Chris Cicconi on why trust is iterative

Chris Cicconi discusses how to earn trust and why patience is essential in sales

Adam Sockel (00:01.229)
You're listening to Bold Calling, a podcast presented by Oram where every episode we're bringing on the biggest and brightest minds in the tech and sales industries for a discussion about their biggest challenges and the unique ways they're working to solve them. I'm your host, Adam Sokol, and today I'm joined by Chris Ciccone, a person who according to LinkedIn wears many, many hats, but I'm going to focus on the fact that you are the head of business development at Unicorn. So first off, Chris, thank you for joining me today.

Chris Cicconi (00:26.986)
Yeah, my absolute pleasure. I'm getting introduced as one of the biggest and brightest of anything I will absolutely take. Loudest and most obnoxious would typically be what I'd be expecting. So I will take that. Compliments will get you everywhere, Adam.

Adam Sockel (00:40.322)
I can tweak the edit if you need me to. In post, I can make sure I'll talk to our editors. We'll add those in there as well.

Chris Cicconi (00:46.958)
Perfect, perfect. Those are better qualifiers.

Adam Sockel (00:49.801)
Yeah, absolutely. So for the first season of our podcast, Bold Calling, we are talking about the things that are stressing out our guests and the ways you're working to solve them. That'll be the second segment. The first segment, I want to hear about your background, how you got to be where you are today. So just walk me through kind of your, you know, your career and how you came to be the head of, you know, kind of business development, sales development at Unicorn.

Chris Cicconi (01:15.692)
Yeah, so it's been an adventure in the best of ways, of course. So if anybody like actually checks out my education on my LinkedIn profile, I studied kinesiology with a specialization in athletic therapy. So in my head, you know, I'm going to follow professional sports teams and I'm going to be on the sideline. It's going to be the best job ever. And then I forgot for a second that I live in Canada where there are like eight professional sports teams.

And even though there aren't a lot of athletic therapists, it wasn't quite going to line up for me. So, you know, I asked myself, what else can I do to actually, you know, get paid and,

Adam Sockel (01:55.114)
I was just going to say, not to cut you off, but a few things when I'm laughing because one, I went to graduate school for sports marketing and I have used that exactly zero times in my 15 year content career. also want to give, and I'm laughing as well because you talked about wanting to be connected to athletic teams and people who watch the video version of this will see this, but you are wearing a Montreal Expos hat, which I just, as a baseball fan, huge baseball nerd, so much respect for that. And I was wondering, it

Honestly, the moment you got on, was like, I need to find a way to talk about the Montreal Expos hat. So just the fact that you're not only, not only are there not many teams in Canada, but you're wearing a hat of one that no longer exists.

Chris Cicconi (02:34.83)
That is correct. I'm a huge baseball fan as well. Was a bigger one when the Expos were still around, got to be their last game. It was a very, very tragic moment. It was right around that time where my friends and I all started getting cars. We were able to get to the stadium and stuff. They weren't doing well attendance -wise, so they had $5 games where you get a ticket for $5 and $1 for a hot dog. So we would just line up and have a dozen hot dogs and watch some baseball. yeah, near and dear to my heart are the Montreal Expos.

Adam Sockel (03:03.259)
Listen, I live in Cleveland. I'm huge Cleveland Guardians, formerly Cleveland Indians fan. We happen to be having a magical season where right now attendance is very, very up, but a normal season in Cleveland, you could get tickets very, very easily. So I appreciate that. Okay, I'm going to stop on a baseball tangent because this could be an hour of baseball. I apologize. I cut you off. You were going to school to be involved in athletics. Found out that would be challenging. And three, two, one,

Chris Cicconi (03:19.864)
Sure.

You're good.

Chris Cicconi (03:31.374)
Yeah, so I was like, well, what else can I do? And throughout my, you know, university days, I worked part time at a sports store, which, you know, led to probably part of my love of shoes, which is another tangent I could go on, but we'll skip that one for today. So yeah, I was like, well, I can sell things, I guess. And then I interviewed for all the really crummy sales jobs, you know, the like no base salary, 100 % commission, or the like, here's a phone book, good luck.

And I'm in these interviews like, dude, I have never taken a single business class in my entire life. I need more training than here's a phone book. So I got lucky. Actually, I won't say I got lucky. I got referred by a friend of my sister's who worked at Aerotech, which is the staffing company. And their whole mantra was we're going to hire people straight out of school. We just want people with the right attitude, driven go -getters. We'll train them. We'll teach them the rest. We'll develop them. that

That was my inn and I had a wonderful mentor, first boss, everybody there was amazing at just helping me get kind of up and running. So that is where I first fell in love with the developmental aspect of hiring junior folks and kind of bringing them along. Then I very quickly saw some success and got dumped into a brand new division that didn't exist in Canada. So I got to start building stuff, which was also a blast.

And that's where I kind of developed my second love and this will be relevant, I promise as we go forward. But I did that for about 10 years and I was like, you know what, this is cool. It's like, it was full cycle sales. It was a lot of leadership. I very quickly had direct reports and it was a lot going on. And I thought, you know what, not that I don't love what I'm doing, but it would be cool to just explore a different option or a different direction and just see what else is out there in the world. Cause all I've done is pretty much staffing

through my network got referred into an HRS company. So I was the first salesperson hired there to again, kind of do that, build, develop, figure out the process, the messaging, all that good stuff. And I was still selling to HR, living in that same world. So that was fun too. We did that for a couple years. And then I realized that moving on to the SaaS side when I didn't have a SaaS background at all was again, challenging and I probably could have used a bit of help.

Chris Cicconi (05:44.846)
And so I got an opportunity to move into an SDR leader role. I had a larger organization where I would have some coaching and mentorship and development and all that kind of stuff. that's where it started all coming together that like, hey, somebody gave me that opportunity at this point like 10 years ago to get into the sales world as an SDR leader. Like I get to do exactly that. I get to hire junior folks, especially at that time, like pandemic -ish time where

Money was cheap and SDRs were getting hired left, right and center. was, you know, find people with great attitudes and teach them the rest. And, you know, seeing people go and get promoted and become account executives and become CSMs and move to other organizations and like watching them see success was so much fun. So did that. The other thing that was fun about it was kind of my creative aspect got to come out a little bit. So, you know, get to, obviously you're doing the email and the call stuff, but got to be a lot more active on LinkedIn. Started doing more video started.

Adam Sockel (06:38.878)
Mm -hmm.

Chris Cicconi (06:40.986)
using direct mail and gifting and all kinds of different stuff. And I was like, well, this, kind of makes sense. So, from there, it turned into me getting laid off at the end of last year and, started us working with another startup in Montreal that, turned out the, company already had no money left when they hired me. And, yeah, it was, it was perfect. I didn't get paid for like two months. Great times.

Adam Sockel (07:05.384)
perfect.

Chris Cicconi (07:10.606)
And the founder was obviously very driven to want to sell. So decided, hey, you need to hire more salespeople. I was like, buddy, I'm not getting paid. I'm not going to hire more salespeople. So I thought to myself, like, maybe we go look at an outsourcing type of sales organization that can support us. And, you know, that way we're paying an invoice and not somebody's salary. It makes a bit more sense. And that's where I got introduced to the gentlemen of unicorn, Zach Walker and Chris Ray, had

met and passing through LinkedIn and chatted with them a bit and went back and forth. And then I called them up with them. I'm look, look guys, I appreciate everything you've done. You've walked me through, but like, we can't move forward with this. We're not going to be able to pay you. Like at the end of the day, I haven't even gotten paid. And they're like, you're not getting paid. Why don't you come here and not get paid instead? That's like, that's the worst sales tactic ever, but it worked.

Adam Sockel (07:50.966)
Mm -hmm

Adam Sockel (08:04.208)
Mm -hmm.

Chris Cicconi (08:04.47)
So here I am, because again, it kind of paints everything together where I get to work with startups and founders every day. I get to get creative with their messaging, test stuff out, get out in front of different folks. So it really builds like that networking side, that building side, that hiring, developing, training side. So I get to touch on all those pieces. So it's kind of how it all came to be in a very, you know, zigzag sort of path. yeah, I love what I'm doing right now.

It's all fractional stuff, which is why you're pricing the 14 different titles on my LinkedIn. But then, you know, it's cool too, because it is fractional that I do get a little bit of leeway to do some advising on the side and do some coaching for folks, whether that's LinkedIn or sales coaching and stuff like that. So I get to mix it up, keeps it fun, keeps it creative and different. So I'm in a real great spot right

Adam Sockel (08:37.199)
Yeah.

Adam Sockel (08:56.858)
Well, and would have to imagine, you can correct me if I'm wrong, because I have only been at one place at a time, but working for a startup now with Aurum and the company I was at before this was called Pluralsight where we had more marketers than we have employees here at Aurum. Like we had, I think almost 300 marketers at the time and it was very corporatey and like had everything had to go through a million different steps for good reasons, but still it really put your creativity in a box. And here we get to try weird stuff.

see if it works, see if it doesn't. Like we're going to have a LinkedIn giveaway that'll come out like the day or two after we're recording this. That would be very, very weird that maybe it'll work. Maybe it won't, who knows, but we can try those types of things. have to imagine what we're realizing as we try these different things is very similar to like what I feel like from a sales development standpoint, like being omni -channel and like going at prospects from different routes to

what interests them, what approach will work. Like have to imagine being fractional and getting to work in all these different spaces, like that probably not only scratches that creativity edge, but I feel like, and again, correct me if I'm wrong, but I'm assuming it kind of makes you a better seller and leader overall, right?

Chris Cicconi (10:15.186)
I would like to think so, but I'm probably a bit biased here. Yeah, no, it is. And it's so interesting because I think to your point, getting to try different things with different organizations is really fulfilling because you can also take some of those learnings and apply them into different spots as well. Like, hey, this worked over here. But there's also the, this worked. Why did this work? What did we do there that's special? How do I recreate that kind

special sauce somewhere else. So you get a lot of different learnings, you get exposed to a lot of different things. And the other part of that's fun is from a fractional perspective, you know, in a world where if they hired me, I would maybe be like an individual or have maybe one person on my team or something. But like now I have a pool of people that I can go to and say, Hey, we're working something in higher education. Who has experience here? great. Three people raise their hands. Perfect. Let's get together and chat about what is unique about a higher ed.

Adam Sockel (11:06.623)
Mm -hmm.

Chris Cicconi (11:12.554)
they don't live on LinkedIn. they hate when you call their cell phones. Okay, cool. Let's pivot and do this differently. Maybe we look for events. Maybe we look for direct mail, like let's figure out different ways of doing things. So yeah, from a creativity perspective, it's so much fun because you get to try different things that iterate different things. The beauty of, you know, startup world though, is you do all of that with no money. So that's the fun part. Would you this? Yes. Does it cost anything? No? Perfect. We're

Adam Sockel (11:33.779)
So.

Adam Sockel (11:37.172)
Perfect. Yeah. I do want to ask you though, you talked about a little bit ago, you basically said like, not only just seeing what things work, but find figuring out the why behind what, how, why they work. And that, that is something that was the benefit of working at a large company is like, we had a market research team. So forget just like doing a survey with Qualtrics, like I could go to our market research team and be like, what's the why behind this answer? And that's something we're working through right now here at Orum is like

do lots of things and we have tools that we really, really love like Dream Data and Mutiny and Wormly and all these other tools that do help us uncover like, okay, here's the content people are looking at and here's the why and here's how it's actually leading to ROI and things like that. But it takes so much time. It takes so much time to figure out the why. So I'm curious for you working at various startups and having, like you said, next to no resources, how do you uncover

like the why and how, it's behind what's working.

Chris Cicconi (12:38.008)
So here is the fun part and I'm going to explain what I do and I'm going to give everybody the recommendation that regardless of where they're at or how big their organization is, you should probably try doing this. So the beauty of being in the startup world and having limited resources and tooling to try and figure all this out is you literally just have to talk to people and ask them.

working with startups a lot of the time. And again, we're talking early stage for the most part, or maybe they've done some founder led sales are looking to make that transition to, you know, a little bit broader, more scaled is like product market that's not quite there. Maybe the product isn't fully developed either. like reaching out to folks and being like, Hey, Adam, so you attended the webinar, I would love to just pick your brain about what you thought, not trying to sell you anything, nothing like that. But like, people are very receptive to

Adam Sockel (13:25.828)
Mm -hmm.

Chris Cicconi (13:29.102)
So all of a sudden, like I'm on the phone with people in my ICP and I'm chatting with them about stuff. And then, know, pitching like, Hey, do you want to just take a look at the product and give me your two cents? Like 30 minutes, just give me your feedback. I'm not trying to sell you anything. If you don't want it, no problem. But then, Oh, take a look. Oh, this is really cool. Oh, I could see where this could fit in or I know somebody who's talked to me about something like that. So it's, it's so hard because especially in like, I, I realize I'm talking to, you know, somebody at Orum where

They've got a dialer and a power dialer and like you can push volume, but sometimes taking a step back and slowing down is so important because you really do get to like, hey, I get proper feedback about who would be interested in this. What's the value in it? Is the product like fully baked? Is it missing a bunch of stuff? Like where are we at? And those natural conversations can really progress just the momentum forward that you're looking to drive to start closing some deals, especially in early stage

Adam Sockel (14:24.406)
Yeah. And, and I will say one of the things that we're really proud of here, like you said, we, we have a power and a parallel dialer and we have a click to call option, but like one of the things we impart upon every customer that we work with and for Fortune, there's over a thousand customers at this point that use our platform is exactly what you said about like slowing down. We are so, so maniacal about like, you need to have the right data. You need to have proper lists so that when your rep calls, like you said,

we try to really minimize the amount of times anyone is using Oram just to like spray and pray. Like we want you to have a list where you can say exactly what you're putting. Like, hey, we saw that you attended our Bold Calling Live webinar or like, hey, we know that like you not just were at this event we were at, but like we remember you came to our booth, you took a photo in our like London phone booth, you got one of our yellow Oram banana phones, like would love to have a conversation and like to your point basically being

Trying to figure out your needs though and see if we can help you. And I do think as I'm creating content more and more for sales professionals, what I have found is like this space is really, A, sellers get like a bad rap about attitude and how they approach their day. Like yes, we all like to make memes and jokes about how bad everything is, but like when you have a genuine conversation with somebody, like exactly your point, like A, not only will they give you genuine and honest feedback about your stuff, but they'll tell

their needs and the things that they're going through and they'll talk about platforms that they've tried and experienced and liked and didn't like and like I just feel like it it does really Benefit you like you said to slow down and be willing to have those conversations I'm I'm curious about your like from a time blocking standpoint. Like how do you focus on time management

all the things you're doing and finding time to have conversations with people and stuff like this and all the goodness around

Chris Cicconi (16:22.03)
Yeah, I, it's funny. I always quote this leader I had at my first role and in sales, this was, this was like face to face sales. So like driving to meetings and being on the road and all that stuff. And that was also very challenging when I have a team at the office, I have to drive to meet clients, have to cold call to book meetings, I have to close deals. It was recruitment. So I had to worry about fulfillment. There was a lot going on. And basically what he told me was between the hours of 9 a .m. and 5 p .m. if you are

Calling clients, meeting with clients or driving to and from a client meeting, you're not doing your job. A bit extreme, but the truth still falls to, hey, if I need to be talking to a client or if I need to be cold calling or doing any of that stuff, I need to block that out during the day. And that's what I'll do, right? It's like, when do I have to actually interact with humans? I need to pick up the phone and I will block those times throughout my day. And then everything else can kind of fit in between. And like, I'm not typically going to cold call

9am because and don't get me wrong, there's very easy to tell like where people are but like if it's skipping every second call because it's 6am on the West Coast, like that's not practical for me. So I'll set up my blog and say like, I'll call typically between 10am and noon. I'll call between 2am and 4pm and in between that I can schedule some of these other things and then it comes down to which clients to have to call for which clients am I writing messaging for which clients am I building tech stacks for and then how does that slot in based on again, who do I have to talk to when do I have to talk to

Adam Sockel (17:50.053)
Yeah, I want to ask kind of the core question of each of these episodes about you what's keeping you up at night and you know, we've been talking for the last 15 minutes or so about a variety of things that in theory could be keeping open and stressing out but you strike me as a person who is very excited about the various opportunities and like you have a Gen like the little bit we've got in the chat like a genuine curiosity and excitement about all of this but that being said you are wearing as I said many many hats not just the Expos one. So what

the thing that is stressing you out most about your job and kind of quote unquote keeping you up at

Chris Cicconi (18:25.39)
Okay, there's going to be, I'm gonna give you two answers. And one is going to be the higher level, more philosophical answer that's keeping me up at night. And then the other one will be the more tactical, day to day, what's actually like stressing me out. I think the thing that is keeping me up at night the most is really reflective of the sales profession as a whole. Because I think, Adam, to what we were talking about before, when we said,

It is important to slow down and take the time to meet with people and take the time to network and build that out and build out. I was talking to a colleague about building a community and right. And you know, you're you're doing things today that will hopefully accelerate the future of what you're trying to do. The problem is most people aren't patient enough for that. Most organizations and oftentimes leadership are most certainly not patient enough for

So a lot of times salespeople, myself included, I've done it a million times over fall back into that. I don't have time to slow down and have the right conversations and do the right thing. So I'm just going to do more of the wrong things. I'm just going to do more mass email and I'm going to do more parallel dialing 17 people at a time to blow through lists or a thousand people in a day. Like I'm going to do more of that, which is more of the wrong thing, which is more perpetuating the stereotype of salespeople being

underprepared, just trying to sell their stuff, don't care about the prospects, don't care about solving problems, don't care about building relationships. That is my biggest thing from a high level philosophical perspective that scares me about sales because we're going down that path or back down that

Adam Sockel (20:06.337)
Yeah, I want to talk about that before we get to your tactical one, because I have a, we've been kicking around a theory on our marketing team around that exact thing, because we, we are running, we're just now getting the data for our 2024 state of sales development report, which is our 2023 one was the first year we did it. And it was very successful. People love the data we had in there. And we were really interested because 2024 has been, you everyone's always like, this year has been so different than everything else. Like legitimately 2024 with, you know,

Chris Cicconi (20:08.162)
Yeah.

Adam Sockel (20:36.319)
whole AI effication of everything and people panicking. We were interested to see what was going on. And what we're seeing is there's all this data that shows that sales development representatives are actually creating less pipeline than they ever have before. In fact, it's not even like the majority, like AEs and CSM and all these other teams are creating more pipeline than SDRs are right now. But at the same time, every organization, like the thousand organizations we blind surveyed, we're like, well, we're planning on hiring a bunch more SDRs in the next 12 months.

And it's just like, we ask that they're just throwing money and we asked them what their top three tools are. And they said the phone, which is great. They said, they said social, which makes sense. And then I said email and they're just like, it's exactly what you said. It's like, they're just throwing money at the problem, trying to figure it out. And I, the re my theory, it's a very long preamble to this is because sales is so quota based and it's, it's not only is it like, what have you done for me lately?

The moment the quarter ends or the half ends of the year ends, it's no longer, what have you done for me lately? It's like, what are you doing for me right now? What's your number right now? And every single person is beholden to a certain number. And if they don't hit that number, a lot of places are so impatient that they just will kick you to the curb. think a lot of it has to do with like, people are so in sales are very afraid to try new things because what if it doesn't

is a thing that you can't really say in sales. In marketing, especially at a startup, we are fortunate to be able to say, if it doesn't work, especially if the cost is zero? So our theory is just like, people are afraid to change because they don't want to know what happens if it doesn't work, so they just keep throwing money at it like they always

Chris Cicconi (22:19.896)
So I'll say something that I don't know where your audience falls in the way of seniority and level in an organization, but I think a lot of it, and I've had this conversation with former leaders of mine. I think in a lot of spots, it's exactly what you said. This is what we, we know how this works. We hire SDRs, they produce X. We hire twice the SDRs, they produce two X. Sales isn't math. That's not how that actually works. And the thing

from a leadership perspective, that's what they did, or that's what they've seen, or that's what's worked for them in the past. So they're doing the same thing where everybody's just protecting themselves. Well, we needed more pipeline, I hired more people. We did more marketing campaigns, we did whatever it is that traditionally would produce that. And then that trickles downward as an SDR. I'm not producing enough meetings, what do I do? I make more phone calls, I send more emails. And when I'm talking to my leadership, they go, well, that's what you gotta do, right? That's what you do when you're struggling, you make more calls.

Adam Sockel (23:17.145)
Mm -hmm.

Chris Cicconi (23:17.26)
you send more emails. So everybody's just so happy protecting themselves with the status quo from bottom to top that nobody wants to take that risk and go, hey, I tried something and it didn't work. Or if you do, it has to be so small and so minimally impactful that even if it does work, you could barely tell. I did something, I got an extra meeting. Cool. Is that worth it? Well, who knows?

Adam Sockel (23:37.025)
Mm -hmm. Yeah. And then if you, from a marketing standpoint, like you said, if you have a play to do, like we're gonna focus on our SEO content, or we're gonna build a state of sales development report. I had the luxury this year of building out a state of sales development report by being able to show the ROI of last year's. I didn't have that last year, it was a big bet. And salespeople, you can't say,

Ask me in six months if the thing I'm doing today worked. I, like I said, I really do think it's that this has always worked. We don't know what's going to happen moving forward. And that's scary to us all. And I think we're in agreement there. That's the big philosophical one that we can't fix. Let's hear the thing that keeps you up at night that is tactical that you think we can fix.

Chris Cicconi (24:28.29)
I think it's the fallout from that first thing that causes me issues in my day to day. So people send more emails. Google goes, you can't do that anymore. Right. And so now we have the same issue where it's like, well, I can take the time and I can write a really nicely well -crafted email and then I press send and then I get a notification being like, you can't send email to this person. You're like son of a B this sucks. And

So again, it makes my job more difficult because when we're selling our services to anybody, now it's not just like, we'll go and we'll, like Unicorn's awesome, we offer everything from rev ops as a service right up to like, we can get you SDRs or closers, whatever. That's cool. But now it's not just we do that. It's like, okay, also you to buy like 14 other domains and like two emails at each.

And it's going to cost you not a lot domains are cheap. That's fine. But like, I need to explain to you why and then they go, I don't I don't understand that. That's not a thing I've ever seen. Let's just do it the way we've been doing it. It's fine. Like it's not fine. But also do I like where where does the line draw where you're like, I have to turn down business because this doesn't make sense anymore. I'm afraid of negatively impacting what you're doing or your domain or all that stuff. So like, how do we set it up so that we can give our clients the best opportunity to succeed?

and have them feel really good about that when they're talking to us. So there's like so much more education that goes into it now. And even then you're still kind of rolling the dice going like, I hope you understand where I'm coming from and why I wanna do this. And it's not because I wanna take your money, it's because I want this to make sense for everybody.

Adam Sockel (26:10.685)
So what are the ways that you're working to convince people?

Okay.

Chris Cicconi (26:16.918)
I can I just send out an open ask on this podcast for people to reach out to me and tell me how to do it. They're like the biggest the biggest challenge becomes and again in the world I'm living in where we're talking to a lot of founders who again a lot of times have been very successful with their founder led sales and made those moves but it's how do you then scale and so it's explaining to them that like you did this really awesome thing.

Adam Sockel (26:20.666)
Sure. Yeah.

Chris Cicconi (26:43.786)
in this really small spot of people who sort of know you, got referred to you, connected with you. You didn't have to worry about cold calling all that much. You didn't have to worry about cold email. You didn't have to worry about volume. And now we want to scale that. But the problem is the niche that you found yourself in isn't necessarily representative of what the rest of the market will be for your product, right? Your niche is people who know

their industry isn't necessarily as relevant as it would be otherwise. The size of their company isn't necessarily as relevant. I'll take a shot on you because I know you, but typically I would never do this based on the size of my company, the industry revenue numbers, whatever. So it's like, how do we paint the picture of you've done something great, but also we're going to ignore that for a second because we have to do all of this. So it's really comes down to teaching like, Hey, here's, here's the game plan. And like unicorn's only been around

seven ish months. So like we don't even have it fully formulated to say that this is exactly what we're going to do. Plus it depends different industries, different products, all that kind of stuff. So for us, it really comes down to like, let me give you a play by play of what this is going to look like, and why each of these steps is important. And being able to really do that versus saying like, we can help you out. Here's generally what we do. There is like night and day difference in the results as well as the patience.

that the founders have when we're doing that. Because if you don't break it down for folks and you're telling them we're charging you X amount of dollars and like two weeks in, they don't have a meeting. They're like, guys, what's going on here? Like I'm spending all this money and you're getting me nothing. Okay, but if you explain to them properly, and they fully understand what week one like we're just setting stuff up, I haven't been doing anything. We two are going to start testing and then we're going to iterate and this is what it's going to look like. And this is what the goal

Adam Sockel (28:32.747)
Mm

Chris Cicconi (28:35.618)
This is what a good reply rate looks like. This is what a good connect rate looks like. This is what a good conversion rate looks like once they're in the funnel. Same thing each step. So like there's so much iteration occurring that you're like, yeah, the reply rates of our first emails, it's going to suck. Like it just, it is, we don't know what works yet, but we're going to take what does work. We're going to A to Z test it, and then we're going to get better. So like, it really just comes down to breaking things down. and the thing, last thing I'll say about this and like, I hope I don't offend any founders who listen to this,

Founders are very, very smart and very, very good at what they do, but the majority of the ones we deal with, that thing that they do isn't sales. And so it's not always easy to have them take a step back and be like, Hey, I'm, I'm a dummy in this segment, but I'm brilliant over here. And like being able to separate those two is sometimes challenging because they think that like, I'm good at this, which means I'm good at all of

Adam Sockel (29:31.209)
Yeah. As you were talking, like the phrase that just jumped out of my mind is like, trust is iterative as well. Like we're really like here at Orum, our founder was, is a salesperson, like headed up the sales development at Rubrik. Like, so he knows that like, okay, if I'm going to scale this, I need other salespeople. need product people. Like I can't do all this myself, but like you're right. When there's other

founders when a founder comes on board and like They code a platform themselves. They start doing founder led sales for several months. They get their initial amount of money It they're like white knuckling that thing so like their grip is so tight that you like trust is iterative you have to like slowly release like one finger off at a time and be like we're gonna exactly what you said like We're gonna show you in week one. What is starting to

now and how we're going to keep working. I think as people get further and further along in the journey, that's why customer stories are so impactful. That's why network -based selling is becoming more more impactful because you can build that initial trust. Then once you have that initial step where it's like, hey, Chris trusts what we've done so far for them, that's why we wanted to reach out to you. They're like, okay, I'll give you a shot and then you at least have that moment.

It's a thing we're all feeling and we're all experiencing is that like, how do we get people to trust us when they're afraid of change because sales is hard?

Chris Cicconi (31:03.694)
Totally. like the way you said that is so perfect because that's why you have to like really break things down. And it's not because again, like so many of the founders we deal with are brilliant. It's not because they're not. It's because you want to be able to build that trust. And if I say, look, week one, we're going to start sending out emails. We're literally going to accomplish nothing. Like I'm telling you, we're not going to get a reply in week one. It's just how it is. Like this is how this is going to work. But then you don't get that reply week one and they're not fazed because they're like, well, Chris told me it's going to be like this.

And the goal is by week two, like, that's when we're going to start getting our first meetings. And then we're going to ramp up by the end of the month that month two is going to look like this. And when we can start breaking that down. And then to your point, you're just, building trust every week. Like, yeah, okay. Nothing's happening, but they told me that, okay. The next week, Hey, we're starting to get something. Okay, cool. Now we're building that trust. And I think to your point, if you're selling through your network, if you're reaching out to people, like you're starting with just a little bit more trust than you would have had otherwise.

If you're cold calling, you're starting from like negative trust, is there just already pissed off your calling them, bugging them, right? So like, how do you build up a little bit of trust in that first couple of seconds? And it is through being properly prepared and knowing what you're going to say and having it be relevant to them. And again, to kind of go back to that first thing, the more people make BS cold calls, send junky emails, the worse you are hurting the reputation of the entire sales world. And you're putting everybody a step back.

Adam Sockel (32:28.048)
Mm -hmm.

Chris Cicconi (32:31.842)
That is my rant about this data sales.

Adam Sockel (32:34.41)
I love this rant. I love this soapbox we get both got to step on together. So I'm right there with you. Let's do a little bit of a less stressful conversation. We can both take a deep breath through our nose. What is for the third round here, for third segment here, what is the first job you ever had? It can be when you were a kid, it can be out of college. What was the first job you ever had?

Chris Cicconi (32:46.146)
Perfect.

Chris Cicconi (32:57.41)
The first job that ever paid me money was actually being a soccer referee.

Adam Sockel (33:03.947)
I assume for like little kids or how, what was the experience like?

Chris Cicconi (33:08.078)
Uh, so at the time I was probably like 14 ish. And so it started with like little kids and then they're like, Oh, well, we're missing a ref here or missing a ref here. And we're, and then all of a sudden it was like, yeah, uh, we've got like these 16 year olds that like need a ref. So let's go do that. And then it was, Hey, we have the senior women's league. Uh, you want to go do that? And, um, it was an experience where like, I,

want to say I learned how to take rejection because it wasn't rejection. I just learned how to deal with all sorts of personalities of people who are, you know, different levels of happiness in their life. And they brought that to the soccer pitch. It was fun. I got to run around outside.

Adam Sockel (33:46.431)
Mm -hmm. was just gonna... Yeah, I was gonna ask how the parents were, but as you can imagine, when they were younger, probably not so great, but you know.

Chris Cicconi (33:58.03)
I always remember this one game. so the way it worked was because again, we're on like fields where there are a game starting at six at seven 30 nine o 'clock. So like you had to be on time and sometimes teams would be late things would happen. So you're like, well, I got to shave five minutes off your game. Like, sorry, it is what it is. I always remember this one coach that had this stopwatch around his neck. And I called the game five minutes early, which was like on time to start the next game. And he just like lost it. And like going back to the trust is iterative piece.

At the beginning of the game, I'm telling you, we are starting five minutes late and therefore this is going to happen. And then you just lost it. I'm like, dude, I literally told you what was gonna happen. But again, you put like a 15 year old kid out there with a grown ass adult and that's what's gonna

Adam Sockel (34:40.232)
Yeah, that makes sense. All what is the worst job you've ever had? You don't have to name names if it's like a organization, but tell me about the worst job you've ever

Chris Cicconi (34:49.726)
It was, I honestly, I've been very lucky in my life. I have not had too many jobs that have been like really that bad. The one job I would bring up that I thought was comically.

bad was I was working, it was right after university when I was trying to figure out what the heck I wanted to do with my life. And I was working in a unionized environment. It was it was in the hospital system here. And the job was actually kind of fun. So basically, you're coordinating patient transport. So like, from the hospital to their home from hospital to a different place, whatever you're organizing with ambulances, all that fun stuff. And

It was just how unionized everything was. So I had a 45 minute lunch break. And so I would go and like walk around outside because we were like downtown was fun, go have lunch, whatever, come back five minutes early. I literally get kicked out of the office. Like don't come back until you were literally ready to punch back in. Okay, cool. Then there was the, the filing system, which was you take all the requests you got in a day, because again, they printed them all out because why not? And you would take them, you would roll the papers up into like a tube.

Adam Sockel (35:56.519)
Of course.

Chris Cicconi (36:00.332)
you would put a elastic wrap on it and then you would throw it into a banker's box. And that would have like the month on it and like that was their filing system. I was like, dude, if you give me like five bucks, I can go get separators, we can put this and make this really nice. And they're like, that's not your job. That does not fit into your job description. If you do that, somebody will be very angry you. Please don't do that. You're just like, guys, like I'm not asking to do anything

crazy above and beyond. Like I'm really just like, just the basics of, you know, being functional at this job. I was like, I couldn't do it. I mean, I lasted three months, so was fairly proud of myself. But just like the level of if you turn the light switch on, you're doing somebody else's job is just mind boggling to

Adam Sockel (36:34.566)
Mm -hmm.

Adam Sockel (36:43.703)
Mm -hmm. Yeah, that's terrifying. What is your favorite app for productivity? It could be Slack, Oboma, Monday. Do you have an app that you use from a productivity standpoint that you really like?

Chris Cicconi (37:00.31)
I share what I've recently started using when I got into this fractional world because now I have my personal calendar and then I have my personal work calendar and then I have my unicorn calendar and then every client, I also have an email address and a calendar. So I had like five different email addresses and five different calendars and I was very regularly missing things, double booking myself and being late for things. And then I went and I messed around with like every calendar app out there, because there's like a thousand of them.

and I landed on, it's called Fantastical. And it's great because I can link all of my stuff together. So it's all in one calendar. It has like a thing to produce a calendly style, like, hey, book a meeting with me here. And it has natural language processing to book meetings. So you can literally type in like, I want to meet with, you know, Adam tomorrow at 1 p .m. And it'll like build out the whole thing. If it knows your email address, it'll throw it in there. I hit the send button and it's done.

and I can do it from my phone, from my desktop, whatever. like tasks are great for that too. Like, hey, remember to do X on Thursday of next week and it'll just pop it in there as a task. Super fun.

Adam Sockel (38:10.54)
That is amazing. Fantastical? OK, that's awesome. I'll put that in the show notes. How about an app for fun? You have a favorite app you use for fun. Are you a TikTok guy? We've had two people already in the first six episodes say the chess .com app, which I wasn't expecting. you have a fun app that you enjoy using?

Chris Cicconi (38:14.114)
Fantastic Hal,

Chris Cicconi (38:32.888)
fun app that I enjoy using. will, I mean, I'll give it a better explanation because just saying Reddit off the top of my head is not like super helpful, but I'm like, I'm a giant nerd at heart. So anything that I do, like I want to know everything about it. So like I'm a big, I'm a big shoe guy. I'm a big coffee guy. So like I want to go and learn everything I possibly can about that topic. So like, I want to know everything there is to know. And so like, I would love diving deep into

You know, whatever subreddit exists around like, okay, Jordans, what's coming out? What's what's worth good money? What clubs are happening? What like I want to know all of those things. So I will spend like hours just reading stuff and ending up in random rabbit holes about things. YouTube will like be the next one on there because like I've learned how to video edit through YouTube. I have learned how to set up multiple domains through YouTube. But I'm trying to learn clay through YouTube, which is less fun than you think it would be.

Adam Sockel (39:26.305)
Mm -hmm.

Chris Cicconi (39:32.002)
But yeah, like I'm just a giant nerd from that perspective. So anywhere I can like get my learn on, I'm

Adam Sockel (39:36.274)
Yeah, I was laughing because I saw somebody like, obviously everyone in the sales space is talking about clay a lot lately. And somebody put a LinkedIn message, like a LinkedIn post the other day that was just like, someone explained clay to me, like I'm five. And it was just very like

Do you have, I'm actually very interested for this one for you because of the way that your work is set up. Do you have an ideal work day?

Chris Cicconi (40:05.078)
No. Honestly, my biggest just challenge is the amount of time I need to be on calls or making calls or anything like that. Because I get very I don't want to say stir crazy. It's not quite the right word, because I don't mind working from home, but I'm very much

Adam Sockel (40:06.685)
Fair answer.

Chris Cicconi (40:28.706)
Okay, I wanna work from my couch for an hour, then I'll work at my desk for a couple hours, then I'd love to go to Starbucks for an hour and do all of that kind of stuff where I can really break my day down to say like, I'm going to do focus work here and then I'm going to go do my calls here and all that. But just the amount of time I have to spend in meetings, on calls, doing that kind of stuff, I just like, can't do things the way I'd like to. It's really just dominated by like, when do I have to be, you know, on the phone calling, doing all that kind of stuff.

Less than ideal, a day where I get like time to actually eat lunch is usually a nice day. So I'll count that as a win, but I'm also lucky. So my, my wife is still on mat leave and my daughter's a year old. So if I can take like 15 minutes a couple of times a day and go bother them and see how they're doing, like that's, that's usually a pretty good work day for me.

Adam Sockel (41:17.264)
All right, last question for you, because we are a phone -led company, I always like to ask, what is a cold call opener that would get you to at least hear a pitch from somebody who called you? Like, what is something someone could say to you that you'd be like, okay, you've got 30 seconds, go ahead and tell me what you want to

Chris Cicconi (41:36.918)
I'm like really, really on this relevancy kick. And I think so many people got tied up in like the personalization versus relevancy thing. Like you get, I'll get messages like, Hey Chris, I saw that you love shoes. Me too. Hey, you want to buy my stuff? Like, I don't know. No, I don't. like, that's actually the opposite. That makes me really angry at you. Like, I don't, I don't want to talk to you.

But like one of my biggest pieces when I'm doing like new business stuff for unicorn is I will reach out to founders and say like, hey, I have been a founding account executives three times in my career. I know it's really tough. I see that you're hiring for one. Here's why I think there are better alternatives out there. So if you can approach me with something relevant as to what I am doing when whether that involves fractional sales, dealing with founders, dealing with outbound, dealing with the sales development world like

If you can come to me with something relevant as to what I am doing right now, that's great. And I honestly think going back to the networking piece I have become because I actually half the time don't know who the right persona is for my clients. Like, Hey, Adam, you might not be the right person to talk to, but here's why I'm calling. I saw that your company does this thing with AI. I'm offering an AI product. Would you be open to taking a look or is there somebody better to talk to? Like,

If you don't know that you have that like product market fitter, I'm the right person to talk to you then just don't tell me that. Just be honest, have a conversation like we're normal human beings. So that's my biggest thing. If it sounds like it's a script that you've called and said 4 ,000 times, then like it's probably not quite gonna get.

Adam Sockel (43:19.104)
That's absolutely perfect. I feel like I could talk to you for another two hours, Chris. I really, love this conversation. Thank you so much for joining me today.

Chris Cicconi (43:27.436)
Yeah, of course. Thank you for for having me. Like I said at the beginning, you know, I'm used to the qualifications being loud and obnoxious. Like I'm happy to chat about anything anytime somebody says, hey, you want to come talk, talk with me for a bit? I'm always like, yeah, I'm down. So I appreciate you having me. It was a blast.

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Chris Cicconi is a wearer of many hats, both literally and figuratively. As a fractional sales leader working with several companies, he understands the essentiality of communication and the simple fact that trust is earned.

“Trust is earned” is a phrase we’ve all heard a million times, but we rarely discuss that complete trust is never earned all at once. Trust is earned gradually, especially when that trust is directly connected to achieving quota.

In the latest episode of Bold Calling, Chris joins host Adam Sockel to discuss how he builds trust working across multiple organizations, the rise of AI, why they believe sales leaders fear change, and juggling the stress of the present pipeline and future aspirations.

In the SaaS and tech spaces, change feels like it's happening at warp speed, especially if you’re hyper online and reading LinkedIn posts all day long from influencers. Is sales development going extinct? Will AI take every sales job? Are these fears completely unfounded, and will AI be a passing fad?

The truth is somewhere in between these extremes. Progress isn’t linear, and genuine change happens at a snail’s pace in sales if you don’t constantly work at it—little bits at a time, iteration by iteration, conversation by conversation.