Career Crashers Episode 16: Kevin Cherrick on Winning Job Opportunites

Success is not final, failure is not fatal: it is the will to continue that counts. Winston Churchill Kevin Cherrick was looking for a sales job. He applied to a role at a startup he liked, but two weeks later, he still hadn’t heard back. So he did a lot of research, went to Costco, bought $150 worth of snacks, crashed the startup’s happy hour, and set up an interview with the hiring manager. After the interview, he was rejected. But he didn’t take no for an answer. He found a way to show who he was in ways a…

Success is not final, failure is not fatal: it is the will to continue that counts.

Winston Churchill

Kevin Cherrick was looking for a sales job. He applied to a role at a startup he liked, but two weeks later, he still hadn’t heard back.

So he did a lot of research, went to Costco, bought $150 worth of snacks, crashed the startup’s happy hour, and set up an interview with the hiring manager.

After the interview, he was rejected.

But he didn’t take no for an answer.

He found a way to show who he was in ways a resume could not.

And he turned a rejection into a job offer.

On this episode of Career Crashers, Kevin, an entrepreneur and currently a digital marketing executive at FreightWaves, shares his story and approach to the hiring process–and how he uses it to win great job opportunities.


  • The process Kevin went through to identify and pursue job opportunities
  • How to research the company and industry you’re targeting to find out if you’re interested
  • Why and how you should reach out to front-line employees at your target company to learn more about it
  • Kevin’s story of joining a company happy hour as a way to get a leg up in the hiring process
  • Using rejection for one position as a doorway to other opportunities at the same company or others


Connect with Kevin on LinkedIn: linkedin.com/in/kevincherrick

Read Kevin’s detailed breakdown of his job search on Medium here.


Also listen to this on iTunesSpotifyAnchorTuneIn, and Overcast.

Full Transcript:

Welcome to Career Crashers, where we tell the stories of those who are not content to wait around following rules and hoping for good things to happen. Great careers aren’t found. They’re forged.

It’s time to crash the party.

Hey, Career Crash listeners, we want to take a second before the episode to let you know that we have a brand new pocket book out called Crash Your Career. You can pick it up on Amazon or at crash.co/crashyourcareer. You’ll learn how to launch your career without waiting on gatekeepers and standing in line, applying many of the lessons you’ve heard from guests on this show. Go to Amazon or crash.co/crashyourcareer. Now onto the episode.

I am really excited about this episode, because just yesterday, I got an email out of the blue from somebody that I had not met in person, I don’t know that we’ve ever even talked before on email or social media.

And it said, “How I turned three rejections into two job offers.” And the email was great was real short said, Hey, here’s the TLDR. I applied for a couple jobs. And I was really persistent. And I got rejected anyway. But I didn’t take no for an answer. I sent some custom follow up stuff turned around, got an offer letter. And here’s a longer article where I detail my process.

And I’m like, Oh, that’s really cool. And the article blew me away the amount of awesome information in there. And just the mindset and the approach that was taken, which is all about what we do here. So I immediately emailed back and said, Kevin, would you want to talk about this? Come on the podcast. And here we are. So Kevin Cherrick, anything you’d like to say to introduce yourself to the listeners?

Well, thank you so much for having me on. I’m a big fan of been following you and TK through all the different podcasts that you guys have set up and your work through Praxis. And, you know, thinking forward, I’ve been in contact with people at practice, and they’re such good customer service and follow up on on that side.

I was like, Well, I’m really just doing research for my nine year old. So we’re not there yet.

But you plan ahead. And so yeah, I, I just kind of documented what I did for my own purposes. And because I kept telling people about it as I was going through the process. And they said, you know, nobody does this, which is you know, typical, in my experience is like nobody does it this way.

And so I first have to ask, why is that? You know, and I couldn’t I didn’t give a good answer. So I just thought I would document it. And it just seemed to really the tagline that you have on your podcast, is you have to really just line up with that, of what your ethos is around Career Crashers. So, yeah, I just reached out and I’m glad to be here.

So you wanted a, you’ve got some experience, you’ve you’ve been in the professional world, you’ve started some businesses, we’re looking at a new job, and you were looking for a sales job in particular. And you were looking at some startups in your area. And you kind of outline here, your process, you have 11 steps outlined.

And by the way, we’re gonna share a link, if you want to read this full article, we’ll share a link in the show notes, I highly, highly recommend it because we’re only gonna be able to touch on the highlights. This is really thorough, really.

So you have this sort of 11 point outline of what you did. Can you just sort of walk through that process of Okay, I want a new job. What am I going to do now?

Yeah, I mean, the most important thing is to actually have a specific target. And I think this is the same way when you’re making educational decisions or career decisions. When you’re trying to plan for everything, you there’s no context and no course to take.

And so, you know, I had been kind of sort of looking for a job and then I this company stumbled across my, my desk, so to speak, and, and I was intrigued by the people first. And then I started to do basically step one, which is research the company, you know, am I interested in this company? What do they do? Are they winning? I have become here now in my late 30s, I have become more and more developed an understanding that industries and then companies make careers, and so you can be Steve Jobs.

If you’re in a broken industry, it doesn’t matter. You will be wasted. You will never develop you know wealth, the lifestyle you want, the career accomplishments that you want to have that you’re pouring your lifestyle into.

Warren Buffett says this so well. He says “when an industry with a reputation for mediocrity meets management with a reputation for brilliance, it is the industry that emerges with its reputation intact.” And that comes from his own experience trying to turn around the original Berkshire Hathaway which is a textile factories I think somewhere in New England and they get into this business and they decide, oh, this is a disaster, it’s just complete money suck, and so they have to get out of it.

So, you know, when I was young, I was fired up, I was like, you know, I can make anything work through my sheer force of will. And now a little bit older, my wife would say, a little bit grayer, you start to say, Oh, I need to convey not only ride that wave, but you know, step on those shoulders of giants, so to speak, so that I can have the opportunity to be successful.

The first thing I do is just research the company and understand the industry, try to understand the company’s competitive position within that industry, basically, are they winning? Okay, that’s what I want to know, first. And then and then after that, I need to understand the role specifically.

So I start to reach out to just comb through LinkedIn, I reach out and ask for informational interviews from basically frontline employees, you know, people my age and younger, who are doing work so that they can tell me about the culture, the you know, the compensation, the day to day activities, do they love it? How is the company really doing and I take those folks out, it might be a phone call might be coffee, it might be lunch, you know, I took a woman out for lunch. Last year, the first time I did this strategy, and it was a two hour lunch, she was just giving me all the information, I’m taking pages and pages of notes, so that then when I climb the ladder, I know a lot of the jargon. I know a lot of people in the organization, I know how the company works, because I found kind of an internal champion who was able to tell me about what was going on.

So. So let me just recap that. So you first researched the company and the industry, get a good idea for what they’re all about. If you’re interested. If you are interested, then you’re reaching out not to the people who are making hiring decisions or high level executives, but to just kind of on the ground workers. And how are you, What are you asking them in that cold outreach? Hey, I’m Kevin, I’d love to just buy you coffee and ask you a little bit more about the company you work for, because I’m looking at an open position there?

Yeah, that’s it, it’s very straightforward, you really have to this is where the mindset starts. Because you might send out 10 emails and get one back, or zero, I mean, if you cannot do send one, oh, I hope this one person opens it and gets back to me. And I do that through LinkedIn, because I don’t normally at this stage, know what the email format is. So I can’t just email people directly.

So I’m just in LinkedIn, I go, you know, this company has 132 employees, I click that button. And I’m just scrolling, looking for titles that are within the department that I’m interested in, my case sales. And I’m starting to build out a little org chart. I’m like, these are the basic sales folks, you know, these are the directors, he’s the VP of sales, etc. And so I understand how the internal politics, if you will, are working,

I love it. And so you also have on here that you develop an org chart. So you’re kind of mapping out based on the pieces you’re putting together, okay, who works, where, who reports to where and as you interview people, you’re asking them these types of things, you’re getting a feel for how it works? Who are the decision makers, the hiring managers learning about the company culture and how it works? And that’s all before you have done any formal application to any job postings they have, right.

Yeah, my feeling is that once you formally applied sometimes people get a little skittish about it. When you just say, Hey, I’m checking out your company, I may be interested, you know, can I buy a coffee? Can I get you on the phone? Somebody is gonna gonna say, Sure, no problem.

This may depend on me, we’re in a relatively mid mid sized city. So it’s a very friendly city. And so people are very open to having meetings with folks. So that might vary, you know, culture to culture within different cities. And New York City might be less willing to take you up for coffee. Yeah, I don’t know.

But, but yeah, this is all ahead of time, because it puts me in the driver’s seat. I’m evaluating this company. Once you’ve applied, that psychology changes. And it, it seems like, oh, now I’m begging for something, and they’re gonna evaluate my candidacy until that happens. I’m in the driver’s seat.

I like that. So you formally applied and in the case that you wrote about here, is pretty fascinating. So you sent out an application. But once you did that, you did not just sit and wait for things to happen. You took some of the information, you knew some of the context you’ve already made. And you you push the line in some things and you talk about this that you wanted to make sure you didn’t come off as creepy or stalkerish. But you did things like show up at some happy hours that you knew that the company was going to be at, from people you talked with.

And one of my favorite story, you actually showed up to the office while your application was in there. You were waiting to hear back at it taking longer than they said, which often people get defeated. And instead you went and spent 150 bucks on a bunch of snacks and showed up because you knew they were going to be watching a basketball game, showed up to the office with food. Tell me that story because that’s amazing and a big part of the process that you put together?

Yeah, thanks. Um, the one thing I always preface everything with is you have to understand the context of what I call your buyer, right in the sales process. In this case, the buyer is the company.

So right at the beginning, I know it’s a venture funded, fast growth startup company, okay, that tends to have a certain ethos, right, a certain kind of hard charging, kind of aggressive ethos. And so you start there. And then I had just after my first informational interview, I had just cold gone to their offices to walk in and then realize they do this Friday, happy hour, I had no idea I was gonna walk into their office place and start asking for things asking for to meet people, because I had developed that org chart, so I knew who was not responding to my application.

Met some people that was great, you know, got some positive feedback. Hey, go ahead and follow up. Nothing happened. So two weeks go by it’s now been maybe about a month since my application that went nowhere. And so it was March Madness. We are in Tennessee, the University of Tennessee basketball men’s program has been ranked number one at points during this year. And so everybody in my cities like the University of Tennessee, basketball is great. And I realized on a Thursday that the next day, the second day of the opening weekend of March Madness, the Tennessee men were going to be playing their first round game at 2:30pm.

And I thought, knowing what I know about this company, bunch of young, aggressive, mostly males, and they took over the sports bar for their offices. And they had Friday happy hour every they’re probably watching this game. I mean, everybody in town is watching this game. So this is an opportunity for me to go back, reinforce some of the connections I’ve already made in person, two weeks previous, try to meet the hiring managers who have not been responding to my follow up emails my original application like, and who knows why right? Like that could be because they looked at it, they carefully evaluated my resume. They did some research online and said, this guy’s a schmuck, we’re not going to talk to him.

Or more likely, more important, more urgent things came up in the day to day business. And, you know, my experience has not been running my own businesses, I realized that’s probably what the case is. And so I don’t take silence as a rejection. And so anyway, I decided, Okay, they’re gonna be watching these games.

I’m gonna go to Costco, I’m gonna buy snacks and food. I mean, when I’m watching a sporting game, you know, I like to have some dip. I like to have some chips. I love to have, you know, pretzels. So I do this, I don’t even have a Costco card, I have to arrange with a friend who has a membership to let me go with her and meet her up there. Of course, Costco busts me and they won’t even let me pay for it. So my friend has to pay I have to Venmo her the money.

Okay, great. So we roll in there, I got this stuff. And I walk up. And I recognize that the CEO of this company is sitting on the porch of this former kind of sports bar space that they’ve taken over the second floor, they’ve got the whole building.

And I go, alright, like, I’m gonna go introduce myself to this guy. So I walk up to him and he’s talking to somebody, they’re sitting down and kind of these club lounge chairs. And I just walk up and I just cold say, Hey, I brought some food. Can I party with you guys?

I’m just on the sidewalk. Like I just walk up off the street. And of course he looks at me is weird, like quizzical look like what? I said, Hey, are you guys watching the Tennessee game? I brought some food. I mean, I literally could just be some guy who’s just looking for a place to watch the game. And he says, he’s trying to like, this is out of the ordinary, right? This is not like a normal function. Like we all have our social cues. Somebody says, How are you? You say I’m fine. How are you? This is this is I’m pattern interrupting right away. And so he goes, who are you? I say I’m Kevin Cherrick.

That’s it. Like he should know who I am. He has no clue who I am. Of course, like he hasn’t seen my resume. He doesn’t even maybe know that this position is being hired. And he says like, and?

And so then I walk up to him, stick my hand out to shake his hand and say, Hey, I’m sorry. My name is Kevin Cherrick. I’ve applied for this position that you have opened, haven’t heard anything. I’m hoping to be able to meet these two people specifically so I can talk about the position briefly set up an interview. I figured you’d be watching this game I brought some food is alright if I come in.

He looks and like, it’s kind of like you see the wheels going. It’s like I don’t, there’s too much information here to evaluate. I don’t know, but the dude’s got some food, like, yes. Bring in your food. That’s fine. So he says, Sure. Come on in. So I walk in and he yells at somebody that I’m walking by. Hey, this is Kevin. He brought food. Show them around. And then as I’m walking out he goes, he yells after me, man, I like your style. Thank goodness. Yeah, like this whole gamble…

It could have gone badly. And like, that’s a risky take it like…

That’s right.

Don’t take it personally… But you read the context, you took an informed gamble, because you knew the culture of this startup. And the fact that you brought some food, you made it hard to turn you away and say, No, you weren’t a weirdo and a jerk about it. So you got it. And then you got you got his endorsement.

I also love that you say in here, so you get to meet all these people. You lay out your food on the table, you say, Hey, everybody, I brought some food for you. You get to chat with some of the people who are reviewing your application. And you said, and they’re hung around for about an hour, hour and a half talk to a lot of people. But then I left. I don’t want to overstay my welcome. I wanted to give just enough get enough information and give enough information to make myself still interesting.

But you did one thing really important with one of the people you met, who was somebody you were trying to get an interview with? Talk about that conversation?

Well, I finally, as an aside, the food is important. And there’s something to talk about is important. It’s a lot easier to set, invite someone over, hey, hey, got this food here, come check it out. And then you have like an easy way to talk with somebody then just going in empty handed and saying, Hey, I’m look I’m so and so.

But somebody finally reroutes me to the hiring manager who I had sent an application to indirectly through their online portal, who I had emailed after meeting everyone a couple of weeks earlier, who I had been assured was going to reach out to me and didn’t. He got busy. So like, I’m super nice. Oh, yeah. You sent me an email, right? I said, Yes, I did. And he said, Oh, send me another one. I just got buried, like, just basically boost that back up to the top of my inbox.

And I interrupted, you know, a conversation he was having with young woman. And he had his phone in his hand. And I said, he said, email me and we’ll set up an interview. I said, Oh, well, you have your calendar in your phone right there, like we all do. Right? We all have smartphones. Let’s just set it up right now. And when I say that the girl who had been talking to him goes, Oh, he’s good.

Because his, again, to me, it’s basic salesmanship, which is, you do not accept vague plans for the future. When you’re in front of the person who has the ability to give you what you need. You press for concrete, yeses, or nos or concrete plans for the future. And so he kind of pause him and he goes, Yeah, okay, great. Because he knew in that moment, he was gonna say, No, no, no, just email me, we both would have known that’s a complete brush off. This is a no. And that would have changed my strategy a little bit.

Doesn’t mean I would have been out of the woods. But But and all through this, of course, I kind of make the analogy in sales. If you’re doing this process, you are showing them how you will do the job.

And it reminds me of Barack Obama’s 2008 campaign for president, a big critique of then Senator Obama, like first term United States Senator was this guy doesn’t have enough experience, how is he you got no, got no bills, no laws. And he’s really done anything with, you know, he gave a great speech in 2004. And he said, if you want to know how I govern, watch how I run my campaign. And so in sales, because it is a sales role to get a job, that is a sales job to get the job. You’re doing that as you lay this out. And so…

I love it. You showed them how you work if they’re, if he’s coming after us this way. Imagine how he’ll go after customers for us, you know, you created value by bringing in food you were persistent. But reading the context really, really, really awesome.

So so you get on this guy’s calendar, you’ve got an interview, and your interview goes pretty well. You’ve done all these things, all the research, you’ve made connections, you come in and bring food, do this out of the box stuff. The CEO even says, Wow, I like this guy’s style. This other woman says she’s impressed. You get the interview. And you didn’t get the job offer, right?

No, yeah, they they coming of the interview, you know, another sales tactic. I mean, you always ask for feedback, try to find out where you are in the process. You know, we don’t just vomit a lot of information at somebody and then walk away and go, Hey, that was a great sales presentation. I hope they call us back. You know, you’re gonna uncover and ask questions.

And so I always ask for feedback. That’s something that when you’re dealing with sales professionals, in this case, I was dealing with a CXO like chief revenue officer who, shortly thereafter was promoted to President on the company, you know, in these smaller startups, you’re dealing oftentimes in the hiring process with with executives, and he’s got decades of experience with sales and building sales organizations, they recognize when you’re doing those things that set apart great salespeople.

So part of this is, you actually do have to know your stuff, right? You cannot fake it till you make it in this sort of a context, you’re simply trying to show who you really are in a way that an electronic resume cannot do.

If you know your stuff, and you know that you have what’s needed for the role, you can’t just assume, well, I’ve got what’s needed. So they’re gonna find it, I’ll sit and wait, they’ll look at my resume, they’ll dig in, they’ll do all the work of figuring out why I’m a good fit, you got to flip that around and say, I’ve got this stuff, they don’t know that. I have to make it impossible for them to not know that, you know,

Yeah, that was one of the lessons of my entrepreneurial experience, you know, I started off going, if I just build the perfect mousetrap, the market will recognize my excellence, and start raining cash down on me, you know, through voluntary mutual exchange. And that just doesn’t happen. Marketing is very important. And this is part this is can be considered, like a marketing idea.

So, anyway, come out, they told me what was going to happen, very positive, here are the next steps, you’re gonna meet with such and such. And then I get a phone call, five days later. So say, we went another direction. And I was like, I felt like I got punched in the gut.

You know, at this point, I’ve been building momentum for over a month, you know, you start to develop this. You know, you just get sucked in, you’re like, Oh, you can see yourself in this role. You’ve talked to a bunch of people, everything’s been great, you start to start to feel like you’ve got the job, and you do the interview, and it goes well, and I had to sit down on a stool of my kitchen for a minute and just hold for about 10 seconds and just go ughhhh, because it felt like I now had nothing because I had invested a lot psychically, and timewise into this.

And then I thought, if I was managing sales people, and a prospect came back and said no, and said, well, boss, they said, No, so I guess, we’re out in the cold. I’d be like, why did they say no, I don’t know, you know, they don’t have the budget this quarter, you know, some flippant nonsense reason that we all have. And we all give, for all kinds of reasons, you know, girls give standard reasons why they won’t go with you, jobs give standard reasons for why they won’t hire you.

It goes on and on and on. And you cannot accept, like face value answers, superficial answers for why you don’t, why you don’t fit. They said the usual, which is we want somebody with industry experience, as somebody who’s moved around in different industries, that is always what kind of trips me up in the process.

So I sat down and thought, okay, now what can I do right now sitting here with a no, to try to turn this around. And that is, you know, as you know, indicative of an internal locus of control. So frequently, when we’re in the job application process, we don’t feel in control at all, we are at the mercy of the opaque machinations of the corporate bureaucracy, that we just zipped a little resume through an online portal to and we just sit back and wait.

If you have an internal locus of control, which is the world is what I create, I craft my world and my experience, then that’s just doesn’t happen. I don’t care what you’re going to do. If I if you have not convinced me that I’m not a good fit for this role. We are not finished.

Preach it, brother, I love I love what you said in there, too. You said, You said I needed to find out if it’s if they think they don’t like me as a person and think I’m a bad culture fit, then I’m not going to pursue it anymore. And I’m not going to try to convince them. It’ll only make it worse. So I need to find out. If that’s not the reason for the No, then I’m going to keep persisting.

And so you asked a couple specific questions when you requested feedback. You said, you know, what did you think of I can’t remember this specific question. And you basically got back from him information that indicated No, we actually like you as a person. But we’re sort of assuming that maybe you won’t be able to do this job because of the industry experience or whatever and that signal to you. They like me, I would be a fit there. They just fail to see how I could overcome this obstacle of lack of industry experience. I’m going to push harder to make them see that.

What what did you do after you got that No, and you got the information about why what was your What was your, your final result?

Well, before that, I do want to I do want to dive deep a little bit on for a follow up phone call.

This episode, it’s gonna be a few minutes longer and it’s worth a great story.

So I get the phone call, not from the guy that I interviewed with for an hour, right I get the phone call from someone one level, lower, you know, still executive. And so I needed to get back in contact with the person that I had developed this great report with, who had told me so many times of things, and these are the next steps. And then those next steps didn’t happen.

I texted and I called I left a voicemail, I called the next day and didn’t leave a voicemail. And I’m tracking all this and eon an Excel spreadsheet, because you can’t be too aggressive, you know, and I can kind of visualize it. And, and so I finally called, text him for the second time. And I tell him, Look, a part of my process is whenever a process does not complete, I do feedback so I can understand what went sideways and how I can improve in the future.

By the way, I took this from what I did in previous sales jobs, right, which is, you’re letting people know, I’m a professional. And even if it doesn’t go the right way, I’m going to take personal responsibility for it and see how can I improve the future? Guess what, right? coachability the ability to improve is what one of those key aspects employers want? I said, Would you consent to talk to me on the phone for just a few minutes so that I can get the feedback so that I can improve for the future down the road with somebody else? And he got back to me said, Yeah, okay, let’s talk.

So then I’ve got this appointment a few days out. And now I write on my little notebook. Okay, how do I want this call to go? And what am i decision trees based on what his responses are? And one is, hey, sometimes you get beat out, that’s okay. Like, did I really get sometimes you get beat on a deal. It’s just somebody else came in the candidate pool was more talented, you know, had industry experience was just as great as I am and smart, and so on and so forth. You get beat? Great. I can live with that. How did I get beat? And what can I do to improve in the future.

Two, I had already set the stage a little bit with this was a company I wanted to work for, I was very confident in their positioning and their growth based off of my informational interviews. And I knew that if I got in anywhere in this company, that I would then have the opportunity to show that all of this bluster and talk on the application process isn’t just a flash in the pan that I actually can produce for them. And then it becomes much easier for them to say, Okay, yeah, we brought him in, they did a lower level then he applied for he showed us he was the real deal. Now we’re going to give him the opportunity before, and if they don’t, I’m still in a better position. I’ve gotten paid by the industry experience. I can take that resume now and go somewhere else.

So my questions were, I needed to know, did I get beat, two, is this all just an excuse? Because I tripped, I tripped a wire somewhere, and they wouldn’t hire me to clean the bathrooms. And that was, I don’t ask them. Hey, do you like me? Right? What corporate folks like to talk about is fit and culture. And that is code for, Do we like you?

Yeah, do I want to be talking to this person in the lunchroom? Are they annoying?

Yeah. And it’s huge, right? I mean, you know, this when I was hiring for my one of my businesses, I hired this young woman. And I said, The best thing about working for yourself, isn’t the money. It isn’t the control. It’s choosing who your colleagues are.

And by the way, if you arenot a culture fit somewhere, if that code for hey, they just don’t like you, that doesn’t mean you are a bad person, it means you would not have been happy there either. Right? Like, that’s right.

There are a lot of good people in the world who are annoyed by my personal habits, who would not want to be around me every day. And if that’s you, I don’t want us to be around each other because we’re both not going to like it. So you don’t take that personally either. But but that’s that’s a great thing that you point out that the need to figure out if that’s what’s going on. That’s not something you need to try to salvage. But as long as it’s not that.

That’s right. Yeah, you don’t want to be there. And that’s something that again, when I was in my early 20s, people would talk about fit, like, That’s nonsense. That’s just like a smoke shield for something else. And now it’s like, oh, yeah, I care about fit, got enough experience have been in bad fits where you go, this is not working.

So I asked him this question, and he almost cuts me off before I get done. He says very much. So we think we love what we’ve seen from you. You know, he’s very effusive. I’m like, Okay, great. So now I’m tacking, What other positions if I can’t get this position, what other positions that have already been nailed down sales in two different departments that I want to talk with him about, and so I start to bring it up. And he says, Yeah, I was thinking about you for these departments.

That’s information you never would have gotten if you didn’t get that follow up.

That’s right.

Because got a rejection. And little did you know, they were like, Oh, we got to reject this guy. We’re just not sure. But man, we’d love to find a place for him. You had no idea how close you were until you got that call.

That’s right. And then he tells me, you know, the hiring manager he tells me, be in constant communication. I always tell people like, Listen, if you tell me to be in constant communication you have now this, I’ve done all these things without permission, and you just gave me permission.

So now I tell my friends when they say, oh, we’d love to host you and your family anytime you’re so great, I go, I’ll be at your beach house. Like, I’ll just be there. So I so I get that, it was exactly what I wanted to get off the phone.

What I got off of that was they were positive about me culture fit, stay constant communications with the hiring manager, but I really don’t have anything it was kind of like, Hey, keep looking out on the website for job postings. Don’t be surprised if we just straight call you, you know about a position, but I’m still sitting here with nothing.

So what I say is when I’m behind the eight ball position wise, I have to go gorilla, which I did already previously by showing up cold at their offices twice with food, upping the the CEO cold. But then when I’m in place, once I have the interview, I go conventional, you know, we dress nicely, I’m going to present correctly.

I love that. I love that in your article that you said you go gorilla, you get the attention. But once you got that interview, you didn’t show up to the interview in a clown costume and do a bunch of antics, you already got their attention. Now show them your you’re also a conventional professional who’s not wacky all the time, right?

Because it can be easy to go overboard. Yes. And a little salt goes a long way. People like a little character a little quirky. But if the guy’s gonna be in the office all the time, always doing weird stuff, always pushing. Very few people in organizations can handle right, they’ll spit you out, go Look, just start your own crazy. We got enough here.

And again, this is all informed by my experience building small organizations.

So what do I do? I had already emailed the hiring manager letting him know I spoken with his boss, and this is what he told me. And I just decided, Okay, it’s time to go aggressive again, or go rogue or go gorilla. I use all these different terms. And I’ve done this before, it worked. This is the latest time. So what I did was, I love Winston Churchill. I’ve read his three volume biography by, what was his name, anyway, Last Line. It’s incredible is incredible story of perseverance. I mean, his stories are unbelievable, everyone should read it.

And one of his famous quotes, he’s got 1000 of them is, “success is not final. Failure is not fatal. It is the will to continue that counts.” And I thought that spoke really well to this position that I found myself in right here. And so I go on to Etsy, I put that quote in you know, here’s 15 different things you can buy from somebody that have the quote really nicely, bought some five by seven, essentially, like postcards five by seven pictures of this quote, framed them. I’ve got three of them. I wrapped them with, like old school brown packaging, like paper, like almost like grocery bags, but it’s it’s wrapping paper, but it’s brown, I get twines, all this stuff. My my family is very crafty. So we have this stuff around the house. You know, I wrap it all in twine. So it looks like like, like a package you would receive in the 50s.

And I send one each to the CEO who I met. But I hadn’t had any more communication with him from that day. But I knew I made an impression, to the guy who interviewed me, the top executive, and to the hiring manager. I send them each these three things, cost me 15 bucks, maybe total. And in there, I put a blank card, which is maybe two by three inches. And I said, “the other candidate would have taken no for an answer.” -Kevin Cherrick.

Now this is really tight. You got to be careful about this. Yeah. Because if they’ve hired somebody, and I’m slagging this person who by the way, the position was a high level position, like it’s above like I could conceivably be reporting to this position. Now that I’m kind of tacking to, you know, my fallback position. So I don’t want to piss this person off. I don’t want to impugn their decision making skills when they made, right so you’re basically telling them they made a mistake, but you have to do it in a certain way.

And this goes back to what my sales trainer told me was the difference between the perception of aggression and assertiveness in a salesperson is his tone.

You know, you can say something to someone’s face, and it can come across totally one way. If you say, in a higher register with a smile with a laugh, the exact same words can be interpreted totally differently. You know, a lot of salespeople understand that whatever it is, 70% of communication is the content of the words, it’s not the tones of the body language, etc, which is why we always try to communicate kind of face to face when, when possible.

So I’m sitting here, like working this copy, you know, my first instinct is the other guy, might of hired a woman don’t say guy, the other candidate, you know. And I’m thinking, this person is probably super well qualified, industry experience, coming from somewhere. If they’ve gotten No, there would have been just fine doing their job the way they did yesterday.

But not me, I needed to get this job, I needed to bring some money in. And this was an opportunity that I felt I had to make a lot of money and help this company a lot. So I write that down, I sent it off. And my options there again, everywhere I’m trying to differentiate, right, I could have like, maybe put it in like a cushioned UP envelope, insured this thing and waited a couple of days. And I was worried to this glass because it’s framed. We have a courier service, here in town that attorneys use to send their stuff back and forth, which I would have used.

But instead, I just sent my 15 year old nephew in there, and gave him the opportunity as a learning opportunity for him to see this crazy, and to be a part of it with nothing at risk for him. So he goes in, I make him take pictures with his cell phone of whoever he gives it to, these packages, deliver it, I get done. Okay, this is the first step in actually a big process that I had already planned out previously.

Basically, I was just going to write handwritten notes and letters to these guys over weeks, you know, every few days, kind of like, you know, we’re all familiar with drip campaigns on email. But email is such a cluttered area with so much noise. I’m trying to cut through that with my communication medium. So I do handwritten mail.

So you were ready to do what the guy told you and stay in constant contact? Yep.

Yeah, exactly. And I had done that. Right. I emailed I had texted and got no response back. No, yeah, thanks, Kevin. Sorry, didn’t work out for this one. You know, we’ll keep you in mind for future, nothing, which is kind of par for the course again…

Yeah. This thing is a pattern, and you are very busy, you would observe that and you had also understood that it wasn’t because they didn’t like you. And so you were able to kind of read between the lines and say, Okay, I just need to do something to make sure that it doesn’t get buried.

Yeah. And so I get these things dropped off. And now I’m just sitting there. And the next afternoon, I get an email with a DocuSign document that says labeled job offer. And I and I was walking into the house into my bedroom to talk to my wife, and I’m looking at my phone and I see this as it pops up on notifications. I can’t even believe it.

Because I had this whole plan. I think this is gonna be a couple of weeks minimum, best case.

And it was a it was a roll. That was not anything they were advertising for publicly correct?

Yeah. I mean, I’m sitting there looking at their, their, you know, their job openings board, there’s nothing there.

You created a role for yourself, you forged a role by being somebody that they felt like, okay, we just can’t pass on this guy, we’re gonna find a way to get value out of him. Even if it’s not for this role, we thought or this other role, we thought, What an amazing thing.

So I want to I want to leave some stuff that people can go read in your full article, because there is a final step where you got the offer.


And then you were like, I want to negotiate the offer. And you said right in there, I didn’t want to bluff because I wanted this job. And I would take it even at the original offer.


But I also wanted to set the tone, that I have confidence in my ability, and that now that you have said you like me, I want to let you know that I want to make sure I’m getting value. And you kind of walk through that process. And I think you handle a really a really nice balance there. Like a lot of the things in here, the line between, you know, respect and restraining order with other boxes, and just all these things you talked about with tone. So I want to throw that in there. It’s worth checking out.

But what an amazing process and journey for a company, you’re really excited about a role you really want and putting in the work to win that versus you could have sent out 100 generic resumes that all looked the same and probably waited around for longer than a month and had more stress and heard nothing and be nowhere by now. And in this case, you’ve got something that is that you results in an amazing job that was created for you.

But not only that, the fact that you’ve written this up in a story and shared it and now shared on this podcast. You’ve documented your process and your work. And how many people are going to see this and say, Oh my gosh, I would love a guy like Kevin. Hey, Kevin, what are you doing next? Right, just showing that is a huge added benefit. So kudos to you.

Thank you. Thank you. Yeah, it’s been a great process, and I’m so happy to share it. Thanks for having me on.

Hey, absolutely. Kevin.

I’ll put a link in the show notes. As I said, I highly recommend reading the article. There’s so much good stuff in there that everybody can learn not just for sales roles, and Kevin I I really appreciate that you just sent it to me that you thought to share it. That’s the kind of stuff we love.

So if you have your own Career Crash stories out there, send them to isaac@crash.co. I want more of them. I’ll bring more people on to interview them or read them on the air. So, Kevin Cherrick, you are the man. Congratulations on crashing your career. Have a good one.

Thanks, Isaac.

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