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Customer Success: Pivot Your Career artwork

Reevaluating Success: Layton Chaney candid and unfiltered

Customer Success: Pivot Your Career · 2026-03-22 · 51 min

0:00--:--

Key moments - from our scoring

Substance score

38 / 100

Five dimensions, 20 points each

Insight Density5 / 20
Originality6 / 20
Guest Caliber13 / 20
Specificity & Evidence8 / 20
Conversational Craft6 / 20

Layton Chaney, an 18-year veteran of customer success who co-founded Better Growth consulting and taught at Pavilion's CCO School, opens up about burnout, redefined success, and the cost of relentless ambition in SaaS. After seven and a half years running Better Growth, Chaney experienced severe anxiety and burnout despite external success - a thriving consulting business, influential speaking opportunities, and the launch of a new community initiative. Rather than push through, he made the counterintuitive decision to step back, eventually selling his shares to his business partner and shifting to independent consulting. The episode explores how Chaney's 38-year trajectory of non-stop work (starting at Bazaar Voice, the early SaaS rocket ship) masked deeper questions about purpose, identity beyond achievement, and whether grinding relentlessly serves the life you actually want to live. His reframing of failure - launching Better Growth U as a learning experience rather than a missed milestone - challenges the SaaS industry's win-at-all-costs narrative. The conversation resonates with anyone in CS leadership questioning their own sustainability and what success truly means after decades of chasing excellence.

Key takeaways

  • →Burnout is a legitimate health issue that requires intervention and rest, not pushing through it, especially after decades of non-stop work.
  • →Success and failure are often misunderstood - admitting when something isn't working and pivoting is a learning opportunity, not a true failure.
  • →The SaaS industry culture of constant grinding and relentless ambition can mask deeper unhappiness and prevent reflection on what truly matters.
  • →Taking intentional breaks from work can restore energy, clarity, and perspective on career priorities and personal values.
  • →Mental health support through therapy and honest self-assessment are essential tools for navigating burnout and career transitions.

In this episode

  1. 1Hosts Welcome and Personal Updates
  2. 2Impact of Alex Raymond's Growth Department Book
  3. 3Layton's Career Journey and Burnout Experience
  4. 4Success Disguises Failure: Redefining Career Goals
  5. 5The Better Growth Community Pivot and Mental Health
  6. 6Work-Life Balance and Generational Perspectives
  7. 7Accepting Failure as Learning and Moving Forward

Mentioned

Bazaar VoiceShopgatePavilionBetter GrowthTrilogyAlex RaymondLayton ChaneySamAlex WhiteDavid LoketsThe Growth DepartmentCCO School

Guests

Layton Chaney

Topics in this episode

Burnout and mental health in SaaSBetter Growth (consulting firm)Bazaar VoiceCustomer Success professionPavilion CCO SchoolSuccess metrics vs. life satisfactionRemote work and work-life balanceThe Growth Department (book by Alex Raymond)Career pivots and reinventionTherapy and personal wellness

Questions this episode answers

What caused Layton Chaney to sell Better Growth and step away from consulting?

After seven and a half years running Better Growth, Chaney experienced severe burnout and anxiety attacks despite external success. He realized he had lost the drive that fueled his 20-year SaaS career and decided to listen to his mental health rather than continue grinding, ultimately selling his shares to his business partner and pausing to reassess what success means to him.

How did Layton Chaney reframe his failure with Better Growth U?

Rather than viewing the failed community launch as a loss, Chaney reinterpreted it as a learning spike in the agile sense - an experiment that revealed it wasn't the right fit for him at that time. He publicly admitted failure, apologized to contributors, and recognized that success isn't always about being the best at everything; sometimes it means choosing what protects your mental health and family.

What is Layton Chaney's background in customer success?

Chaney started in CS at Bazaar Voice, one of the first SaaS rocket ships in Austin, when the role was called 'community manager.' He's since worked at Shopgate, served as dean of CCO School at Pavilion for five years, and founded Better Growth consulting, building a career driven by competition and excellence across 18+ years in the industry.

What is Layton Chaney currently working on?

Chaney is now an independent consultant through Leighton Chaney LLC, working with a company he describes as doing good for the world. He's also writing a book called 'The SaaS Truth' about his 22-year experience in software startups and the realities of grinding without sustainable boundaries.

How does Layton Chaney view the relationship between burnout and success in SaaS?

Chaney argues that SaaS culture has conflated continuous grinding with success, allowing burnout to hide behind external wins like revenue and growth. He contends that real success should include mental health, family presence, and sustainable ambition - not just career achievement - and that failure to maintain that balance is a systemic problem in the industry.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

5 / 20

The episode is largely personal reflection on burnout, mental health, and career reevaluation with recurring platitudes rather than actionable B2B insight; the few operator-relevant ideas (the 'Sunday method,' culture affecting CS outcomes, CAC/renewal math) are thinly developed amid long emotional tangents about childhood, ice fishing, and school start times.

What's your total customer acquisition cost if it's over a year? The most important thing is getting that renewal, otherwise you've lost money
I call it the Sunday method... if you get to that point where you cannot take your weekend without that feeling coming up on Sunday, that's when you got to

Originality

6 / 20

Much of the content recycles well-worn tropes (deathbed regret, 'fail fast,' work-life balance) rather than fresh thinking; the 'Sunday method' and reframing failure as success are mildly distinctive but not deeply argued.

when you're on your deathbed, I've never heard anyone say I wish I worked more
they always talk about fail fast, learn from it, and move on

Guest Caliber

13 / 20

Layton Chaney is a genuine practitioner with 18+ years in CS, an early Bazaarvoice employee through hypergrowth, a Pavilion CCO school instructor, and a consulting founder - relevant and credible, though the conversation leaned on his personal story rather than operational expertise.

Leighton has been in customer success for over 18 years, working for for such companies as Bazaar, Voice, Shopgate, a dean at the CCO school at Pavilion
I taught CCO school, Chief Customer Officer school at Pavilion for five years

Specificity & Evidence

8 / 20

There are named companies and some concrete personal details (Bazaarvoice growth to 800, Dell hiring story, six figures in his 20s, five years teaching), but the episode offers almost no hard business metrics, dollar figures, or data that a CS operator could benchmark against.

I got there early. I was within the first 30... of employees at a company that would... be up to 800
I made six figures in my 20s

Conversational Craft

6 / 20

The hosts largely affirmed and mirrored the guest with their own anecdotes rather than probing or pushing; there was almost no productive disagreement, and questions were open-ended and supportive rather than sharp.

Yeah, so. So mine's a little bit different
See, I think that's healthy when you can express yourself

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A46%
  • Speaker C34%
  • Speaker B21%

Most-used words

success33customer28back27leighton21career20best18culture18started16alex15life15important15start14last13feel13family13podcast12

Episode notes

In this episode of the Customer Success Pivot Your Career Podcast, hosts Alex White and David Lokietz welcome Layton Chaney, an 18+ year customer success veteran for a candid, unfiltered conversation about burnout, mental health, and redefining success. Layton describes how he recently paused and labeled a personal failure, only to find relief and clarity. The discussion explores how SaaS grind culture, shaky leadership values, and weak psychological safety impact CS. Learn practical signals like the “Sunday method” to know when it’s time to reevaluate your priorities.

Full transcript

51 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign.

Speaker B: Welcome to the Customer Success Pivot your career podcast. I'm Alex White and my co host is David Lokets. Our podcast is focused on people looking to get into the customer success profession or move up in customer success if you're already in the field. Welcome back. David, I know you weren't on the last podcast. It's great to have you here. How are you doing, Alex?

Speaker C: I'm doing great. I thought the last podcast was fantastic, by the way. Maybe it's absence of David made it even more brilliant, but that was fantastic. Overall, I'm doing great. How are you doing?

Speaker B: I'm doing good. A little, you know, a little, uh, some things health wise as far as knees and stuff like that, getting that looked at, try to get that fixed and all the other things, but I have no complaints. Life's good.

Speaker C: Yeah. Hey, welcome to the aging process. Things that, uh, we did early in our life, some were athletic and some were just pure reckless, are coming back to you now. Have to pay the piper, so to speak.

Speaker B: Yeah. So what are you thinking about today?

Speaker C: Wow. You know, really? For the forefront of my mind is your last podcast with Alex Raymond. It was a fantastic podcast. Not only that, but his book, the Growth Department. I flew through that book and both the podcast and the book had a profound impact and really got me thinking.

Speaker B: Yeah, I was excited about the episode as well. And even before the podcast I had read like 2/3 of the book and I'm like waiting for the last part around expansion and the uh, amplify method. And it was, it was every, everything and more of what I was thinking, but articulate in a way that had a roadmap that you could go out and execute on how you change the CS narrative to. We're a revenue department and we're just as important for as sales, if not more important because how. What's your total customer acquisition cost if it's over a year? The most important thing is getting that renewal, otherwise you've lost money. And that was all wasted time as far as all the people. So I got a lot out of it myself.

Speaker A: Oh.

Speaker C: Uh, and I've already started applying some of the concepts behind it. So first and foremost, the book is so well written, it's not written with a lot of extra fluff. It's very prescriptive, it's very much thought provoking. And I've already started scheduling meetings with my customers, the ones we've just finished engagements with, to talk about what is next, not just a review of. Oh, well, how did we do? Kind of make us feel better. But, hey, we did a great job. Now what can we do for you? So I've already taken some of that and I've also shared the book. I've sent off four copies of it and one Kindle copy to some colleagues and people I coach. So making a big impact on me, at least to start with.

Speaker B: Great. Yeah, we missed you. It would have been great to have your perspective in the conversation. You should reach out to Alex and talk to him. He's a good guy.

Speaker C: Oh, I will. It seems to run with the name Alex. Profound thinking and good guys.

Speaker B: So hopefully everyone could tell our voices apart because we're like, Alex. Alex. Didn't notice it until afterwards.

Speaker C: Oh, uh, yeah, no, it was absolutely fantastic. I was glad that you were able to pull up and have the conversation with him. I thought the one on one was quite effective as well, by the way.

Speaker B: So great. Okay with that. We have a great guest today, so why don't we get started?

Speaker C: Looking forward to it. Let's go.

Speaker B: Our, uh, guest today is Leighton M. Cheney. Leighton has been in customer success for over 18 years, working for for such companies as Bazaar, Voice, Shopgate, a dean at the CCO school at Pavilion, and also the co founder of Better Growth. Welcome to the podcast, Leighton.

Speaker A: Yeah, thank you. And thank you for your patience as we had to reschedule a couple of times thanks to a, uh, kid going back to school and petri dish of germs coming back and forth.

Speaker B: Not a problem. We're glad that we persevered through it. We kept rescheduling. We made it happen. So I'm glad able to do that. So to get us started, why don't we have you talk a little bit about your career and how you got into customer success and what you're doing today, and we'll go from there.

Speaker A: Yeah. My career has been a slower coaster, Like a slow roller coaster. Right? Like where it's like, things are good and then it's like m. And right now I'm in one of those roller coaster moments. So since we talked last a couple of weeks ago, getting ready for this actually sold Better Growth to. I sold my shares to my business partner because after seven and a half years of running this consulting business and grinding and working with some amazing clients, I just. I went through burnout. I went through burnout. And I'm somebody who takes mental health very seriously. And so I was like, I'm going to give myself a little pause. And so I am now just a consultant for, for Leighton Chaney. Llc, which I've had as a backup company for since before I started even this. And so I was going to take some time off and then as life happen, I ended up throwing a tantrum on LinkedIn, which I do sometimes. And, ah, someone reached out. And now I'm consulting with an amazing company and my heart's in a great place because they do good for the world. I keep my clients private just because I am very opinionated on LinkedIn and I never want people to have to feel like they're associated with my loudness. But someone's gotta be loud.

Speaker B: Yeah, awesome.

Speaker C: See, I think that's healthy when you can express yourself and get into some sort of ferocious debate. Even in a platform like LinkedIn, it stimulates thought. It really captures the imagination of others that say, hey, maybe I want to talk to or work with that person because where they're coming from, they're going to be transparent. It doesn't mean it's an absolute. It doesn't mean there's a wrong or right. It just means, hey, Leighton's able to express himself. We need some of that. Because often as a consultant, everybody thinks, well, I have to come in and tell them what they want to hear. No, more times than not, they want to hear what they need to hear. Kind of like the Emperor's New Clothes. Right? I think that's a healthy way to just behave. Being respectful, obviously, but being open and transparent with thoughts and that are provoking, I think is really important and a nice sort of align in that area.

Speaker A: I appreciate that, man. And like, look at us. The three of us are Gen Xers. I think we've come a long way from drinking out of water hoses, but maybe that's why we ended up the way we are.

Speaker C: Exactly.

Speaker B: And ah, Leighton, I can relate to the burnout part. I left my job back in September and I made a vow to myself and my family that I'm just going to focus on everything except work for four months. And it was the best four months I had. It's amazing how much energy you can get back. I'm, um, energized. I can add a lot of value to a company. So if you come out and you have a little bit of a break, you didn't take a break, but you got into a good situation, so that can be energizing as well.

Speaker A: That's awesome, man. I didn't know you did that. Okay, so let me ask you this because I know so many people that are doing this. Pause. Like now I'm interviewing Y', all, this is what I do. I take over. Sorry, but I know so many people that are taking these pauses. Do you think that the pandemic taught you that? Because it did me. It taught me that. Oh, when I'm forced to sit in my own company, I actually can get in touch with myself and figure out what I need to do. Whereas I think I've always been such a. I don't know if it's ADHD or what, but I've always just been like, I can't stop. I go, I go, I go, I go. And. And 2020 made me, like, sit in a room. What made, you know, you needed that? Because I think a lot of people are there right now.

Speaker B: Yeah. I mean, in my situation, it was a little bit different because I was actually working at a company when the pandemic hit that I was already isolated. I was all my team was around the world. They'd say, you have to go into the office. You show up in the office, and then you go in a conference room all day, and then you go home and you're like, why am I coming in here? I guess I get free food. That's great.

Speaker A: Yeah.

Speaker B: But there, ah, was. I was already isolated, so it's like, welcome to my world, everybody.

Speaker A: Yeah.

Speaker B: And so that didn't impact me as much. I had been working, God, uh, how many years was it straight? It was something like 38 years without a break. I'd always end on Friday and start my next job on Monday. And then the last two roles I had were directly in the CS Headlights, and it's underappreciated. So in my instance, I. I just, um, you know, questioned a little bit where customer success is going, all those type of things. I'm just like, you know what? This is the time I'm financially in a place that I can do this, and I'm going to take advantage of it. So it's been great for you, man.

Speaker C: Yeah, so. So mine's a little bit different. Leighton finding that time. About four or five years into my career, way, way, way back in the early 80s, I had what I would call my first real mentor in the business world. And we had a long drive to go visit a customer. And what I learned, the guidance he gave me, was about really forcing yourself into balance. And there's a lot of things that you can get encumbered with at work, wound up around the axle, and then you lose sight of your relationships, your parenting, whatever it might be. He really hit me up hard, and it sort of Planted a seed. And then over the next six months that we worked together, I continued to pick his brain on that and we kind of implemented that. So I try, because I traveled for the better part of 35 years, tried to balance it. So if I was home on Friday, Saturday, Sunday, there would be the balance. My second mentor and Alex. This is where we worked together for the first time in mid to late 90s with my mentor there just said, learn to contemplate your navel. I'm like, what does that mean? Learn to chill, just learn to let things go. And then the pandemic brought out more. What the pandemic did is I'm an introvert. So I'm a raging introvert. So now we get the pandemic where we get to work from home. I don't have to get on an airplane. Oh, I really liked that. So it wasn't a bad thing for me. And it's sort of the world I live in now, working remote and distributed. The rest of the world is caught up to where I wanted to be, so to speak. So that's sort of how I feel.

Speaker A: I hear you and it has been fantastic. I was not, I was a uh, in office person. But now I'll never go back because I get more done. I do understand you have to be self disciplined. I think it's probably not great for everybody, like I'll give it that but for me I get so much more done and I, I will never grow up. I hate mornings like I like to. I'm a night owl. I get most of my creativity at night and so now I can work on my terms where I get my best work done. Whereas before it's like I forced myself to fit in this box of get up early even though you ha it because you got this report you got to do or this thing you got to do. And then I felt like it was like half ass compared to when I can do it when my brain works best. So I hear you.

Speaker C: Yeah, that uh, that's an underlying issue with, and studies have been done with kids when they go to elementary, mid school and high school. We force them to start off at the crack of dawn because mom and dad are going to work where their brains and their tech, their best learning doesn't begin before 10 o' clock in the morning. So again we haven't adapted well from a learning perspective. So you're not alone in that.

Speaker B: David. I don't know if that is the same in Southern California, if it was a California or just a Northern California. Thing, but they actually required all the schools to start later up here. So now they pushed everyone back an hour. And now all the sports have to push back after school and everything. But they did that up here just because of that reason.

Speaker C: That hasn't proliferated through Southern California. It hasn't proliferated through the rest of the United States. And I'm saying that just with my limited observations. Keep in mind, I've got grandkids that are going to school in other places, so I'm not really involved in that. But it's a good thing.

Speaker B: Do you remember going to school as a kid and it was dark out? I remember that vividly. Where you're walking to school and the sun wasn't up. I'm like, so I looked on the sticks too.

Speaker A: So I'd have to go to the bus stop and just like whistle to myself, like, see this movie. M. I don't make it. Yeah, during the height of milk box kids. And here I am walking half a mile down a gravel road to the bus stop.

Speaker C: Somehow I've seen that horror movie.

Speaker A: I know. And that's how my mind works. My mind likes to mess with me ever. Even when I was little, it's, hey, you know what we should think about right now? The clown from it. Let's think about that. Right?

Speaker B: Okay. So, Leighton, one of the things I saw you had posted around Better Growth U and you started looking into doing that and this whole thing, we talked about what we're going to talk about on the podcast and you talked about success disguises failure. Can you explain to our audience a little bit about that post and the feelings and what you were going through at that time?

Speaker A: Yeah, absolutely. I think that it is. This goes back to some of our earlier conversations too. But I'm somebody who has been driven in SaaS software as a service since I was in my early 20s. I got a little lucky and a lot of hard work to end up in a spot where I ended up working for a, uh, company in Austin that was one of the first real startups that ended up actually being a rocket ship. Like my first experience to software was what we call wait to have in our career. And that was bizarre. Voice. I got there early. I was within the first 30, at least, maybe even sooner than that of employees at a company that would, within my time there, which was only a few short years, be up to 800 and then national. And it was an actual rocket ship. And from the time I got there, I was going 100 miles an hour and I have been in customer success that whole time. We didn't even know what to call it then. We actually called ourselves community managers, which are now completely another title that goes with another job altogether. But at the time, it was. We didn't know what to call ourselves, so we were community managers. And so I worked with a lot of very ambitious people. The people that started Bizarre Voice, the had a lot of them were from Trilogy or the success group from Trilogy. And then I was successful at that company because as a young individual contributor, I worked my tail off and I got to know our customers really well.

Speaker C: And.

Speaker A: And I had this desire to do. I always wanted to compete in a healthy way ever since I was young and did a lot in speech and debate and won a lot of things with that. And so I found myself competing to make my customers do the coolest things, right? And so from a very early age, I was always just go, go, go and win, win, win, and be the best and be the best. And. And for me, it was never a financial goal. I mean, yes, it's there. It's great. Like, that was a part of I'm doing this, that my salary would go up and that I made more and more money in my career and stock options vested and stuff like that. But it was never carrot was just being the best. Like, I don't know why, but I just wanted to be the best at whatever I did. And I, uh, think if I would have been a janitor, I just would have wanted to be the best freaking janitor. I wanted everyone to be like, leighton is the best janitor. Right? Like, it's just a part of my drive that I think a lot of us have. But I did that, and I never slowed it down. And so now I'm 46, right? Like, I'm not in my 20s, and I've been in customer success this whole time. And I think I started to see my mentors, people that I looked towards, really change lately in this kind of. I'm a part of diversity. I believe diversity makes us better. And. And I've just watched a lot of leaders in this current political climate just switch hats and just either ignore it or not go forward. And so I started to be like, what is the grind worth? If we don't stand for something, what's all this worth? Because I'm watching the richest person in the world not be happy. So, like, why am I doing this? Like, why am I grinding my ass off ignoring my not ignoring because I'm a family guy, but not giving 100% of my attention to my family and those that deserve it, and putting it all into this career. What is this end goal that I'm going for? And all of a sudden, I just could not for the life of me find it. And so I was desperate to try to get that passion back. And I loved my time at Pavilion as the. I taught CCO school, Chief Customer Officer school at Pavilion for five years. Sam saw something in me early in my career, and I'll always thank him for that. The CEO, uh, of Pavilion. And he gave me this opportunity to be a professor, and I loved it. And so I was like, I need that passion back. I'm going to start a community, and I'm going to flip recruiting on its head, and I'm going to teach classes, and I'm going to work with some of the biggest people in the world or in my world to do this. And so I was like, this will bring that passion back that consulting isn't. So I called and people answered. Some of the top influencers in sales and customer success and product engineering, and even CEOs were like, yeah, we'll do this. We'll teach for free for you. And so then, even with all that, I just. Every morning I woke up and I was like, I can't do it. Like, I can't find this fire that I've always had. Like, where is it? And then I was like, I started to really panic, if I can be honest with you. I started having anxiety attacks. I was like, the thought of doing this was just giving me pure anxiety, even though I had everything laid out. And so one thing about me is I really believe in therapy. And once a week, I, uh. Now it's every other week. But, uh, for five years, I've gone to the same therapist, and she's amazing, and she's helped me through all kinds of things. And this. It was just something I had a safe place to go to. And I just really realized that burnout is real and that I just needed to listen to my mind and I needed to take a break. And so kind of to what you did, right? Like, I was like, I'm just gonna stop. So I. I stopped, and I didn't respond to the community for the month that I had built up. And I was like, okay, now you're just doing wrong. You've got it. You gotta face this.

Speaker B: But I was wondering. I was like, what's happening? I'm not hearing from Leighton.

Speaker A: I was waiting for it to come back. I was like, you got this. And Then finally I was like, hey, dude, you know what you did? You failed. You failed at something you wanted to do. And that's okay. Like, people do it all the time. You failed at this. This is something you failed at. So just accept it. And so I wrote that post days before I posted it because I was just like, uh, and. And then I did and I immediately felt relief. And then I went into the community and I posted and I said, listen, I failed. I sent that post, I put it into the community and then I reached out to some of the most, some of the people that I had the longest relationship with and I'm still working through to just apologize. But more than anything, what I said was it was a good idea. Someone should do it. Right? Like someone should do this idea. And if you do, I'll do it for free. But I have slept like a baby since I've admitted to myself that I'm just not going to be the best at this. This isn't the thing. I have to be the best. I don't have to be the best at this. This is. Maybe I don't need to be the best at anything. Maybe I just need to be a 46 year old dad who is going through a career moment of what do I want to be when I grow up? And maybe that's okay.

Speaker C: Yeah.

Speaker B: One of the quotes I've always thought of, I don't know who said it. They said, when you're on your deathbed, I've never heard anyone say I wish I worked more. And I always think of that. Time passes, you're stressed out about how am I going to fit my vacation in and get this done and all that. And then three months later, it doesn't even matter. It just evaporates in the time. And m Making sure that you have those special moments with your family and friends.

Speaker C: Yes. So looking through a different lens and uh, again, let me. Allow me. When we do software development in an agile world, and I won't get into all that, a lot of times there's a lot of unknowns and we will often try to get the developers, product owners, whoever it might be, to run a spike. Okay, let's experiment, let's learn. And sometimes the learning is it's not worth doing or it's the wrong decision. So that to me is a positive. So the fact, Leighton, um, that you recognize what the community needs, the fact that you came to conclusion that it's ripping me up, uh, inside and out, hey, it's not the right fit for me. I Don't really consider that a failure in the sense that, well, what is success and what is failure? Because you could have stayed at it and been diligent, it could have just emotionally just drained you. You would have had to go to therapy five days a week, which is not what we want. Your family suffered. So I sort of see this as loosely defined as a failure, more as a learning and getting you on track with what do I want to do, what makes me happiest, how can I have that balance in life? So, again, I'm not here to challenge what's a failure, what's not. I'm, um, turning it around and I think it's a positive. You're your mid-40s and you've got a long life ahead of you. Why sit in this role and suffer for the next two, five, ten years? Because we're stubborn and I got to carry the torch. If you're able to hand the torch off, hey, you've planted a seed. You started something. That's fantastic. It's needed. I'm dropping the mic. I'm going to get back to being latent. And being latent is what we all want to achieve or strive for. To Alex's point, nobody on their deathbed has ever said, well, I wish I worked more. Yeah.

Speaker B: Uh, and Leighton, I'd be curious to hear what was the response of everybody? Were they upset?

Speaker A: No. Overwhelmingly kind. And I mean that the thing that is. And to everything you said, I knew that because I sat on it before I posted it, that actually this had ended up being like a win for me, that I put myself before my ambitions. Or does that make sense because you are your ambitions? I don't know. But that I actually listened to myself instead of just going for the grind. And it was like a. It was a real eye opening moment into what is failure and what is success. And I think that is something that we have done wrong in software as a service. One of the many things right is I'm writing a book right now called the Sassy Truth, which is, here's the truth about software. Here's been my experience for 22 years in this grind of working for different startups and for starting my own company and being successful in that I was successful for seven and a half years in my own company without ever not paying myself once. I never didn't pay myself, not one month. And it's because I worked my ass off and never slept. Right. So towards the end of this, when I started to drain myself out and get to this point, Winning started to look a lot different. I actually sat down and was like, what is the ideal spot for me to be in in my last 10 years on this earth? And it was being with my family. So to your point of working your way backwards from the deathbed, like in the hospital, it's like being with my family. Fly fishing. I've never freaking done it, but it sounds great. I just want to fly fish. I don't want to touch the fish. I'm worried about things that are slimy and move. But I want to try it. I want to like, maybe be in a cabin, like, I don't know, ice fishing. I don't know. But it's a whole lot of nothing is what it is. And so I think I started to really. And, uh, maybe it is midlife crisis, I don't know. But I started to really put together what is important. Why do I have to be the best? Why do I even have to be in the top 10? Why do I even have to be successful? Why can't I just be? That's why isn't that enough? And so I've gotten really comfortable in that space. And if I can help anyone else to realize that about themselves, that like, maybe the best thing in life is not that you're the best, that we're not, we don't need a trophy, that this is like, uh, an experience. Like, uh, customer success is making sure that our customers have the best experience. Maybe I just need to look at my own journey map and really put in the time that I have for customers all these years and for businesses to make sure that I'm successful, that the steps I'm doing make me actually happy. Like I've redefined success.

Speaker C: Yeah, I don't think that I'd call that midlife crisis. I think I call that something along the line of mid career normalizing. I think competition's good, but when we become overly obsessed with what and who else is doing something, we try to set a bar that's not in our wheelhouse. And by wheelhouse, I mean not less your core competency. But am I going to be all encompassed in this? Is it going to just suck the life out of me? Now what I think you're doing is you're saying, okay, I'm going to compete with myself. What does that mean? I'm going to set bars. What I want to achieve professionally, who do I want to consult, work with? Because I have a lot to offer, but I want to do it on my terms. Because you know what? There's these other things I want to do, it's my family, it's my ice fishing is a goal I want to do. So, uh, to me that's not a midlife crisis. It's just a mid course adjustment and learning to compete with your own established criteria as opposed to what somebody else might expect you to do artificially.

Speaker B: Anyhow, I was thinking something similar around the line of, you define your definition of success, and what it was before was something that you made up. It's the peer pressure in society that says you have to make the most money, you have to get the most trophies, you got to do all this. But does that make you the happiest? And really successes to me is finding something that you're passionate about that it doesn't feel like work, you really enjoy it. I really enjoy doing customer success stuff. I have to figure out how I get more appreciation for the work I do because that's rewarding to me for people that say, wow, that you're really making an impact, that's important for me to have. But, uh, when you get that, I think that's, that's the definition of success. Define it for yourself. Success to me is helping a company grow, being with a bunch of people that are really good people to have the right values. And we work hard. When we work hard, we take vacations. We're encouraged to take vacations and spend time with the family. All of that and how you define it to make it a, uh, enjoyable life, you spend a lot of time at work, need to make it enjoyable.

Speaker A: Absolutely. And what I'm finding in that is that I'm more successful with this mindset I mentioned a minute ago, this book that I've been working on. I'm probably going to fail on it. It's probably going to end up being a diary. I've been working on it for a year and a half already. But I don't have that look as a disappointment anymore because in doing so I've come up with opportunities like in just focusing on myself and having a place to put my thoughts that could turn into something or could not. And so refocusing on what success is and trying not to achieve it. It's almost like I feel like I can relate this also to when dating. It's like when you're not looking for it, it comes. And I think that's your career too. I think when we are and that comes from a place of privilege, I know that right now a lot of people are like, I just need a job. I've been out of work forever, so I understand that my. My heart goes out to that because I have been there, and I know what that feels like. I think when we do get to a place of comfortable privilege where we can pause, all the more reason to do it, because it is the chance to just let it come to you, as opposed to you're just waking up every day and putting one foot in front of the other. And that's survival. How long have we all been in survival where it's just got to get up, got to get through this day. I got a long day of meetings. I just need to do this. And every day you're doing that, and every day it's just got to get up. I'll get to the other stuff I got to do later, but just got to get through this. Got to get through this. I don't know about you, but I did that for 20 years straight.

Speaker B: Yeah.

Speaker C: I won't get into how long that's been my life. You know, it's interesting. You're talking about you're writing a book, and it may just turn into a diary. Uh, a little side note, we took a road trip this past weekend to drive to St. George, Utah, to. Our eldest granddaughter was in a volleyball tournament. So my wife and I, we take these road trips and we listen to books, audiobooks at the time. And we actually, on the way there and back, we finished an audiobook called the Correspondent. And I don't know if you've heard about this book, but it's written in the context of all these letters over the. The narrator's life, who's 75, 78. It's actually brilliant. So when I, uh, was saying, hey, this may be a diary, I got news for you. A diary format for a book with the title you have would be pretty powerful because there's going to be these ebbs, the flows, the emotion, and everything else. So I got to tell you, just getting it on paper and you satisfied with it, whether it's published or not, I think would be a success. But just that type of format to me is so raw and so organic and just wonderful to read. And I'm connecting those dots, so maybe I'm pushing the envelope, which I.

Speaker A: That's like. I like that. Like, yeah. Uh, yeah, yeah.

Speaker C: So I just think conceptually, your experiences, your world, customer success, what does it mean? How have I invested in this to the point of overflowing? How do I throttle it back to the balance of life? There's just so much richness there. And In a diary format, sort of. It's enticing.

Speaker A: I love that. And that's helpful because I have been kind of in a spot of. I am writing it like a diary. And I've also talked to other people because you talked about being painfully introverted. I have always forced myself to be an extrovert. I was a comic for the first five years of my professional career. I still do it on the side. I emcee a lot. I volunteer my time a lot for stuff just so I don't have to feel bad about being a shitty comic. I can just be like, well, I'm doing it for free. Pressure.

Speaker B: Pressure's off.

Speaker A: It's not like a pain for this bad joke. Get over it.

Speaker C: Um, but it's fun. It's. It's fun one way or another, right?

Speaker A: It's fun. Uh, and so I do. I MC a lot at local charity events and I do stand up from time to time and have since I was 19. I was on Last Comic Standing when I was 20 something and made it to right before the house. That was my 15 minute of fame the second season. So still very early, but yeah, so I have put myself in a spot where I dropped all of those hobbies, all of the things I did like stand up and just. That's how I got into sas, actually. I lived in Austin and I went to apply for a job at Dell because that was the only. That was that Dell was right. Like, they used to play highway to Dell for everybody in Austin every morning because 90% of us work there that were in this industry. And I remember and you had to drive to Round Rock and it was like through traffic. But I applied for a job at Dell right before I graduated college. And I was not qualified for it, actually went in and it was like one of those where there's lots of people in a room. And it was for electronic and accessory sales, was what the position was for. And I walked up and I handed in my little resume. That was ridiculous. It was like dragging out that I had bartended and stuff forever. And, uh, so I go in there and the lady, literally, she was kind, but she was like, you're absolutely not qualified for this. And I tuck tail and was walking out to the parking lot and this gentleman in a Livestrong bracelet, because this is back when he was still a superhero, uh, chased me to the driveway and was like, were you on Last Comic Standing? And I was like, that depends why? And he was like, well, because I watched that and that's cool. And I was like, cool. And he's like, hey, come back in. I want to give you another chance. And they hired me. They hired me just because they'd see me on tv. And so I have spent my career trying to give that to other people. Right. Because I shouldn't be here. It's so hard to get into tech. And I made six figures in my 20s. I wanted to give that to my dog walker. I wanted to give that to people that I met that I knew had the talent and just didn't have the entry. And so I've spent the last two decades. What I'm most proud of is I've spent the last two decades getting hundreds of people into customer success. My sister is a csm. She's great csm. She's an enterprise. She kicks ass. Like it's a family business at this point. And so watching where we are with customer success and watching companies just go into AI without any information on what it is just to do it and watching all of this happen, I feel an obligation to stand up right now, say shame, because I brought a lot of people into this. So if you're not going to. And a lot of the people I brought in were marginalized in one way or another. And so I feel an obligation to raise my hand right now and call foul to CEOs that have given up on making their culture the most important thing because customers feel this shit. If you are not going to have a good culture. If there's anything I've Learned in the 20 years of doing customer success, which let me remind you, I have been married thrice, I have had 100 different hobbies, I have done a million different things. But I have stayed in customer success since day one of starting the job at it. All of these years, I've stayed in it. And so I really feel passionate about right now saying customer success cannot be successful. Your customers will not be happy if your culture sucks. If I've learned anything, that's what I've learned. So to see these companies giving us on. I'm not talking about the ping pong tables and the bullshit. I'm talking about psychological safety. I'm talking about keeping your team in a bubble where mental health does matter and where, remember like, we, we got to the point where it's like, you can take mental health days and now it's like we just stopped. That doesn't matter anymore. And so watching this abrupt change, if I don't stand up after 23 years of this and call foul and complain about it, on LinkedIn for everyone to read that wants to, then what am I doing here? Like, I'm mad.

Speaker C: So. Yeah. So, uh, dead on. I'll second what you just said with a big hallelujah. The one part of it that I try to encourage individuals is nobody's going to own their own career other than them. Nobody's going to care. And I'm going to read into this and you can shoot me down, backhand me or whatever you like to. Leighton. But, uh, irrespective of the culture you're in with your company, you take it upon yourself to at least create that culture within your circle of influence and with your customers. So you're not going to let the lack of a culture within the company impact your relationship with your customer and your partners within the company. You bring that to the table now, it creates a huge headwind for you, but through listening, through your passion, where you've been the last 20 years. And Alex and I would argue, uh, for both of us, that we share the same type of DNA and the same approach, but we can't always rely on our company or that's out of our control. So what we can control is our circle of influence with customer and our context. So just having that embedded in yourself, and that's what I share with people when I coach them. It's, hey, own your own career. Try to push aside the noise, don't lose your passion, don't let them beat you down, but at least try to do that. So I sit there and I agree with you a hundred percent. But I also try to encourage people, don't take a backhand on this. Own it and move on. Now, we all have to pay bills. We all have to do that. So sometimes you have to compromise a little bit to stay within an organization like that until you find something. But at least you know that you're true to yourself and what you believe. So it's what you said and 100%.

Speaker B: I'll add another voice into this. I've worked for a company that's unethical earlier in my career. Never do it again. I remember coming home every day to my wife and saying, I've sold my soul to the devil. People are making promises and then walk out the door and say, we're not going to do that. You go ahead and now deliver that message back. And I'm like, wait, we were in agreement with them and now you're saying we're not doing it. Now I have to go fix it and keep them. Wait a minute. So there There's a balance of. I can understand a culture that is. I don't know where to go with this, but I can understand. I can relate to what you're saying, David, in certain circumstances, but there's also extreme circumstances where you get into some things where you can tell there's less empathy for the employees and just get it done. Get me the money in the company. We'll get through this. But it's my job to do that in customer success, and that is draining.

Speaker C: Yeah, yeah. Uh, and I think you're just adding a little bit of additional color on the edges to what Leighton and I are saying. That's critical. You have to recognize. Is it so extreme that it's abusive and I need to get the fiduciary out of it? Is it unethical? I need to get out of it. Those are just, to me, characteristics. And I believe I understand who you're talking about, and I agree. And none of us want to get into that ever, but you at least have to recognize it. And it's such a strong characteristic that we need to be able to recognize. I think, unfortunately, a lot of folks, and granted, we go from old to older and oldest on this call, and I'm definitely the oldest, the wisest.

Speaker A: You're wise now.

Speaker C: Yeah, my wife would completely argue that point, but let's not go there right now. No, but I think we've got a little bit more maturity and maybe financial stability where unfortunately, some people turn a blind eye or gloss over that just because they're getting a paycheck.

Speaker A: And.

Speaker C: And unfortunately, what I've seen. Alex, to support. What you're saying is they're told and constantly told, oh, we're doing ethical business. And the people that are saying that are just brainwashing them into saying, okay, we're doing the right thing, we're doing the right thing. I'm getting a paycheck, I'm getting a paycheck. They don't see the turmoil that they're in unless somebody helps them or they have some sort of life changing event or career changing event. It's well said. Uh, unfortunately, I think there's quite a few people that get caught up in that for financial reasons, lack of confidence. It's a sad state of affairs, to Leighton's earlier point. And you talk about therapy. I see coaching and mentoring as a key in that as well. So if you think about what am I looking for? You're looking for that sounding board. You're looking for that pressure release. You're looking for something that may be prescriptive, that I can try in the future. Or you're just looking for somebody to encourage you or to stretch your way. You think so? Whether it's a therapist, whether it's a coaching or mentoring, I think all those feedback loops are critical for us individually to get over this hump of negativity, or we're suppressed in the mindset of, well, I have to do this is the way it's going to be. And then all of a sudden, you wake up on your deathbed, as you said, Alex, and say, oh, I wish I worked more. No, uh, I wish I had done something differently. And I think being able to reflect on that earlier on, like Leighton, you're doing, I think that's pretty bold. And we need to encourage others to reach out, to figure out what that is. Knowing there's a ton of external influences that are hard to deal with.

Speaker A: Absolutely. And what is so apparent about this, just in this conversation, is like, customer success requires a lot of empathy. Anyone I know that has been good at customer success? There's a lot of empathy there because you got to understand the customer. We're all customers. What would we do? What would we want for ourselves? How do we help the company to do that? And so it's not. It's not surprising to me that a lot of people in customer success have reached out and like, that we're talking about all of these things because we feel it a lot. And I do think that there's this fine line I tell people with, no, nowhere is perfect. Your company isn't your family. Regardless of how cutesy we like to say that sometimes. I mean, sometimes it literally is as a startup, but, like, for the most part, it's not your family. And so you're going to go through times where everyone's not going to do it the way you would do it. And so there is this understanding of that. Right. Everyone works differently. Not everyone's. Not every CEO is going to be as empathetic and all of these things. But there's also a fine line where you need to leave. Going to your point. I've worked for just beep m. Right. And so at the end of the day, what I did, which in my early career is I was like, well, I can't leave. My customers need me. Right. Like, the whole company would fall. Like, just. And so here you give up your whole life trips, you would have taken time with family and all of these things that on your deathbed, you wish you could come back and have. And then what happens the day you leave and your email is cut off? The company keeps going without you start to cut. You got to step back and reprogram yourself. And so my advice is that you find a fine line, that you start with a fine line when you take a job with customer success. What is my line? What am I willing to accept and not accept here? And that you try to get through that in the interview process, but it's hard to. And then when you reach that point where you're. I call it the Sunday method. And I've talked about this on LinkedIn before. As a CS leader, I used to always ask my teammates on one on ones, how was your Sunday? And the reason why I asked that is because I spent over half my career wasting. We get two days off and in software it's not even that. And so I'd waste the whole one, uh, 50% of my time being anxious on Sunday about all I had to do on Monday. And how is that good for the soul or for our customers? And so if you get to that point where you cannot take your weekend without that feeling coming up on Sunday, that's when you got to. That's a good litmus test for step back and reevaluate. And so I've used that and I encourage others to use that if it's just an annoyance, if it's just things are hard, life's hard. But there is that line to not work for, as you put it, the devil, or to continue to do things that just drain and suck your soul, which I've done way too much of.

Speaker B: Well, Leighton, I think that's a good way to wrap up this episode. I think it's really good advice. I think weekends should be your time and that's really good advice for our listeners. So we very much appreciate your time. Your honesty, openness and vulnerability on the show, uh, it's brings a lot to our listeners. I'm sure a lot of people will listen to this and not feel alone.

Speaker A: So, um, thank you guys and I appreciate your time as well. Hopefully I don't end up having to live on one of your couches as I continue to be loud about all this.

Speaker C: I have enjoyed this and I sort of see a mental doppelganger for me. As Alex, uh, would say. I do have a high risk personality and I. Sometimes it comes out and I just appreciate the open candidness that you have. And I'm definitely going to start looking at your link in with you so I can start tracking all this stuff. But it'd be refreshing. And be careful what you say, because I may come over the top and be just as aggressive.

Speaker A: Well, I hear it. And yeah, I mean, I thank you guys for even reaching out. Most of the time, people want me on podcasts is when everything's at the top. And again, that's just not reality for a lot of people. And I think a lot of people feel for the three of us to all be saying the same thing. Hopefully other people can listen to this and be like, okay, cool. Like, where I'm at is okay.

Speaker B: It's okay.

Speaker C: Okay. I do a coaching circle and they do tag us and they listen. But this is the one episode, Alex, I think that they're going to come over and interesting enough, there's six of them, five women that are very bold and strong personalities. This is the one that they're going to start raving about more than anything else, because it's going to hit home and resonate. When you start to talking about culture, what you start talking about what's important, I think it's going to resonate. So you're going to make my next coaching session once this is broadcast quite easy. I'm not going to have to do much thinking.

Speaker A: Well, I truly appreciate you. Thank you guys for keeping SAS in a good place, for keeping it place for people. All right, thank you very much.

Speaker B: Awesome. Thanks, Leighton. Bye. Well, David, that was a great conversation. A different kind of topic than we have done in the past, but I think very relevant for people to think about. What are your thoughts?

Speaker C: That was fun. I really enjoyed that conversation. It was a new approach. I thought Leighton's energy level was fantastic. It just brought out another layer of energy for me. Lots to unpack in our conversation. But the two things that absolutely jumped out at me were, first and foremost, I think culture and how important there has to be in a cultural fit. I really pondered that quite a bit while he was talking. It is important. I don't think we call it out as much on how it impacts us individually. We may think of culture from an organizational perspective, but not necessarily the impact on me per se. So I love to unpack that, uh, with you.

Speaker B: Yeah. And culture is defined differently by everybody. It made me think about all the companies that I work for, my career, and which ones that I really enjoy. And if you think back to those companies that you just, you couldn't get enough work because it was just so much fun, you start to think about the culture and you're like, oh, yeah, there was this and there was this and There was this. I was like, understanding what's important to you and not just taking a job, but really getting cultural fit can make the difference. Difference.

Speaker C: You're right on. And as I'm listening to you and I'm reflecting on what Leighton was talking about, for me, culture is so important to be able to express ourselves, to be able to have a ferocious debate. When you have the right culture, you and I can have a very animated disagreement. But it's for the purpose of moving forward, and the right culture makes that acceptable, and we're all better for it. A negative culture would sit there and say, well, why are you challenging me? Um, on that? Or, why are you, you know, pressure testing something? Or why do you have passion around something that's decisions could be made by somebody else? So being able to have that culture, really, as I was listening to him talk and your statement, it really means a lot to me, and it impacts my enthusiasm with getting up in the morning, to be quite honest. To work.

Speaker B: Yeah, absolutely.

Speaker C: The other thing, Alex, that. That was profound, of course, his energy level. But the other thing that was profound was not being afraid to fail. And you sit there and think, okay, well, we all make mistakes, we all fail, but to learn from it is critical. And, uh, if you look at sports, for example, how many times does a hockey player take a shot on net when it actually goes in? Now you got somebody there to defend it. Or a baseball player. How many hits does a baseball player get out of ten? If you're successful three out of ten times, you're making $100 million every couple years. So we've defined success by a lot of different things, but we hardly ever talk about failure and improvement. So I thought that was really, uh, the other part that was profound for me.

Speaker B: Yeah. And they always talk about fail fast, learn from it, and move on. And people really need to have that. They have to think, if I'm not failing, at least on something, maybe I'm not taking enough risks and trying to push the company forward enough. Maybe I'm just doing the. What it takes to get things done, but I'm not helping my company progress and mature and get better. Take a step back and reflect on that and say, I'm going to do this one thing that I wouldn't do that's risky, but let me see what it does and measure it and see what happens out of it. And if I fail, we at least tried, and we know that didn't work, but try to push the company in

Speaker C: new directions, you know, that's A good point, because nothing ventured, nothing gained. And I can't tell you how many discussions I've been privy to listened in when a client left or a client didn't sign off on ah, an sow. And the question is, why didn't we know? What could we have done better? Well, when you start listening to some of the things that Leighton brought up and you're bringing up, did we ask? Did we push the envelope? I mean, and if you don't ask, you're never going to know. And then when something occurs that surprises you or negative, you shouldn't be shocked. But to be able to ask a question and push the envelope, even if you get a negative answer, at least you have an answer. Being not being afraid to ask or to have that negative response or to fail, I think is a shortcoming. So it's well said.

Speaker B: Yeah. And I think the last thing that I'll touch on is just if you're a coach or a mentor or a manager, know that your team has a lot of things going on in their lives. And understanding them at a human level as well as a work level, I think is important to be able to understand. Maybe someone just had a baby, so, you know, they're not sleeping much. They might make more mistakes. Not failure, but just mistakes, and that's going to be okay. But to get them on the right path or maybe take some things off their plate and have other people chip in for a little bit until they can get that stable, I think is important. And that all goes back to just the mental health of employees. And it's great that as a culture we're emphasizing more on that because I think it's hasn't been emphasized enough that we are humans and we're not machines. And at the end of the day, we have to be compassionate to each other and understand that we all have different things going on in our lives and just to be aware of that.

Speaker C: So well said.

Speaker B: Well, that's a wrap. Thank you all to all our listeners. If you could take some time to rate our podcast, that is very important for us to get ratings as well as comments on our LinkedIn post. Just appreciate the podcast. Anything will help us. And we appreciate everybody's time. Until next month. We'll talk to you soon.

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