From Early Childhood to Talent Tech: Allyn Bailey’s Career Crossroads

Gerry Crispin: I am pleased to be here with Allyn Bailey, who I’ve known for some years. To start this off, this is part one of the Career Crossroads podcast series. It began when I started thinking about how career crossroads affect both employers and candidates—looking at the decisions people make about their jobs, careers, and life stages.

So I’ve got five questions for you, Allyn. They’re all easy questions.

Allyn Bailey: Oh good.

Gerry Crispin: The first one is: how and when in your career did you first decide to get involved in talent acquisition?

Allyn Bailey: That’s actually a fascinating question.

Gerry Crispin: A while ago, right? How did you cross that line? Because most people don’t go to school for talent acquisition.

Allyn Bailey: No, I didn’t either—surprising, I know. It was a long and winding road. I was doing a series of work at Intel around employee experience, trying to understand what made employees tick, how we could understand them better.

Gerry Crispin: What was your job at the time?

Allyn Bailey: At that point, I was a consultant—contracted in. I’d been in and out of Intel several times. I had my own business and was doing experience-led research for the HR organization. I was proud of the work—we interviewed nearly 5,000 people globally and had this incredible breadth of data. I was so excited.

But it literally went nowhere. There were some interesting tidbits here and there. They’d call me in occasionally for a use case conversation, but it would die on the vine. It was frustrating.

Eventually, there was a woman named Delete Broch in the talent acquisition organization who had convinced leadership that experience mattered for candidates. She managed to build a small group—originally four of us, including her—to look at candidate experience.

She had seen my work with employees and said, “I think some of those strategies could apply to candidates. Can you help us understand them?” And I said, “Sure,” because, well, nobody was listening to the employee stuff and I needed the work.

So I got into it. I took the job, worked with her and others across regions, and started looking at candidate experience. Then I had a moment where I realized: we’re asking all the wrong questions. We were focused on making people like us more, improving brand reputation, and helping people feel better about job hunting. But that wasn’t the issue.

The experience was a problem, but it wasn’t a candidate problem. It was the system—the whole ecosystem of how work was being done just didn’t work. And that’s how I ended up there. I spent the next seven or eight years deeply involved in understanding the experiences of hiring managers, recruiters, candidates—everyone. We transformed how we thought about talent acquisition.

Gerry Crispin: What company was that?

Allyn Bailey: That was at Intel.

Gerry Crispin: So Intel was your first?

Allyn Bailey: That was my first, yes.

Gerry Crispin: Yay.

Allyn Bailey: Yeah. Before that, my work was in L&D—learning and development.

Gerry Crispin: Ah, okay.

Allyn Bailey: My background is actually in early childhood development. My degree is in Child and Family Studies.

Gerry Crispin: Why do I think that’s relevant? It is relevant.

Allyn Bailey: It was hugely relevant. I spent a whole career—there’s a whole group of people who know me from my work in early childhood and infant development. I worked on building better infant and toddler care programs. I did that for about 12 to 15 years.

Eventually, because I worked with teachers, people assumed I could do L&D. My first corporate gig was with the Intel Inside Program, teaching OEMs how to follow marketing rules so they could put that little “Intel Inside” sticker on their products.

So yeah—long and winding road. Nothing was a direct path. But it’s all been connected by a core understanding of the human condition: how we think, learn, grow, and connect to our work. Whether it’s learning work or other types—it’s all the same. It all connects.

So while I didn’t start in the TA space until 2010, I’ve been trying to understand why people do what they do since forever. Because I’m old.

Gerry Crispin: I love that. So, in leaving Intel—which is relatively recent—was that a push or a pull? What motivated the shift?

Allyn Bailey: Transparently, it was realizing that we had done some really great work—made big shifts, retrained our entire org, rebuilt processes. But a new leader came in who was focused on efficiency and rolled things back, hard. I saw the team getting dismantled.

I had an epiphany: I could stay and try to save what I could, or I could take what I learned and try to help others. That was the decision. I’ve had many disappointing career moments—“God, we worked so hard, why didn’t it stick?” But that’s the way the world works. Sometimes decisions get made that you can’t control, and you have to decide your own value in the conversation.

Gerry Crispin: Right. Things don’t last forever.

Allyn Bailey: They don’t.

Gerry Crispin: So you create value in the moment. When the moment ends, you move on to the next.

Allyn Bailey: Exactly. At that time, I was working a lot at the intersection of systems design—process, role, tech. I was collaborating with vendors, learning how their products worked. I saw a gap in the conversation: not enough people were discussing how tech actually supports or transforms organizations. That frustrated me.

Gerry Crispin: So the opportunity to go to SmartRecruiters was a bridge?

Allyn Bailey: It was. Though in between, I put out my own shingle again—I’ve done that many times.

Gerry Crispin: An interim solution.

Allyn Bailey: Exactly. But I’m terrible at it. I hate schlepping for money. I want to be in something, not selling it. Business development is not my strength.

Eventually, I did some contract work with a group called Genius Group—an entrepreneur building a new learning framework. I helped build their HR function. But I realized TA and HR weren’t where I wanted to be long-term.

Then I had the chance to join SmartRecruiters. Jerome and others invited me to help build out their hiring success consultancy. I thought, “Sure, that sounds interesting.” So I jumped in. Winding road, Gerry.

Gerry Crispin: And that worked out. I love the winding road visual.

So where you now sit in that winding road—you’ve gone from SmartRecruiters, which is now part of SAP. How does that look?

Allyn Bailey: I get asked all the time, “What’s your job now?” It’s hard to explain.

I’ve done a few things—ran services for a while, then moved into marketing. I spent the last year focused on helping people understand our story and what we’re building. It was a brand role—filling out our narrative.

Now, I own our brand and experience base, which means I help leaders like Rebecca and Sharon communicate what they’re building and why. The best analogy I can give is—I’ve been watching way too much West Wing—I’m like a staffer. I listen to ideas, bring in outside perspectives, craft narratives, and help them land.

Gerry Crispin: What strikes me is you’re really good at seeing what’s in front of you and figuring out how to contribute. And then, if it doesn’t coalesce into something, you find the next interesting thing.

Allyn Bailey: I get told a lot that I’m very pragmatic. I always look for the business answer, how to solve big problems. But underneath it all, I’m driven by one thing: where can I help influence the conversation?

It’s about contribution, and understanding how people work together. Anthropology, really. Right now, I’m excited by conversations around how tech—AI especially—changes identity and connection to work. That shifts how we manage human capital.

We’re a systems-driven culture. We work the way the tools allow us to. If we can fix the tools, we can fix how we think. But first, we need to ask: what is it we’re trying to accomplish?

Gerry Crispin: We need to step back and reimagine what we could be doing. So, thinking about your fourth question—where might you go from here?

Allyn Bailey: Personally, I’m doing more writing, more translating complex ideas so others can understand them. I’m moving from building to explaining. That might define my next chapter.

I tell people I don’t have a path—I have tentacles. I put them out into the world and wait to see which ones tingle. Right now, the ones tingling most are the opportunities to start larger conversations. I think I’m good at that, and I want to do more.

Gerry Crispin: I love all of that. So, last question. We’re in a world of uncertainty. I’m not asking what advice you’d give your younger self—but if someone like you were just starting out, what would you tell them?

Allyn Bailey: The number one thing: no decision is permanent.

I grew up in a hierarchical, structured environment—very black and white. Performance reviews, right and wrong ways to do things. But when I broke free of that, I realized the world isn’t so rigid.

There are always outside forces telling you what you should do. They influence your choices. But don’t get so caught up in trying to make the “right” choice that you become paralyzed.

Move. Even if you’re not sure it’s the perfect move. You can always move again. Too often we stay stuck because we’re afraid the next move might be worse, or final. But that hasn’t been my experience. Movement is important. Otherwise, you stagnate.

Gerry Crispin: Love that.

Allyn Bailey: Systems are designed to keep you consistent. If you stay within them, you’ll get really good at being consistent. But that’s boring as shit.

Gerry Crispin: That’s a wonderful stopping point. Thank you very much. I think you’ve given all of us a lot to think about.

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