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Episode #72: How All Roads Led a Gainsight AE to UpdateAI ft. Kristie Gaunt (UpdateAI)

Send Kristi, Jon, Mickey & Josh a message – https://www.speakpipe.com/UnchurnedPodcast

Watch the banter on YouTube – 
https://youtu.be/N22Id931Tb4

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Mickey is back! & Let’s welcome Kristie Gaunt to the UpdateAI Squad!

Kristie had been an AE at Gainsight for the past 2years.

Join Josh SchachterKristi FaltorussoJon Johnson  & Mickey Powell  to learn more about
14:10 – Working at Gainsight
16:55 – The Work Culture at ClientSuccess
18:00 – Navigating Strengths on the Career Highway
23:05 – Getting Hired at Gainsight
25:45 – Bidding Adieu to Gainsight
28:30 – Hiring for a New Role at a Startup
30:36 – Cons of Startup Life
38:30 – Cultivating a Growth Mindset in the Startup Jungle

12:00 – Big Shoutout to Hamish Stephenson (Selr.io) (Check out the episode “Who Wins the Tug-of-War, Team Customer Success or Team Sales?“)

👉 Get the advice and insights you need to thrive in Customer Success. Subscribe to the CS Insider Newsletter

Listening to Unchurned will lower your churn and increase your conversions.

Unchurned is presented by UpdateAI.

Josh Schachter:

Thank you. Tryptophan. I just learned over this weekend from my brother, who’s a doctor, that tryptophan becomes melatonin. That’s why it puts you to sleep. I did never learn that.

Jon Johnson:

Your body processes it.

Mickey Powell:

Yeah.

Josh Schachter:

As melatonin. Okay, so we’ve got an exciting episode. Yeah. We’ve got three Update AI ers on this episode. So we’ve outnumbered KF and JJ. There’s two exciting ones here. So, first of all, we haven’t brought this up before. Mickey, as many people know, has been out for the past five or six weeks.

Josh Schachter:

He’s gone through nightmare and back in that time, the most horrific things with his family, the death of his mother and his brother, and the community has been so outreaching towards Mickey. Even through me, every call that I get on with a prospective customer or with a current customer, the first thing they ask me is, how is Mickey? How is Mickey? He’s been very open about his journey and the community in kind has been open about their care for him. And he means so much to me, to all of us, I know speaking for Christy and John and to the community. And so, Mickey, it was a surprise to see you come and join the episode. We hadn’t rehearsed that.

Jon Johnson:

I would like to make it very clear that he just showed up. We’re grateful that he’s here, but hey.

Mickey Powell:

Mickey, I did a reverse exit.

Jon Johnson:

I haven’t done the updated yet either. So for everybody that’s listening, we’re all going to be doing this together. So I’m really excited that Mickey’s here and I’m excited to kind of talk a little bit about what’s going on.

Mickey Powell:

I’m doing great for the first time in about six weeks. Yeah. So to quickly fill people in on my mom’s side of the family, we have a genetic mutation that can lead to aortic aneurysms. And we’ve lost family members to this. And due to some really amazing research by folks in Washington and at Stanford, dr. Liang calling you out. They identified the genetic mutation, which has kind of allowed us to keep an eye on it, but my mother had the gene. I actually found out two weeks ago that I also have the gene.

Mickey Powell:

We can talk on a later date what that means, but shitty genetics led to my mom having heart problems for many, many years. She actually had her aortic valve replaced in 2014, which you can imagine is a really intense procedure. So she just always had heart problems, even though by all other measures, she’s been very healthy. And she had a heart attack while visiting my brother Reed in Santa Cruz. She was without oxygen for like 15 to 20 minutes, which unfortunately, you just can’t really survive. Also, kudos to Josh’s brother Dan, who got on the phone with me like a day later because he’s a what is he, Josh?

Josh Schachter:

He deals with stroke.

Mickey Powell:

Yeah. So he kind of like, talked me through some of the things, but it was pretty clear that once she had that heart attack and she was down for 15 to 20 minutes, there wasn’t really any way to recover. So all of our family, we all, from everywhere we were, showed up in Santa Cruz, said goodbye to my mom, laughed and cried and were angry and were sad and drank and ate and slept and did all of those things together. My mom is Portuguese and Italian, so you can imagine that food. Yeah, lots of food, lots of drinking, lots of boisterous, lots of Portuguese Italians, which is great. And my eldest brother Seth also has the gene, has had decades of health problems and he was really struggling. Know, for anybody who’s a first child, I’m not. I’m the youngest of four boys, but what I have seen is that the oldest have a special relationship, especially with the mom, and he really struggled.

Mickey Powell:

And when we got home the Friday after my mom passed, he ended up having a brain hemorrhage, which means he’s bleeding in the brain. And at the same time, he also had a dissection of his carotid arteries going into the brain. And what that meant is that to treat one, you have to do something that’s going to make the other worse and vice versa. So we had this really amazing doctor who just happened to be in my hometown, even though he’s the professor of neurology at USC, and this is Visilia, California, where I’m from, where he happened to, you know, about the best doctor you could hope for in that moment. And he basically said, hey, it’s like the same situation with your mom. He’s essentially, for all intents and purposes, brain dead, and the best path forward is actually to let him go. So we did that on Saturday night. So not even three days later.

Mickey Powell:

I know on LinkedIn, I post four days, but I think I just didn’t do the mental math. It was three days later. So I just kind of disappeared because all I could do was process and be with my family and try to help them and try to lean on them. And now I’m starting to feel ready to come back, in part because I’ve had such amazing support from everybody around me in the way that I’ve needed it, whatever that is. Some people it’s emailing me, some it’s text, some it’s a phone call. Some people it’s just sending me a message and saying, no need to respond. But I’m thinking about you and I’m grateful for everybody here, including our newest member, Christy Gaunt, who came on in the middle of this her interview. I was, like, walking around being like, yeah, so, like, my mom and brother died and I’m totally distraught, but let’s talk about you joining the So, which is crazy, but I really appreciate and love Christy for that.

Mickey Powell:

And now I’m coming back. I’ve had a lot of time to think and to process and to see how we can all grow together. Josh, you’re more than welcome to announce my promotion if you want. Otherwise, I’m going to do it.

Josh Schachter:

That’s why Mickey really came on the.

Mickey Powell:

Been a it’s been a really horrific five, six weeks. I’ve come to terms with the fact that that pain will never fully heal and that’s okay. And I’m really excited to get back to work while, of course, still doing all the things that will come up and yada, yada, yada. So I’m going to stop there, otherwise I’m going to nervous talk for the rest of the episode.

Kristi Faltorusso:

Well, we’re happy to.

Jon Johnson:

All right. Goodbye, everybody. Yeah, have a good day and good night. Well, no, but I can say this because I’m the other guy on the microphone. It’s been not the same without you here.

Mickey Powell:

Thank you.

Jon Johnson:

I’ve missed the hell out of you. Missed you, too. So it truly is not the same group. And I got kind of tired of Josh and so I wasn’t even here.

Kristi Faltorusso:

For half of the episodes. Relax.

Jon Johnson:

I know we’re going to get to our guest, but her name is Christy, too. So this is going to be a really great listening experience for our listeners. Christy. Christy, christy.

Mickey Powell:

Yeah. Should we do a round of introductions again?

Josh Schachter:

Sure.

Jon Johnson:

Who are we today?

Josh Schachter:

I just want to add, though, one last thing on this. So really, Mickey, I’m not just saying that in almost every call that I got on over the past month and a half, people were asking me the first thing they were asking me was about you. What do I say? He’s good. He’s okay. No, he’s not okay. What I did say, because I felt like this was the best representation and I said in a way where I hoped it wasn’t. Reductionist either, is like, all things considered, he’s amazing because what you’ve gone through, what you’re still going through, what you will go through is obviously horrific. Somebody actually told me last year they had lost both their parents and they said that I’m going to go on a tangent here.

Josh Schachter:

They said that one of the worst things you can do is tell somebody that they’re being strong, because that is like I have. So I won’t say that. But even just the way that you were communicating with me behind the scenes throughout everything and your presence to talk to Christy as she was going through the process and your openness with the community and your openness right. Like, to me, I’m just dumbfounded by it. I’m so impressed by that. And it’s inspirational and I just commend you and I don’t know how you do it, to be honest. All that you are going through and have gone through, it is incredible. And I do strength, whatever word you want to use in place of that.

Josh Schachter:

It is tremendous.

Mickey Powell:

We’ll figure that out. But I’m really excited to chat with Christy. So Christy with a G and an so I say we get into that.

Josh Schachter:

All right, Christy, tell us a little bit about yourself, your background here, kind of where you’ve come up through in your career. Tell us a little bit about Gainsight and what you’re doing today with us at Update AI.

Kristie Gaunt :

Everyone here knows Gainsight.

Jon Johnson:

Is that could you explain what do they do?

Kristie Gaunt :

Yeah, what?

Kristi Faltorusso:

No, let’s not make we’ve learned that we can never assume anything. We get yelled at by Josh’s listeners, only Josh’s. Our listeners are great, but the ones that Josh knows, they’re not as kind. So I think we should explain.

Kristie Gaunt :

Going to have to dig into that in a little bit, but sure. I am the new senior Ae. I have been in sales for about ten years and have done a little bit of everything, but always with a seller’s hat. So I started by being a selling manager for Anthropology. I moved into It Sales, and then I forgot my three and a half year stint as an investor relations and marketing manager for a private equity firm. So that was interesting. Then I pivoted really into sales. So it was it sales, then it was Medical Device sales, and then most recently Gainsight, where I pivoted from medical device.

Kristie Gaunt :

It somehow translated that into being chosen to be an Ae at Gainsight and then fell in love with customer success, gainsight as a whole. I had been there for a little over two years until Updates Recruiter Creatively reached out to me. Hamish. Shout out Hamish.

Jon Johnson:

Good old Hamish, Christie’s best friend.

Kristie Gaunt :

Oh, I actually watched that podcast. I’m sorry about that.

Kristi Faltorusso:

I think that’s the most.

Josh Schachter:

It actually is the highest rated, the highest, most views.

Jon Johnson:

Wait, so Hamish is your recruiter?

Mickey Powell:

I know you hired him. We didn’t treat him like we like him.

Jon Johnson:

But I’m outside of the Update AI bubble, so I only have the experience on the podcast.

Mickey Powell:

Do you want to come into the bubble?

Jon Johnson:

Josh and I already talked about Mr.

Kristi Faltorusso:

C. Josh, stay outside the bubble with, please, John, please stay with me. I didn’t know that you guys had hired him.

Josh Schachter:

We’re not letting this derail into a conversation about Hamish, no matter how many more eyeballs that gets the episode. I love Hamish.

Jon Johnson:

He’s a great guy so much.

Kristi Faltorusso:

Yes, he did a great job.

Josh Schachter:

No, listen, I’ll tell you what. I’ll tell you what. Hamish came to me. I told Hamish we were looking for this role. We had dabbled, I guess, a little bit in trying to look for the person our own, on our own, hadn’t gone full throttle, but had struggled a little bit. And I told him what we were looking for and he said, great, I’ll get you the perfect candidate, and I’m going to line up half a dozen folks and one of those people is going to be like, your absolute person. And he was so confident about it. And then I think Christie’s profile was the first one that came back to me.

Josh Schachter:

They all came back in a slew, but I think hers was the first one that I saw. And I was like, oh, my like, whatever. You’ve just been so confident about delivering. You have delivered. So we were thrilled with bringing Christy on board. Christy felterusso now’s your chance to know every deep, dark secret about working at Gamesight. All the competitive intelligence that you can.

Kristi Faltorusso:

I feel like I don’t not know. I’ve been buying Gamesight for ten years. I don’t know I feel of anybody. I feel that probably I know enough as an outsider, so I don’t need to probe.

Josh Schachter:

Josh, what was the highlight? Christy Gaunt. I hate this. Kg KF.

Kristie Gaunt :

That’s what we’re you can call me Kg. That’s fine.

Josh Schachter:

Okay, Kg.

Kristi Faltorusso:

You can just call her Christy and I can be chaos.

Kristie Gaunt :

It’s fine.

Josh Schachter:

I’m not getting into this. You derailed him.

Jon Johnson:

I saw his brain stop.

Josh Schachter:

Leave me outside that bubble. Kg, what was the highlight of your working at Gamesight?

Kristie Gaunt :

Well, honestly, all of it. It really is what people say it is. It is the best company I’ve ever come in contact with. I couldn’t believe that I got hired there and then from the moment, even in my interview process, every single person was as cool, if not cooler than the last, and very smart. So I was like, whoa, I just want to learn from this, so we’ll see how it goes. And then I think closing my first six figure deal in the first six months as an Ae was shocking and also like, oh, shit, now I know why they hired me. I just needed to believe it myself. So that was a big deal to me.

Josh Schachter:

What was it about the culture? Because it sounds like Culture is a huge fan. We’re not also going to go into like, a 30 minutes derailment about Nick meta, but what was it about the culture at Gainsight that was so appealing?

Kristie Gaunt :

Well, I won’t go into the derailment but it does start at the top. He is exactly how he is and portrays himself to be internally and externally, 24 hours a day, seven days a week. I think there’s twelve of him.

Josh Schachter:

Do you think he sleeps? He strikes me as the guy that doesn’t.

Kristie Gaunt :

Maybe a four hour sleeper. I’m not sure. I’ll text him. We’ll see. No, I’m just kidding. And I haven’t even met him in person, guys. So that’s the craziest part. He was able to influence this kind of culture throughout 1000 plus person company and make everyone feel like they were someone and something really important.

Kristie Gaunt :

And where I was in my life personally, I really needed something like that. I just didn’t even know that it existed. But the most supportive people we have, instead of HR, it’s called Teammate Success. Our sales team literally had one person that was responsible for ensuring that we were happy, even though I had already put my two weeks in. I had just hit my two year anniversary and a Gainsight brand as Theragon showed up at my doorstep, even though I had already put my two weeks in. Just little things constantly sprinkled throughout. And obviously, Josh, we talked earlier and you’re like, I’m glad you have the same humor as a five year old. Well, one of Gainsight’s values, one of their five or six is childlike joy.

Kristie Gaunt :

And they literally sprinkled that shit everywhere. So I loved it.

Mickey Powell:

That’s great.

Kristie Gaunt :

Yeah. Do you want me to dig into any of those aspects?

Josh Schachter:

Christy felterusso KF, what do you like the most about the culture at Client Success?

Kristi Faltorusso:

I would say for us it’s the human first culture. Like working for Dave and that team. I’ve worked for as many CEOs I have, and most of them talk a good game. Right. But to what Christy said, and I know this about Nick, I’ve had a long standing relationship with him. He is very much who he portrays himself to. There aren’t two Nicks. I like to say the same thing about Dave.

Kristi Faltorusso:

There aren’t two Daves. It’s like what you see is what you get. And there is something I really appreciate about those types of leaders, and I do think they’re few and far in between. So if you ever have the privilege of working with somebody like a Nick, like a Dave, you take that and you go on that journey for a bit.

Kristie Gaunt :

Agreed.

Jon Johnson:

Awesome. One of the you know, we’re reading through all of our prep document and just for the listeners, we just got an intern and it’s making our jobs so much easier with all this prep documentation. I just want to give a big shout out to Josh for organizing all of that and getting this in front of us.

Josh Schachter:

To Daniella for actually doing the work.

Jon Johnson:

Daniella, she’s my favorite person right now and I’m so grateful. And I was reading through your prep doc and one of the things that kind of stood out to me. No, I actually really like this one thing because you mentioned it early. You said when you closed your 1st 100,006 figure deal, whatever that six figure deal, you’re like, oh, shit, this is why they hired me, right? You needed to believe in yourself. You talk a little bit about your experience with anthropology back in the day of maybe not feeling like you’re meeting expectations and kind of believing in yourself and reading through almost everything in here. There seems to be a theme of finding out who you are and identifying not just what your strengths are that you see internally, but what others see externally in you. And I know I’d love to hear you just kind of talk about the path because you mentioned that you maybe wanted to be a doctor and move into some care. You did some hospice work.

Jon Johnson:

Walk me through that journey of, I think finding yourself right where you’re at today in this role. You’ve had these wins, but you’ve also had a bunch of roads that maybe didn’t go where you thought they would. But as we know, life is not it’s a journey, right? And we get to where we’re going. So I know that’s kind of a meandering question, but it’s something that stood out in your intro and then just kind of the documents that you shared as well.

Kristie Gaunt :

Awesome. No, I like that. I like that question a lot. And to be totally transparent, I don’t think I’m exactly who I am for the rest of my life. Today, I think we’re ever evolving, ever growing. And if I’m not growing, I’ve learned I don’t like it. So if I get too cozy, I used to just want to be settled and comfortable and stay exactly where I was because I don’t want to change this moment. But there’s no fun in that.

Kristie Gaunt :

There’s no growth in that. But, yeah, going back to Anthropology, all my friends had these corporate jobs and at the time and I graduated in 2008, 2009, and at the time, everyone was moving to New York or doing nets, and I’m like, I’m going to work part time in Anthropology at 22 because recession is about to hit. And here we go. But I very quickly moved up there. That being said, I still in the back of my head heard this voice being like, you’re not enough, like, you’re not doing enough. I want more for myself. And so I was like, what does that even mean? I ended up moving to downtown Philadelphia and could not afford living downtown on a retail salary. And a private equity firm took a chance on me and was like, you’re going to be a marketing manager.

Kristie Gaunt :

This is age 24, 25. And I had this office and I’m just like, impostor syndrome wasn’t like a thing back then, but I was like, I have no business being here. Everyone to Wharton. I, like, scraped by at St. Joe’s, like, what the f am doing? But I learned so many things that I hated. I learned so many things about myself that I really needed to work on, and I had to grow up very quickly. And from there, it was just like, I know that marketing and sales is really my forte. I just don’t know, how do I get there? There’s just so many things, and the world is like, do this, do that.

Kristie Gaunt :

No, you can’t do this if you do that, that’s not cool. Blah, blah, blah. I’m like, when are you going to trust yourself? So still didn’t really trust myself at that point, by the way. So then I worked for Apex System, which is a recruiting firm, and I was pretty good at it. I was an account manager. Took on some really big accounts there, and just felt like I still wanted so much more for myself. And my family is big in healthcare. My dad was a healthcare executive.

Kristie Gaunt :

My older sister, who Josh met randomly on Bluetooth the other day, kate, she’s in healthcare, and she’s done really well. And my little sister’s in healthcare and brother. And so I was like, I need to do that too, because I do what the Hobans do. Of course, again, not me. And so I worked in Med Device for three and a half years, and then we moved to for during COVID and from Philly. I felt like in Philly, I just wasn’t getting out of this bubble that I had comfortably gotten myself into, and I was really I don’t think I’m happy here. So I ended up serendipitously somehow they opened up an opportunity at my Med Device sales company to move to Charleston, and I did that. And then I was driving all over the place, like, hours and hours.

Kristie Gaunt :

I had a three year old, and I really was unhappy again. And I’m like, Shoot, this is like I moved my husband and my little son here. I’m not even happy. I need to pretend I’m happy. I went through, like, a little slump where I was just like, what did I do? We should move home. No, I don’t want to go home. So one of my new best friends that I had met, I knew nobody here, but you can make friends really quickly with like minded individuals who take a risk and move to a place they don’t know anyone. And she’s like, I work at a company called Gainsight.

Kristie Gaunt :

I’m like, what the heck is that? And she’s like, oh, we’re a customer success. SaaS platform. I’m like, I really do want to get into SaaS, because my husband’s in SaaS. He’s sitting in his office being ten times more productive than me when I’m on my stupid car rides to Savannah, Georgia. I can do that. What he’s doing? And so she’s like, I’ll get you an interview. I’m like, okay. And then interviewed 13 rounds.

Kristie Gaunt :

It’s normally not like that.

Kristi Faltorusso:

13 rounds normal. 13 rounds is like there was, like.

Jon Johnson:

A record when you said that.

Mickey Powell:

For the record, I gave Christy two thumbs up after one phone call. 120 minutes. Phone call.

Kristie Gaunt :

Thank you.

Kristi Faltorusso:

Wait, without completely derailing, who did you meet with? Like, without giving every name, like, a woman for the roles, like, 13 is so much okay.

Kristie Gaunt :

My friend Jen, love you. Jen accidentally referred me to an enterprise account executive role where most of those AES were veterans of SaaS and B, two B tech or B, two B sales and work for Zoom or all these big tech companies, and they’re like, why is we like you? We really do, but we don’t think you’re going to like this enterprise position and you’re just not qualified. But you have gainsight in you. And I’m like, oh, okay, like, whatever that means. Let’s cut some success.

Jon Johnson:

You have gainsight in you. That is the most aspirational interview.

Kristie Gaunt :

Like, no, but I can you’re definitely part of it. Like, you have that. We just need to find your place. And so I interviewed with the account management team and then the mid market account executive team, which is actually where I landed. I wanted net new sales, but I didn’t want to do enterprise at that time. And so it was perfect. I ended up getting hired in the mid market account executive, and then everything just changed. Like, the amount of growth I had from 22 to 35, those 13 years of going through different industries, I mean, I think I grew like, tenfold in the two years that I was at Gamesight.

Kristie Gaunt :

I don’t know how, but maybe the things that I was going through at the time personally made work. Just feel like I just could not wait to wake up every morning, grab my coffee and take my son to daycare and hop on the laptop. So I have felt that all four days here now at Update as well.

Jon Johnson:

We’re four days, baby.

Kristie Gaunt :

Sorry, I feel like I just talked for 27 minutes.

Kristi Faltorusso:

No, it’s okay. You did, but you’re supposed to do that. This is your episode. So, Christy, when did you know it was time for you to make a change? Right? So you talked about loving this journey at, right? So we also mentioned you don’t want to get bored, you don’t want to get stagnant. You like to be challenged. What was it that you said? You know what, I did what I needed to do here, and it’s time for me to make a change?

Kristie Gaunt :

That’s such a good question, and I think about it a lot still. Over the summer, I moved to the strategy for sales strategy, and so I didn’t really talk to prospects anymore. I started to lose that muscle, and I lost very quickly felt like this journey that I was on and this growth journey that I was on, and so I was like, wait, what is it? Is it Gainsight or is it this role or what do was? So Hamish somehow knew that I was going through this reflection.

Jon Johnson:

No, I love this.

Kristie Gaunt :

And I got, like, a voice memo in my LinkedIn inbox and I didn’t even know you could do that, even though I didn’t for a living. You have to do it from your mobile device.

Kristi Faltorusso:

That’s why it’s a mobile thing.

Kristie Gaunt :

Oh, cool.

Kristi Faltorusso:

It’s not available on the desktop. You can only do it from your mobile. Oh, yeah. Anything you want to know about LinkedIn?

Kristie Gaunt :

Okay, we’ll circle back.

Jon Johnson:

She’s a bit of an influencer.

Kristie Gaunt :

I know. I follow her on LinkedIn.

Jon Johnson:

Let’s see, for everybody who’s listening and.

Josh Schachter:

Can’T oh, is this the part of the segment where our guest is then going to go like, oh, I can’t believe I’m talking to Christy Falterusso. I follow you, blah, blah, blah?

Kristi Faltorusso:

No, she’s telling us no. Hamish reached out to her. She got her voice memo. Stop cutting her off. I want to hear this story. So, Christy, so he pitched you and his voicemail.

Kristie Gaunt :

Good on you.

Kristi Faltorusso:

I know, it’s not his color.

Josh Schachter:

I’m an influencer, too, by the way.

Kristie Gaunt :

I know you guys are all influencers. I am not one. So let’s help me be like you.

Mickey Powell:

No, I’m just kidding.

Kristie Gaunt :

So, Hamish, yeah, he gave me a voice memo. Very creative. I pushed play, heard an Australian accent, heard AI, heard founding Ae. I was like, It’s going to be hard to get me to leave Gainsight, Hamish, but I’ll give you a conversation for that creative way to reach out to me.

Josh Schachter:

Do you think the word founding made a difference in your initial impression and reaction to the opportunity?

Kristie Gaunt :

Well, yes, because I knew founding means you’re not really just an Ae. Your customer support, your customer success, your marketing, your everything strategy. And I wanted it all.

Josh Schachter:

And there’s room for growth, right? And that’s actually, like, the first tactical thing that Hamish and I talked about because we actually cowork from time to time together in New York, and I was sharing with him my job description, and he’s like, change that to founding Ae, and that’ll get a lot more.

Mickey Powell:

Intrigue from the right people, because right is the right people. We wanted somebody. One of the things I always look for, and this is why I think Josh and I hit it off, is like, I look for people with founder mindsets, even if you’re not a founder right now. So as soon as I can’t remember what you said, Christy, but you made it very clear that you have that whatever that was. So I was just like, yes.

Jon Johnson:

You’ve got update AI in you.

Mickey Powell:

You’ve got update AI in you. That’s right. I won’t tell you which part where.

Josh Schachter:

But it’s in Christy. Christy was so savvy. I think it was inadvertent, although perhaps it was part of her master plan. But I was in a slack thread. With her, and I think she hadn’t even started officially yet, although she was already helping us with stuff and somehow organically through a slack conversation, within like, 30 seconds, it was like, okay, we’re going to change your title to Senior Ae. I was like, wow, if she can negotiate that well with our sales prospects, then this is going to really yeah.

Mickey Powell:

A little tip for all of the potential customers out there, josh is bad at negotiating. Seems like you can pretty much do negotiating. So, like, if you want a discount, go talk to Josh. He’ll give it to you.

Kristi Faltorusso:

That’s why I don’t call you.

Mickey Powell:

You don’t even have to ask. He will negotiate with himself.

Jon Johnson:

Yeah, he’ll just negotiate with himself.

Mickey Powell:

You know, I think I can do better. I’m going to sell you more if you come and talk to me.

Josh Schachter:

I want to bring this conversation to a topic here around because our supposed listeners are, in theory our listeners, in theory, want to understand ways to grow their careers and they listen to these stories about our guests and our own experiences as benchmarks to their own growth and development professionally, not personally. And Mickey, Christy and Christy, you guys each took a leap. You left more established companies and you joined fairly small startups. And what I want to understand is what are some of the trade offs that you all had to make when you were considering that opportunity? Because that’s something that I think many listening to this can relate know, they want so desperately to go and do their own thing as a solopreneur or for a startup. But there’s trade offs, there’s a mortgage, there’s kids, there’s this, there’s that. Christy, we can start out with you, but then I want to let Mickey and KF respond as well. And you can be honest, if it was like, I just wanted a slice of the pie.

Kristie Gaunt :

Can I go last?

Jon Johnson:

Yeah.

Josh Schachter:

All right. So I’ll respond as Mickey. Mickey. This is how Mickey responds. I just wanted a slice of the pie.

Mickey Powell:

There were three things I wanted to take a risk, so I took as much risk as I could with the support of my Kai. Like, I really probably pushed it to the limit of what she would tolerate in terms of risk taking because I have a mortgage and cars and a daughter and a family and a wife and yada, yada, yada. But yes, I wanted a big slice of the pie because if I’m going to pour myself into something, I want to know that it has an impact. And the best way to represent that right now is by owning a piece of the pie. So that’s one of the reasons why I joined. The other reason is that it was very clear to me from the very first time that Josh and I spoke is that we were willing to go to places to explore weird avenues that could be beneficial or could be BS. And I was pretty confident that if we did that long enough, we would land on like if we could stay there long enough, we would land on something really big, which I think we have. And I got fired, so I needed a job.

Jon Johnson:

Yeah, but also like those big swings, you never know what you’re going to get. Right? You could land a great Ae or you could get banned from Pulse.

Mickey Powell:

Yeah. Are we allowed back?

Josh Schachter:

I don’t know. I think I’ve mended that. I think so. Okay, good.

Jon Johnson:

It’s my favorite story, by the way.

Kristie Gaunt :

I’m laughing, but I have no idea what you’re talking about.

Kristi Faltorusso:

We’ll fill you in on all of our backstories so that way you feel.

Jon Johnson:

KF, I want to hear you. What is a trade off? This is a really good question.

Kristie Gaunt :

Life is a trade off.

Jon Johnson:

Oh, wow, we got deep, guys.

Kristi Faltorusso:

No, I mean, honestly, we’ll start with Comp, right? That was the biggest visible trade off, right? I took an extremely significant cut to come here and equity is great, but equity is only great if the company does something that makes that equity worth something. We’re very small right now, client Success. And so it might be listen, unless we had acquired right, that might have a different outcome for us, but otherwise it might be a long road ahead before any of that materializes to something. So for me, it was the pay cut, right? That’s the first thing I had to do as a trade off. Second thing is resourcing. Every team I’ve been a part of, I’ve had resources. Now every company is varying degrees of that, but I’ve had budget, I’ve had people, I’ve had technology. I’ve had a lot less of that here at Client Success.

Kristi Faltorusso:

But I’ve been able to be very creative, right? And so I feel like I’ve done a lot with a little and have been successful in doing that. So I think for me, I’ve learned how to do things without, which has been cool. But knowing that I came into an organization where I would not be able to just hire a ton of people and buy whatever technology I thought I needed and do all of the things right, even travel to go see customers as much as I want or participate in events the way I’d like to. Those were all things that were trade offs for me. But I will say, at the end of the day, none of that, right. When I left my last company in Teleshift, I made a cognizant decision that I wanted to go back to doing work that I loved for a community that I felt connected to. So it didn’t matter if I was getting paid a dollar. I wanted to go work for customer success, right? As an industry, I wanted to serve customer success professionals.

Kristi Faltorusso:

And so whether that was Client Success or another company, that was what I was focused on finding is a role that would allow me to serve our community and make a living doing it right. I was doing all of it by myself on the side anyway, not making any money doing it. And I felt like this was going to be that next opportunity if I was going to take one. So those are some of my tradeoffs. So I would say Comp probably the biggest one. And then bandwidth like personal versus professional.

Kristie Gaunt :

I love that. I love that story. Honestly. What both of them, both Mickey and KF have said has definitely resonated with me. Along with going from a company like Gainsight that you can call someone, know, do a cold email or something, and they’re, wow, you know, I’d love, but, you know, we don’t have budget until and I’m like, wow, I came from a company that everyone’s like, who? What’s that? What are you doing? And then it’s nice. So just like that market, the market leader. Can I say that?

Kristi Faltorusso:

That’s what Gainsight was, right? So it’s nice to work on Freudian slip.

Kristie Gaunt :

Should we pull?

Kristi Faltorusso:

Definitely. Anyway, no, but I agree though, in customer success, very few companies who have customer success teams don’t know who Gainsight is. In fact, when I try to tell people who client success is, I often have to say, are you familiar with technology like Gainsight? And they go, yeah, I’m like we’re like that, but different. And let me tell you how so they are the brand, when you think about customer success, they’ve done a great job with that. I don’t think there’s any competitor in the space that’s done marketing like Gamesight and building the brand and the presence in the community.

Kristie Gaunt :

Absolutely. And I think just knowing now that Update is doing everything that we can to provide the value that customer success is creating for their companies and just all of that is really one of the big reasons why I chose Update. The product, the people, the culture is something that is going to be cultivated. But just from talking to Josh and Mickey, I was like, absolutely. It reminded me of my interview process at but I guess you know, the brand name and I was comfortable, I was cozy, it was consistent. And that’s one thing that I realized. That’s where the growth comes in when you’re not comfortable. So trying this on and really leaning into this is I’ve already learned an.

Mickey Powell:

F ton, you can curse on this podcast.

Kristie Gaunt :

Even before I started at Update, I remember learning a lot. And then just like in my first day, we had a full hour pricing session on how to go to market with this pricing, and I’m just like, wow, I would never been involved in a conversation like this. And I actually have some things I need to share, and they’re listening. So there’s trade offs everywhere. But I think I felt guided in this way and I went with my gut.

Jon Johnson:

Can I ask a question on that?

Kristie Gaunt :

Sure.

Jon Johnson:

Kind of going back to what we talked about at the top, this impostor syndrome. You’re sitting in rooms right now where your voice is not only appreciated but needed. Right. This founding position or senior position. Right. What’s something that you go through every day where you’re sitting in those meetings where in the past you haven’t had this experience before. Right. Where you just get told what to sell and how to sell it.

Jon Johnson:

How do you pep yourself up? How do you get yourself into the mindset to say, I have opinions. Maybe they’re not the right opinions, but they’re opinions and part of this job is figuring out how to get these opinions and these strategies aligned with your leaders. How do you get yourself out of that mindset of an IC of saying, I’m going to do what I’m told. Not that I don’t know what your job is like at Gainsight, but into a space now where they’re presenting you with opportunities to possibly change what’s being presented to these customers. I think a lot of people I asked this because I feel like our listeners might be in similar situations where they’re going smaller and yeah, there’s trade offs, but there’s also you are ten voices instead of one. Right. And there is a weight that you carry in the role that you’re in right now. So how do you break out of that mindset before and kind of show up in those moments?

Kristie Gaunt :

I was never scared to speak. I’m sure Josh and Mickey can tell you I was never scared to be the one who was everyone was going this way and I was the one who know sometimes it was really uncomfortable and I’ve also had conversations with Mickey saying, we might disagree, but I really want to hear what your side like? I always want to hear every single, otherwise the solution just feels it’s probably maybe it works short term, but it’s not going to work long term. So I just continuing to trust my voice. But also I think we’re all winging it a little bit. And before when I was, wow, Chrissy, you’re like hopping industries. The theme was always in sales, but I did jump around to industries. But changing your attitude, changing your mindset, that’s saying like, wow, instead of having a fixed mindset, having that growth mindset being like, yeah, now you know a lot about a lot of industries and you can take a little bit from here and a little bit from your private equity background and help with fundraising. You can go take a little bit about your healthcare experience and have that empathy that customer success is so good at and then all of that selling experience to hopefully close some deals.

Kristie Gaunt :

So it is really nice feeling like I came back to a place where I’m not only heard, but also it’s being taken seriously and being put into practice, and we’ll see if it works. But I don’t know. It feels good.

Josh Schachter:

I think your washing machine is on.

Kristie Gaunt :

My garage door is open.

Mickey Powell:

Oh, your garage door is open.

Kristi Faltorusso:

There’s a six year old walking in.

Josh Schachter:

Hi, Nolan.

Kristie Gaunt :

Here we go.

Josh Schachter:

And I want to say also, we all have imposter syndrome. One of the things that Christy’s that is Christy’s first day of work, officially.

Jon Johnson:

You brought her on a podcast on her first day.

Josh Schachter:

Here’s the thing. Here’s the thing. And listen, I’m not necessarily saying that everybody has to be so generous with their time and attention as Christy has been. It doesn’t feel like to any of us that it’s her first day because she’s already set up on everything for weeks now. She’s already been working on stuff. She’s already been in calls. She’s already a trusted again, like, people have to have their own personal decisions on boundaries, but she has just leaned all the way in. And so for me, if she’s faking it, then she’s making it, because if she feels a monster citrus, she’s overcome that with enthusiasm and with brute force proactivity, for sure.

Jon Johnson:

Well, I think the sooner that you can realize coming out of more defined roles into less defined roles, the sooner you realize that literally everybody is winging it and relying on no, but that’s not a secret. I think there’s wisdom here, is that we are winging it and relying on our experience and others experience of those around us. Thanks for cutting me off.

Mickey Powell:

I was just going to say that we think alike. I love you.

Jon Johnson:

I know. No, but that’s the thing is I feel like people think this is like a big, like, oh, my gosh, everybody is winging it’s. Like, no, we’re creating things out of nothing. There are zeros and ones. That’s why we have GTM models. It’s why we have all of these things, because we’re just throwing things against the wall and seeing what sticks. So I really like your mindset here, and I think you are setting yourself up for success, not just with Update, but with what comes next, too. To say, hey, I’m acknowledging that we’re just going to rely on the experiences.

Jon Johnson:

And my experiences, that’s the key. My experience are valuable as well. And as soon as we can get ourselves to have that internal dialogue, to say what I’ve experienced and succeeded in is valuable and offers me a seat at this table. And I think you’re proven that just the fact that it’s your first day and your boss brought you onto a podcast about customer success, and you’re like, yeah, okay, let’s do that. That’s part of my onboarding. Let’s do this for every new employee. Josh first day, every new employee at Update, AI. Joins our in if he’s like, maybe not every employee.

Josh Schachter:

No, I don’t want to bore you guys. If we want to make every episode an advertisement for update.

Mickey Powell:

AI sure, but I don’t because we will support you emotionally and sometimes financially.

Jon Johnson:

And occasionally get a paycheck.

Josh Schachter:

I keep telling you, it’s in the.

Kristie Gaunt :

Mail on that one.

Josh Schachter:

All right, guys, I think it’s a wrap. Christy, welcome to the team. Mickey, welcome back. It’s so good to be here with all of guys today. Okay, until next week, happy post Thanksgiving, everybody.

Mickey Powell:

Happy Thanksgiving.

Kristie Gaunt :

Happy Holidays.

Josh Schachter:

Love you.

Kristie Gaunt :

All. Bye.