The Breakthrough Hiring Show: Recruiting and Talent Acquisition Conversations

EP 208: Turning AI Into a Strategic Engine for Talent

James Mackey

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0:00 | 53:09

Daryl Escoto started with a mindset shaped by constant motion and perspective, and carried that into a career spanning Amazon, Microsoft, Uber, and now leading Talent Acquisition at Bill. In this conversation, he explains that the real opportunity with AI isn’t automation; it’s building a continuous system that identifies objectives, implements solutions, drives adoption, and constantly asks what’s next. It’s a look at how TA evolves from a reactive function into a strategic arm of the business, powered by repeatable learning, smarter workflows, and a relentless focus on impact.

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SPEAKER_04

Hey everyone, thanks for tuning in. Today we have Daryl Escoto on the show. Daryl is currently the head of TA over at Bill. Daryl, it's great to have you.

SPEAKER_00

Good to be here. Thanks, James. Thanks for the invite. Yeah, of course.

SPEAKER_04

And you're local. You're right here in the uh DMV market where I am too, which uh it was great. We had the everybody tuning in. We had the opportunity to meet up for coffee recently. So it's nice, it's nice finding people in tech in the DC area. We don't get a whole lot of that, it seems like.

SPEAKER_01

So I would agree, hence why when I got your invite, I said, Oh, he's local. Let me take advantage of this. Absolutely. Always always happy to expand my my network here in the local DMV area. It is home, so yeah.

SPEAKER_04

Yeah, yeah, for sure. Well, today uh I we're all very excited to learn more about you. Um, so where are you from?

SPEAKER_01

Here in the deep, right here in the DMV area. Grew up here, went to University of Maryland, had a little foray to Seattle for a few years, but this was home, came back um after about three years in Seattle. Um, and you know, love it here. Uh been in Arlington for about 24-ish years. Great place to live. So, yeah, right here in the DMV.

SPEAKER_04

Nice. So, you um did you grow up in Maryland?

SPEAKER_01

Yeah.

SPEAKER_04

Okay, cool. Nice, good stuff.

SPEAKER_01

Uh, so what were you like as a kid? I was pretty even keel. Love playing with my friends, loved being outside. I was um out a lot. My mom, she was a stay-at-home mom, always was telling us to go outside, you know, enjoy the weather. Got into you know sports at an early age. Yeah, loved being outside, loved, you know, never liked to sit still, very much like you know, certain certain animals, certain things, like if they if they sit still, they think they're gonna, you know, pass out and die. I was very much like always have to be on the move, so out and about.

Immigration Stories And Perspective

SPEAKER_04

Yeah, yeah. And you were saying that um your your parents immigrated here, right? I think you were saying too, right? Yeah, my dad did. Your dad? Okay, where is he from initially?

SPEAKER_01

He's originally from Cuba. Oh um, he lived there until he was uh, I believe about 12-ish. And then they escaped, uh, went to Spain for believe a school year. Um then my dad came here to the US when he was a teenager, and then uh he went to the New York area, lived there, and then he went in the military. And when he was in the military, is when he and my mom met and pretty much when they had me.

SPEAKER_04

Nice, nice, good stuff. And um, you know, I'm curious, like, do you feel like that background, particularly your dad coming from Cuba? Do you feel like that has impacted you in terms of how your values and how you think about even like you know, how you think about hiring and building teams today?

SPEAKER_01

I think about hiring, probably. I would think around in terms of like my values. Um, it did it impact me? Let's just say it was a blueprint. It was very much a dinner table conversation. It was very much a we saw it, we heard it, we understood it, we know exactly what my dad had to go through, what my grandparents went through. Um, and in light of that, yeah, it did instill a lot of like, you know, there's never a way that you can't. If I can escape a country, if I can escape communism, you have no excuse to complain about school being too long or boring. You know, you have no excuse to think about this, or think about, you know, if there are constraints, navigate around them. That I would say I definitely did bring into my professional life. And it's like, you know, is it really as hard as we think it is? You know, anytime I'm facing difficulty, a new scenario, a new challenge, something that may not have existed before that we're coming up upon. And it's like, okay, so you know what? In light of the work, in light of things that could be worse, this is really nothing. So it did instill that from a very early age in me. I've always challenged status quo. I've always thought, well, you know what? If escaping a country can become um an accomplishment, so can anything else.

SPEAKER_04

Yeah, I uh I've actually I've been thinking a lot about lately for whatever reason, like this the concepts of like what we find as to be like discomfort or putting like what we perceive as like major adversity. Um and it's I think it's interesting because it's it's very it can be very easy to I think lose perspective and to truly like when when people are talking about like certain obstacles that they might face, like for instance, like even in our industry or tech or certain obstacles that they're facing in life, sometimes it's like there is, I feel like almost like uh there could be, and it's very normal. I think we all do it to some extent, but we a loss of perspective of understanding like what true hardship really can be like, yep, in so many different places in the world. And when we say like we're we're sad, or when we say like it, you know, we're there's this insurmountable obstacle, it's like, well, actually, people have had to overcome like way, way worse. And that's not to say that our I don't know, there's there's a big today, it seems like there's a lot of like people saying like everything's valid, everything is maybe so, but I think maintaining a perspective of like what what you said, like your dad went through, your family went through, is really important when we're navigating our own challenges. Like, okay, wait, like is this really a huge deal, or is this you know essentially almost like a good problem to have? Like it's you can navigate it and you can overcome it, right?

SPEAKER_01

Oh, absolutely. What do we call that here? First world problems.

SPEAKER_04

Yeah.

SPEAKER_01

Yeah, exactly.

SPEAKER_04

Yeah, yeah, for sure. I think that's like it's main finding a way to maintain that perspective. Like learning that as a kid seems like a really valuable uh value system or philosophy to have, right?

SPEAKER_01

Yeah, I was I I would say that was ingrained pretty much from birth. I mean, I grew up with that. It was like anytime we would, you know, that's not fair, this is too hard. We would get just what you said. Well, let me tell you comparatively what could be hard, but you don't have that problem. So, you know, you grow up thinking, you know what, he's right, and it is right, it is true. And I've done the same to impart that upon my children. It definitely is a good classroom to have, um, especially when it's at the dinner table, very apparent to you. You see, you hear the stories, you see exactly what you live now in your midst of, and you're like, well, okay, so I see the fruits of his labor, I see his accomplishments. He's not wrong then.

SPEAKER_04

Yeah, for sure. Yeah, I think it's like I I think about that too. Like when I'm raising my daughter, it's like I definitely want to be like empathetic and lean in and like give her the support she needs. And at the same time, it's like, you know, trying to guide her and help her understand, like, okay, this isn't like actual, like real like pain, or it's not like you know, human beings are capable of doing so much and overcoming so much, and and often have needed to. And it's like that balancing act of like helping helping kids without perspective gauge like what actual adversity really is, you know, versus just like in their own little world.

SPEAKER_01

Exactly.

From Economics To Recruiting

SPEAKER_04

Yeah. So uh you went to University of Maryland. What did you end up studying there?

SPEAKER_01

So it was there, I was studying economics. Um, my long-term plan was I want to be a stockbroker, wanted to go, you know, be on Wall Street, live in New York, and then uh one summer got a job as what we called a research analyst back then that was sourcing, loved it, turned that into my full-time career. Then I was like, well, I mean, this the age-old adage of I fell into the recruiting. No one ever says, Oh, I went to college to learn how to be a recruiter. Like that never happens. Um, totally pivoted, but yeah, I was studying economics, and I knew, okay, if I can just make it through this, you know, happy, you know, there the my goal at the end of the tunnel is is definitely going to be fulfilling, but it was just so boring. It was so dry. Um, and it was like I literally had to just keep pushing myself to remind myself what I was going towards. But then when I found something new, I was like, I like this better. Um, I don't have to force myself to like it. I don't have to force myself to really enjoy what I'm doing. I don't have to force myself into pushing myself every day. Um, so uh yeah.

SPEAKER_04

So when you started out in recruiting, were you um were you on the agency side or were you did you go in-house?

SPEAKER_01

No, I was on the agency side. We were a boutique shop and we were doing full desk or split desk, full-on head hunting. There were some people there that they went out and they got requisitions from customers and then came back and did the recruiting themselves. Then we morphed, we evolved into an actual solutions provider. We were doing some consulting work as well. Um, but we were a boutique placement firm that I joined, which was, I mean, again, for any of us who've started out on the agency side, that is, I would say for all recruiters, that's that's your classroom.

SPEAKER_03

Yeah, for sure.

SPEAKER_04

Yeah, it's uh I mean that's where I started. Oh I so yeah, I started at K Force. Yep. Big big staffing company.

SPEAKER_00

They were in refresh my memory. The original founders of K Force branched off from where? Tech Systems, AeroTech.

SPEAKER_04

I K Force was initially founded in the 60s, but there's been so many acquisitions and you know, sell-offs that it's you know, which one is the real I I do know that I know that there was uh one guy who sold his business to K Force and then became president. So I honestly I I knew more about I forget the name of his company, but he was a he was a really cool guy. Um, but yeah, it's just it's one of those companies there's been so many acquisitions, it was it's hard to know exactly.

SPEAKER_01

Yeah, you have to go back and check. But K Force is uh I mean they're a well-known brand, so yeah, I get it.

Lessons From Amazon And Microsoft

SPEAKER_04

Yeah, yeah, for sure. Um, well, cool. So then you but you moved up pretty fast, if I'm not mistaken. And and you so you were a recruiting manager over at uh at Amazon, right? I was so how was that? What was that like?

SPEAKER_01

Amazon was a great classroom. I mean, when they tell you it's like, yes, it's always day one. So, you know, for being a big massive company with established processes, it's never gonna be so bureaucratic where you're just you know mired in the red tape. Um, but it and it is it is aggressive. I mean, it is literally, you know, hey, we've got an opportunity Monday morning, it's Thursday night, turn around this strategic white paper, you know, start thinking about, you know, how we're gonna bring this to pass. And that definitely does teach you not just how to make decisions, but how to get to the point of decisions, how to even design like what your solution is gonna be, how to really think through things and think through things like very quickly, almost working backwards, like defining excellence, how you're gonna back into that and getting things in motion. Um, that's a skill that was a classroom that I have taken with me every day since it definitely does help, especially now in the you know, in our current environment of AI and automation and you know, it really accelerating things. Amazon's a great classroom to have. And that was the reason we moved to Seattle.

SPEAKER_04

Nice.

SPEAKER_01

Yep.

SPEAKER_04

But then you then you moved on to to Microsoft. What so what I'm just curious, like from a TA perspective, the if there were any kind of differences between like Amazon's and Microsoft's environment.

SPEAKER_01

So I would say yeah. I mean, Microsoft's Microsoft's was at that time uh very mature systems as well, a lot of service lines. So whereas Amazon, it was like you could identify an opportunity, you could basically um really look to see, okay, who's done what already? Who can I jump into this? Microsoft had very established processes and it had very, you know, exact recruiting. It had events for like batch interview batch days, sourcing teams already in place. And of course, when you're recruiting for those two types of things, you've got a lot of inbound. You've got global brand recognition. You're probably one of the top five brands that everybody recognizes, you know, immediately. I would say they both are the same, they're the same, they're two sides of the same coin. Um, very innovative companies chasing the same talent, just very different daily lives. Whereas Microsoft, you you had they had come from the Bill Gates era. There were, I mean, there were people I supported, there were hiring leaders that remembered that would tell me, like, oh yeah, my my interview coming out of college was was with Bill Gates himself. Um, you don't have necessarily that it was, yeah, that was cool. Like to hear that type of story, like, this is Bill Gates, like, wow. But uh, yeah, it was they I would call them two sides of the same coin. Um, you know, very, very uh fast moving. Microsoft was a little more, I would say, polished. You had to almost be on your political game at all times. Amazon, yes, but not really. I mean, there was more, it was it was about the results, as it was at Microsoft, but Microsoft was a little more, how does this look? What are the optics on this? But both were great classrooms. Microsoft is where I learned how to do, you know, global hiring. It's where I really got, you know, my got my feet wet into how to scale globally with peers and counterparts and stakeholders across other companies, even though we say, all right, we've got these, you know, established processes and cycles around headcount planning. Yeah, but that's gonna go out the window as soon as you know more headcount comes in, and it's gonna be like, hey, we've got this, and hey, we've got like it was it was a great place to really have to think on your feet, all solutions on the table where you could experiment, you know, really try things, take your learnings, retool. And I met a lot of great people who um are still, you know, influential in my career. People who I still work with, even here, even here at Bill. Well, one of my former teammates from Microsoft works with me here. A number of our uh hiring leaders also came from there as well. Amazon as well. I mean, but uh yeah, those were two great, two great classrooms for me.

Recruiting For Self-Driving Cars At Uber

SPEAKER_04

That's awesome. That's awesome, man. And uh you've worked at a lot of big names, so I'm just curious. Like, I mean, so then you went to to Uber and you were part of Uber's advanced technologies group. Uh so that was like autonomous vehicles, like what or what, like what were you guys uh doing over there?

SPEAKER_01

So, yes, uh self-driving cars. There were a number of other things as well. There was our freight group, there was um our new modalities or Nemo, as we called it, jump bikes. Um, I was in the self-driving car side, which was amazing. I mean, literally, I remember my first day there, I was like, wow, this car really is autonomous. We had operators, but the operator sits there basically, you know, tracking all the data points coming in. There was a point where we were downloading more data from the car's routes when they would drive around Pittsburgh and San Francisco collecting data points. We were downloading more data off of the cars than Netflix was streaming in a day. I'm sure Netflix has since surpassed that, but to hear that back in 2017, 2018 was incredible. That's cool. Um, and that was also you talk about really teaching someone how to stretch their strategic mind. I mean, that was a great place. I mean, you're looking for skills that don't exist yet. I mean, 2017, looking for people with AI, ML, autonomous, they existed, but and they were still academia. Um, they were still happy there. So it's like, how do you call them and say, hey, listen, new opportunity, come here? Like, yeah, sounds great, being very interested, very intelligent people, very innovative people. And I love some of the people, I still keep in touch with a lot of the people I met in that area. But yeah, that was that was one of those you talk about as recruiters. We always want to work for a company that has, you know, a new disruptor product, something we can say, hey, I was able to recruit for this at a time when I mean imagine the for the recruiters who were um hiring for Google at a time when they created Gmail. Okay, something like that. So um that was incredible to be part of, to watch that grow, to come to scale and just still be able to take the learnings from there because a lot of the AIML, um, what I was able to learn about that tech stack and that talent community, um, you know, now it helped bring bring here because that was a major focus of ours uh about two years ago here at Bill. And I was like, hey, I remember people in that area. Hey, I remember some of the tactics and the playbook that I had. Let me just repurpose some of this from memory. And I I hadn't I've been able to because I lived that for a number of years, and it was great.

Bill’s TA Team And Mission

SPEAKER_04

Yeah, it's uh it sounds like a really cool time to be part of Uber. Yep. And so, and now you've been at Bill for almost five years.

SPEAKER_01

Yeah, going on five.

SPEAKER_04

That's pretty wild. Um, okay, and then you know, you've you've had a uh held a few different positions there currently head of TA. I remember when we met, you have a pretty interesting perspective on AI and recruiting. I know that's sort of like your obsession right now is figuring out how to, and I'm gonna paraphrase, but my understanding is figuring out how to effectively leverage AI to actually achieve strategic initiatives, like and really figuring out high impact areas to that allows your recruiters to be more strategic. You know, you've you've given a lot of thought to this, and and I was impressed with with what you shared with me when we met up. And I would love it if you could share that with our audience, just how you're thinking about leveraging AI at at Bill, and maybe some background on like the size of your team and uh just just some context for folks that maybe aren't as familiar with Bill.

Redeploying Recruiters To Build AI

SPEAKER_01

Yeah, so Bill, we're a fintech platform, uh accounts payable, receivable, spend and expense. We're very uh very big with our banking partners, accounting channels, um, focused on small medium businesses. I mean, that is our um, yeah, that's our focus. Um, and we are about, I think about 2200 people, um, 21, 2200. Um, it's in our annual report. We're a publicly traded company, so you could look it up. And my team is about 20 people, and that encompasses our center of excellence, which is our events, branding, all of our operations. And then on the industry recruiting side, we have um our tech recruiting, we have our non-tech and revenue, uh, revenue being our biggest priority, one of our biggest priorities. I mean, they're all big priorities, but that's like one of our biggest priorities uh right now, this quarter. And um uh early careers. So if you look at like, you know, the whole portfolio of a TA organization, traditional in this in a certain sense, non-traditional, and how I had to redesign certain things last year uh to get a little more lean and agile, especially now as more and more things are becoming automated, um, as more things are basically ever running in the background, as I I say to my team all the time. So that's in essence who we are. Quick overview on where my team um we reside in the people organization. Um, and uh yeah, that's that's my team within Bill, our focus, um, where I'm in, you know, instilling AI. I had an opportunity about a year ago where we were in the midst of a hiring pause. So I uh re-deployed some people. And one thing I love about Bill is like there's always work, there's always avenues where, you know, if one side slows down, we but you've got you know capacity, you can jump in and help. No one has ever been like, no, you're recruiters, you don't need to come to you know within engineering and learn how to code. What is that? No, I was welcomed. Um, my CIO at the time was building out his foundation around AI, how he was gonna roll out the tech stack, training, ongoing governance. One day I was just, you know, he and I were one-on-one, and I asked him, I said, Hey, listen, how are you gonna stand certain things up? He was like, I have to do this, I have to do this, but I need some headcount. I said, Well, how would you like to have you know five head count for my team? And he said, Oh, that'd be great. Are they gonna be able to be technical? I said, these are the five people that literally can learn anything and have have demonstrated that, you know, consistently. So when those five people went into that team for, I believe it was a God, I don't remember, it was the summer, um, all last summer, so three, four months, um, they learned, you know, how to build agents, they learn how to build gems, how to code an app script, how to really interconnect our tools across our entire tech suite, how to take, like on this on Zoom, how to take the AI companion and the AI companion tracker, turning that into not just a doc, but then creating an agent to go through all your docs, create to-do lists, create, you know, automate messaging, literally start to automate manual tasks. As they were, you know, in the the whole benefit of this was for me to say, hey, listen, you're gonna go into the business for this time, but it's not just you're gonna go into the business. It's not like this is the this, these are the learnings that when you come back, we need you to bring back because then you're gonna teach our team. It's gonna be teach back, it's gonna be ongoing forums around opening up fluency, showcasing that type of thing. And then how are we gonna go about building, you know, manually automating a lot of our our current tasks, having things ever running in the background? And then how are we gonna, you know, not just within TA, but all across people and then all across Bill? Like, how are we really gonna scale that, you know, company wide? And we've been doing a lot of things. We've built out agents, not just for us, but for our internal stakeholders as well, is like, hey, when we're going to build out requisitions, we're not just automating the intake process. We're now automating, okay, intake, getting ready for the eventual interview pre-brief to all the interviewers. We've built out our interview rubrics as well, mapping, you know, the the interviews against the rubrics of everything is as automated as we can get. So when people, interviewers are in front of a candidate, they can just focus on the candidate. Like, no more note taking. You're just no more. Let me think about the next question I have to ask. No, none of that. So, this has definitely become creating learning as a repeatable process, but not just learning a new skill, like meta skills, like how. How are you starting to group things into meta skills, learning new dimensions at a time? And it all started with you know that hiring freeze came up, opportunity to redeploy, you know, five people in the business, having those five come back with their newfound knowledge, teaching it back to us, really upskilling the entire org, and then teaching everybody else to keep that going. Um, and then I also, you know, just gave them an objective like, hey, listen, can we go through, like, like let's inventory all of our you know manual activities? Can we find at least a third of our yearly work hours that are opportunities for automation? Like, how would you like to get a third of your year back? You can use it for other things, you can use it to spend more time in front of your candidates, turn in front of your hiring leaders, you know, look at data points, think strategically, I innovate new solutions and ideas, but also live your life. Um, like how many times has everyone been busy at night? You're going through and you're getting ready for tomorrow. Like, how'd you like to up, you know, automate those things? And now you've got time back to um focus on you know, interactions, strategy, data points, and and living your life. And man, did that come together very quickly? I mean, people heard that and they were like, absolutely. We didn't just automate, you know, because you figure a year of your third of your work yearly work hours of what 687-ish hours? No, we've now looked at all right, if these were all our manual activities, we've we've automated about 2,100 hours worth of previously manual activity, and it's great. You asked this morning how things were when I came back from vacation. I mean, it was wonderful. Um, through AI, I was able to have the agent I have for my to-do list, which goes through all my workspace tools and everything. I had my top 10 things. I had already responded to what I had to. I was, I got through my my, you know, for a week, I got through all my emails in less than an hour. And as soon as you and I are done, I'm already set for my next two meetings this today and the rest of this week. So I I look at it, and that's one thing where I'm telling my team is listen, you've learned this now. So the rollout, the foundational piece is in place. Learning is now a repeatable process. Teaching is now a repeatable process because I want everyone as whatever you're learning, you got to teach and share your teammates, not just within TA, but across other people, organizations, and the company. And uh look at AI as a companion. It's always gonna be a work companion, it's never gonna replace you. There's always gonna be a need for that human judgment uh that AI just doesn't have yet. Will will AI be able to make judgment decisions in the future? Maybe. Um, but for right now, it is the ultimate companion. Use it to live your life. And everybody has jumped on that, myself included, and it is definitely up-leveled us in many in many in by leaps and bounds.

SPEAKER_04

So for leaders tuning in that want to go in this direction and are thinking about okay, building agents or leveraging AI and automation appropriately, where do you think they should start?

SPEAKER_01

Uh, I would say YouTube. And I say it sounds very simple. Well, it is. When prompting first became the thing years ago, with you know, what, two, three years ago with ChatGPT, I was no good at it. I would go to and say, hey, give me a list of this. The output was not optimal. I was like, uh, this isn't really what I want. And almost got to a point where I was about to give up, like, I'm not good at this. Do I really need to use it? I'll just go back to doing the things that I'm good at, the way I'm good at, I can get through it. But I was like, no, if I learn how to, if I invest in this now, learn how to do it, I can do it, use it for so many other things, and raise my own game, if you will. Um, and I went to YouTube, started looking at all right, what are some prompting best practices? And they had all these prompting acronyms and frameworks and you know, repeatable frames. And I was like, let me memorize these and let me start the trial and error. And I it got really good at that. But again, I'm bilingual, so I almost learned it the same way I learned my my second language, where I'm just like, okay, here are the the fundamentals. Here's how to speak in prompting language. We're here, we're a Gemini, uh, we're a Google shop. So we have Gemini, we have Notebook LM. And because of the everything I had done when prompting first came up, did the same thing with Notebook LM. Notebook LM for me was a learning opportunity. I struggle with that. Now I use it for everything. Um, you know, the team, same way. We have an AI fluency hour. We host that every other week where people first it was TA, now it's everyone across the people team can come in, showcase their things. Like, I'm building a new agent, I'm building a gem, I've got a notebook LM project, I'm I'm going into a QBR and I got to do a slide deck. Like, how do I attach all the tools? And it's becoming now such a you know repeatable behavior day in and day out. People wake up and think AI. And that's where I would say the big thing has been is like, okay, where do I start? Well, come up with like just just an idea, something you want to prompt, you want to ask. Go to YouTube, okay. Type in prompt engineering, type in notebook LM. Look at, read the comments, see who the speakers are, follow those speakers on LinkedIn. That's what I do. I I a lot of the people who post videos and best practice, I follow them on LinkedIn. I see some of their other articles or some of their, you know, rubrics, they're they're they're posting for their companies because your company is going to teach you your initial training. We did that here. We had a summer of AI where we rolled out here's the training on each of the tools. But then what? Like you didn't just complete that training now, like there's got to be that self-ongoing training literally at all times. Um, so I would say YouTube's one of the better ways. Reddit, a lot of people post in the forums, and then just again, using the the tools. Uh, I'll be honest, there's just there's so many out there. How do you make sense of them? Just try again. Like I tell people here, you know, no one could be worse than me when I first started using AI. I was like, I don't even know what I'm doing. But hey, I took all my, you know, that prompt didn't work. Great. Well, it's not that it didn't work, it taught me a new way not to do a prompt. Great. So took those notes. Just get in there and start. What you may think is a fail, F-A-I-L, first attempt and learning, it's actually helping you get towards where you need to be. So I like to think everybody now is at least trying it, taking their notes, trial and error, learning from it, getting better. Um, because I see a lot of the automations. Um, we have a dashboard that every morning I can go on and see who's built what new agent, what new gem. I can also, you know, repurpose some of those things as well.

SPEAKER_04

Where are you building these agents? Like what tools are you using?

SPEAKER_01

So we use a tool. We have a tool called Glean. Um Glean. Glean. Um, I'll be honest, I am not very good at App Script or some of the logic. I still go to Gemini. I'm like, I'm building out this agent. Here's what I want the age to do. Can you give me the instructions? And Gemini spits out the instructions. I copy and paste. And yeah, I copy and paste it what Gemini gives me into Glean, and I have my agent. So it's like, you know, every you just got to get in there and start. Get in there and start, take your notes, break things, play around, go to YouTube, follow, you know, uh, watch some videos other people have done. And you know what? Eventually, as you start to get more and more repetitions under you and you get better, you're gonna come up with oh, you know, some some light bulb moments of your own.

SPEAKER_04

And so it sounds like with the way that your team thinks about AI and automation, which you know are two separate, they can be separate things, but how you think about optimizing your your workflow essentially, it sounds like you're doing it a lot, like throughout your entire workflow. I I and it, it's it's almost like that compounding motion of doing all of them, it sounds like is what's driving a big impact for your organization. But are there any specific automations or AI enablement that you would consider like the highest leverage in terms of where people should start?

SPEAKER_01

Yeah, I would say your to-do list. And here's why. If you automate your to-do list, okay, you've got an agent that goes through your whether it's Slack or Teams, whether it's your email, everything. If you can at least get that, you know, those guardrails in place where every day you wake up, your to-do list is nicely generated into your Slack. Oh, by the way, here's what you have today. Here are your meetings, here's your agenda. I've drafted this, help you get ready. Um, that was that's gonna be the most natural starting place because that's what's gonna keep you organized. That's what's gonna start to first. Everybody thinks AI is all about just automating activities. Well, yes, like that much. Then what happens when you automate activities? What are you gonna do with where are you reinvesting the the newfound capacity, the time back, uh into strategic objectives, partnering with your internal hiring leaders, you know, uh partner communicating with your candidates, um, you know, attaching your OKRs? Like again, if I've got more time back to reinvest into my can experience, am I seeing my can experience uh scores increase? We are here. Um, am I seeing things when I do go into you know QBRs? I'm able to say, because we've automated this much um upfront activities, now we've got more time to focus on A, B, C, and D, other trends. We've now removed previous concerns from the process, you know, areas you have provided feedback, um, you know, some of the tools that we're using around um interviewing, my God, uh, that was right there, probably the biggest opportunity because now interviewers, um, like you've got a recorder, no taker, interviewers, your notes are taken for you. Um, when we go in a debrief, every debrief now is perfectly prepared. All all feedback is there. We can actually come to an outcome 100% of the time. So I would say if anyone's looking to start, don't swing big, don't be like, I'm gonna automate anything and everything. No, start at the very beginning. First principle thinking what are you breaking? What is it that you need to break down into its core parts? For me, it's how the scope and scale, especially of my job. I mean, I'm getting, I mean, and I'm sure you to you talked this. I heard in some of your other podcasts we talked to heads of TA. We get a lot of things coming at us. Great, but how are we already? We've already counted for those things. We're already out in front of them. I mean, what we're dealing with is scope and scale is so wide, it's so massive. How are you staying out in front of those things? You know, for me personally, it's I need my to-do list generated where it's accurate and I wake up to it. So what used to take, you know, two hours in the morning now takes 20 minutes. My day is set, my day and my week, and I'm actually helping focusing on my longer-term OKRs throughout the physical year.

The TA Tech Stack And Analytics

SPEAKER_04

Okay, yeah, that's that's great. So, what is your um what's your tech stack right now?

SPEAKER_01

So our tech stack for um uh you mean TA tech stack?

SPEAKER_04

Yeah, T A T A tech stack because I was like you're using a few different tools, right?

SPEAKER_01

Yes, we use greenhouse as our ATS. Um, you know, I know a lot of people are like, well, this ATS is better, and this ATS is better. If you were to ask me which one is better, I'm just yes. It's how are you using it? How have you learned how to use it? Where are you customizing it for what you need? So we use greenhouse our ATS, we use Good Time as our interview scheduling tool, we use Bright Hire as our interview AI tool. We use uh Workday as our employee management tool, H R I S. Um, we use Slack as our communication tool, and then of course for AI, we are uh Google Suite, so Gemini, Notebook LM, um Appscript, and then Glean is another tool. Okay. Yeah. Oh, and Tableau for Analytics.

SPEAKER_04

Okay. And that that's plugged in directly into greenhouse.

SPEAKER_01

The Tableau?

SPEAKER_04

Yeah.

SPEAKER_01

It's plugged into it's kind of like a center point. It's plugged into all of our repositories, if you will, because it's, I mean, it aggregates everything into our views. I mean, I live in Tableau because that's the that's another thing I automate every Monday morning is I'm looking up. I'm like, okay, what are my standard reports? What are the trends I'm seeing week over week? What are these trends? What do I need to? How does that look from last week? What do I have this week to drive to completion or what meetings? So, yeah, Tableau. I'm gonna be honest, I'm not very technical. So I don't know how it's connected on the back end, but it is because I've got my data points readily available and I need them.

TA Leadership Beyond Filling Reqs

SPEAKER_04

That's awesome, man. Yeah, nice. So, hey, like let's just kind of like zoom out for a minute. You know, at this point, you've been a recruiting leader at a lot of category leading defining organizations from large enterprise to what might be considered like more um scale up, growth-oriented, uh, mid-market. Um, you know, I I'm curious like what your top takeaways are as a a TA leader at this point. So for fucks for people looking to level up, right? What would be like your top kind of lessons learned?

SPEAKER_01

My top lesson learned is don't just focus on TA is filling racks. Like, how are you translating TA to solve business uh small problems in other areas of the business? Whether that's through you know, an events model, whether that's through partnering with you know business development teams as to what the way they're doing their lead generation. Um, you know, how are you partnering with other groups such as you know, Corp Dev, when they're doing like MAs? One thing I've done in the past, we did this at Uber was when we were looking at um, you know, we were looking at doing acquisitions. We didn't acquire the company, um, didn't want to acquire their IP, but wanted to do a you know, at least acquire their workforce, recruiting would partner with the corp dev team. We would do what we call an acquisition hire, acqui hire. That was such a huge offering, if you will, to the business. So I would say, you know, when you're really looking at TA, it's like, okay, how am I really focusing on translating TA into a strategic arm for the business, solving other problems? Yes, um, you know, hiring the people we need, but not being necessarily, you know, just a just-in-time uh rec-driven function. But, you know, how am I looking at the orgs that I support, the scope and scale, their capabilities? Are they optimally staffed? Are they in front of their roadmap? Um, and then um, you know, continually focusing on you know data patterns. What else am I seeing? What the patterns that I'm seeing within TA, because again, we're one of the first, you know, eyes and ears into the open market. What else are we seeing? What other competitive intel are we gathering? What other new products, new companies, a series A, B, C, and D that you know, is coming on that people are you know interested in? Because again, this was one of the things that you know got us into AI very soon was things we were hearing in the industry years ago. And it's like, oh, I've just read about open AI. Now they're they're going to hiring, you know, oh, let's see what's going on with Chat GPT. Um, so I would say if you're getting into TA, you don't focus on it as, okay, I'm gonna be on the phone, I have to make my 200 calls a day to hit my 20 leads, to get two submittals, to get one hire within the next 30, you know, the next 40 days. That's a component of it. And yes, that is our our end goal, but it's that's the that's transactional, that's just in time. You know, look at it as okay, how does TA really drive quality of hire? How are we really bringing in and shaping the workforce that Bill and Uber and all these companies really need to drive what they're building, to drive for their customers, to drive for their investors? You know, when we go in front of Wall Street every quarter, what are we reporting? And then what's TA seat at the table for that? I tell my team all the time listen, we're not a transactional model. And when people look at TA, they should know they're part of our business. They're not just that they're so far down on the totem pole, like by the time something gets to them, it almost doesn't matter. That's not true. So those are the three things I would say. What else can you translate TA into? Really understanding, you know, the business you support, how are you shaping, you know, for your company, almost existing with your business?

Redefining Success As Adoption

SPEAKER_04

So let's let's zoom out even more. Uh yeah, you know, I'm curious at this point in your career, again, you know, you've leadership roles at category leading organizations. I I'm curious, like for for you personally, just has your definition of success started to change over the years based on where you are today in your life? Or how do you see like success in your career and in your life today versus maybe when you were starting out back at uh the agency or even back at uh when you're at Amazon or Microsoft?

SPEAKER_01

Yeah, so success is not necessarily a zero-sum game. That is one thing I had to learn early on. I had to go through some very hard lessons, but again, great classrooms, as I'm sure all human beings do. Now it's what are the takeaways? What did I learn along the way? What did I learn what not to do? What am I now? What's helping me get towards my end goal? Early in my career, it's like if you didn't, you know, an agency, think about it. Every wreck you get, you're not gonna be the one to fill that because 10 other agencies got that same wreck. And you know, you're by the time you call Canada, it's like, oh yeah, so-and-so already called me about this. And they're like, Well, they submitted your resume. So, you know, if you didn't get you, you know, you didn't get the fill on that, you're like, okay, that's that's a fail, that's a loss. Well, that's not really true. And I actually was able to take that away and say, okay, what was the silver lining? What does that silver lining add up to? Um, what is it that you know I can really use to say holistically, I've seen these things, I've heard these things, I've encountered these things. What am I next doing? I forget where I was when I heard the same. One of the most enlightening things was Einstein's definition of insanity, like doing the same thing over and over, expecting different results. And I was like, that's actually pretty good. I'm I'm gonna keep that with me so I can make sure that no matter what I'm doing, anytime I have a learning, I don't make the same mistake twice. Um, and uh I'm able to evolve beyond it, take, you know, take my learnings, move on, it has served me well. So I would say my definition of success really, you know, grew out of that. There's a lesson there. What's that lesson? What am I taking away? Uh am I even the course that I set my original hypothesis, is that even correct? Is the data telling me it's gonna even be correct? Do I need to pivot? Do I need to change course? I would say success now, I look at it as adoption. Okay. It's like you you if we look at like design thinking, what goes into a lot of these solutions? I mentioned earlier when we first opened the call around one thing I learned at Amazon was how to really design a solution. Well, you can design the best solution if it doesn't get adopted. That's not good. That I would say succession for me now is really coming to the table with a solution, getting adoption. I've succeeded now in gathering the right data points, understanding the right strategic objectives, working backwards from those, engaging um the right uh stakeholders that are responsible, accountable, consulted, and form. I still, you know, use Racy as a guardrail all the time. Um, and where I can, you know, where we're driving adoption and it scales the business, that to me is success now. So not at all a zero sum game.

SPEAKER_04

Yeah, for sure. For sure. That and you know, when I talk to you too about where you're going, right, in terms of like how you want to continue to evolve, uh, you talk a it's like similar, right? Like a similar vein in that you talk a lot about just continuously finding ways to innovate um and make improvements, which also sounds like it's essentially what you're already doing, too, like thinking about automation and AI and working more effectively and really tying it back to strategic value for the business, like hours returned to recruiters to work on more strategic initiatives. What I'm gathering from you is like that's almost like your the core way you think about your role. Uh, and this kind of goes outside of even TA. It's just like to be a successful executive or successful, like impactful business, someone impactful in the business, regardless of what your title is. It's like just pushing for like the most impactful innovation and adoption of it, right? Like deciding the strategic course, finding ways to get better, and then making sure you're driving adoption within the organization. Does that sound like Yeah, definitely?

SPEAKER_01

And then, you know, this year, like what's next? I mean, it's it's not gonna be static. Um, whatever we're everything, yes, you recapped it well. Um, what are we driving in the business? Then what's next for next year and the year after that? And then what's gonna be the next iteration, the next gen of this technology, of these problems we're encountering? So that's the other big thing that I'm always imparting on my team is and they always tell me, they laugh at me, but they can recite it. Like, I got this great idea, and they'll go through great, and then what? What's next? What does next gen need to look like on that?

Using AI At Home And For School

SPEAKER_04

Yeah, it's constantly asking, like, well, what's next? What's next? That's awesome. So, what about like you like holistically? Like, how else do you see yourself developing as a person?

SPEAKER_01

I mean, as a person, I would say, you know, much like you know, within my professional career, it's like, yes, how am I using what I'm learning now to scale my job, you know, faster to higher quality? Um, because again, faster is not always necessarily better, but you know, elevating the quality, increasing, improving the quality as well. And then how am I turning that into my personal life? Like, how am I then saying, okay, so I've now got time with my family. How am I, you know, also teaching my kids the same things that we're doing at school or we're doing at work? How am I really teaching them, like, hey, listen, when you're planning a vacation, when you're planning, you know, how to run your household, when you're you, you know, you're trying to learn how to fix a garbage disposal or anything else. A lot of the same things I told you about how I I first got into, you know, how do I prompt? And I went to YouTube. Same thing for how to take care of my house. Anytime I have something broken, and I'm just like, okay, I gotta learn how to fix this. I go to YouTube, I watch this, I'm like, okay, great. Really, again, it's like work is a classroom, but then you've got all these new skills and these new, you know, abilities. Like, how are you turning that into your personal life? My children are also, you know, they um a lot of schools right now, and I get it. Um, they don't want kids to uh exploit AI, but I feel like they they're gonna have to start teaching them, okay, how to use it responsibly. What are you using it for? Let's face the days of sitting in a lecture hall, um, that for many of us remember when we were an undergrad. You know, if I can sit in a lecture hall now, record something, create an agent to help summarize my notes in the format of how my brain processes information, that's gonna help me study and retain information a lot better.

SPEAKER_04

I think like customized education is like a a huge potential benefit of AI. Like, for instance, for me, like I seem to learn best when it's interactive. Yeah, like problem solving. When I'm talking with my team, when I'm in person, like my brain engages in a way that it just is different. It's just I I learn at a deeper level, I problem solve better. I mean, and these types of things, like you can literally have conversations with AI, like just put it on voice, and like you can, if that's how you learn, there's just different ways you can leverage it to make sure that you're able to retain the information. Uh I so I I think like, yeah, that like customized approach to education is like that's a really valuable use case that you know people should be thinking about.

SPEAKER_01

Yeah, or I want to see myself, you know, really growing professionally and personally is a lot of the same things that I use at work to really automate my my work life. Hey, I can do the same thing to automate my personal life. A lot of the things that I get busy with on weekends, what can I automate? What can I do? That's again, same way that I want time in front of my candidates and my stakeholders. I want more time, you know, my wife and my kids focusing on their interests, their activities. There are things that my kids tell me now. I'll be honest, I don't understand a lot of it. I have to go to Gemini and say, what does this even mean? Can you give me a video or give me some of this? And it fine, it helps. So if anything, I mean, a lot of the solution mindset I've learned over the years, I've adopted to both personal and professional or life.

SPEAKER_04

Yeah, I love it. I love it.

SPEAKER_01

Yeah.

SPEAKER_04

Um, I'm just curious too. It's like, so is this basically when you're giving your kids advice on like their future career, like also very is there any other like advice that you're giving them as they're because they're they're approaching college age. Is that right? I can't remember.

SPEAKER_01

Yeah, one one's uh one is done in college, the other is getting ready for college.

SPEAKER_04

So yeah, yeah. So one that's done with college, has she landed a job yet or is she in the process of she's in the process?

SPEAKER_01

She is um also you were using AI very heavily for her job search. It's like, you know, let's go through your resume, let's ask your resume to recommend jobs, let's look at what else is out there. Because again, I mean, your agency, we remember, um, you know, at one point you go to Monster or you know, career builder um or any other job act, indeed, simply hired and you look for jobs. Now, God, you can go to you can go to Gemini or Notebook LM, put her resume in, recommend, you know, find me job postings across the the you know, um across the globe that may match this resume. And oh, by the way, tell me what kind of cover letter I have to prepare from this resume, get ready to apply for this. And it does that. So it has been a godsend, whereas it's funny, yes, I'm a recruiter, yes, I know how to find candidates, yes, I know all the resources about you know posting and getting my job out there. Don't ask me how to write a resume.

Writing With AI Without Losing Voice

SPEAKER_04

Right, right. There's so many tools, like it's it shouldn't be, it's not too hard these days, I guess, right? Exactly. On the flip side, though, I I do like when it comes to writing, and I guess it's a little different with a resume, but I try not to leverage AI too much, like in my emails or on anything I'm putting online, like any kind of post, stuff like that, because I do feel like it's it ends up being sort of like generic content that isn't like even when it picks word choice for you, like we don't necessarily impact. Think about how like we have our own way of speaking and our own vocabulary and our own phrasing, and not everything needs to be. I feel like there it does take something away from communication a little bit when it's leveraged too much. Um, so I I hesitate to, I mean, I do use it at times, I suppose, like, but honestly, I I end up writing, I think, still most of my own stuff almost. I use grammarly, you know, just to point out like you know, grammatical issues. And even there, I'm I'm somewhat hesitant at times. If I feel like it's like my form of if it's in if it's a more casual email or whatever else, I I hesitate to use uh too much automation there. I don't know what your thoughts are on that, just like when it comes to writing and like cover letters and stuff like that, how much you can just kind of leverage AI versus if if you see value in like actually writing it, right?

SPEAKER_01

So I I again I do see more value in writing it. And this is why I believe AI does not have the certain judgment that humans still need. It's always better to sit down, write it out by your genuine thought, what you're trying to convey. If you were in front of an audience, how would you be speaking it to them? How would you explain your in your natural delivery? But then I can use AI to say, now, in this tone and format, reduce the word count, scale this down for me. So I'd use it, yes, to draft certain things in my own word in my own thoughts, but I'll use AI to tighten things up, make it easier to consume. Um, if I have to put it into you know, taking it from white paper or email into a slide deck, AI can help me with that. Um, but yeah, the the what you're really trying to convey, your own thought, again, AI doesn't have the judgment. It can't make a lot of the judgments and the interpretations uh that we still uh human beings still need, but it is again, it's a work companion. It's a tool you use just like anything else. I mean, AI today for recruiters, it's basically when the first ATS was created. You mean I don't have to print out resumes anymore, I don't have to put them in a uh a file cabinet anymore. I got an ATS and I can source the ATS, it's gonna automate things. It was a work companion. Similarly, that's what AI is. And there's always gonna be that review tax, if you will, that time of, okay, I just wrote this in AI, I still have to go through and review it. I can't just say, okay, copy, export to a doc and send it. Like, hey, I haven't read this yet.

SPEAKER_04

Yeah. Yeah, for sure.

SPEAKER_01

Yeah.

Closing Thoughts And Thanks

SPEAKER_04

Well, awesome. This has been a lot of fun. I'm I'm really thankful that you were you came on today and just told us more about you and uh as well as just like giving your advice and in terms of for leaders that are stepping up and looking to advance in their career. I feel like we covered a lot of a lot of ground and and you gave some really the level of clarity in terms of like how folks should be thinking about implementing AI, um, which I I genuinely enjoyed and I've I've learned a lot as well. So um, yeah, thank you very much for joining us today.

SPEAKER_01

Thank you for having me, James. This was a lot of fun.

SPEAKER_04

Yeah, it was a great time.