, 2021

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Book Your Meetings While Being A Force For Good with Scott Milener


welcome to another episode of the peak performance selling podcast, where we interview top sellers and sales leaders to learn the different tips, tricks, and mental strategies that they use to create sustainable peak performance. Let's get rolling.

[00:00:30] welcome to today's episode of the peak performance selling podcast. Today, we get to welcome on Scott Milener, who is the CEO and co-founder of Intro Snap, which is a really cool tool that he'll tell us a little bit more about to help. Organizations give back to get better meetings booked to drive more success as a whole with their investments in driving more sales engagement, and prospect meetings.

[00:00:57] Beyond that, Scott has an incredible background. Leading sales organizations, is that an individual contributor as a VP of sales multiple times, and has really worked across the spectrum of. Small-scale startups early stage taking on different funding from companies like SoftBank and other organizations to working at places like Oracle, being one of the top sellers, there actually number one for the Oracle marketing cloud out of about 350 different reps.

[00:01:29] And then running enterprise sales, across many different organizations, helping triple revenue. All sorts of different things that he has done as a seller, as a sales leader. And Scott brings a wealth of knowledge to the table for us, that I'm super excited for. As we get to start to learn more about how you can move into sales leadership, and even all the way to co-founding it and starting and running your own business.

[00:01:53] So Scott, welcome to the show. 

Great. Thanks Jordan. I am really excited to learn from you as. Not only is the new project that you're working on really, really interesting with intro snap and what we'll learn more about that as we get into it. But seeing the experience you have as a seller, as a sales leader, I'm really excited to learn more about that journey and how you think about the mental game and ultimately sustaining performance through your career.

[00:02:23] The first place we always have to start though is understanding. How'd you end up in sales. What got you here in the first place and talk to us a little bit about your, your career journey to where you are. Yeah, sure. You know, I, um, I joined a startup, uh, right out of college, um, with school in New York, a friend of mine had already just gotten this company started off and, um, uh, I came out to Cupertino.

[00:02:53] Uh, California, uh, had always wanted to come to the Silicon valley. And, uh, we were selling a product that was a combination of a Mac and a PC and a single box. He had invented this thing where you could basically toggle between either OSTP and run any app you want to do. It's amazing actually. Um, and so right off the bat, I had to sell it.

[00:03:16] So he had built it. It, the job one was let's go, let's go sell it. So, uh, it started right off there. And then I went on to run BDS for two other firms, uh, including a social media marketing firm and where I learned a lot about social and modern digital, uh, and then, uh, onto Oracle marketing cloud, as you mentioned for a few years, and then, uh, uh, and then, you know, a couple more companies and here I am.

[00:03:42] So it's been a natural trajectory for me. I think. Um, you know, I asked myself what it is about that. I think I just, I just love people, love working with people. Um, and, uh, it's fun to talk about a cool new product and how it can change their lives and men when they engage and they realize, okay, they also agree that it's going to change their lives and improve their business.

[00:04:06] And, uh, it's just very satisfying. Um, and, uh, I like storytelling, which is an important part of sales. Good sales. Um, so just sort of a natural fit for me. That's really great. It's a really hard thing for folks as they go through the traditional college path to see themselves in sales. I've talked to a lot of folks within academia now that are actually bringing sales into the college curriculum, which is really exciting, but it wasn't there for me.

[00:04:42] I'm guessing wasn't there for you. And so did you know you wanted to be in sales initially or was that. Just how the opportunity presented itself. I'm not really in college, at least. Yeah. When I went to college, they didn't have sales courses or it is funny because they don't teach you how to present an idea, how to run a sales cycle, how to talk to customers, how to price out of negotiate.

[00:05:06] It's all like economic theory and, you know, art history, which that's nice. But, uh, yeah, so I, I didn't really understand. Uh, enterprise selling or any of that, I just had to dive in and, uh, just learn by doing, yeah. It's a really interesting space, especially as you've grown in your career now to leading. I think one of the things that intrigued me about sales early on was, well, any business has to.

[00:05:36] Drive revenue in order to be successful. And so it seemed like a really good path to understanding, you know, how do you communicate value to others? How do you connect with people? How do you provide feedback to your product or to your account management team about how can the organization run and grow more effectively?

[00:05:55] And as you've transitioned into VP of sales roles, and now actually sitting in the CEO seat at intro snap, talk to me a little bit about some of the skills or. Mental models. You've had to update with yourself, moving from that individual contributor role to leadership and then ultimately to the CEO seat.

[00:06:16] Yeah. You know, the, um, I think for me, I think about some. Uh, traits or core, uh, day-to-day kind of actions and how you see yourself. Um, I think the, no, I think the number one thing is really simple, but really important. You've gotta, um, gotta stay positive no matter what happens. You got to stay positive because you have a purpose, you have a mission, you have a great product.

[00:06:39] I mean, it's not a great product, you know, you probably shouldn't be trying to sell it. So you assume you have a pile, you know, a good product. Um, You got to remain excited to tell others about it, remain excited to have your team tell others about it, continue to work on it. Uh, cause then that just that enthusiasm is contagious and is contagious to the team.

[00:06:59] It's contagious to yourself. It's contagious to the customer, to the, to the, to the market, uh, to social media, all that stuff. Uh, so staying positive, enthusiastic, uh, is, you know, is really important. Um, there's a saying that's a. Sales depends on the attitude of the salesperson. Not really the attitude of the customer, right?

[00:07:22] Yeah. You need to win them over, but, uh, the, how you approach every day, uh, uh, and, and approach each customer with that, that right. Sort of enthusiasm that's contagious is super important. That is so powerful. And. I find, especially from the startup world, when maybe you're in the earlier stages of the product and you know, the vision of where you want to go, but maybe it's not.

[00:07:53] Best version where you're still in beta, you're still in V1 or V2. How do you maintain that in the startup world? How do you keep that enthusiasm and that positivity when you know that your product is on the right path, but not quite there yet. You know, that's a good question because that's, that's sort of this, this, the, uh, elusive product market fit that a startup like ours.

[00:08:17] And really, I mean, companies for years, years, and years, especially in complicated areas like MarTech and, uh, and, and, you know, analytics and big data and these other very complicated, uh, to really get that. That, uh, ball rolling, where things start to come a little bit easier and everyone understands the product and really, they already start to look for that.

[00:08:43] Um, and we're certainly in that phase now. I mean, we've got customers and happy customers, but we have a long way to go before we, uh, before I would say that we're there. Uh, but it's going really well. So we, in the meantime, I think one of the biggest things that. Everybody moving in the right direction is customers.

[00:09:02] So even if it's early, go get customers. It's very energizing when everyone says, wow, you know, so-and-so company is using, is just agreed to use our product. It's very energizing because then they realize we're not just making a product. We're not just talking about it. Other people are putting up money to use it, to achieve what we've said.

[00:09:25] We believe they can do with it. Get customers, get them on board and then, um, respond to customer change. So customers will give you feedback. Uh, Hey, w we wish it did this, or how do we do that? Or can we integrate it with this? And so we work tightly to, uh, To improve the product and our processes based on customer feedback, which is also energizing because it's real, we're not just sitting around thinking, oh, we should do something.

[00:09:54] It's actually a customer said it, uh, or more than one customer has said it. So that I think is, is, is the couple of most energizing things is get customers and respond to customers. Um, everyone's down for it. Yeah. That ability to grow, to learn from the feedback to move out of the theoretical sketches on a whiteboard or mock-ups or wire frames of what that product will look like to actually say, Hey, we've got customer 1, 5, 10, and knowing that you're not going to be at your best version of your product.

[00:10:29] I hesitate to say, but maybe ever as our products are continually evolving, we're continually iterating and redesigning and redeveloping to make them faster, more efficient. We're user-friendly and so I think that's a really good point. Yeah. You're never going to be able to get user feedback if you're not bringing on any users.

[00:10:51] Correct? Yeah. So that's, that's, that's critical. And so that's what, you know, I think it's it's and so having a team that understands that, uh, early on, so, um, you know, I think there they're sort of two different types of founders or, uh, business leaders. There's sort of the operational, uh, business leader.

[00:11:11] Maybe if there's three types, there's probably a simplification, but there's the operational very good at sort of the COO kind of things. The capital raise and the disbursement and the hiring and the structure, and, you know, and that's important. Um, but it's not a sales function. And then there's this sort of engineering founder, which is great at the engineering, understands it inside now, but there also isn't a sales function really built in there.

[00:11:38] And then there's sort of the sales. Yeah. Leaders, uh, sales, founder, sales CEO, uh, or, or there's the company comes in from a sales side where right off the bat it's we know how to go get customers. That's what we're going to focus on. Of course, we need to build a great product. And so I think each of those types of leaders are important.

[00:11:59] Um, I would put myself more in the sales camp. It's just natural for me to say, okay, we're ready. We've got to go and get customers on this thing. And, and, uh, it keeps us, uh, energized and moving the right track. I think that's a really fantastic point as I've been part of early organizations that have maybe had one of those three leaders as part of the founding team and seen the challenges that can come from that from having a limited perspective.

[00:12:27] And so I see that you, you are a co-founder in intro snap. And so what did you think about. Trying to create with that leadership team, as you were ready to go out and really start building your own business and your own product. Talk to us a little bit about how you thought about finding those types of leaders or was it mainly just you saying all right.

[00:12:48] I, I know I'm a sales founder, but I can flex into the engineer or COO roles also. How have you think about that? Yeah. Um, I think. Two things that are important, uh, were to have a team that understood the problem set and understood the customer pain points. So I didn't want to bring in people who just out of left field, just because they were good, maybe even at what they do, but, um, it's so much easier when you have a discussion.

[00:13:19] W when everyone totally understands the pain points that you're trying to solve. And generally, if you're going to sell some SAS, you better be solving some clear pain points or you're going to have a tough time. Right. Um, so it's hard to, it's hard anyway, even if you are solving pain points. Um, so that was a key thing.

[00:13:36] So my, my co-founder and head of growth is Zander, Zander Robey. He also came out of SAS sales, Oracle TripActions, lattice engines. Um, yeah. Understands the pain points in spades of the sales cycle, on the outbound and the prospect engagement and sending something personally convinced he and I both understood.

[00:14:02] Um, and then from an engineering standpoint, you know, we've got, uh, uh, great people who also have internal yeah. And understand the problem set in there and are a hundred percent behind it. So those are, I think, really important because then we're you come to the market with. Of knowledge base, uh, and you don't have to figure out all those things.

[00:14:21] It's, it's, you know, again, that's why we started it. So that's really how I, how I, how I looked at it to start with. That's really cool. And you talk a little bit earlier about maintaining this level of positivity, this enthusiasm. One of the questions that I love to ask folks is. Even though you're number one in sales at a massive company like Oracle competing against lots of different people.

[00:14:54] I'm pretty sure there've been times in your career where you've maybe had a bad quarter bad month, bad year, even. I'm just going to guess it's happened once at least. How do you bounce back from those times? How do you get back to that level of enthusiasm or positivity? And what's the unique mix that maybe you have found this worked really well for you over your years in sales or leading others to really help them bounce back.

[00:15:21] If they're struggling. So, yeah, I think this is important. Um, for number one, you, you got to figure out what went wrong. So if you, if you have a bad quarter, let's say, um, usually that means you didn't close as many deals or the amount of deals as everyone had hoped. Um, so you've got to analyze, well, what went wrong?

[00:15:42] Why not? Um, and then you got to learn and adjust. You have to be ready to learn and adjust. In fact, you have to be, you have to expect it. Change there was this, there was this founder, uh, who invested in a different company years ago, who invested in one of my companies. Um, and he said, you know, uh, he was in a fast moving business that he ended up selling, uh, in analytics.

[00:16:05] And he said every Friday, they had a change meeting with the whole class. Uh, as they were growing, uh, and it was just to talk about what they saw in the market and what was different that literally that week that they should think about in their marketing and their sales and their pricing and their product, because he wanted to, you know, try to internalize that you got to expect change and improvement, not just be reactionary to it.

[00:16:32] Right. And so very, very important. So, well, what are we going to change? What went wrong? And then in a sales effort, it's typically. Um, if you have a good product that does sell, if you have a bad quarter, uh, let's say, have a sales cycle less than 90 days, that probably means something happened two or three quarters, or leave one or two quarters prior where you weren't filling the funnel you want.

[00:17:01] Engaging enough with those prospects that were in the funnel, uh, either balls were dropped or we didn't, you know, we just, weren't doing the work, the tenacious work to make sure that the funnel stayed filled. Cause that's usually if you've got something that's again, has some win rate. You got to look back and say, what did we do to not keep a healthy pipe or take care of the people that were in the pipe?

[00:17:30] It's kind of comes down to that. You know, like the, the, the, the top in the middle of the funnel is kind of where the action is because it's, you're, you're, if you have a decent product and a decent process, you're going to get a decent wind rate out the bottom. So what did you do in the, in the middle of the funnel?

[00:17:46] And that's actually one of the reasons for interest snap, cause that's where the massive pain point is. You had an inbound be lost them, or we had a good outbound, but we lost them or we were in process, but they went cold, you know, use something like an interest map where you can send them a charitable donation because you learned about them earlier in touch and get them warm again.

[00:18:08] And, and, you know, that's exactly what the whole point is right. Is to, is to do that. So, uh, that's really probably where the analyst analysis has to be. What did we not do in the funnel? In a quarter or two ago. Cause that's why, probably why we are where we are now. Totally. And I think there's so much good sentiment as you think about looking back.

[00:18:34] And realizing that, well, it probably wasn't what you did last week, or maybe even last month, but how do we take that step back or that bigger view to look maybe a quarter or two back, and you mentioned interest's nap and I think it's a really exciting company and product and what you're working on because I find it's really easy to burn out and sales to only have my mission be focused on.

[00:19:02] The dollars that I'm closing, because that means it's the dollars that I'm putting in there. My pocket, uh, as somebody who my dad was in the nonprofit world, running a nonprofit for 30 plus years, and sometimes feel a little guilty about not giving back more outside of dollars or some consulting or sitting on a board.

[00:19:24] And so talk to us a little bit about intro snap, because I think it actually brings this value to feel like. Not only can we ideally have more meetings, more effective, more quality meetings, but bringing in this concept of being able to give back, can you just talk to us a little bit about interest Napa and where that came from it and what the intention of this company is?

[00:19:46] Because I'm super excited by it. Yeah, sure. Um, numbers that you touched on it. Thanks. That's exactly it. So, um, the. The need today is to reach out in a personable, personal, and more meaningful way, uh, where you are offering something outside of a pitch outside of a poke, right? Or features, you know, feature, feature, feature, don't you want my features?

[00:20:16] And the problem is that there's just way too much of that going on. There's just too many empty emails and in-mails and, and stuff going out, um, that, Hey, please listen to me while I allow the wrong about, about how we're, you know, uh, how we can do whatever we do, uh, without first doing something meaningful.

[00:20:34] And so, um, What interest app is enabling is, is a touch point or multiple touch points where you can provide something personal and meaningful to the prospect. And that is in the form of a charitable donation to a cause that they care about. And there are, and millions of causes, uh, effect interest map is integrated with over a million causes, uh, basically all north American charities.

[00:21:03] And so. You can, you can, instead of just saying, Hey, let's talk about my features. It's like, Hey, let's talk about where you live or you have kids, you know, oh, you know, your kid goes to what school, all that's great. You know? Um, oh, I just searched and a mentor snap and you know, there's a fund for that school, you know?

[00:21:25] Yeah. It's called the such and such fund. Yeah. Great. So next touch, um, Jordan, I'm going to put it. Uh, as a thank you and to give back a hundred dollars to the school, did we talked about, uh, where your son goes, you know, imagine the, the belt it's like, okay, you've got me. Right. You just, you know, as opposed to, uh, okay.

[00:21:47] A nice chat we had, uh, I forgot to tell you that on page five, you can send an email automatically trigger, you know, think about the difference between those two touches. Right. And so, um, Uh, so were you able to give back while doing business? And the thing is that the value of these interactions is so high, right?

[00:22:09] I think we talked about there's $2,000 for a meeting, $4,000 typically of marketing spend for an opportunity. The spend is there. In fact it's way too much. So we're trying to enable less spend much better touches, uh, uh, and, and have it be meaningful to the prospect. And, and they love it. You know, they, they really, they really respond very, very well.

[00:22:32] And then the, the, the next meeting is, starts off on this warm footing, you know, Hey, thanks so much for putting a hundred bucks to my kid's school. That's awesome. Right. And then you start off on that footing as opposed to okay. What are you gonna pitch me? Right. Um, big difference. And so that's, that's really what.

[00:22:51] That's great. And then I think I saw somewhere that you guys have a pretty lofty goal of how much you're trying to get back over the next few years. What's that goal that you guys are shooting for? Yeah. So with interest snap, we, uh, we want to donate a million dollars to charity just as a matter of course of business, you know, over the next two years, that's our goal.

[00:23:14] And so the one cool thing is. Uh, the sales person or the marketer can offer this to prospects and prospects can also just accepted or even they can also say to a sales person. Yeah. You know, I'm interest now, go ahead and put it through interest. Uh, and, and, and we'll book your meeting. Sure. No problem.

[00:23:38] All right. So everyone gets to benefit from helping, helping to reach that goal just as a, uh, as a matter of, you know, that's just as a matter of course, of doing basically just doing the meetings that they're, that they're likely to already be doing. This is great. I'm such a big fan of finding ways to contribute as the.

[00:24:00] Ethos of the business as that core. I think when we were talking a little bit beforehand that you mentioned, you know, how do you weave things in? And I really liked that word because I like to think about integration and really weaving that into the core of your business and how you operate and the value you provide.

[00:24:18] Now starts to help expand on the mission because I think in sales, it's really easy to just get stuck in the quota dollars. Are we hitting the mark metrics for the board? So I think that's a really cool mission and we'll definitely link to interest Napa and share that with some folks, um, to check out because most of our sellers, uh, Are having meetings with different people.

[00:24:41] Uh, but a lot of times they're not showing up a lot of times they are not highly engaged and they're just expecting the sales pitch. And if you can really lead with that, Empathic or compassionate, uh, start that that's a, a really, really beautiful starting point. Yeah. Yeah, no, that's, that's that's right.

[00:25:00] And you know, one of the problems that you've touched on is, uh, salespeople are, are, uh, also, you know, you know, in a huge hurry, uh, they're under constant pressure. Um, despite modern thinking about how to manage sales teams, which is which. Well, you know, the, the servant leader and all that, which is very important, uh, you know, help the team.

[00:25:24] Don't just press the team. Nonetheless, the reality is half the time, what comes down from the top is what's your number? What's your number? You know? Um, how are you doing in the quarter? What about the forecast? How's this deal? How's this deal. I mean, that's ends up what's happening because there's just an insatiable appetite for more revenue.

[00:25:46] And, and so the sales team feels right. Every day and yes, they want to put money in their own pockets, but they're constantly depressed. And so that makes them, you know, hurry an interest nap and things like that are good for building relationship and getting that cycle. You're rich. Uh, and so it's easy to do and it's quick to do, but part of it is salespeople have to pull themselves a little bit out of buy my stuff, buy my stuff, you know, I have to get a number and, and, and be a little more patient.

[00:26:18] Slow down a little bit mentally. And, and I think this allows them to do something that's different than just poke, poke, poke. Um, uh, and you'll still probably increase your sales, uh, using something like that, uh, and try to get away from that pressure, which I think is part of the problem of empty pitching all the time.

[00:26:41] Cause they're just in such a kind of a forced hurry instead of a natural. Uh, the natural sort of process that feels better for both parties. Yeah. There there's so much opportunity is I think sales is really becoming redefined as a profession, as an operating function in a business, as we move through, you know, the last 10, 20 years, really.

[00:27:09] And you talk about this point around sales leadership, and. It's so easy to fall into the, talk to me about the deal. Talk to me, you know, push, push, push, push, push. What have you done as a sales leader to try and help your direct reports and your teams maybe slow down a little bit or find that space for themselves to show up with more quality work versus just more work.

[00:27:37] Yeah. Or just, yeah. Um, It's it, it has to do with, uh, uh, literally sometimes I'll say, you know, slow down mentally. I know what's going on. I've been there. Right. So it's like we wearing red, I got a dog got up, just hurry. Um, and so if I don't want people operating and if they're under tension, people don't operate well.

[00:28:05] If they're tense for a short bursts, We got to crank this out. It's Thursday, we got to get it done by end of day, Friday, whatever that is. Yeah. People will crank tense fear for a few days, plus something out that's different, but like day in and day out, month after month tension is not healthy, mentally healthy, or even from a work standpoint, people don't operate well when they're tense and you can prove that that's true.

[00:28:30] Like. But managers will think, oh, I want them to, I want them grinding, but that's, you know, they're not robots with people. And so, um, you know, if you think about when you're great at something, uh, it could be a sport or anything you're good at singing or writing when you're in the flow, when you're in that zone, are you tense?

[00:28:50] It's the opposite. When you're really great at something and you're doing it well, you're loose and it's relaxed. Cause you're just, you're just firing on all cylinders kind of in an automatic way. And like, you can't be great at, at, at, at singing or a sport or whatever it is. If you're tense, it won't, we won't happen.

[00:29:06] Same thing in sales, you've got to have a relaxation. So you're thinking about the customer thinking about, about what I could do better next. How could I build a more relationship by, uh, doing things like chatting with just, just chat don't even bring it. Business at all, try to get to know them a little bit, maybe on LinkedIn or follow them.

[00:29:26] I'll follow them. What's the result of that going to be, I got to hit a number, you know, that's the problem. So slow down mentally, relax, take the time to do the right prospecting, to do the right research, to follow through with them on social, to send them an offer for a donation, you know, and let that just be all you do with them in the next couple of days, whatever that.

[00:29:51] That's critical. Um, and I've had salespeople tell me, you know, as long as down was a really, really important thing. And I didn't realize, uh, so I think that's a big one. Um, and then the other is have a process that works because the sales people don't necessarily know what the best process is to sell your product.

[00:30:10] So you can get them into a process that's consistent. It'll also help people relax and get into a flow that, you know, works. Uh, but I think those are both really good. Yeah. I love having that foundation of a process to fall back onto when times get tough or when you know the process and you know, that it works.

[00:30:29] It makes it so much easier to focus on that connection versus, oh, did I ask the exactly right closing tactic question here or qualify for budget exactly how I'm supposed to when you have those things and those foundational skills understood. Mastered, it makes it so much easier to then really get into that humanity of sales to get into the, well, what does this prospect actually care about?

[00:30:57] How do I actually understand their goals or their challenges, and then work to really bring the right solution to the table for them. And this thought of moving away from tension. Yeah. You think, you know, maybe since you're in Marine county up there, uh, you know, Steph Curry is probably not tense when he's going in to shoot a three pointer.

[00:31:20] He is smooth, silky smooth, and that's because he's put in the work in advance and he can then trust the process. I love those thoughts. Yep. Talk to me a little bit about the personal routines that you may be, have to help you show up at your best day in and day out, you know, w what do you do to take care of yourself, uh, and really help support your own mental health or physical wellbeing, uh, to show up as a leader, as a seller, uh, throughout your career.

[00:31:55] So, yeah, 1, 1, 1 thing to do is I just, I, I made sure to build in, um, uh, exercise sports, um, outings, hikes, whatever it is, you try to do something every day. We are crazy busy, but it's too easy to say, oh, we've got more to do. Of course you have more to do, but you know, it's, it's five 30. You've worked hard.

[00:32:17] Go for a run, go for a bike ride, go for a hike, go hang out with the family, go to the backyard, whatever it might be, but to try to get some, especially some exercise, um, a good runner, a good, a good bike ride, uh, does a world of good for you mentally and physically. Um, and it also helps you. Uh, purge a little bit mentally.

[00:32:37] So, uh, also part of that is another one is get up from the laptop and stop, uh, reacting to emails, reacting to InMails. Like it's so easy to think that that email just came in. It's too important. Um, is it that, you know, you have to create new thought, you have to purge existing thoughts in the sense of, I mean, we're like processed thoughts.

[00:33:01] So get up from the laptop and let your mind. Think, uh, uh, cause otherwise it's all consumption and reactionary, which is not really a great way to build a business, to react constantly. You've got to be creating new thought. Um, and when you exercise, uh, it could be mild exercise. It could be a walk or it could be a hard bike ride.

[00:33:25] I find that my brain then says, okay, now I've got time. I'm going to start really cranking out these ideas or these problems, uh, because you've gotten me away from staring at the laptop and my heart's pumping. So you kind of get a double, you get a, you get a good, almost like a Zen like time while you get the exercise.

[00:33:43] Uh, and it helps you process, uh, challenges and whatever else is going on in the business. Yeah, I'm a big proponent of physical health is the first major step to mental health and wellbeing. And exercise has so many benefits that we've known for a long time, but now you're seeing more and more from science on the neurochemical actions that happen when you exercise and you actually take a step away.

[00:34:07] We've all heard forever. People's best ideas, somehow show up in the shower, which is so contrary to what we all feel programmed to do around push, push, push, push, push grind harder instead of the laptop. And that I love your thought on. If we're sitting at the laptop, we're just consuming constantly and we're not creating, we're not thinking as much when we're just in the work, especially in today's day and age, with all sorts of.

[00:34:37] Notifications and things that come in, uh, every second of every day as a whole, I'm curious about a couple rapid fire questions from you that I always love to ask people and I think really are some keys to, to performing really well. The first one that I I'd love to start with is do you love winning or hate losing.

[00:35:07] I hate losing and I love winning. Uh, so I think the winning, uh, I love, I would say I love winning more than I hate losing. Uh, just because there's the positive feelings are much better than the negative feelings. Um, back to the staying positive also. You winning, propels you in a way losing makes us analyze winning propels us.

[00:35:36] And, um, one of the cool things about being in sales is that you have a moment like that. You have, you can say we got win. Uh it's uh it's again, it's one of the fun things about sports, right? Where you, you have a moment at the end of the day. Of the game where there's a winner and hopefully you're on that team, but you it's a very finite, like we have a win a lot of careers or just a lot of things we do, which kind of just grind on where there isn't that low mint.

[00:36:05] Uh, so what's one of the great things about sales. Yay. We got the deal. People high five, your rhythm money goes into pockets. Uh, customers are happy. It's a very, you know, it's a very good thing. So the wind is a, is a, I think is, is a big deal. People talk about the challenges of sales and it's a grind. So you have to have that reward.

[00:36:23] Yeah. The financial is one part, but honestly the calling it a win, especially when you beat competitors, uh, and help the customer. Uh, that's really, that's really, I think one of the big drivers, I love hearing how different folks think about that question. And I love this concept of. Winning is this propulsion where losing gives us the ability to analyze where we can learn and we can grow.

[00:36:47] Um, but I haven't heard it defined like that. And I really liked that one. Next one. What are your top one to three qualities in leaders that have helped you succeed the best that you've worked with or that you try and emulate as a leader now?

[00:37:10] The, uh, ability for them to understand your own approach and be empathetic to what you're trying to do and be helpful around that. Um, as opposed to, you know, uh, you know, something that's more analytical or short or, well, I don't know, just go get the deal done or whatever, someone who's essentially steps in as a.

[00:37:38] Partner in your, uh, as a team member and partner and, and figuring things out together because we don't have it all figured out. Nobody has it all figured out. Uh, that's a really important trait because that is a constant challenge and you need, you need a team. You need team help, not downward pressure.

[00:37:58] Um, I think that's been, that's been the biggest thing. And then, um, another would be, uh, just, uh, ideas and knowledge. Right to fill those gaps of what about this sales process? What about this negotiation? What about this messaging and someone who's willing to roll up their sleeves and get in to, and you can really learn from who's done it before.

[00:38:21] Um, uh, are both really, really important. Those are great. Last two here for ya. What's your favorite interview question to ask either a seller or sales leader that you're looking to hire? Uh, pitch me, number one, pitch me. Uh, uh, so they've been selling something, so it doesn't matter. You don't have to know my product.

[00:38:49] You know, pitch butter you've been selling for the last couple of years or whatever it is, uh, I want to, and I'm going to toss questions out and I want to see how they are in that environment. If they're in like an AEA, who's going to be closing enterprise deals or whatever, that that's really important because then suddenly all kinds of stuff comes out.

[00:39:06] How do they really come across? Do they really know the product? Do they really have a process? Do they really know how to handle questions? Are they comfortable? Do they come across, you know, in a genuine. You learn a lot from that. Um, and then, um, you have to ask open-ended questions that find out things about how they have power.

[00:39:28] If are they self starters or the, do they have hustle? Are they tenacious? Uh, those are some of the key qualities that you gotta find out and you can't just say, so do you get up and hustle? Like that's not, that's not going to work. So tell me a story about how you outhouse. Uh, uh, and, uh, to, to win, you know, tell me about some deal wins.

[00:39:49] And then I get into that. How did you, how did you hustle to win that deal? There were three competitors in that deal, and then they actually have good stories about what they did or how did you get to that customer? You said that was an outbound win. How did you do it? Well, it had to do this, this and this.

[00:40:03] Oh, good. They're you know, they're tenacious and they have ideas or not. So those are some of the, some of the things that I think are. Those are great. And the last one is somebody that's been in businesses, large and small. That's sitting in the CEO co-founder role today. It advice to sellers to help set themselves up to sit in that co-founder CEO role.

[00:40:29] W what would you tell them to work on, or what would be your piece of advice for folks looking to grow their career in that direction? Yeah. Um, you, uh, I try to spend some time outside of just the role you're in because there's against very easily caught up in the pressure of that role and just do that all day long, which means maybe join meetings between AEs and VPs or, uh, maybe join, uh, meetings around enablement, uh, meetings around management, anything that you.

[00:40:58] To listen to how the rest of the org talking to each other and thinking about the problems and addressing the problems. That's when you realize, oh, that's how they that's. How management thinks about us or thinks about the process or thinks about forecasting. What are that? You know, there's lots of learnings.

[00:41:16] So I think that's a really good corn one, get out of beer spot and go listen to as many other things as you can manage the time. Uh, and then the other is you've got to absorb and read. Uh, and because you've got to be educated on processes and what's happening in the market and, and, and be ready to, to take those learnings, um, get training, you know, there's a lot to learn outside of just what your own experiences are.

[00:41:41] Um, And then generally you have to move up through the, through the ranks. So you've got to go from wherever you are now to whatever the next role is and the next role. Um, great thing about being in sales is often great sales leaders end up in the top roles because, uh, if you're successful in sales, you probably know the business inside and out because you know, the product and the customers and the pressures and the features and the price.

[00:42:09] Um, you know, the trends you're, you're on the front lines of the whole thing. So it's a great place to be. Uh, but you just got to keep moving up, moving up those ranks. So you learn step by step. Uh, you know, instead of just thinking, just going to hop, uh, uh, uh, I think those are the, probably the best, uh, the best.

[00:42:28] Those are really, really helpful points. And again, thinking about Jeff, you're going to see great sales leaders moving up in the organizations. Well, Scott Milener, thank you so much. I know folks can find you We'll also link off to your LinkedIn at any other places you'd like having folks follow you or connecting with.

[00:42:49] Twitter is at milliner. So it's my last name. Um, but yeah, LinkedIn and Twitter are the best, probably the best ones. And um, yeah, w obviously anyone who's listening would love to get your feedback. Uh, one, one cool thing about interest app is you don't have to do a SAS license. Anyone can go to interest

[00:43:07] Just start for free. Uh, there there's buttons on there. You can, you can start using it and send out donation offers to customers at the right times and, and, uh, uh, super easy to try it out. Uh self-serve so, uh, and then glad to hear, you know, feedback about how that goes so awesome. Well, until next time, let's go make it a great day.

[00:43:29] Awesome. Thanks so much, Jordan. It's thanks to help from listeners like you. This podcast can continue to grow and help others. If you found anything helpful in today's episode, please take a second. Share with a friend and leave us a five star review on iTunes or wherever you get your podcast today.

[00:43:43] Thanks.




Scott Milener on LinkedIn


About Jordan Benjamin

Jordan is the founder of My Core OS. After spending years in sales, working with sellers and studying peak performance he found an opportunity to help sellers level up to not only build peak performance at work, but to also create harmony between work and life so you can sustain performance over the long term.