From Early Childhood to Talent Tech: Allyn Bailey’s Career Crossroads
What happens when an expert in infant development rewires recruiting? Allyn Bailey shares her career journey and the systems thinking reshaping TA.
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Featured Guests:
Carmen Hudson – Talent acquisition leader and recruiting consultant (companies mentioned: Capital One, Amazon, Starbucks, Microsoft, Yahoo, Recruiting Toolbox)
Hosts:
Gerry Crispin – Co-founder, CareerXroads
Episode Overview:
Gerry Crispin sits down with Carmen Hudson to explore her career journey in talent acquisition, from her first exposure to recruiting in the late 1990s through leadership roles at major organizations and into consulting and entrepreneurship. The conversation focuses on how career decisions are made over time, what Carmen learned from working at different companies, and how curiosity and willingness to try new paths shaped her work. Carmen also shares what she’s focused on now and the advice she would give to professionals facing uncertainty in their careers.
Key Topics:
Discovering recruiting through early internet sourcing
Early sourcing roles and remote work
Career moves involving Capital One, Amazon, and other large employers
Evaluating teams and managers when choosing a role
Transitioning from in-house recruiting to consulting
Work with Recruiting Toolbox across companies of different sizes
Exploring entrepreneurship, writing, and technology
Pulling away from recruiting and writing a historical fiction novel
Advice for navigating career uncertainty
Notable Quotes:
“I didn’t even know there was a job for people to help find candidates.”
“After a few years, I became very good at determining whether I would enjoy working with this team, this person, these people.”
“There was no other company I wanted to work for.”
“Give yourself permission to try something else.”
“Eventually, you do. You figure it out.”
Takeaways:
Carmen Hudson’s career reflects an openness to experimentation and learning across roles, companies, and career stages. She emphasizes the importance of understanding work environments, giving yourself permission to try new paths, and learning from both successes and setbacks. Her story highlights how career decisions evolve over time and how curiosity can shape long-term professional growth.
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Gerry Crispin: So we are now recording, and it’s a wonderful day. It’s actually Friday here, so thank God it’s Friday. It’s kind of cool out. I’m with Carmen Hudson, who’s one of my favorite people and who is perfect for this idea that, when we started Career Crossroads, we wanted to think about the decisions not only of employers, but of candidates—how they learn to make better choices about jobs over the course of their careers.
There are few people out there who’ve been in more interesting companies doing interesting things than Carmen. So I just think it’s kind of cool to hang out with you for a few minutes, Carmen.
Carmen Hudson: It’s exciting and fun, and we’ll just explore.
Gerry Crispin: We’ll explore. I’ve got five questions, but they’re easy ones. The first is: how did you get into TA in the first place?
Most people don’t start off in life and say, “Oh, I just gotta be a recruiter.” So tell me—when was the first time you thought, “Oh God, I’m going to go recruit”?
Carmen Hudson: It happened for me soon after the internet—so late ’90s. The internet happened and my mind was blown. I didn’t care about anything else. All I wanted to do was play on the internet and see how it worked. It was an amazing thing.
A friend of mine got a job at another firm not far from where I was working and called me and asked if I wanted a job. I said, “Well, what is the job?” She said, “Well, you’ll get to use the internet, and you have to use the internet quite frequently.” I said yes. I did not know what the job was.
I got there and it was an assistant recruiting role—I don’t remember what we called it—but I searched the internet for candidates. That’s what I did. I didn’t even know there was a job for people to help find candidates. This was my first exposure to recruiting overall, and I loved it. I simply loved it.
The woman who hired me for that job and I have gone on to become friends. She’s done other work, lives in California now, and we still talk every week.
Gerry Crispin: So you obviously did that for a while, and then you suddenly realized there had to be something more there. How did you make the choice to get from there to your next job?
Carmen Hudson: Well, my next job—we actually decided to move to Seattle.
Gerry Crispin: Wow.
Carmen Hudson: This was around 1999. I found a job that required me to work from home. Everything was set up for me, and eventually I sourced everyone from home. It was a sourcing job, but that wasn’t great for meeting people and getting to know the new place I lived.
I always like to tell this story that I decided I was tired of William, and that was it—I was going to break up with him. I got a job in Florida with Capital One. Again, it was sourcing, but it also gave me my finger on what else was happening in the world. I found myself going to different conferences and being totally immersed in staffing.
That didn’t last long, because William called me—actually, I got a call from Amazon. And that’s how I was recruited back to Seattle. That was the beginning and the end of that story.
Gerry Crispin: Now I see some of this linkage—Amazon, William, you, et cetera. I get that.
Carmen Hudson: It was all linked. Yes.
Gerry Crispin: So you’re beginning to make better decisions about your stage of life and all of that.
Carmen Hudson: Yes. I will tell you that my time at Capital One was invaluable. It was six months, and I learned so much about recruiting from so many different sides. Had I stayed there, I would’ve had a fabulous career. I’m pretty sure of it. But I didn’t—I moved back.
Gerry Crispin: You certainly had a succession of Capital One, Amazon, Starbucks, Microsoft, Yahoo. It’s not like you didn’t go to interesting companies. You had a bunch of them.
Carmen Hudson: Yep.
Gerry Crispin: How did you think about those choices?
Carmen Hudson: I figured out how to take stock of the company I was deciding to join. I loved Amazon until I got to the point where I had a boss I didn’t enjoy working with. That was my mistake, because I probably would have millions of shares of Amazon stock and be talking to you from a yacht somewhere.
But after a few years, I became very good at determining whether I would enjoy working with this team, this person, these people. That became very important to me.
Gerry Crispin: Learning the kinds of questions that would determine whether the environment was one you wanted to be in.
Carmen Hudson: That’s what I had to figure out. By the time I made it to Yahoo, I had it figured out. I knew very much what I wanted to do.
Gerry Crispin: I love that.
Carmen Hudson: Yeah.
Gerry Crispin: So what caused you to shift from the light side to the dark side of providing services?
Carmen Hudson: After Yahoo, where I had a fabulous career, I decided there was no other company I wanted to work for. There was no other place that was going to give me what I was getting.
Gerry Crispin: You’d been to every major corporation by then.
Carmen Hudson: Not every one, but plenty of them. Most would’ve given me the same type of work. So I decided to join John and take on the recruiting world through Recruiting Toolbox.
That was exactly what I needed to be doing. I got to work with tons of companies—from very large enterprises to very small startups—who just wanted to figure out how to do recruiting better. That was incredible work.
Gerry Crispin: It also gave you flexibility to think about writing a book, working as an entrepreneur, building technology. You’ve crossed into almost every facet of our industry.
Carmen Hudson: And that was what I wanted to do. I probably couldn’t have named it at the time if you’d asked me why it was important, but it was important for me to try something new, do something interesting, and push myself to create.
Gerry Crispin: You were always willing to embrace the unknown and figure it out like a puzzle.
Carmen Hudson: And I still am.
Gerry Crispin: From where you sit now, having done so many things over a long career, what’s left? What do you see in front of you?
Carmen Hudson: What’s interesting is that I’m pulling away from recruiting. I thought I’d be completely grabbed by AI, and I am interested in it, but not as much as I would’ve been five or ten years ago.
I’m in the middle of writing my novel.
Gerry Crispin: I love it.
Carmen Hudson: It’s historical fiction—straight-up fiction—based on my father’s story of leaving home very young and joining the Army when he was 12 or 13 years old.
Gerry Crispin: How did he get into the Army at 13?
Carmen Hudson: That’s exactly chapter one. It was a blend of not paying close attention to ages and some boys deciding to put their ages up.
Gerry Crispin: I can’t wait to read that.
Carmen Hudson: That’s what’s happening now.
Gerry Crispin: I have one more question. There’s a lot of uncertainty in the world today—challenges around work and career choices. If you saw someone like yourself today, facing “What do I do?”, what advice would you give?
Carmen Hudson: I’d say: follow your dreams. Follow what you want to do professionally. But give yourself permission to try something else. Give yourself permission to say, “I’m going to try this.”
It’s going to feel scary. I’ve walked into jobs thinking, “Can I actually do this?” or “Do I really know this person well enough to deliver what I promised?” Eventually, you do. You figure it out. Sometimes you’re the hero and people applaud you. Sometimes you don’t do as well as you hoped—but you learn the lesson and do better next time.
Gerry Crispin: I think that’s great. You’ve had a fascinating, winding road.
Carmen Hudson: Yes.
Gerry Crispin: But one that’s constantly fascinating to me. You always had enthusiasm and curiosity about where things could lead, and you embraced that with passion and engagement.
On that note, thank you very much. I appreciate your time and the impact you’ve had in our field. You’ve made a big difference.
Carmen Hudson: Thank you, Gerry.
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Tagged as: Career Crossroads, CareerXroads, Sourcing, Talent Acquisition, Yahoo, Curiosity.
What happens when an expert in infant development rewires recruiting? Allyn Bailey shares her career journey and the systems thinking reshaping TA.