The Executive Search I Survived, and the Map I Wish I'd Had

I have spent the last 20 years mentoring people through the big moments, the career pivots, the hard resets, the relationship decisions that reshape a life. So when my own executive search came around and I decided to run it full send, I figured I had a head start. I didn't. I still ended up buried, juggling accounts and tabs and half finished documents at midnight, thinking to myself, I build software for a living, why on earth am I doing this by hand.

So I did two things. I finished the search the hard way, and then I built the system I wish I'd had the whole time.

This is the honest version of the hard way. Every step I actually took. No secret sauce held back, because the sauce was never a secret, it was just a mountain of work. Read it, follow it, and you can absolutely do this yourself. Most people who do it by hand succeed eventually. I just want you to see the size of the mountain before you decide whether you want to climb it alone or take the path I cut afterward.

One note before you start. I ran this as a full time effort because I was between roles. If you are gainfully employed you can run it part time and that makes complete sense. But if you want to go full send on landing the next role, this is what full send actually looks like.

First, get your house in order

Set up several email accounts you can use. I ended up running four. You will understand why by the end of this, but for now just know that a serious search generates a serious amount of traffic and you want lanes for it.

Sign up for the AI chats. All of them. I use ChatGPT, Grok, Claude, Copilot, and Gemini, and I do not use just one, because they each give you something a little different. My method was to have one draft something, then have two of the others critique it, then I would settle on the bits and pieces I actually liked. This works. It also means you are now managing five tools, five logins, five sets of free usage limits, and a lot of copy and paste. Hold that thought, it matters later.

Get your resume revamped properly. A professional executive resume revamp runs about $400. That is real money, and it gets you one strong static resume. Keep your base resume handy and do not gut it, but understand what that $400 buys you and what it doesn't. It doesn't solve the part that actually wins interviews, which is a resume tailored to the specific problem a specific company is trying to solve. More on that near the end.

Fix your LinkedIn. I used the AI chats to help me rewrite mine, same method, one drafts, two compare, I keep what fits. And get a professional photo. Not a cropped wedding shot, not a selfie in your car, an actual professional photo. People look you up before they ever talk to you, and the photo is the first handshake.

Figure out who you are and who you are actually targeting

Write out the role titles that match what you want to do. This is the quiet beginning of the most important document you will build, your personal career focus. Nail the titles first.

Then write out what you do really well for those titles. I spent a couple of days on this, wrestling with it, pulling apart my best skills and matching them to the roles. This is harder than it sounds because you have to stop describing your old job and start describing the value you carry into the next one.

Decide the size of company you want. Early stage up to around ten million, small around fifty million, and up from there. You have to pick, because it tells you who to target and how to talk to them. A ten person startup and a Fortune 500 do not want the same executive.

Build your target company list. With your skills and your company size and ideally an industry, you can start listing the companies you want, and then the specific problems each of them has. This is where you start building a value statement, the company has a problem, you have the solution, and you can say it in one clean line.

The networking part I genuinely dreaded

I am not a natural networker, so I had to find a way to do it that fit my personality instead of fighting it.

I went where the people already were. Industry seminars, meetings, even sales pitches, and I asked every former vendor friend I had to invite me to everything. Then I started reaching out to my connections directly, and here is what surprised me. Nobody was worried I was going to ask them for a job. They all just wanted to help me get into the next role fast. I do not know why so many people treat being unemployed like something shameful to hide. Sometimes it just happens. I hit it head on instead of hiding, and the response was genuinely great.

I took notes on everyone. Every event, every meeting, every real conversation went into notes. Good conversation, I asked for email and phone. Shorter one, I asked if I could reach them on LinkedIn. Those notes became my prospecting list, and that list became warm leads later.

I lived on LinkedIn. I got familiar with companies, people, and open roles. And I will say the thing people tell you never to do. I applied through job boards. Everyone says don't, but my process turned more than 40% of my applications into a conversation, and the current average sits around 10%. The board was not the problem. What I did with it was the difference.

Apply, and apply smart

Do not be shy, just apply. I chased leads that were not a perfect match, and I followed them anyway, because here is my theory. Every interview is one interview closer to the best interview, the one that ends in a job. You get sharper each time. But before you apply, there is a move worth making.

Warm the lead first. Before I applied, I would reach out to the hiring manager or the executive, and I kept it light. Nothing like hey I heard you're hiring and I happen to be exactly who you want. More like, hi Name, I really admire the work you're doing in this area, I'd value connecting with you. It was rare not to get the connection. Then I would apply, and message that same person, and now my application landed on someone who already knew my name.

Post meaningful content where people can see you. I only really use LinkedIn, so that is where I post. Anyone looking at you specifically should be able to watch from the shadows and get a feel for who you are before they ever reach out. Let the quiet observer see something worth calling.

Get ready for the room before you are in the room

Build your About Me document. This one changed my prep. You want a document that captures who you are, the real answer to who are you and why you. (Build and download your own, free, right now.) I used mine, plus the AI chats, to run myself through interview questions over and over. I would drop in a real project I had done and have the AI ask me questions about it, the kind a live interviewer would ask. You already know how to do these jobs. The work now is being ready to prove it out loud, under pressure, on demand. I even practiced with random people in normal conversation, answering like I was in the interview, so that when the pressure was real my answers were already natural.

Know what you are submitting for, every single time. If you are a CIO and you fire your base resume at a company hunting for sports venue experience, you have not answered their real question, which is how do you fix our problem. A strong candidate still gets that interview, but it does not go far. It becomes, we want to test our top choice against someone, and you are the someone. Great practice. That is all it is.

That means custom, every time. Custom resume and custom cover letter for every role you are serious about. Online applications, solicited applications, referrals, all of it, tailored to the specific problem in front of you. This is the part that actually converts, and it is also the part nobody has the stamina to do by hand for the fortieth application.

And here is where I broke

Remember the four email accounts and the five AI chats? Here is why. The chats only give you a small slice of free compute, and the kind of tailoring work I was asking for would eat an entire account's free limit on a single submission. So four accounts, five tools, constant copy and paste, version chaos, and me at midnight trying to remember which chat had the good draft of which cover letter for which company.

Somewhere in that mess I stopped and thought, this is insane, I build systems for a living, why am I hand assembling this like it's 1998. So I built the thing that does all of it in one place, tailored resume and cover letter per role in minutes, the About Me and interview prep, the target work, the value statement, the whole process I just walked you through, sequenced into manageable pieces so you are never staring at the whole mountain at once.

That is the difference between this guide and the system. This guide is the mountain. The system is the path I cut through it after I was done bleeding on the rocks.

You can climb it by hand. I did. Or you can try the whole thing for 14 days, and if it isn't for you, you get your money back, no wrestling required.