You are probably a weird special case too
Last year, I published a lot of data about the job market and the experience candidates were having (getting ghosted a lot). But I didn't share much about my own recruiting experience.
I started a new job just before Thanksgiving. I wrote about my role, as well as some others I'd considered, when I first announced it. This week, I wanted to share some data from my job search.
I was a long-time founder and startup person who was interested in seeing an enterprise from the inside again. I write a lot in public and I have a strong and relevant network. For these reasons, you might argue that my recruiting process was a weird special case.
But in this market, I believe most people are weird special cases whether or not they realize it, and maybe sharing my data can help someone else.
Hello? Is this thing on?
I didn't start out looking for a job. I was happy making nerd processor, coaching startups, and building stuff. In fact, I was planning to start another company this year. But in May 2025, I got a call about an enterprise role in AI transformation that was interesting enough to consider.
That initial outreach call is the only one I received directly from someone with a recruiter job title in all of 2025. This is common for founder-CEOs; recruiters don't know that you'd be open to an operating role, so they rarely call.
That particular role wasn't the one, but it opened me up to considering other operating roles. All of a sudden, I was running a job search.
It's people all the way down
There are many consultants and AI tools promising to help with your job search. Awesome! But the main thing that helped with my job search is talking to everyone I have ever enjoyed working with in the past.
If you take nothing else from this piece and you're looking for a job: your network is your most important asset for finding the right role. Not the job boards or the AI tools. It's the people.
After that initial recruiter call, I talked to a lot of people to figure out what I wanted to do. Between that first call and the day I accepted my current job, I had informal conversations with 32 different people about my job search.
A few of those early conversations focused on specific opportunities, but 84% of them were more open-ended brainstorming (not even counting the conversations I had with AI).
Those open-ended conversations helped me clarify what I wanted. However, only 15% of them turned into something concrete, such as discussion of a specific role or a relevant introduction.
Although I considered CEO/other exec roles at smaller companies, I was pretty sure I wanted to be inside an enterprise. But of the eight positions I considered in earnest, only two had existed prior to my pitching them on opening the role.
In other words, even though I would have been open to considering pre-existing roles, I didn't really get recruited for them. On the other hand, I was able to co-create most of the roles I ended up considering. In at least two cases, the company has now hired someone for the role that I designed, even though I do not work for the company myself.
Interviewing takes a long time
In the end, I had meaningful conversations with eight companies about working there, five of them deeply. This resulted in four interesting job offers.
Only one process moved fast: I got an offer three weeks after our initial conversation. The other four (including the one where I did not get an offer) all took 4-5 months from start to finish. In these lengthier processes, I met with 8-15 people as part of my interview. This is a long time and a lot of interviews, even for exec roles.
I had previously collected data from other job seekers about their processes, so I expected to spend a long time. But even I was surprised at how long everything took.
What I expected vs. what happened
It didn't matter that I had accomplished a lot and had an industry reputation. My particular experience made me a weird fit for many conventional recruiting processes. I found many people excited to hire me! But I had to work to find them. If I hadn't hustled, people wouldn't have expected that I was open to being hired.
Only a small portion of my early conversations turned into something tangible. A lot of people who said they would follow up did not. On the other hand, someone I knew only slightly made multiple intros that led to job offers. You can't know ahead of time which conversations will be the most helpful, so you need to have all of them.
The bottom line: Exec searches take more time than average. But even if you're not looking for exec roles, a job search is a major endeavor. I ended up having many more conversations than I'd expected when I decided to look for a job. Most of them helped me refine what I was looking for and I'm grateful to everyone who spent time with me. Few of them turned into concrete opportunities, and I couldn't have guessed ahead of time which those would be.
It's still people all the way down.
Kieran
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