Cristyn Girolami, welcome to the show. I appreciate you making today happen. As I was telling you before you were the first person, I reached out to what I was thinking about putting this whole show together. So it's makes me really happy. Here we are. I don't know how many months later, but that this has come to fruition. So thanks for coming on.
Thanks for having me. Adam. Sorry, it took me so long to commit,
You know, you're in demand just is what it is. I felt like I was at the supermarket. I don't know if they still do that back in the day where they give you a number, and then you get to come back. They still do.
Yeah, they do. Yeah, I think they do do that.
Okay, well, my number finally got cold. Here we are.
You're too kind.
So for those who don't know who you are, if you don't mind, give a quick synopsis as to you know, who you are and what you're doing these days.
Sure. So my name is Cristyn Girolami and the chief people officer at Upside Business Travel. And we are a business travel company for travelers who really don't want to spend a lot of time thinking about how they manage their business travel, we have dedicated agents who support savvy business travelers and make sure that their experiences are really positive one across the board from A to Z, and they're on their travel. And we have a team of about 100 people all over the US, we recently took the team remote, fully remote. And so that's been fun. And it's been a good ride the last five years, I've worked with the co founders in some other businesses prior to this one. And this has just been really fun to build, build out.
So you've been I guess, head of HR Chief Administrative Officer chief of staff. What is the difference? as a chief people officer?
Yeah, I mean, I think, look, there's a definitely a common thread. For me, through my career of what I've been doing, I've always wanted to work in a role where I can support people in one way or another. And whether that was in a chief of staff role for the business. And for the leaders of the business or in a in HR people function. I've been fortunate to be able to do exactly what I love to do, which is get to know people understand their values, their mission, where they want to go, and how do I support them in getting there? So I think those have been kind of common themes for me my entire career since I graduated college.
Yeah, I mean, would you say that your superpower?
I suppose I feel more It's like my, my calling is to support people and figure out how to help them in one way or another. So yeah, I guess if you wanted to say, superpower, you could or I just feel lucky, I get to do that. Because it's something I've always been drawn to.
Yeah, well, luck is the residue of hard work. So I really don't like the term luck. And I know that you've worked hard, and you've built some amazing relationships and really left your mark on a lot of different organizations. Although you've been working with the same people for the past few years. that right?
Yeah, yeah, the co founders that I work with are really first and foremost, amazing human beings. And I think what's really cool about working with john and Jay and Scott, is that they personally put people first, right, so for someone in my role, that is, you can't ask for something better than that. And a lot of founders and CEOs talk about that, but don't live it. And I think that's what's really unique. Second, they're entrepreneurs to the core, they figure out how to make things happen, nothing can get in the way of where they want to go. And if it does, they figure out another path. And so that learning in that experience for me, and working with them has been just invaluable as far as what I've experienced. And I think being able to pivot and shift when things aren't going the way that we planned is just huge. So yeah, I've been working them for about about eight years building a couple of different businesses. And another one I've been in, I've been in for about five years.
Talk about having to pivot.
Yeah. So look, john, one of our co founders always says, success is never going to be in a straight line, you're gonna see all these kind of jagged movements when you think about the path and how you want to get somewhere. And I think that's true. And I think one, that's what makes it fun and interesting. And I think why there's a little bit of crazy and in wanting to be in a startup and in that environment, and also, I think it keeps you on your toes, and you'll learn more the pivots, allow you to learn and make a mistake and adjust and then learn again, and then adjust. And, to me, that's what life is all about. I mean, it's about figuring out how to how to adjust constantly.
Yeah. So this show, the format, I like to do what I call a rapid fire. I want to warm it up a little bit. I want to let the audience get an opportunity to learn a little bit about you as more of a person and then I'd like to roll into what I call the main segment where we're going to kind of get under the hood and and get into some meaty topics. You're ready to get rolling.
Let's do it.
All right, early bird or night owl?
Oh my god, early bird, I could get up at 4:30am or 5am. I'm an early bird.
And are you setting the alarm clock? Or is this just happening?
No. natural, natural
Okay, what do you do to stay sharp mentally
yoga and exercise. And I eat pretty well eat mostly plant based diet.
Good for you tell me a habit that you have good, bad or indifferent,
leaving my phone in another room when I go to sleep. It's been a game changer for me. I think it's a lot of people use it as an alarm clock. And I think that's sort of a BS reason to keep your phone there. But you just get an alarm clock then, because you're owned by the technology. And I don't want that to own me. So it's bad enough during the day that we're kind of owned by our technology. But at least for the seven hours, I'm going to sleep or the six hours because I'm one of those. I can leave it in another room. Nothing's gonna blow up at that point.
Good for you. I think was it you that referred The Social Dilemma to me?
Yes. Oh.
Yeah, I watched it. And I made my kids watch it with me. So thank you for that, by the way.
What did you think?
Yeah, I mean, it was on point. Do they own you? They were they really do they? I mean, a lot of this stuff was stuff that I knew. But it was great. Just to see who the people were, that were being interviewed on these shows. I mean, they're the people that, you know, it's hard to argue with the people that designed this information and hearing about why they did it. And what's happening. It's an eye opener, so I feel like it's something that we all should watch. But anyone that has kids, I mean, it was really good for my kids to watch it.
Yeah. Great. I agree.
So what makes you forget to eat lunch?
I guess this could slice either way. I think having like a really passionate discussion or a really good conversation with somebody that you don't want to like, break up or too much on my plate. So it just becomes an afterthought a little bit. So not stress, per se, but almost like the volume of work sometimes.
Do you have was there a turning point in your life that you can point to?
Yeah, I think when I went to grad school, I lived in New York, and I moved to Arizona for grad school. And I went out there by myself. And a lot of things shifted for me. In that two years, I was out in Arizona and went to school, I lived in a new place. I was going to grad school, I was working for the New York Giants at the time, I was working part time for a HR consulting firm, and I was going to school and I just learned a lot about myself in that time period. And also, having that experience alone was really kind of cool. challenging, but cool. So something shifted for me. When I came back to the east coast. I don't know I got a level of confidence, I get a little level of calmness. It was just like, wow, I could I was able to handle all that and what else you got? What do we have next?
Was it just the independence that sparked that?
I mean, it was independence. But it was also just dealing with a lot of different things. a long term relationship, grad school, working for a major NFL organization. I mean, I never thought I was going to be able to get that gig and I kind of somehow convinced them to bring me on as an intern was kind of my story. But I think that and trying to keep all those balls afloat. Working, I started doing yoga became a vegetarian at that time. So there was also physical and mental shifts, I started to do a lot more meditation. So stuff shift physically metaphysically, mentally, and just I was learning a ton from a growth perspective. So I think it was all of those things. I mean, that's a great question. I mean, I never really thought about it like that. But that's I do think about that time period is a real pivotal time in my life. That was really kind of character building.
Yeah, I mean, it sounds like a perfect storm of all these different things that happened, and obviously put you in a position to get this good job. And it looks like with your career really just kind of took off from there.
Yeah, I mean, look, I've been fortunate people believed in me, I worked really hard. And people believed in me, I was not afraid to ask for things and speak up. And I think that's something I really believe in not only for women, but for men as well to really speak your truth and talk about what's important to you, what you're passionate about and what you need. And, and so I think that's definitely part of it.
So in your opinion, you've worked with some of the top people in the world, I mean, entrepreneurs and you've just other you've worked with other top performers. Is there anything in particular that you've noticed that other top performers do differently than average people?
I mean, there's definitely traits for sure. And I love to read about this topic. My background is in performance psychology, and that was the route I took the degree was about sports psychology and but I transitioned and use that sports psych in business. And look, regardless of how you define success. I think there's a lot of people in all different industries, whether it's art, whether it's in sports, whether it's in business that I think have been successful in their field. And a lot of them do things like making sure that they're committed to their health, their mental and psychological state, they have rituals that they do, whether it's sleep, food, different daily rituals. So definitely some of those that I think about, I think you can learn, like relentless behavior, you can learn how to keep going after something that that's me, like, I've seen people in startups learn that. So I don't know that it's always personality driven, you see all different personalities that are successful. And so I think a lot of these things are, how badly do you want it? And how badly you going after it? Right. And so there's a passion piece of it. And that's why I really think it's important for people to do the kind of work that they're naturally good at where their strengths lie, how they, what do they gravitate towards? Because when you gravitate towards things that you're passionate about, you're more likely to have a bit of fire in the belly.
I think that's a great answer. And I completely agree, I'll tell you something I think you're going to appreciate. So back in the crash in 2008-2009, I had owned an executive search firm at that time. And I mean, or, you know, companies were getting wiped out as a result of the crash and not just direct finance roles. I mean, there was obviously a domino effect. And what was happening, what I was noticing is that I mean, there are some positions and companies are just going to get wiped out just because, but what there was also happening when organizations have to cut people, which they do and could be performing fine. But they have to look at the bigger picture. And what I was noticing is that there were a decent amount of people that were really smart, we're talking went to great schools, or a lot, actually, a lot of lawyers, I mean, there were a significant amount of people that were highly qualified, that were getting cut. And as I kind of peeled back the onion, what I was noticing is that these were people that were just smart and just good, it wouldn't have mattered where they went in life, they just would have done well. But they weren't necessarily passionate about what they were doing. And as a result, they were happy with let's call it getting a 90 on a test instead of getting 100. So getting the 90 on the test would have gotten them a good job and a decent bonus as opposed to the 100 on the test, which you know, got them to the next level just because they wanted it more. Does that make sense?
Yeah, totally.
So, I completely agree.
Yeah, there's something to be said for passion and drive. But if you don't know what you're passionate about, well, you kind of need to start there. I think that's where sometimes there's a disconnect.
Yeah. And you've taken some pretty good assessment tests. What are your thoughts on those? And are there any in particular that you recommend?
Yeah, I mean, I had to take all of them basically got my master's degree psychology, but I think I like Myers Briggs, but Myers Briggs, to me is not as great as any Myers Briggs is different. But strengthsfinder is my tool of choice right now. And I think it's because it gives people a language really to talk about what they're good at. And what's really nice about this, and I was I didn't know much about it. And then when we did it, we did kind of a demo kind of session with our leaders. And
did you do 2.0? Strengthfinder
Yep, yep. And we got this awesome coach, Michael Dauphniee, who is just spectacular, and is this coach, he does strengths, but he does other stuff as well. And the team just really loved it. And they were like, this language works for me. And it comes up in, in normal dialogue now. And so you can see, it's really ingrained in how we talk about ourselves and each other and that kind of thing. And so, that's a great tool. I'm a huge fan. And I'm not really the biggest fan of assessment tools. But this one, for some reason, it just it really resonates with me and with the people I've been working with,
because it was strengthsfinder that that's that I know there's different levels, but it kind of tells you your dominant characteristics, right? So it tells you
Yeah dominant strengths out of like 34. So you can like look at the whole 34. But if you take the basic one, it gives you your top five, and usually the top five are pretty accurate as far as close to who you are. And so then the question you have to ask yourself is, am I living these top five in some way whether it's in my work in my life in my hobbies, and yeah, I think it's a great tool
for me, so I did mine but I remember a couple of yours better than my own. I remember it being so accurate. I remember you were a learner. You were positive.
Wow, good memory.
Cheever. Don't quote me on that one.
Yes.
And then network are connected or something. Like that. Yeah. And I remember like, oh, man, that is good. It's a great point. Getting back to what you said before about being passionate, and then tying it back to what you're good at. I think that's really important, too. And are there things that you've implemented in the organizations that you've worked with that have kind of reinforced this stuff?
Yeah, I mean, a big part of this is, and the thing I like about strengths is for me, when building a culture, it's really about how do you allow people to have a common goal that they're going after, but also make sure that they feel like they have individuality and autonomy. And I think the reason I like that tool is because that tool allows people to interpret it the way they need to for who they are, it's not the only thing. It's not the end all be all thing, but it allows them to individualize what the whether it's their career or their life, what they want to do next. So I think, I don't know if that's answering your question. But we think about kind of the culture and the company in a broader sense of not whether or not someone's gonna fit in here. But whether somebody can add value, they make us better. And they can only add value, if they have individuality if they're different. Right. And so there's a conceptually, I think that's how me and our CEO, Scott, think about just people in general, right? Like, how do you make sure someone could be an individual, but still add to the greater goal of mission?
That's good. So I want to talk about something that I know that's also near and dear to your heart, and something that you've been a huge champion of, and that's gender equality, what does that term mean to you? And what is it about gender equality that you're so passionate about?
Yeah, so I guess I never realized until kind of, probably the last 10 years that I was so passionate about it, you know, I grew up my mom was just a real feminist at heart. And I, when I was younger, I didn't have girls soccer league. So I played with the boys at a young age. And so I had a very kind of interesting and cool upbringing in that respect, where I had these unique experiences to play sports around guys to be in business around men. And I think that gave me any personal perspective. And it also made me strong, and it made me kind of have a voice in a different way. And so when I think about gender equality, it's about how do we get women to be at the same place that men are, and women are still getting paid less on the whole, in every country less than men, that's painful on this day and age to know, right. And I'm not wanting to say like, I'm a victim, or, or me or any of that. But you do see small idiosyncrasies in business with being the only woman in the room and how that can be challenging sometimes when your voice on something. And so I feel really passionate about the issue, because I feel just passionate about the issue of equality in general, right, whether it's gender or anything else. And so I think the more diverse and the broader we get, the better we are as a company, as a nation as a society. Yeah.
You talked about gotta pay equity, how equal or unequal? Is it out there right now? And how much is it moving in the right direction?
Yeah, I mean, look, as an optimist, my positivity strength, I see getting a lot better. When I look back earlier, my career, there were times I was like, wow, why? Why is that happening? And you know, when you're an HR, when you're in the people function, you get to see all the numbers of that stuff. And that just blew me away. early on. I was like, No, no, that does. That's not right. So I think I had kind of a special view into it. And I think, look, I am somewhat biased on the topic, because I'm so kind of bullish about this topic, when it comes to our business, our work, doing comp studies, looking at our population, and making sure that people are doing the same job or in the same ranges. And that's really important for me, but even outside of the business. I coach a lot of women on how they negotiate their salary, and what does that look like, and what should they be asking for. And a lot of women don't know how to do that. And they don't know what to say they don't want to ask, and they're just kind of taking what is offered to them. And that's not really the same thing as what a lot of men do. Now, I'm not making a blanket statement. I'm making it a generalization, but you do see themes there with how men and women handled those conversations. So you know, I think pay equity is getting better. I think there's more awareness, there's more transparency on it. what's what's really nice is that the data is out there and people share it and so so I think that helps this issue get better. I mean, look at the women's soccer team, right? I mean, they just, they were not letting their foot the US women's soccer team. They just were not letting their foot off the gas on that topic, right? And that was like, a really pivotal thing for us as a seeing a women's sports team fight for that,
as a soccer player, I'm sure yourself you're pretty excited to.
Exactly, exactly.
So as an HR professional, you ever find yourself at odds between protecting the best interest of the company versus making sure that people are being treated fairly?
I don't anymore, I think when I was in larger companies, where I couldn't make the impact, as easily or at all, because I didn't have the ability to do it. Now I don't, to me, it's about look, we're fair. And we do what's right for the person, we do what's right for the business, we balanced that carefully. I don't run into a moral dilemma on that too often. I mean, I think, you know, for doing right by people and asking them, what are your expectations? And yeah, there's difficult things that have to be that have to work through and figure it out. But that's not something I run into, or I have money to that much in the last few years.
That's good to hear. Those that are listening, that are not properly represented, where can they find their market value? And what should they be doing? Not everybody, you know, they might not have mentors out there, or they might not feel as confident. So what would you recommend to them? whoever's listening right now, they're interviewing for a job, or they're going up for promotion, or they're looking whatever it might be? Are there resources or places that you could point them in? What steps should they be taking?
Yeah. So for people that are in underrepresented groups, I always recommend that they do research, I guess, someone recently on doing research and kind of walk them through how to pull the research from a bunch of different places, and then pull together an average Look, it was a bunch of different data, it's not super cut and dry. You can't just plug a job title in and say, Okay, now I should be making 100 grand, like, it doesn't really work like that. There's a lot of different things, how many years experience, what size of the company? Where are you located? I mean, that's huge, right? New York, and La are going to be different than Iowa. And what's really nice about this market now, where people are remote, and a lot of companies are going remote is I think some of that stuff's gonna get screwed up a little bit. Because it doesn't really matter, kind of which location you're in. I think that's sort of an antiquated way of looking at it like, well, your base there, so you should make less, I think there should be more equality across the board on that someone's doing the job, they should get paid to do the job. So I think that's one I think doing the research is really key. And then I think talking to people who do the role out there and understanding what are some of those ranges, every company is different, every role is a little bit different sometimes in that company. And sometimes there's a higher supply, you know, there's a higher demand in a company for x experience. So I think the research is big, you know, I think there's a lot of articles on this stuff. There's a lot of articles on negotiating. I don't really love the idea. Like when I say negotiating, I say it in a more of a collaborative sense. I don't like the idea of like, having to go back and forth on salary with someone and having someone do that. It should be straightforward. It should be like, whatare you looking for in your next role? and someone says x, and it's like, great, you know, x is in our range, or you know, what, x is a little bit higher than our range, but it doesn't knock you out of the running for this. That's one of the first conversations I have with people. I don't want there to be some weird back and forth like, well, you asked for this. And, you know, it's like, Who needs that? That's not like, that doesn't feel collaborative, right off, right out of the gate. And so I think it's about understanding what the person's expectations are, and making sure you have that dialogue upfront.
Yeah. How did you know how did the underrepresented get more representation in the room?
Yeah, that's a good question.
And the reason I asked that, well, there's a lot of reasons but there was someone who's on my other show by the name of Dr. Dawn Graham, and Dawn's amazing. She's got her own show on career transitioning on Sirius XM, and she's the adviser to the Wharton School of Business. And she told me something that was super powerful. And it's a quote from a gal by the name of Carla Harris, who I think is the she's like one of the senior most people at Morgan Stanley, and she's diversity candidate. And she said that most of your career decisions are made when you're not in the room.
Yeah. I was gonna say to you what's really looking at I've been fortunate, I think having an advocate white men run most of our businesses right now, unfortunately, that's shifting. You've seen this many female CEOs and underrepresented groups, lead companies as you do right now. And so that's hopeful, that's hopeful trend that we're seeing, I think I've had a lot of white males be an advocate for me. And so I think having an advocate whether it's, if that's all that's represented in the business and that can help you grow But I've had great women, I worked for two female CEOs that were phenomenal. And most of the leadership team was female. And so I was fortunate to work in an environment where women were supporting women. So I've had advocates across the board, all different types of people. So I think making sure that someone's invested in you, I think, particularly for people who are newer in their career, where they can they have somebody that can help represent them, or can speak to their experiences or mentor. So those are some of the thoughts.
I think those are great. And we're cutting tight on time. Two more questions for you. If you're still okay, great. So in the spirit of having an advocate, a mentor, or whatever it is that you'd like to label them. What's the best advice that someone ever gave you?
I think the best advice someone ever gave me was, put your head down and just go for it. And I think, having played soccer at the collegiate level, I learned that also in sport, but early on, that was the strong message from my mom. And then it was a strong message from other people in business that I really, really respected. Like, no, is not really an answer, like, figure out a way to do it. And I think, yeah, like CEOs that I work with, they're like, okay, you're saying no, but like, what about this? What about this? What about this? No, how about this. And so I think it's kind of like, put your head down and just keep going and just keep pushing through. And so that's really stuck with me.
Love that. We I don't know if you've heard the saying, if you're going through hell just keep on going. I keep a quote in front of my desk. And it says successful people begin their days where others end and failure. And yeah, go for it. I know, I'm sure I didn't make it up. But feel free to run with it. Oh, my God. And then last question. And then you are free to part ways outside of your family. Who's had the biggest impact on your career?
Oh, wow, that is a tough one. That is a tough one I had, I had a great mentor, who taught me HR but taught me HR and very entrepreneurial environment, even though she learned it in a more traditional environment. So she was a huge mentor for me, I worked for two different companies, and then eventually kind of, you know, back filter and enroll, and so, but I think but my current CEO is an unbelievable leader. And I watch him every day, push people, but also balance that with compassion and, and thoughtfulness around people. I think those two people I know most will stick one. But people for those reasons,
they can't be co CEOs have your biggest impact about that.
Thank you. Those of you who have dealt with significantly impacted my life and there's no way I would be who I am right now. Without without that
there was it the push that they do that they kind of tested your day they stretched you is that what made
them push and it was more observation, like it was more watching them be the leader that they are more the time. So for Gina who I worked with, it was watching her balance, really, really smart solutions with kindness and supporting people. And with Scott it's the same thing. I mean, I guess my values are the same. I mean, Scott's really he's hungry for change and movement and the ability to shift things, but then he's really compassionate on the other side. And so I guess those things really resonate with me, which is why those two people come up. For me, it's less about pushing me it's more about watching leaders lead and learning through osmosis, I guess.
So it wasn't necessarily any one thing in particular, they said this was you just having a front row at the game?
Yeah, it was a front row seat. And it was kind of like, Oh, I want to be like that. Yeah. Okay, I get that, that that worked out. Well, I watched that play out. And I watched how they did that. And I'm a real observer of kind of human behavior. And so watching people at the top of their game like that really just allowed me to emulate that.
Yep, pulling it back to the strengthsfinder you're a learner. Oh, man, Cristyn, I really appreciate this. I've had a lot of fun. I've learned a lot tons of morsels of wisdom that you've shared.
thank you for doing this and for inviting me as well.
might have to do it again.
For sure. For sure. I appreciate it. Thanks again.