Stop Recruiting, Start Searching

How the Custom Search Works

Step 1: Start with a fresh map, not a rolodex

The default move is to activate a network. Who do you know? Who have you placed before? What rolodex can you work?

Caroline starts with the market, not the rolodex.

For every search, she builds a fresh map of where the right person might actually be — and that map almost never looks like “find me someone who’s done this exact job at a similar org.” It looks like five or six different categories of places where someone with the right combination of skills, instincts, and motivation might be hiding. Different sectors. Different stages. Adjacent work you hadn’t thought to consider.

A sample Market Map for a high-growth Healthcare AI Startup.

The point isn’t the categories. The point is: don’t assume the candidate looks like what you think they look like.

And the beauty is that, when you don’t assume, you end up in places you hadn’t considered. You find people you’d never have known to call.

“A common theme for nonprofit clients is that they want someone who’s done this job before at the same kind of org. And every time we encourage them to look wider — different sectors, different stages, different adjacent experiences — we find someone better than what they thought they were looking for.” 

2. Treat every conversation as learning, not pitching

Here’s where most recruiting goes wrong: you’re so focused on convincing people to take the role that you stop hearing what they’re telling you.

Caroline’s approach flips that. Every conversation is intelligence gathering. She’s not just asking “are you interested?” but:

• What matters to you right now?
• What kind of role structure are you actually open to?
• What’s making you hesitant? What would make you say yes?
• What’s true for you that might also be true for other people in this space?

And then she brings what she’s learning BACK to the org. “The market is telling us X. Here’s how that might change how we’re thinking about the role. Here’s where we might need to flex. Here’s what’s shifted since we started.“

That’s the four-sided alignment in action. What she hears from candidates and the market reshapes what she tells the organization about what’s realistic, and sometimes reshapes what the role becomes.

3. Adjust as you learn (without losing the thread)

The piece that took me a while to really appreciate about Caroline’s process is that it’s iterative, but it’s not chaotic. Every week, she’s adjusting. But she’s adjusting based on real pattern recognition, not vibes.

• What language is getting responses? 
• Which categories of candidates are engaging more? 
• What reasons are people giving for no? 
• What’s showing up over and over that nobody predicted?

Her Health of the Pipeline Tracker captures all of it — not just “where is each candidate in the process,” but “what the market is teaching us, and what are we adjusting this week because of it?”

Every time we encourage [orgs] to look wider, we find someone better than what they thought they were looking for.

What Expansive Thinking Gets You: Sebastian Johnson

The hire that still makes me laugh at how unlikely it was on paper — and how obviously right it was in practice — was Sebastian Johnson, who Caroline brought us to lead the Center for Lived Experience at Think of Us.

The Center was a new thing. We were building it to center the voices of people who’d actually been through the foster care system — not as advisors after decisions were made, but as leaders of the work itself. The person running it needed to be able to translate that work in a LOT of different directions at once: to philanthropy, to policy, to research, to media, to the field, to the young people themselves. They needed to hold real credibility with funders AND with people with lived experience. They needed to know how to run multi-party campaigns across the aisle. They needed execution chops — someone who could actually build the thing, not just talk about it.

If you’d asked me to draft the job description from scratch, I would have gone to the lived-experience world. I’d have looked at advocacy organizations. I’d have done all the obvious things.

Caroline brought us Sebastian who, at the time, was coming out of Arnold Ventures, a major philanthropy organization. On paper, the jump from being a funder to running a lived-experience-led center at a nonprofit is weird. I don’t think I would have generated him as a candidate in a hundred years of drafting.

But once Caroline pulled back the layers, it became clear that Sebastian’s proximate lived experience would be a major asset to the role. He’d been at a major funder, so he understood how philanthropy operates. He’d done deep policy work. He’d led multi-party campaigns that moved bipartisan legislation. He’d held Chief of Staff roles, so he could actually execute. He understood research. He could translate across every audience we needed.

All of the pieces were there. They just weren’t in the place I’d have thought to look.

That’s what an expansive search gets you. Not a different kind of candidate — an entirely different CATEGORY of candidate. Someone nobody in the room would have proposed if we’d started from a job description and a rolodex.

And once we saw Sebastian, we couldn’t unsee him. He was exactly right for that moment

What Rolodex-Hiring Costs You: A Cautionary Tale

I want to tell on myself here because I’ve made this mistake a lot.

At Rev Foods, we were scaling a school food company fast. We were the scrappy alternative to the giants — Sodexo, Aramark — who’d been running cafeteria food in schools for decades and whose entire model we were trying to disrupt. We cooked real food. We sourced local. We worked with smaller districts and built trust one tasting at a time.

We were hiring new account managers after a restructure, and I felt SO clear on what we were hiring for. We wanted to “professionalize” a little. We wanted experience, discipline, diligence.

I met a woman who checked every box. Older than our team. Industry background. Very professional. She felt like a safe hire.

By the third round of interviews, I knew. She wasn’t going to be a fit. She wasn’t scrappy. She wasn’t creative. She knew the process, AND she couldn’t mix and match — which was basically the entire job at Rev Foods.

I went to my general manager and said I wasn’t sure. They said, “I’ve gone to bat for her. You have to hire her.”

So we did. And every single day, it felt like a mistake.

The same pattern played out again and again before I clocked it: we’d say “we need someone from Sodexo or Aramark, they know school food, they’ll come teach us.” We’d get them. They were good humans. And they brought the worldview of the thing we were trying to disrupt. None of them moved us forward.

Meanwhile, the hires that actually built Rev Foods? An ed reform person who understood school districts from the inside. A former Target general manager who could run operations at speed. Folks from restaurants who knew real food at scale. People I never would have pulled off a list — because no list would have had them on it.

The lesson I keep relearning: when I’m matching a checklist I drafted ahead of time, I’m hiring from scarcity. When I’m actually curious about who might do this work brilliantly, I’m hiring from abundance. Those are completely different searches. They produce completely different humans.