The Breakthrough Hiring Show: Recruiting and Talent Acquisition Conversations

EP 212: Managing Expectations in a Job You Can’t Control

• James Mackey

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Mallory Planck started her career in the middle of the 2009 recession, figuring things out in real time without a clear path. That grind took her from door-to-door sales into talent acquisition, where she now serves as Head of TA at Drata. She talks about managing expectations in a people-driven role, the pressure to keep up with AI, and why learning to slow down might be the hardest skill to build.

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Welcome And Midwest Roots

SPEAKER_01

Hey everyone, welcome to the show. We got Mallory Plank with us today. Mallory is currently the head of TA at Drata. So Mallory, thanks for joining us.

SPEAKER_00

Thanks for having me, James.

SPEAKER_01

Where are you from?

SPEAKER_00

I'm from a little town in Midwest Ohio called Kettering, Ohio. Um, was never gonna leave Ohio and I am no longer there.

SPEAKER_01

So yeah, we're uh I'm definitely looking forward to to learning more about that. So um okay, so small town, and you were the eldest.

SPEAKER_00

I am the eldest of two daughters. So I have one other sister.

SPEAKER_01

One other sister? Okay, cool. What's the what's the age gap?

SPEAKER_00

We are, oh goodness, 21 months apart. We were, I mean, there was a lot of being raised as twins and a lot of capacity, and so is the oldest really irritated me, right? Like she got to do everything first before, you know, I had to wait till I was 16. She did it at 14, you know. So okay.

SPEAKER_01

Yeah, I got you. Um, and so as as a kid, you were, I think you were telling me you were uh into sports a lot, right?

SPEAKER_00

Mm-hmm. Definitely. I mean, I'm six foot, so we had to use the height for something. And my dad had two daughters and he needed to coach sports, you know, so so there we went.

unknown

Yep.

SPEAKER_01

What uh so what sports did you play growing up?

Sports Childhood And Finding Volleyball

SPEAKER_00

We were the only sport that didn't click for me was soccer, which is funny because both my daughters play, um, and my youngest says it's her favorite. I'm like, really? Soccer? Um, but we were softball, um, basketball, and then I danced. And then when I did not make the cheer uh the cheerleading team in high school, I pivoted to volleyball and actually found my like true love. And that's the sport that I'm coaching with my oldest daughter right now.

SPEAKER_01

Oh, cool. Yeah. Um volleyball is a good sport if you're tall, right?

SPEAKER_00

That's uh you don't even have to be able to jump that high in high school and you can just be tall, you know, and I do not have a vertical, so it helped.

SPEAKER_01

That's awesome. And so that was like playing volleyball was a uh somewhat of a formative experience for you, right? Particularly as you approached your senior year.

SPEAKER_00

Yep, it was. So I was able to make JV as a freshman and play varsity moving on. And then again, not because I was the best player on the team. I think being tall in high school helps. Um, but then I had a freshman take my starting spot as a senior. So that was definitely a kind of like a moment in time that's like, huh, being tall is not just gonna get me places. She was taller than me.

SPEAKER_01

So so tell us more about like what that taught you and how you kind of responded to that situation.

SPEAKER_00

Yeah. I mean, I think for me, I remember having this conversation with my mom a little bit later, you know, in like early adulthood and talking about that. But at the end of the season awards, the coach had get, you know, hands-out awards to all, you know, not to everyone. Um, and he ended up presenting me with the coach's award, which and what he said was kind of stuck with me as an 18-year-old. It was like, you know, that I could have gone two different paths. I could have been very disgruntled. I could have let my team down. I could have been really upset about about that, like kind of feeling like something was taken from me. And instead, I just decided to be the hype girl, you know, like really making sure that my my teammates felt supported, felt encouraged, like, and took on more of that like leadership seat from the bench. And I remember talking to my mom about it as a as an adult, and she like in her and how I don't it sat with me as an 18-year-old, but I think hearing it from her lens and how proud it made her in the sense of like, you know, you're gonna be okay, you're gonna be a leader, you're gonna be an okay adult because you can handle adversity, um, really kind of sits with me.

SPEAKER_01

Yeah, for sure. And so like that also probably set the foundation for like your career, right?

SPEAKER_00

I think so. I think it definitely I knew that like I want you didn't have to be the best at anything to show up and use your strengths in other ways, right? Like I couldn't jump, I wasn't the best volleyball player on that team, but I used my strengths in other ways to be a leader on that team.

First-Gen College And Moving West

SPEAKER_01

I love it. I love it. And then so what was uh college like for you? That was another, you know, as for most people, like a formative experience, but for you, you were first generation uh to go to to get a four-year degree. So so what was what was that experience like?

SPEAKER_00

Yeah, that was uh uh navigating completely uncharted waters, right? I mean, I had I have um two amazing working class parents, right? Like they and so it was they went to respiratory school and they got associates' degrees and they met at the hospital. And so it was like you in my mind, you became a teacher, you went, you became a nurse, you know, you did something along those lines because salespeople were door-to-door vacuum salesmen and like business people, you know, carried a briefcase and like wore a suit. Like that's what I knew of that world. And so I didn't know, I just thought I wanted to be a teacher. So I that was the plan, that was the march. And I had a um an amazing seventh grade teacher that actually became a friend of mine. She was my language arts teacher. Um, and I won't, you know, I want to be Mrs. Montero when I grow up, right? I ended up going to the same college that she went to randomly enough. Um, but that's just what I was gonna do. And I knew my junior year of college that I didn't want to teach, but I had no idea what I wanted to do. So because I was paying for college, it was like, well, let's just finish. And I didn't even at that point know that, like, didn't really understand that you could go to a guidance counselor and like talk about what you like and like figure it was just like that was the plan. So you just execute on the plan, which is you go to school, you get your degree, you become a teacher, you teach, you stay in Ohio. Like that was my plan. But junior year, like realizing that that's not what I wanted to do long term was a weird, not identity crisis, because I still finished the like I executed on the plan. I finished the four years, got the degree, moved. Um, and I graduated in 2009 when, you know, the during the last big recession where there were, you know, five jobs in America. All my roommates ended up living with their parents after we graduated because we just couldn't, we didn't have jobs. So I was bartending and living in, you know, actually the guest room because my parents had converted my bedroom already. I was like, what the heck? And my younger sister still had her room. It's like, what is going on here? But I met my husband in college and he got a job offer out in Southern California and he calls and he's like, You want to move? And I was like, I mean, I guess let's do it. And kind of never looked back.

SPEAKER_01

I love that. And so you and your husband moved to Southern California, right?

The Sales Grind And Work Ethic

SPEAKER_00

Yep, yep. We moved, so we packed up. So he um the year before the couple months before we moved, he was studying abroad in China. So we planned this entire move across the country via Google chat. But because, like, you know, that was back when texting overseas was you had to pay for every text. We were doing all that, right? So you had we were like Google chatting like the time difference, like planning this move. And we moved, we packed his two-door Honda Civic. He's six five, I'm six foot. We packed a two-door Honda Civic. We had, I mean, it was the cliche, our clothes are in trash bags, like as much as we can pack, basically. Our parents were gonna mail the rest when we found we didn't have a place to live. So we moved out there and we had no job, he had a job. I did not. We had no place to live, one car, and I that was not my plan. Like I was going to stay in Ohio. Most of my best friends from high school moved to Columbus, which was like a 45-minute drive. It was the big city, separate from Kettering. And so they a couple of them are still there, right? And so I was gonna move there with them. We were that that was the plan. And so this just took me completely off course. I think it shocked my parents because no one in my family had done anything like that before. Um, and it was scary, but it was, you know, I kind of looked at it and like, well, I can always come home. Like if I go out there and like this relationship doesn't work or, you know, I hate it, like I can always come home. Um, and so we got totally catfish when we first moved out there. Like the apartment that we've like, or the we were gonna stay at an extended stay hotel until we found an apartment. And the pictures that we looked at online, we roll into this hotel and I'm like sobbing. I'm like, I can't do this. It was the the nastiest hotel ever. I was like, I can't do this. And so that was a you know, really great first full four hours of our uh of our life in California, but it was a really fun adventure, and I think I mean it definitely changed the whole trajectory of my life, truly, because I wasn't a teacher out there. I tried to get a teaching job, I didn't land one. Um, and so I kind of stumbled into sales, and you know, that's kind of where my career took a different path.

SPEAKER_01

So when you went into sales, was that um in staffing? I I think you started in staffing, right?

SPEAKER_00

Well, I started my sales career at Xerox, actually. Um, I sold copiers, which nice that's a grind.

SPEAKER_01

I'm sure that was a grind.

SPEAKER_00

Oh my gosh. Like, you know, the amount of walking door to door in cheap heels because I couldn't afford nice ones, and you know, you had to be business professional at the time.

SPEAKER_01

It was like you were going like door to door, like uh door to door, like consumers like being knocking on doors with my business card.

SPEAKER_00

Like, do you have a Rico or a Toshiba back there?

SPEAKER_01

That must have been what was that's that's a that's a brutal entry to sales right there.

SPEAKER_00

That's honestly, it was a wild ride. I was good at it though, which I think surprised me a little bit. Um, I ended up being, I was in the orange in the orange county office and I ended up being one of our top reps. And I don't know why, because I really hated that job. I'm sure you like it isn't it?

SPEAKER_01

It's work ethic, right? It's like putting your best foot forward and just you kind of have to have this like almost baseless optimism like I can make this happen. If other people made it happen, I just will grind until it happens, right?

SPEAKER_00

A hundred percent that competitiveness, like that internal fire. And it's funny you say work ethic because I remember when we were like starting to get ready for the move. My father-in-law, who's a very successful business career, he looked at me because I was nervous. I didn't have a job or anything. And he's like, You're from the Midwest. Orange County's gonna love your work ethic. And like, it's true. I mean, I had, I mean, I had a teaching background. Now, granted, I had always been I'm a server and a bartender. So like I always had that sales attitude. And I always loved within sales or with like waitressing and serving that like I could make more money. Like I had to every spring break that I wanted to go on, I had to work for those tips to pay for those spring breaks and like all those trips and stuff that I wanted to do in college was on me to like save all my birthday checks. You know, I remember my grandma calling and being like, Are you gonna cash that check? I'm like, no, I gotta save it until I it's time for this, you know, amount of money to be moved over for the trip. But I always loved that mindset of serving and knowing that like the more I worked, the more I could make. And so it made sense with sales, but I never put the two and two together. Like, truly in my mind, sales were like car salesmen and like door-to-door, like vacuum sales people. You know, it wasn't like a career path until I kind of stumbled into it. Um, hated it, but was kind of good at it.

SPEAKER_01

So yeah, that's where I got my start was in sales as well. And I think I I like for for me, I I would write, read a bunch of books on like, okay, how to be successful. A lot of those, like, you know, the like the self-help category, and like in the like if you're ambitious and you really want to get started, you want to get started quickly and make a lot of money. And every everything was just leading towards sales, was like, okay, well, I guess this is where I'm gonna start. And I had a I I don't know if my job, well, my my I don't know if my first job was as brutal as yours, but I started out in uh at K Force, like a big, you know, yeah, yeah, yeah.

SPEAKER_00

AeroTech competitor. Yeah.

SPEAKER_01

So I started there as an intern and uh ultimately convinced them to give me an SDR role. And I it was outbound. It was like a hundred cold calls a day, three meetings booked, and and I had to go to in-person meetings.

SPEAKER_02

Yep, yep.

SPEAKER_01

Uh and I yeah, I I almost got fired from that job. I was I was close. I was so close because I had six months and they were very blunt. They were like, because they they didn't even have a typical SDR role. They gave me one, but they usually they only had AE roles, and they didn't want to hire me as an AE, but they're like, All right, we'll give you a shot. It was like six months. You're either gonna like make it happen or we're gonna burn out, yeah. There were no like straight up, like you're just not gonna be here. Yeah, I was very honest, and I appreciated the opportunity.

SPEAKER_00

That was that time frame, though. It was just like entry level was like turn and burn, truly. And that's what like my first well, I mean Aerotech, that's what I was hiring was entry level sales, and then Townsquare was entry level sales, and it was just like the whole model is based on like hiring X amount, knowing X amount aren't gonna make it, and you just base your revenue numbers off of that, which is wild nowadays because I don't know what the SDR program's even gonna look like in the future with with all the automation.

SPEAKER_01

It's it's so different, it's so different than what like when we were starting out, it's kind of wild.

SPEAKER_00

But I think like that SDR grind and like the door-to-door grind, like it's not earning your stripes, but it is like teaching you, it is there is a foundation that I think is so important when you're starting out, just like being in an office, like now, and you know, as a working mom, being remote is what I need, but like I know for a fact I would not have been as successful in my career in office.

SPEAKER_01

You gotta be in person when you're like you're starting out. Like I for um my company's my GTM team is sits with me full time in Tyson's and they're in the office with me from nine to six, yeah, Monday through Friday. And interestingly enough, like I don't think, I mean, I don't know, maybe at this point they would like some remote flexibility, but like you know, I think they also see the values like you just you can learn so much faster.

SPEAKER_00

Totally. Well, I think too, because like I again going back to like I am not, I'm not the best recruiter in the world. I'm not the smartest person in any room, but I will outwork you and I know my strengths. And I think that that's what came through, especially in my um my earlier career at AeroTech. I kept getting placed with account managers that were building new territories. And so I'd watch all these other people walk in and like walk to the account manager that had this beautiful book and they were getting recs handed to them to fill. And then I'm working with two different account managers that are building a territory from a ground up. I'm like, why is it me? Why is it always me? But I think it was because of the work ethic and just like the grinder mentality of like she's just figured out, like she's gonna get it done.

SPEAKER_01

I think also I'm curious if this is relatable to you. Like, I did ultimately do well in in sales, but I think like getting back to that STR role, there were so many people in that role that I honestly didn't feel like they appreciated it because they were just like, Oh, this it's not what they wanted to do, it's not why they went to college. It's not and I mean, I think it's it's like maybe even if folks do appreciate maybe they feel a little of that in that role. But I do feel like one of the things that set the top performers aside is like they truly kind of appreciated that they understood like the working towards, yeah.

SPEAKER_00

Right.

SPEAKER_01

It wasn't just like I don't want to be here. Like it wasn't that kind of you know what I mean?

SPEAKER_00

It was like all right, it's like the instant gratification of like, well, I should just be making six figures because I'm in sales, and it's like, no, that's not how it works.

SPEAKER_01

You got to start and build and build just because you have a degree doesn't mean you're gonna start it, you know, exactly under 50. Like, that's just not how it works.

SPEAKER_00

And I think that's what we were sold, right? Like, we were sold you go to college, you get your degree, and then you're successful. And like, then what I mean, I again it graduated in 2009. That's not how it worked for us.

SPEAKER_01

Oh, yeah, that must have been kind of brutal, right?

SPEAKER_00

There were no jobs, like our parents is like literally my friends' parents are being laid off, and we're like, well, we're trying to get jobs. Like, and I think there was that scared moment for me too, because like my parents' jobs were safe because of where they worked in the hospital, and teacher jobs at that during the recession were safe. And I was like, Okay, well, maybe I do need to stay down this path because this is the safer path, even though I knew it's not what I wanted to do. Um, California had no teaching jobs, and so it just kind of like took my path the way that it needed to. But I think had I stayed in Ohio, I probably would have taught longer.

SPEAKER_01

Yeah, honestly, though, like looking back, do you think starting your career in 2009 was almost like a blessing in disguise because it teaches you? I mean, not only did you go into that sales job, which is like really hard, but you're also entering an economy that's very challenging. It's like as a foundation that you know, they like I don't know, I don't know if this is the right analogy, but you know how they say like so many Fortune 500 companies were born in the Great Depression? Yeah, if you ever heard that. It's like when you start out in this area of adversity, it's like you have nowhere to go 100%.

SPEAKER_00

Yeah, and I think it level sets expectations like that sales job's base salary in Southern California was$27,000 and I had to negotiate for 33. I was like, please, like, I can't pay my bills off of the, you know, and like now when I you're in and you interview entry level, they're expecting six figures because of the market and because SaaS is complete, and especially because of what COVID area, like 2021 to 2020, early 2023 did to salaries. Like, yeah, they're expecting like six figures is like the baseline now. And like, based on what? Do you realize that I made like and you know, it's like, and then you sound like I sound like that old, that, you know, that old person that's like back in my day, but it's truly like I do think to your point, it's set like a level set expectations. And so you're a little bit more grateful for where you like where I am now because of like understanding what those paychecks look like early on. Like, I was like it's bartending I was making more money than teaching. And so that was like a level set very quickly that like, okay, first of all, teachers are drastically underpaid, but that's a whole other conversation.

Drata Hiring Plans And AI Pressure

SPEAKER_01

It's true, yeah, for sure. Well, I'd love to transition into where you are today. You've clearly come a very uh long way in terms of professionally. And uh you know, Drada is a uh a very successful scale up organization. How many employees does your company have at this point?

SPEAKER_00

Right around 600 right now.

SPEAKER_01

600, okay. And so you're in the head of town acquisition role, so you run the show on the TA side.

SPEAKER_00

Um they let me fumble around and try to pretend I know what I'm doing, at least.

SPEAKER_01

I love it. So, what's your obsession this year? What are you working on?

SPEAKER_00

Oh, it's I you know, I we were talking earlier day by day, truly. Like, I feel like, and that's the scale up startup life. Like you could be marching towards one thing, and then you know, you get a slack at 2 a.m. as you're laying awake thinking about all the things, and it's like the whole path changes. Um, I think for for us this year, there's two big things. It's um, well, the company as a whole scaling an enterprise. And so we have to figure out what that looks like from a headcount perspective. But then just like every other business out there right now, it's figuring out what how AI and what tools fit into our game plan and um how to do more with the team that I have, like, especially in TA, by no means do I want to be replacing humans with these tools, but how do I make the humans that we have more efficient so we can do more? Like, you know, it's our CEO, um, Troy, his little picture next to his name on Slack is just this guy screaming more. Like, how do we do more? And it's just like that, that's just it's like see the little picture, it's just this guy going more. But that's I think we are in a make or break year, and the companies that figure it out will be the ones that get to rule the space and rule the show, and so it's making sure that we're we're in that that those those top companies that get to do that.

SPEAKER_01

Yeah, that makes a lot of sense. And so to get a little bit more tactical for other town acquisition leaders that are tuning in, uh where are you in that journey and and how are you thinking about this problem solving in this area?

SPEAKER_00

I could spiral for days about how far behind I feel in this space, truly. And I think it's kind of like we were talking about earlier. It's like, I feel like the people that are getting the farthest ahead in this space are using their free time, right? To be able to build agents and play around and do, and like if you looked at my calendar, every hour is accounted for with a meeting or an interview. Like I carry a recload as a scale-up, right? So, like, even though I lead town acquisition, I've always been the type of leader that's like the player coach. So, like if my team's feeling underwater, I'm gonna take recs on to take things off their plate. So not only am I carrying a rec load, I'm sitting in strategy meetings. And so, like, there's no time for me to block a whole day to sit and build an agent. So then you to do that in your out of office time. Well, I have two small kids. And so I hit the ground running from, you know, the little bit of me time to go to the gym in the morning to like getting them in bed at night. And then I'm like, oh, the last thing I want to do at 10 o'clock is figure out how to build an agent. So I feel behind in a lot of ways. And I think it's a scary feeling because of what I just said. Like the People who figure it out are the ones that are going to be successful, and the ones who don't will be the ones that are left behind.

SPEAKER_01

Well, that that's just so you know, like this is how like basically every millennial is feeling right now. Yeah. You know, because like we're all in this like place where it's if things are moving so fast, everybody almost feels behind. And it's almost like this, you know what you see always saying, like more and more like we're all like in this kind of place where it's like we're we're feeling pressure to like uh adopt this technology in an effective way to make sure we're seen as that forward-thinking leader, but we're also like you're kind of strapped with these higher recloads, recruiting teams are kind of leaner than maybe they were in 2022. Totally. There's it's time is it's it's hard to to come by, right?

SPEAKER_00

Um hundred percent. And then it's I think I think millennial to your point, like we're also kind of craving a slowdown a little bit. Like, you know, we were the last childhood that was like they just sent us outside and let us run without technology. And there's a little bit of uh, like me at least, that craves that just like slowdown of like you know, I don't want to learn anything in these five minutes. I don't, I just want my brain to chill for five seconds, you know.

SPEAKER_01

Do you ever try to like get away to just outside of like um I don't know, do trips like or weekends away in the in the trees or something, you know, something in nature or whatever?

SPEAKER_00

We we take a family trip every March instead of like it's like my girls, we give them their Christmas present and like they get to their from us instead of a bunch of junk that's just gonna end up with in my dog's mouth. They get a trip from us and we go in March, and it's like I take Slack off my phone, I take email off my phone, and I I mean we went on when we went on the cruise. I'm like, neither of us are even buying the internet package. Like we are truly just like just um disassociating from life, right? But I think it's important. I the balance of like showing my girls that you can do it all, like you can be successful, you can work hard, you know, you can do all the things and still be a mom, but also like not missing out, but also showing them that it is important to like slow down and be present. And that's like a constant internal battle of like being at work and thinking about all the things on my mom to-do list and then being in mom mode and thinking about all the things on my work to-do list.

SPEAKER_01

You know, it's kind of interesting. It's like most of the most successful people I know that like sold a business, like the first thing they do is buy a house in the countryside, just to like run away, like they buy like acres of land in the middle of the thing of chickens and garden and some like crazy tech guy with like a big beard.

SPEAKER_00

Yes, like burnt out.

SPEAKER_01

They're just like, no more, no more, no more.

SPEAKER_00

Yeah, right.

SPEAKER_01

Or they just become like those eccentric people that talks about just life-changing technology, and it's like, dude, it's a scheduling app, like it's not yeah. Um but but yeah, that's uh you know, I I do this this kind of crave the same in a sense. Like I like you, I I feel you know, I'm very ambitious and like work-driven to succeed. But I also try to do these like weekend trips away where I just like I'm in Virginia, so the uh a lot of folks don't actually realize this, but West Virginia is gorgeous, it's just mountains, beautiful, yes. So I'll just go into the mountains, like in a cabin with my daughter and girlfriend, and we'll just kind of go for the weekend and and just kind of it usually there isn't cell reception, which took some getting used to. It was a little scary at first.

SPEAKER_00

That's where we live. So we so I I grew up in like a big suburb, like I graduated with seven kids, so it was like a big suburb, right? Yeah, then we moved to Orange County, like I the amount of time I spent around people and on the 405 is insane. Then we moved to Chicago and lived like in the city, and so then we moved to Charlotte, but then we moved, I live in a tiny little town called Denver, North Carolina, which is a lake town, and there's nothing that we don't even we don't have a target, like we so that was a culture shock for me. Like, what? But we live on a lake and we have a uh like we get to, you know, we're fortunate enough that we have a pool, and so like that's my kids are growing up, like living this very like outdoor life that like I certainly did not grow up doing.

SPEAKER_01

Yeah, no, they go to horse camp.

SPEAKER_00

We did not go to horse camp, that's for sure.

SPEAKER_01

Oh, yeah, yeah. These these days they got all sorts of cool opportunities and totally yeah, yeah. Um, well, that's awesome. So it does sound like at least you like have that outlet to get away from the craziness of working in tech, you know.

SPEAKER_00

Yeah, it's fun. My youngest daughter will literally be like, Is this a is this a do nothing Sunday where we just like do nothing? Because our lives are so chaotic between their school, sports, work. She will ask at one day a week, she'll be like, Is this a do-nothing Sunday? And I'm like, It is, girl. Like we are sleeping in, we are, you know, pajamas until noon. Like those are the type of days that she craves at seven, which is kind of scary, but also at least knows that she like appreciates the slowdown too.

SPEAKER_01

Oh, yeah, for sure. That's like I think a good habit to develop in our kids early on, right? Like, not everything has to be go, go, go, go.

SPEAKER_00

Not everything. My oldest is the complete opposite. She's like, I I'm bored the two seconds after she wakes up. I'm like, that's because you're the oldest.

SPEAKER_01

Right.

SPEAKER_00

Your brain is already running.

SPEAKER_01

Like five in the morning.

SPEAKER_00

Like, yes, yes, she's an early riser. Yep. Like, go back to bed.

SPEAKER_01

So to zoom out a little bit for like what's your advice on what's most important in terms of like what makes you successful as a talent acquisition leader? You had mentioned to me uh during our prep that managing expectations is right at the top. So could you explain what that means?

SPEAKER_00

I think there's two different ways that I look at it. Like, for me personally, managing expectations for myself is like respectfully, like this company could decide that my job is redundant tomorrow. Like, I don't think they will, but I have been a part of two workforce reductions in the past. And that really put things in perspective. That it doesn't matter how it does matter. Like doing a good job matters, but not at the sake of like managing the expectations of like, I do have to go be mom. Like I can't miss out on their childhood because the slack's pinging off, right? Like we went, I worked for a global remote company. So like Slack's never off completely. It's but I have to manage my own expectations of like just because there's a notification on the Slack doesn't mean that I have to answer it today, like in this exact moment. Um, and so that was a that was an expectation switch for me that really happened in like 2023 when I was um impacted by my first riff because I was doing a great job. Like all my performance reviews were great. Like I've never not done a good job at work and never not given my soul to being good at what I do. Um, but that's the end of the day, business is business and it's not personal. Like, and I don't think Drata's going to do that to me tomorrow by any means. It's just like you just don't know what you don't know, right? And so those are how I have to manage my own expectations. But then I think we have to flip like the job that I do in leading TA is literally working with the most like unstable, unpredictable product in the world, which is humans. Like I have hiring leaders that I have to manage expectations with, my team that I have to manage expectations with, candidates that I have to manage expectations with. And all three can be on a different page at any given time. And it's just honing in on that piece that I think is the most challenging part of my day-to-day. But psychiatrist put therapist on my resume. Right.

SPEAKER_01

Oh, yeah, for sure. It's like everything in one. It's funny you talk about like the most unreliable product. It is, it's like it that's like also I remember in the old school staffing days, like you probably feel it at like AeroTick. It's like, okay, you like there was this, I always crave to like sell like software. Yes, because it's like, okay, it's predictable. Because I'm dealing with like these unpredictable hiring managers, like you know, are I'm you're dealing with the people that you're trying, yeah, you're trying to like put this stuff together, and then you know, even like in the in-house roles, right? In-house leadership, it's like I mean, it really is the same. Maybe it's a little a little better, a little easier in a sense, but I mean you it's it's hard. I mean, that's where it's like with uh hiring plans trying to help like you know, folks understand. It's like, yeah, we're not gonna be able to get the start date down to like predicting the week. Like we can predict, we can predict the quarter, like we can do that, but like it's not like that's just not how this we're not rolling we're not releasing like a like a small feature. Exactly.

SPEAKER_00

We're not a roadmap that it's like here's the sprint, here's the deadline, and like we do run sprints, we're gonna we're running now, but it's right you have visas, you have vacations, you have all the things that like you just can't control at the end of the day, and then you have the human element of like some days, like, and I feel this myself, like when I'm in an interview, like some days I am in it, and other days I am phoning it in. And like that is just the human reality of what we do. And so I can't expect my hiring leaders to be a hundred percent on every time they jump in an interview either. And so it's like you could give them the exact same candidate on a Monday, and then they interview them on a Thursday, and you get completely different feedback based on the reality of their life, right? Because they're humans and they are working parents and they have to manage their own expectations. And so there's so much that you can't control in this job that that's like managing your own expectations, like being okay with that. I think didn't happen for me until the last really like three to five years, like because I'm such a type A control freak, you know, be like, take it so personal if someone, you know, declined my offer. It's like, I did everything that I could do. I, you know, I pre-caught closed them and I, you know, negotiated this and I did all this. And it's like at the end of the day, they just didn't want my job. It had nothing to do with me. But I think the earlier um like adage of like, you know, people don't quit jobs, they quit their managers, and you're told it's early job and a recruiter that like they'll take the job if they like the recruiter. I don't think that that's true, especially now. Like nowadays, that that whole market and uh and you know, SaaS in particular, all of that mindset is completely shifted.

SPEAKER_01

It's also like a massive like oversimplification, like 100%.

SPEAKER_00

And when you do that in this type of job, it takes away all the nuances and all the humanity of it, and it just it's not realistic, yeah.

SPEAKER_01

For me, like the biggest like aspect in terms of managing my own expectations, or that's like the hardest, like as somebody who also I consider myself like pretty type A and like ambitious, and like I the one thing you're talking about, it's like a people business, and and it can be unreliable at times, is like you can check references, a person could have a perfect background and match everything, but like you may not be able to tell that they've entered a different chapter in life. Yeah, things have changed. Yeah, there's some stuff that you don't you know on the back end, and so their performance, even if you do everything like perfectly, you could it's sort of like draft picks, right? Like it prefer like you could do all of the things and look at all the stats, and like you still can't be certain that that person's gonna work out.

SPEAKER_00

Yeah, that is annoying, like it is so annoying, and then you add the layer of fraud, like the fraud that we now have to deal with. Then you add that layer, and it's like seriously, you just literally have to just lay it's kind of just like hoping and praying.

SPEAKER_01

I know, I'm like, and I'm kind of going full circle. I'm just going back to like gut, right?

SPEAKER_00

Like, I'm really all the trainings and the years that we spent training hiring leaders to not do that now. I'm like, I don't know, how do we all play? I know, but like I'm just going back to gut and behavioral fit, like but it's interesting because I had a the president of Townsquare Interactive, um, which is really where I like grew up in like startups and all that. He pulled me into his office and he was like, How do we teach people to have the gut that we have, right? Because it's like he knew he could sit across from somebody and just be able to kind of tell if they were a good fit or not. Not obviously like going through interviewing and that he's like, and you have it because you know you know how to hire salespeople. How do we how do I teach entry-level recruiters? Because that's what I hired and built my team of there was like they maybe had been in SDR and decided they wanted to get into recruiting, but I was teaching them all how to become recruiters. He's like, How do we teach them to have your gut? And I was like, they gotta be salespeople, like they have to kind of just have that instinct because you can't teach that. I can give them a the script and I can give them the how and the why, but at the end of the day, there's if they're if they're the right person, they're gonna know.

SPEAKER_01

I mean, I think also probably like we develop practical wisdom and like we've seen so many movies that we're just like we kind of dial in, but exactly. Yeah, I mean, I don't know. I feel like so much of it is like how somebody engages like in an interview, like the types of questions they ask, like what is their level of awareness, they're like no matter their role, like what's their business strategic acumen? Do they understand why they're here, like why we're hiring? Are they asking right questions? Like, is there like a really dynamic, engaging back and forth?

SPEAKER_00

Like, but then some of that starts to add the layers of like, which I know is like can be a hot topic at times is D E and I, though, because then you start to like my gut is attracted to people who are like me, right? So, like, how do I like eliminate that gut bias to make sure that I'm not, you know, only bringing so there's like layers there, and so then you can go full circle. This job is not black and white.

SPEAKER_01

If that is definitely not, and then you also have like obviously it's gonna be a different field talking with potentially a really strong engineer than a really strong like recruiter or GTM individual. So yeah, there's definitely those.

SPEAKER_00

Yeah, sorry to me to interrupt you, but I always say it's harder to be a go-to-market sales recruiter than it is a tech recruiter, in my opinion, because where yes, tech is very hard right now, but you're screening for specific things like skills. Like, okay, what do you code in? If you have like where what kind of LLMs have you been building? Like you can screen for certain like your rag and all of that, but like with sales, it is so much of the soft skill that again, you can't teach that piece to interview for.

SPEAKER_01

No, you can't. And it's also really hard because it's like people have been successful or not successful at previous companies, but right, so it's also like dependent upon the product. So it's like you can have a you know, a salesperson that didn't hit quota at a previous company, but the product market fit wasn't there, or like a competitor swooped in and like just or an LLM came in and just totally ruined the, you know. I guess like a good salesperson would be able to articulate that, but then it's also challenging. It's like, okay, like I believe your story, and also like you haven't hit quota at your last three jobs.

SPEAKER_00

At the end of the day, your your CRO is gonna be like that's an underperformed build rep.

SPEAKER_01

It's it sucks, it's unfortunate, but like we can't help. Or you know, you can have somebody who performed really well, but it's like also maybe it's like how much is the product? And I don't know, it can it's just it's very it's very challenging, and then that's where it's like getting back to of course checking references, looking at the similarities in sales cycles, emotions, and these types of fundamentals, but it's like getting in like behavioral fit, kind of understanding where they are, like in terms of their headspace around their career, and yeah, like it's yeah, it's it's it's tough. It's it's really I mean that it's fun, right? But it's also it's so it's a layer.

SPEAKER_00

I think there's like a layer of crazy that all of us that like love to be in the TA space and you know, scaling in startups, it's like there's just a level of chaos that like yeah, you have to kind of have to thrive in.

Success Without Titles In The AI Era

SPEAKER_01

Yeah, you gotta accept it for sure. Um well, yeah. So hey, I you know, when you think about your own professional development and what comes next, and like how you how you want to continue to grow, like, where's your head at right now?

SPEAKER_00

I have no idea what I want to be when I grow up. And I think that that's okay. Like, I think especially right now, um, I will turn 40 this year. So that's like a big pivotal, like, where am I in life kind of moment. And I thought leading into this year, I would feel this. I gotta have it figured out and I gotta know what's next. And it's the complete opposite. Like, I truly just feel like as long as I'm solving problems every day and I'm like I'm showing up and being like, and I'm just being true to myself at work and at home with my family, then like that's success for me right now. Like I climbed the ladder, I wanted the titles, and I now I don't care. Like, I truly don't care what title you give me. Um, you can call me the janitor, as long as I am feeling like fulfilled in work and like my paycheck validates the work that I'm doing, right? Like, if I'm gonna give you 80 hours a week, like I would like to like at least feel like the paycheck affords the life that I want to be able to provide for my kids and kind of show my two daughters that you can do it all. But it's it's less of climbing the ladder and more of just feeling like proud. I think of like how I'm showing up both places, and I think that's success for me right now.

SPEAKER_01

I I love it. Yeah, I love it. I you know, and that's actually like I'm hearing from it's interesting because I I speak with a lot of successful uh TA leaders on this show, similar to yourself. And it's like so many of them answer that way. It's like there's this kind of pivot away from title. I mean, like we still want to be recognized and there needs to be clarity around it, but like you know, of course, like money's top of mind. Like, we're usually pretty ambitious people, we care about providing good life uh for family and being able to do these things, but it's like when they're focusing on their development, it's like just solving important problems. Yeah, it's just a really like this this like this fundamental curiosity and problem solving that seems to be a very common trait of like a lot of people who come on this show.

SPEAKER_00

Yeah, and I think this industry in particular is one that's being affected so drastically and so quickly in this AI movement that I think we have to protect the humanity piece of it. And I think that's why like less of us, like you know, I can't speak for anybody else, but for myself, it's like so much less about the title and the this, and then it's like making sure that like I feel like humans are still getting a seat at the table to do things that robots can also do. And like, how do we combine the two? Because I worry about my kids and I worry about we talked about how like SDR programs and like what's gonna happen to them right now, and like that just makes me worry for like what does that mean for AE positions? Because like SDR is such a foundation of like the sales career path. How are we gonna teach salespeople? What does that mean? Like the ripple effect that that has and go to market motions and revenue motions, and so that affects TA teams and what they're hiring for. So it's a whole like ecosystem that gets affected just by this one job. And so, I mean, I like I said, I could spiral for days and days on all of this, and I do sometimes at 2 a.m.

SPEAKER_01

So yeah, I mean, I it's um it's gonna be really interesting what happens to the job market, particularly for junior talent. Like I was telling my GTM team, it's like because they're like 22 and 23. And it's like, you know, you guys are to an extent, like pretty lucky that you kind of like just got in right before there's gonna be this potentially huge issue in the labor market for junior talent that are trying to enter like into uh caller positions.

SPEAKER_00

Like it's that that's gonna start well and like what does that mean for the college landscape? Like, do you need a college degree anymore? Like, there's so much of that is gonna change too. Like, it's crazy.

SPEAKER_01

Yeah, I mean, I I've always had like the view on the college degrees of um like they're they're incredibly valuable, but I don't think necessarily from the perspective of like ROI in your career. Like I think there's this intrinsic value in education. And um I I think people, if you have the opportunity and the means to go to college, do it.

SPEAKER_00

Right.

SPEAKER_01

Grad school, do it. Um but I don't necessarily think folks should be looking at it from like an ROI perspective, unless like there's certain traits, like as a lot of but you know, I I mean, even as an engineer, like but I mean it's it's again, it's and there's always gonna be the companies who they they care about like that kind of pedigree or like the you know, and but particularly I would say it's like look, you know, if you get into Stanford, I know it's super expensive, but like you should go, yeah. Take and and this is maybe not like contrarian to take the loans, like figure if you can get like an engineering degree, like you know, so do it right, right?

SPEAKER_00

Like where there is like truly an ROI component, like um, but I think about the life skills that I I mean, clearly I'm not using my education degree, right? But like I met my husband there, and the whole path of my life changed because of that. And like, you know, I think I grew up there in so many ways, and so like I want my kids to experience that.

SPEAKER_01

There's the social development, like so. I'm a college drop pal, I'm like very traditional entrepreneur path, and I was like hyper ambitious, and I just wanted to get started, like, and that was the path that I took. And I ended up getting the job that you needed the degree for that kind of thing. And and so I I it and and I always I loved school, it wasn't that, it was just like I was thinking in terms of ROI and like where where I'm at. Hindsight, I kind of wish I had slowed down because there's there is a social piece, like professionally, I thrived socially, but personally, when I looked at my peers that went to university in their personal lives, in their friend groups, they were so socially beyond where I was. Like they were they and it's taken me a long, long time to catch up.

SPEAKER_00

I think I'm like there now, but it's like but it took them time to catch up to where you are professionally, so it's like a given. Yeah, exactly.

SPEAKER_01

No, that's 100% true. But um, you're right, you're actually completely right. Um but it's there is this like social dynamic piece where it's like I think it is really important for folks like they're and again, it's not everybody has the opportunity, but it's like if you're lucky enough to have the opportunity, like take it, you know.

SPEAKER_00

100%. A hundred and I but it's like also remote learning's a thing now. So it's like, what do you which we mean? I think well back when I was in college, like one call one of my classes was online, and like I definitely phoned that class and like I was like on Google, like you know, like so I didn't learn anything in that class. But um and you're a kid, so I didn't even think about the ROI piece of like I'm actually like paying them money to learn nothing from this class. Like you know, when I think about it now it's not a great use of my money. And I still have one little loan that's just like kicking it. I'm like I just it's kind of fun to just see it sit there now. So I pay it every month instead of paying it off, you know, whatever.

SPEAKER_02

Right. Yeah. Yeah.

SPEAKER_00

It's uh but to your point like you know you can't have it all you say it's like you either go one path or go the other I guess.

SPEAKER_01

Yeah I don't know I just see I I do and I think it's very fr like even I I have a feeling my GTM team like uh two of them uh have degrees one of them still in school um and I think there was this element when they started of like you know how hard the job market was and like what they thought like their degree was gonna like yeah how you know it's gonna we were fed a certain like recipe like you do the XYZ and you get this at the end.

SPEAKER_00

Yeah.

SPEAKER_01

And there's so many folks like at that age right now that just aren't getting the job like it just can't it's worse than I think when I graduated in 2009 honestly it might be.

SPEAKER_00

I don't know because no one knows what is the next year and a half is really going to look like and I think that unknown is making businesses very like hesitant to to pull triggers. And I also think it's TA's job to to gut check when a hiring leader comes to you and says they need 30 heads it's like well hold on a second we've gotten into this like motion that like workforce reductions are just part of business but at the end that's the humanity piece that sometimes we lose it's like those are people's lives. So can we can we automate 50% of that and it's a balance for TA because you don't want to work yourself out of a job but you also don't want to affect other humans' lives and careers because we overhire and then we reduce and we overhire and the the kind of like the cycle that we've been in since 2020 we haven't level set as an industry yet on that kind of like circular motion.

SPEAKER_01

Yeah for sure I I do have a question for you just like because we're talking about like kind of education and just get this generation coming up but I I'm wondering how old are your kids nine and seven nine and seven okay so I have a six year old daughter and it's sort of crazy like what how do we even think about preparing them for their their careers I I have no idea well it's wild because even when you do their homework now right like we I I mean growing up our teachers were like you're not gonna have a calculator in your pocket you're like I actually have the entire internet in my pocket now so literally right I have a robot in my pocket who can do the things for me.

SPEAKER_00

And so I don't know like and I don't know the answer to you know when they when they say like my kids are still young enough and yours probably too like they still want to be a veterinarian or a doctor and they haven't like thought long term about like they don't know what they don't know right but I don't know how to prepare them. I don't know what I don't even know what high school will look like for my kids because that's still you know a few years away and I don't know.

SPEAKER_01

I I guess you just like I don't know just thinking out loud here is teach them values. It's like fundamentals right like how to be a good person. Yeah like just how to be a healthy person. Yeah understanding your role and your family and your community and like those fundamental things and then there's there's the behavioral stuff which I guess we kind of we're fortunate enough because we see what some different habits behavioral traits of folks that seem to do well and so it's like we can kind of guide them there. But yeah it's it's gonna be really interesting to see what happens to the employment market. And you know you have the CEO of Anthropic that's I don't know coming out talking about like how jobs can be completely slashed and I don't I don't know um I for junior for junior roles particularly but uh I'm that's probably what I'm most curious about is like the next one to five years what happens to junior level positions.

SPEAKER_00

And the things that I've been reading are saying that the the individuals that have the human soft skills will be the jobs that are the safest because humans aren't like leaving the planet right and so we got to figure out how to continue to keep you know the economy rolling and things like that. And so I mean you could but you could read another article that completely negates that.

SPEAKER_01

So it's like you just kind of have to like find the the philosophy that grounds you the most in this whole kind of like well I mean like I think the one thing that kind of counter uh like counters the doomsday thing is like humans like want what's in our best and like we want AI to the majority do yeah want to be like yeah for our entire like civilizations to just be like right so obviously we have all of the right it's like well maybe I guess you have like you know some big outliers I'm sure yeah right but like overall like we we almost like okay we we are in control here right we obviously want you know at least hopefully and I think especially kind of like what we were talking about it's like the millennial demographic in particular like we're craving that slowdown as much as we're craving the what's next and so be like we're making up the majority of the the quote unquote workforce right now.

SPEAKER_00

So like maybe that's maybe maybe it's all up to millennials. You know what I mean?

SPEAKER_01

I don't know holy put more on our plates why not I'm like so so I tell you like one of my companies is the AI screener and interviewer June and it's really exciting because we're we're um gonna be making some announcements of like some like a really really well known tech company we're we're kicking off a pilot with uh and then we're also like we have probably eight companies that we're gonna be kicking off with hopefully the next like month or so like mostly in the tech space. But it's it's interesting it's like when I'm talking about the TA leaders they're like talking about reallocating recruiter time to more strategic motions to kind of eliminating some of the the the huge bottlenecks at like top of funnel and it's about like being like there's like the strategic element which I think also brings balance. Yep. But then of course it's like you have the COOs and the CFOs are just like okay yeah like also though like how does this like tell me how we're gonna hire twice as fast and tell me how we're gonna cut our spend in half.

SPEAKER_00

Yep.

Boundaries That Let You Lead Better

SPEAKER_01

Yep do more with less do more with less yeah so like and if you can't articulate that ROI. So it's kind of interesting speaking with the different people right because it all the talent leaders again they're just like okay look like we have these huge bottleneck issues we want to help our recruiters we want to free up their time we want to do this and then yeah you then you have the other folks at the org that are just like yeah but also how do we like not spend all this on you know all this money on job sponsors especially when humans are the most expensive you know expense within a business it's like of course that's where they want to cut first but also like you need the people to click clack on the computers to do the things and so it's just yeah it's like the chicken and the egg yeah it's kind of an interesting place. Well I'd love to zoom out for a minute and you know when you think about the next best version of yourself like who you want to become you talk to me a lot about slowing down. Um could you let's talk a little bit more about that like do you have like how how are you gonna how do you do you have any kind of strategy for being intentional around that or like how do you I would love to say I did I would I would love to say that I have like this I would love to I could love to build an agent that can help me slow down right can you can you do this for me?

SPEAKER_00

I think for me like it's it's being more intentional and more like and less reactive like it's like knowing that like because I'm a control freak and I'm a type type A person like I hate seeing like the little red bubbles on my phone. Like that's something that has to be done. I'm action oriented like that is someone who needs me let they need an answer for me. I'm impacting them by not giving them the answer. And so like it's a spiral to go down where it's like it's it's the boundary piece of like understanding that I can I can get back to you in two hours not two minutes and like this the the world isn't gonna end.

SPEAKER_01

Um two hours is so that's so funny though because like that's such a tech mentality because two hours is still so freaking fast.

SPEAKER_00

And that's how I say slow down like to me two hours is like long time. Yeah that's why you're so successful. Like that's like it's all but I have to remember that like I I am a middle piece of a lot of puzzles in this because I have to like manage expectations for my team. And if I set the expectation that two hours is too slow, then they're gonna be in this constant flight or fight or flight mentality. And then you're not getting the best version of your team if they feel reactionary to that too. So it's like being intentional with my slowdown helps the people that I lead. It also hopefully helps like set the tone for the hiring leaders and just and you know the candidate again like my job is such a nucleus to kind of everything that happens with these very unpredictable products, these humans of ours, you know? And so for me, like what's next is just and I I think when we talked earlier, it's like I don't want to use the word content because I don't I'm never going to be content like that it's just not in my DNA. Like I'm always gonna be like wanting to know what's next and growing but it's not the job title like this is the longest my husband and I have lived in a house. Like we've moved constantly we've been in this house I think eight or nine years now it's being okay with that.

SPEAKER_01

Again it's not content but I can't think of the word that I want to use you know I don't know like I don't know about you but it feels like the rate of change just seems to continue to accelerate in life and there's always these massive challenges to solve for and it's it's hard. So it's like wherever I can slow down I I try to because there's just so much going on controlling what you can control right yeah particularly if we choose to be in tech right which there's reasons we choose and it can be financially it could be because it the problem solving is fun the pace is fun it's challenging but it's fun but yeah like I I'm trying to be way more intentional as well and just like slowing down where I can. Moving is a big one. Like I want to move I want stability I want like consistency in at least some areas of my life to balance out working in tech.

SPEAKER_00

A hundred percent and I think like controlling what you can control because there's so much that you can't like I mean like we like I've been a part of two workforce reductions and it had nothing to do with my work. Like it had nothing to do I worked myself out of a job at one point because I overhired right and so it's like I was too good at my job. And so I couldn't control that piece but I had to like it it's so it's that's what perts in perspective perspective like what matters right like and it's the kids and it's the house and it's the life and it's your health like I luckily am a morning person and so I hit the gym in the morning before you know my kids wake up in the morning but like making being intentional for that time I can control that and I know the difference in my mindset if I do that or if I don't and so like in I you know again because I'm a type A and I like to control like that input will hopefully make make me have a longer life that I can live with my kids and my grandkids and and you know making sure that the inputs that I put in have some kind of positive output.

SPEAKER_01

Yeah no for sure. Yeah it says we're actually in pretty similar places when it comes to that so I'm like totally and we're both 2 a.m spiraling so we have to figure out how to stop that. Yeah this is definitely no uh yeah I'm I'm working a lot right now just uh but I don't see that stopping anytime soon.

SPEAKER_00

No I think that's just you have to be you're just wired a certain way and it's you you know you either are or you aren't yeah we're right in the middle of it too. Like where we're at is like we're right in the middle like of of of life and responsibilities and just like I don't know if you feel it with your daughter too what they call like May Sember where it's like everything the school crams into the last week of like last month of school too. So it's like that always happens right at the peak of like busy time at work. And so it's just like everything's on fire and you're just trying to you know keep your head above water.

SPEAKER_01

Oh yeah I remember one of the funniest things I heard it made me laugh uh at least was uh I was speaking with a revenue leader this was earlier on in my career probably eight years ago and this guy he was ex-military and and uh you know he he was like talking about being a startup executive and he'd been a startup executive at a couple really successful companies and he was like look like my job is like any every day I go in like working in tech as a startup exec he's like there's a hundred fires and he's just like you know my job is to pick the top three and let the rest of those burn and he cursed a lot more in that like he was like like let the rest of those MFs burn yeah you know and and uh it just kind of made me laugh because he was so passionate how he said it but yeah it's like look like there's just gonna be all that you just have to pick you like what are the the the couple you know most that you got to work on and then everything else is you know I think that goes back to what we were saying.

SPEAKER_00

It's like the level setting of expectations it's like today like this is what I can get done and like that just has to be enough.

SPEAKER_01

Yeah yeah awesome well hey Mallory this has been so much fun yeah thanks James yeah thanks for joining me today I had a great time thanks for having me yeah me too um well hey everybody tuning in thanks for joining us and we'll talk to you next time

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James Mackey

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