WHAT IS WORKING TODAY IN B2B SALES WITH CHRIS JANNUZZI
10 Dec 2025 · 40 min
Chris Januzzi, a B2B sales leader who worked at Oracle, Epicor, and Symphony AI, explains why pre-sales engineers often make great salespeople and why most reps give up too early. He credits mentors for teaching him ethical leadership and shares the 9-13 touch rule: persistence beats three attempts and moving on.
Chapters
Hey, Chris, thanks for joining us today. As a way of getting started, give us a little background on yourself. Yeah, for sure.
Well, you know, I guess I always talk about how I had career ADD. You know, I got hired out of college into a buddy of mine's dad's computer software company, and I was basically like a little marketing rep sort of thing doing, you know, the days before there was even PowerPoint, there was all this persuasion. I put together like a slideshow for the company. You know, deck, you know, sort of thing. And, you know, got bored at that, got into, got into like help desk sort of stuff, helping people with technical issues that rolled into training, that rolled into pre-sales. And then one of the clients, you know, hired me out of there into an IT director role. And so now all of a sudden in retail and manufacturing, I was, I was running an IT shop. And, you know, that rolled into, it was a, it was an old Junior's line called Rampage Clothing. You probably never heard of them because they were mostly, you know, young girls wear. That rolled into me running Vans, the shoe company's IT group and, you know, growing them in stores from, I think it was, I don't know, maybe 50 stores at the time up through a couple hundred. And then I got back into the presales role. with a company out of Ohio. I was a remote employee and, you know, was going around just demoing and stuff like that. And then a VP of sales kind of said to me, you know, you're a better seller than the person that you're supporting on the sales side. And that kind of launched my sales career. And, you know, basically that's, you know, with the exception of taking a few years off to run company with my wife, clothing company with my wife, I just generally have been in either sales or sales leadership since then and, you know, worked with mostly technology firms, worked with Micros Retail, with Epicor, rolled into Oracle and then went into a company called Symphony AI, which is, was my last kind of role as a VP of sales.
And what was that first year like going from pre-sales to sales?
It was, I would say it was pretty natural. The one thing that I will say is I had an awesome sales leader. Guy's name was Rick Shevlin. He's now retired. Good for him. But, you know, he taught me a ton about reading deals and, you know, things along those lines and He also was, you know, he was a seller. He wasn't a forecaster. He wasn't a— and at the time, you know, the company was DataVantage before being acquired by MicroStrategy. So we had no, we had no, what do you call it, pressure around quarters. It's like, you know, when is this deal gonna come in? You know, when do you really think this is gonna happen? Okay, we're gonna push. We're gonna push for it, but, you know, it isn't like, all right, let's offer—
Yeah, the panic.
You know, let's offer $100,000 off if they'll do it by May 30th instead of, you know, June 3rd. You know, and actually, it's funny, that was a shock to me when I went from DataVantage or Micros actually at the time to Epicor and for the first time had quarter quarter pressure and, you know, the ridiculous things that we would do. Oh, we're gonna, you know, we're gonna give Crocs, you know, half a million dollars off to sign tomorrow. I was like, guys, they're not ready and they're gonna sign in like 2 weeks. And, you know, let me do some math here what that half a million dollars is gonna take out of my pocket, not, you know, not even, you know, mentioning yours. So obviously You know, as I as I've seen your videos over the years, I I have a lot of laughs. You know, oh my gosh! I think you know he feels my pain sort of thing.
And you saw a lot of that type of stuff—the quarterly hurdles and backflips that people do. Yeah, yeah.
And you know, honestly, it just got worse and worse over the course of my career. As you as you go into bigger, more you know you know Epicar was certainly public, but then you know Oracle. You know, really, really public.
Really public.
Yeah. And, you know, definitely very, very, very quarter-driven. And, you know, even the funny thing about that is the way they've done that, because their fiscal year is June 1st, that makes, you know, November really, really crazy. You know, you're trying to get stuff done.
November is your December. Yeah, exactly. Thanksgiving's easy.
May 31st is year-end and you're dealing with Memorial Day. So it definitely adds a level of stress to your life.
And when you're in sales, did you feel it naturally? Was it your thing? Was it your kind of, you found yourself?
Yeah, I do think so. I would say sales Sales overall was something that I was drawn naturally to, which I never thought I would be. You know, just as a quick aside, and I won't take up too much time on this, but when I got out of college and I didn't have a whole lot of direction as far as where I was gonna go in, I went to a bunch of those interviews where they were like for selling insurance and stuff like that. You'd go in, you'd get into the room.
Get in the room, they close the door.
Yeah, like 80 people and you take this test and it's like, you know, you got the bubbles and, you know, you're 1 through 7 and everything. And I failed miserably every single time, right? It's just like they would call, all right, if we call your name, stay here. If not, well, thanks for coming. And they never called my name. So I just in my mind said, ah, I'm not a sales guy. I'm not cut out for sales. You know, and I got a little bit of a taste of it at Island Pacific when I, you know, went into pre-sales and I was pretty good at that, but I wasn't, you know, trying to close the deals. But But then just as my career went on, I was like, no, I'm actually actually a like it and and b I'm pretty good at it. But I think again, I think the coaching from Rick and the way we went about deals, and it was not high pressure, high you know let's let's get this deal right now tomorrow. You know made it so. I could kind of mature at a younger age to this is what sales is about, you know. And that's not to say getting a deal off the street isn't important. It certainly is. But—
Getting a real deal done is nice, you know, giving them a sneak peek at what pricing they could get in a month or so isn't good, right?
Right, exactly.
Now, why do you think so many pre-sales people make great sales? People, certainly in technology?
Yeah, yeah. And that's a really insightful question. And I think it's because, if I had to guess, I think it's because the pre-sales people really focus on value. And again, maybe they get a little bit of pressure on it, but they're not dealing with the You know, the T's and C's of how do we get it there. And, you know, I guess it's the, you know, the pressure, a different pressure of being a, you know, a skilled player on the outside versus being the quarterback, you know, hey, I run my route, I catch the ball.
Yeah, because you think of a salesperson in a technology, that's the space I came from. And a lot of the the AEs, what can they talk about? They can talk about the company, the product, other customers, some use cases maybe, right? And then pricing and availability, right? But but an SE can talk about how it's used and how it compares and what the issues are.
Yeah, and that's that's the real differentiation because obviously not all are that way. You can get an SE who will teach. You how to, you know, who will train you how to use the product. Oh, if you arrow up to here or if you click on this, you know, you'll do this. Whereas, you know, I think of some of the best, Scott Scherler as an example, you know, he was like, you know, he could frame something, you know, this is the value of what this or the user gets the benefit of this versus, you know, something that would have taken them 5 other steps to do. And generally those people get excited about what that is. The last company I was at, there was a woman named Hannah who, she would get done demonstrating a generation AI or generative AI sort of piece and she would almost like, in fact she did a couple of times go, isn't this awesome? Like, isn't this cool? What, you know? And, and she was legitimately enthusiastic. She had an infectious enthusiasm about what the software could do. Um, so I think that also, I should— she would make a great salesperson someday, although she probably would never want to be.
Yeah. And also the inverse is true. A lot of the SEs that become salespeople don't learn the complex sale.
Right.
They learn they get the technical sale, but not the economic sale.
Right, right. Which is a whole nother world, right?
Which is what really matters because, you know, winning the trial and they don't buy from anybody does nobody any good.
Right. Yeah, for sure.
How did you— sounds like you had a good mentor with that.
Yeah.
I mean, I just, I've worked, I've been fortunate to work with Some really great, great mentors over the course of my career. There's probably at least, you know, three or four that I could think of. But, you know, it's all it's all about that evolution. I mean, even there was a guy I worked for in IT, this old guy who was from Arkansas, and you know had all these crazy sayings and everything. But you know he taught me kind of patience and levelheadedness. And then like I said, Rick gave me the art of the deal and and. You know, and then Kyle, who recruited me over to Oracle, you know, also was, was a great guy, surfer guy from Chicago, originally from Chicago, now lives in San Diego. But yeah, but he's, you know, he was kind of a, he was kind of a guy that, you know, could handle the, handle the pressure from, you know, the general manager, but didn't transfer that down. You know, to you. And, you know, I model a lot of my sales leadership over the years. A lot of that is based on how Kyle, you know, interacted with his people and, you know, provided the air, what we called air cover and those sorts of things. So, yeah.
And so why did you get into sales leadership? What was the driver there? Were you just burnt out as a rep or you wanted to kind of build a career?
Yeah. So, you know, over the course of my career, whether, whether it was in IT where I had, you know, a very large staff, you know, systems operators and point-of-sale people and business analysts and all that stuff, as well as when my wife and I had our own company, I always found that I, I was really drawn toward helping people you know, get— achieve their goals, providing a lot of coaching, you know, well, have you looked at it this way? That was the stuff that if I really thought about it, I found is rewarding, maybe even more so than closing a deal. I know the hardcore individual contributors, some of the people I've worked with, you know, are just You know, jazzed, right? Every time they close it, and it you know, I worked with one guy years ago who you know we used to joke. I won't tell the it's a little off color, so I won't tell what it is. But basically, he was the guy who you know if he could close a thousand one hundred dollar deals, it would be better than closing one one hundred thousand dollar deal. And you know, I was never I was never that guy. Like in fact, you know some of the biggest deals I closed. It was almost more like, all right, finally got that thing done. Let's, let's move on. And I, you know, my wife would always talk about like, why don't we ever celebrate? Like, why don't we, you know, you just closed that $5 million deal with Crocs. Why didn't, why didn't we go out and celebrate, you know, sort of thing. And it's a good question. It's, but that wasn't where the jazz—
Stay even keeled or?
Yeah, no, it just wasn't where the jazz was, you know, I get, I get more I get more rewards from the coaching side and seeing other people, you know, be successful. And then, you know, of course that brings success to you, right?
But that's hard to do. It is the right reason to become a sales leader, but then you've got air cover to give.
Right, right. Well, and, you know, I mean, that's, that's the joke, right? You, uh, you know, you lose your hair, your cortisol spikes, um, you know, you, you get a belly, you know, because you're spending so much time, you know, uh, you know, kind of eating what you're taking from above and, and not giving it to other people. But I'm pretty good at that. So.
I wish more people were because that's a skill.
Yeah, it's something. I don't know. I don't know. But I, you know, I'm not trying to blow my own horn. I think if you ask most of the people who reported to me over the years, they'd say that's probably one of my biggest strengths.
Because, you know, salespeople having a little pressure is good, but it should be internal. It should be like, you know, I want to achieve this, not, oh, my boss is on my back. Right. Then people do things for self-preservation versus the smart thing. Right.
Yeah. And, you know, that's the, you know, also, I think there's a thing that, you know, I've said for a lot of years is in some cases, leadership is telling you to lie to them. Right. So, you know, at my last gig, we had a division president who You know, decided he didn't like things the way things were going, usually somewhere about week 4 into the quarter. And, and he would implement this thing where it was like he wanted an email from every rep on every deal, you know, daily at the end of the day. And, you know, and it was going to sales ops and sales ops was doing this whole thing. I was like, we're, we're just not. Doing. That's probably one of the reasons I got fired. But, but it was like, no, guys, like, you know, send your stuff to me, you know, I'll, I'll combine it, you know, I'll do whatever, I'll put my spin, I'll read it because some of the things you don't necessarily want to say to the guy, not gonna name him. But, you know, and let's do that versus, you know, the pressure of having to have some sales rep, you know, emailing the division president, you know, every day about, you know, his deal that probably isn't going to close until week 12.
And, you know, my way of getting around that was just changing the name of the same file every day because I knew they didn't read them.
Oh, yeah, I guess in this case it was read. In this case, it was read. You know, I take a lot of heat for, you know, why, why did, why did Kirk do this, you know, sort of thing?
Why didn't he leave another voicemail?
Right, right, right.
And what makes a great salesperson? You must have a kind of, you've hired a lot, you've managed a lot, you've seen good and bad.
Yeah, you know, I think, you know, I'm probably stealing this from some of my good friends, but, you know, I think there's a lot of attitude in it. you know, wanting to achieve certain things. I'd say when you really get somebody who you know is gonna perform, it's, you know, you sit down with them at the beginning of a fiscal or at the end of a fiscal and you start talking about the next year and you say, hey, you know, what do you wanna achieve next year? Well, whenever I do get my quota, which in some cases, you know, could be— It's cool, yeah. Could be, right? True story. Yeah. You know, I want to make, I want to make 300% of my number. I want to hit $1 million this year. And I already have in mind how I'm gonna do this. I've got, you know, I gotta close this big deal. I've gotta close a couple of these medium ones. You know, I've gotta have 6. I'm not exactly sure where some of that's gonna come from. So I'm gonna have to, you know, we're gonna have to attend these conferences. You know, I'm gonna have to find a, you know, a better stakeholder at this place. You know, when they start talking about all that stuff about what it is that I can do and that, you know, the material things to get to my number or to get to where I want to be, you just find like, okay, well, that guy's going to be successful, right? Whereas, you know, the person who just gets their number and goes, well, that's unrealistic, and sometimes that's true.
How am I gonna do— what am I gonna do with this?
Right. But I mean, you know, I went through a reorg one time and, uh, it wasn't all that— I mean, it's pretty recent and, and I get it, you know, the reorg, we did all the, all this changing of, of accounts and everything and we gave this guy and he did get a terrible, terrible patch. But he, you know, he called me on PTO and said, you know, hey, Chris, like, You know, this, this thing you guys gave to me, I, I can't make my number. I'm not going to make any money this year. And I kind of said, well, I get it. But so I guess what you're telling me is I should collapse your territory. And, you know, and we'll, you know, you can go find another job and I'll move your accounts to other people. He's like, whoa, hey, hey, hey, hey, you know, don't rush things. Well, well, well, maybe I could make some money with these guys, you know. Sort of thing, you know. And, and look, I felt, I felt terrible saying it because I did, I did want to have some empathy for him of, yeah, it's gonna, it's gonna be a tough year for you. Um, you know, you got, you don't have any meat to chew on, but, you know, but ultimately you gotta, you gotta figure it out.
Right. And most people do figure it out. And that, that is a big adjustment part of the year. And it's hard being a manager doling these things out and Because sometimes you believe in it and sometimes you don't.
Yeah, I've got a good friend who's a very well-known sales coach, does a lot of speaking engagements and stuff like that. And the first time that I met him, sorry, not the first time I met him, but rather the first time he invited me to one of his seminars and it was, you know, on a sales leadership thing. And he talked about how, you know, you get these guys who these sales guys who they'll make the same amount of money no matter what their territory looks like. If he hits his number the one year and he's got 50 accounts and you think, gosh, he's really not working all the accounts and you cut him to 25, he'll still figure out how to make his number. When you cut him to 12, he'll still figure out how to make his number. So, you know, that was really insightful to me.
And I think it's true and Not many reps would agree with me, but, you know, because I've been at like the startup where they hire like 3 to 5 people to cover the whole country. And then the second year, the guy who has the West Coast gets mad because he only has California.
Right. Been there.
Then the next year he gets mad because he only has the Bay Area.
That's LA, right? Yeah.
But it's really focus and that's hope because anyone can take an order, right? The inbound, the easy stuff, anyone can do that.
Yeah, for sure. For sure. And I've seen that, you know, and it's very interesting because I think you're giving me a bit of reflection. I think when that happened to me, I mean, I went from having everything west of the Mississippi to having, you know, the West Coast to, oh gosh, I mean, there was one time that even, you know, I had most of my, most of my current business was going on in the Bay Area, like you said, because we were selling to retailers and there were more there. And then we had an acquisition and then they took their West Coast guy and they said, well, we're gonna give him the Bay Area, we're gonna give you Southern California. And then you guys both have Texas as well. So we're gonna give him Dallas. And you can have the rest of Texas. And I was like, are you kidding me? Like, you, you just took away like 3 quarters of my business. But, you know, and I've still, I've probably still been angry about that to this day, but I still, still did all right. So.
And there's always that shuffle, the people who just can't get over it, which it is kind of a weird conditioning because, you know, every year you get a new comp plan. Base typically stays the same, quota goes up, territory goes down, right?
So of course it hurts. Yeah, right. Yeah, well, that was a shock to me the first time that it was, um, when I saw the percentages on my comp plan. Now I'm getting paid whatever, 2.5% to 3.5% on a deal, and I'm like, wait, why did that go down? And somebody had to explain to me, it's like, oh, because you're your, uh, your quota went up. And I'm like, well, wait a minute, I don't understand. Like, you know, sort of thing. It's like, this was weird enough. It used to be, hey, if you want to make more, you gotta, you gotta sell more. And then it became, well, if you want to make the same, you got to sell more. Like, oh wait, I don't understand that. But, uh, but yeah, definitely, definitely a thing. And, um, you know, hey, look, company's got to make money and that all makes sense. But, but, uh, Yeah, salespeople definitely take the brunt, right?
We do. And what do you see people asking you when they come to you for advice that if, if they only took it, but you're scared to give it because you know you're going to hurt their feelings?
Um, you know, I'd say probably the most prevalent thing is, um, is if people take a really hard look at themselves, they don't persevere. And I don't know if you're gonna agree with this because I think I've seen some videos from you where I don't— you may contradict this, but, you know, I find that the people who struggle the most are the ones who say, hey, I've, you know, I've marketed the heck out of this company and they won't, you know, they won't give me You know, the time of day. And I say, well, you know, okay, let's just talk about whatever, the CIO. You know, how many, how many times have you tried to reach out to CIO? Well, I sent him an email in April and, you know, I didn't hear back from him. So I sent him a follow-up in, in, you know, 2 weeks later. And then, and then I got busy and then I hit him with another email in August. And I'm like, well, of course, you're not making any, you know, any headway, right? So I think one of the big things is people give up. Again, my friend who's a sales coach talked, he probably one of the first things he said is, you know, people don't even notice you from, you know, the first 9 to 13 touches, you know, sort of thing. And most salespeople give up at 3.
Yeah. I mean, my disagreement is only on what those touches are.
Okay, sure. Right. Well, that's true.
You know, if, if they're talking at a show not about you, your company, or your product, that's a very different touch than sending a, you know, request for a presentation to give to them.
Sure, sure. Yeah, yeah, yeah, for sure.
Perseverance, I agree with completely, because to become that creative, to become a little bit different, to stand out Requires pushing yourself, right?
Yeah. And and hey, look, nobody likes to do cold outreach. Well, some some people do, and I can't really identify with those people. I I mean, I know some I know some very nice people who you know that's their thing. You know, they're lifetime business development people, and they just really love it. And God bless them. But uh. Yeah, that's most salespeople I work with are not, not really into that.
And if you watch them and you watch their recordings and stuff, it's probably 90% personality. They really, they, they're able to break the ice with somebody. They're able to take it to another level, something that's most people, if they read the exact words, it wouldn't come across the same way.
Right, right. Well, yeah, I mean, this is There was a lot of years ago, but I remember this gal who would— she had just such great relationships with these people who hadn't bought. She'd been talking to them for 3 years, you know, and she'd call them like every 6 months, you know, and, hey, Chris, how you doing? You know, no, we're still not ready, but gosh, it's great to hear from you. You know, what have you been doing this summer? You know, sort of thing, you know. And she had a level of comfort. Again, there wasn't pressure to close anything, any court. in a quarter, right? So, so she was, she was building the relationships and let's face it, people buy from people they like, right? So it's, you know, it's how you get them to like you is the, is the big—
Ask about them, talk about them.
Yeah, right, right. Yeah. I mean, I've got a, I've got a good, good friend now who's the CIO of Skechers. That, you know, he and I started out with, you know, their company hated us, hated our company. And, you know, we got thrown out early in a deal that we probably should have won from a fit standpoint. And, you know, and I took him to beers maybe a year later. And now he and I and, you know, his wife and my wife get together, you know, for dinner sort of thing. You know, he never bought anything from me. Someday he probably will.
Cool. Hey, Chris, I really appreciate your time today. Where can people go to connect and follow you?
Gosh, I don't know. I guess LinkedIn. My name is Chris Januzzi, J-A-N-N-U-Z-Z-I. I'm not a, you know, I'm not a celebrity or anything by those means, but, you know, just a guy getting my way through the world.
I was just going to give a bit of a testimonial, if that's all right, just to kick it off. Just—
Only if it's positive.
No, it is positive. It was a— yeah, just because I started the course, I think in June of last year, 2021. I got a few more months left of access, which is good. But I feel like it's been a transformative experience in my own personal and professional life. I was able to go from a period of a low sales slump in the middle of last year, in the summer and early fall, and then really was able to then come back and exceed my target by the end of the, by the end of the 4th quarter. And so the only other thing I would say is that it's also really differentiated me amongst people on the sales team in terms of focus and clarity of what's important. And now I feel really good about what I'm doing in terms of the approach of reaching out to customers and having those conversations and being focused, as opposed to just doing a lot of the other busy work on the side, like organizing resources and doing business analytics and all this other stuff. And so it's really been a noticeable difference with our executive team at my company. And so I just want to thank you for the content and for these opportunities. And so I hope that helps if there's anybody new. It's— I'm a work in progress, but it's getting better.
Good. Yeah. And you're selling pretty hard stuff.
