Client Case Study

FROM SURVIVING TO THRIVING.

Kevin was a CISO whose weeks were, in his words, five Mondays and two Fridays, looking for a way out without giving up his income. He left with a hybrid structure built around what he actually produces, and got his weekends back.

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The Challenge

Kevin was a CISO working 120 hours a week, seven days a week, a pace that had already put him in the ER once.

The Shift

He stopped customizing resumes and cold applying and started reaching out directly to the leaders he wanted to work for, backed by real research on each of them.

The Outcome

Weekly hours projected to drop from 120 to roughly 45-50, with income potential doubling if the pending offer closes.

Olivia Gamber

A Note From The Founder

Olivia Gamber, CEO

When I first talked to Kevin, my first thought was: this is a busy guy. I have no idea how he's going to commit to this, but he will. He was running a security organization with no weekends, five Mondays and two Fridays as he puts it, the kind of schedule that had already landed him in the ER once. He wasn't looking for a bigger title. He was looking for a way to breathe.

What struck me was how little he thought of his own output. He'd built a career on being the person who absorbs the workload nobody else can carry, and somewhere along the way he stopped seeing that as valuable. He'd say things like I'm not a toot my own horn kind of guy, and mean it. That's not humility you coach around. That's a block you name directly.

The job market he was walking into didn't reward the old playbook either. Customized resumes and cold applications weren't moving the needle for someone at his level anymore. He needed to reposition himself as the asset he actually was, and he needed to believe it while he did it.

Five Mondays, Two Fridays

Kevin

Yeah, I get it 100 percent, but I am not a toot my own horn kind of guy. That's not me.

Kevin

As I put it, we have five Mondays and then we have two Fridays. So that's where my weeks go. I don't even have weekends. It's just constantly going over and over and over again.

The Market Doesn't Work Like It Used To

Kevin

It's been a frustrating, exhausting journey, as the kids say nowadays... So you can't just go out there and customize every resume. You can't just go out there and cold apply. You can't go out there and do all this normal shit that you have to typically do before the last couple of years, right? That doesn't work anymore. It is a lot of reaching out, selling yourself more so than anything.

“You can't just go out there and customize every resume. You can't just go out there and cold apply. That doesn't work anymore. It is a lot of reaching out, selling yourself more so than anything.”

Owning the Value He Produces

Olivia Gamber

I'm not a workhorse. I'm a thoroughbred. I know my role. You know, you guys were going to be a good partnership because you hadn't owned the value of what you produce. It's just in your blood. And it's so rare to produce at that level. And being in a place where you can package and position, if you're going to work that hard, you should be getting that kind of upside, right? Because when they lose you, I mean, man, they're going to feel it.

Kevin

I helped automate quite a bit of it. So I leveraged some AI to help get some of the basic constructs down just due to time... I worked with and leveraged some Claude prompts that I built to help sketch things out and do some research for me. And that's what seemed to get better responses, is by doing a little more research on them as people.

“This video actually saved my life... In order to do that, find your why. And that's what keeps you going through those hard times.”

Offers, and Weekends Back

Kevin

If sword does come into play, then it'll double what I was making. It'll double my income. And that's not including bonuses... if the bonuses work out on the schedules that have been approved on top of bonuses, it will be seven figures. And then two of them have profit shares for IPO that are locked in for sharing as well.

Kevin

It's crazy because the market is so weird... but it does take resilience and not giving up because there have been plenty of days I wanted to say, fuck it, I'm done... but the next day it's like, OK, no, got to get up. Got to get going. Got to try this again.

Ready to Stop Applying?

Kevin spent months scrambling between offers instead of applications, because he stopped selling his time and started owning his value. If you're carrying a workload that's quietly costing you your life, your next move starts with a conversation.

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Read the full transcript

Kevin: I am not a toot my own horn kind of guy. That's not me.

Kevin: It's been a frustrating, exhausting journey, as the kids say nowadays.

Kevin: as I put it, we have five Mondays and then we have two Fridays. So that's where my weeks go.

Kevin: you can't just go out there and customize every resume. You can't just go out there and cold apply. You can't go out there and do all this normal shit that you have to typically do before the last couple of years, right? That doesn't work anymore. It is a lot of reaching out, selling yourself more so than anything.

Olivia: Oh, yeah. I love that. That's cool. I haven't I was trying to watch it. There's an ad. I'll watch it after this. There's that.

Kevin: this video actually saved my life. In order to do that, find your why. And that's what keeps you going through those hard times.

Kevin: if sword does come into play, then it'll double what I was making. Wow. It'll double my income. And that's not including bonuses. Bonuses, if the bonuses work out on the schedules that have been approved on top of bonuses, it will be seven figures. That's incredible. And then two of them have profit shares for IPO that are locked in for sharing as well.

Kevin: I helped automate quite a bit of it. So I leveraged some AI to help get some of the basic constructs down just due to time. Because by putting all the effort in me writing all these messages and tailoring everything, it's time I didn't have, unfortunately. I didn't have to take it away from someplace. So I worked with and leveraged some Claude prompts that I built to help sketch things out and do some research for me. And then

Kevin: those Wednesday meetings, I wasn't there able to attend yesterday, unfortunately. But I really like those because they're hugely valuable for the ability to bounce ideas off of people. I've

Kevin: I did some digging on each specific leader to go a little deeper. Not to the point it became creepy, but to the point where I got enough information to be able to kind of get some personal connections and ideas with them that way. And that's what seemed to get better responses, is by doing a little more research on them as people, not

Kevin: as you guys say, trust the process is trusting the process because it does, it does work.