The Exchanges

Q a emblematic Give the culture that you have. And I, I want to ask, cause as I said, both Ryan and Jake said about the incredible culture you have. It's often quite a fluffy thing though. And I often find that actually there's not huge strategy behind it, but I know there is with you. So how have you been purposeful and maybe very deliberate in building a strong culture?

A Yeah, I appreciate that question Cause, because it is a drastically overused concept in terms. So for us, we manifest culture into our company values, and there are six of them, and we live by them. And so we write them, we revisit them once a year. They are both symbolic of behavioral styles that we believe are important. I, I spouted off some already, you know, not, don't take yourself too seriously, embrace the journey, but writing them is really just the first step. The actual important part is how they actually get reinforced in the company. And that's what we spend a lot of time on and why I think people do say the kinds of things that they said to you there, you know, it starts at the interview process. We do a pretty structured scorecard interview. But always there's a culture interview as part of that. And the culture interview is done by someone who's not on the team that they're hiring for intentionally. And that culture interview, if everybody's a yes and culture interview thumbs down, then we don't move forward with the candidate. And I talk about it as 51% culture fit, 49% skill and capability. And I think if you're willing to be that unwavering about it, and then you're also, if you're willing to correct when you get it wrong, which unfortunately, you know, can happen. That protects it. And I think that can put an upper threshold on your rate of hiring. So you ha…

AI assessment note: “it starts at the interview process. We do a pretty structured scorecard interview.”

Q a emblematic Give the culture that you have. And I, I want to ask, cause as I said, both Ryan and Jake said about the incredible culture you have. It's often quite a fluffy thing though. And I often find that actually there's not huge strategy behind it, but I know there is with you. So how have you been purposeful and maybe very deliberate in building a strong culture?

A Yeah, I appreciate that question Cause, because it is a drastically overused concept in terms. So for us, we manifest culture into our company values, and there are six of them, and we live by them. And so we write them, we revisit them once a year. They are both symbolic of behavioral styles that we believe are important. I, I spouted off some already, you know, not, don't take yourself too seriously, embrace the journey, but writing them is really just the first step. The actual important part is how they actually get reinforced in the company. And that's what we spend a lot of time on and why I think people do say the kinds of things that they said to you there, you know, it starts at the interview process. We do a pretty structured scorecard interview. But always there's a culture interview as part of that. And the culture interview is done by someone who's not on the team that they're hiring for intentionally. And that culture interview, if everybody's a yes and culture interview thumbs down, then we don't move forward with the candidate. And I talk about it as 51% culture fit, 49% skill and capability. And I think if you're willing to be that unwavering about it, and then you're also, if you're willing to correct when you get it wrong, which unfortunately, you know, can happen. That protects it. And I think that can put an upper threshold on your rate of hiring. So you ha…

AI assessment note: “we manifest culture into our company values, and there are six of them”

Q It's not in San Francisco. And really for me, whenever I speak to founders and people outside of the core tech hubs, they always reference, and also people within the tech hubs also always reference really fundraising and then Hiring and adding to the team. If we start on adding to the team, would you disagree with the perception that location really impacts your ability to hire the best people?

A I definitely disagree with that perception. Yes, very much so. I think that it is a net positive. It is a unique advantage to be building a company outside of a tech hub for several reasons, but to stick with the talent one first. If you look at engineering talent as one important barometer for a company like ours, I think our engineering team is absolutely world-class and You know, 95% of the engineers work here in Philadelphia and are, like I said, the best of the best. And so I have zero view or conviction that that is a thing. Now, like we did with Boomi, we have an office in Philadelphia and we have an office in San Francisco. And so I think the talent strategy as you grow can be a great way to continue to build out the team and continue to bring in skill sets, especially specialized skill sets. And so if you, for example, want to Bring someone onto the team that has done really focused on, let's say, like a product onboarding experience. Well, that's a really small population to begin with. And so, yeah, you really do want to not hinder yourself by location by only considering a certain geography, in my opinion. And instead, you know, try to increase your odds for success by connecting with folks that might be in tech hubs where maybe they work for that company that had an amazing onboarding experience and you can bring it to Guru. Again, those are kind of specialized ski…

AI assessment note: “I definitely disagree with that perception. Yes, very much so.”

Q It's interesting. You mentioned the culture there. It was what both Rick and Jake said was really exceptional about Guru's day. So we're going to touch on that later. On the flip side though, what didn't work at Boomi that you're maybe not doing at Guru?

A The first chapter of Boomi, Boomi's always been focused on integration, but in the early days was focusing on an on-premise application integration problem. And we really didn't effectively Understand our market, how to position, how to differentiate, and ended up in a very unfortunate position of having to compete with big incumbents like IBM and Microsoft and Oracle and, you know, TIBCO and all these vendors. And, you know, I think ultimately completely shifted the business as the world was moving to cloud and took a big bet. But I think what that kind of burned into my, my brain was just the criticality of positioning and how to tell your story in a unique and It's still something I personally struggle with, but have worked hard to bring really talented folks over to Guru because I've just seen the consequence of not doing that well.

AI assessment note: “have worked hard to bring really talented folks over to Guru because I've just seen”

Q question that I always have when it comes to adding to leadership teams is often there's people Internally, if you think of themselves as having the potential to upscale, How do you think about that debate between internal upscaling versus bringing in external talent, and if bringing in external talent, how do you think about that communication with that individual who's internal, who maybe didn't make the grade this time?

A That's a fantastic question, and I've thought through and lived through those many times at Boomi and at Guru, those moments of those conversations, to your point. I think There's one clean one, right? And to use Anne as an example of the several amazing things Anne has brought to the team, one of them is she's lived through a more product-led growth, go-to-market motion in her past. Her time, she's lived in the consumer world, but then in SaaS with her time at SurveyMonkey and some of the boards she serves on her time at Zendesk, you know, these are all companies that have a product-led motion where people can engage with your product before they actually talk to a human and just The way you think about your go to market in your business is very different in that world. So when you think about bringing someone in, in that context, that's a good example of like, Hey, on the team today, we don't have that learning or skillset or competency. And the company will be in a better position if, and when we can bring that competency, that skillset compliment into the team and into the company. And so, okay, that conversation tends to go really well because yes, the person I'm talking to, okay, you're, you'll now, Report to this person. Maybe you used to report to me, but I don't think anyone is unexcited to report to a new leader so long as that leader is someone where they still feel …

AI assessment note: “on the team today, we don't have that learning or skillset or competency.”

Q now that I really would love to double-click on. The first is you mentioned sometimes when it's not a fit. I always really struggle with this, Rick. I'm inherently uncomfortable with conflict as a person. How do you feel with those moments and what would you advise me on kind of your lessons on the right way to maybe let someone go in an empathetic and kind of vulnerable way?

A I think the vast majority of situations when someone's being let go, it might not feel this way in the moment, but ultimately it is the best path for both. It is the best path for the company and it is the best path for you as the person separating from the company. Again, oftentimes it doesn't feel that way, but that's always the mindset I go with because look, If there's a cultural misfit, then you're experiencing it, right? Like if someone comes into a company, and they do take themselves seriously, and they're used to a company where everyone's showing up with the best debater wins mindset, like, I'm not going to say that's right or wrong. I'm just going to say that's not how we do it at Guru. So if that's what you like, right, then you're probably hitting walls all the time walking around here, right? And so it's not good for you. And it's not good for the company, right? That Mental shift going into the conversation. And I genuinely believe it when I have to have that hard conversation does change it a little bit and it does make that concept a little bit better. But look, it sucks. It's awful. No one likes doing it. It's the hardest part of the job, right? Like I think people, lots of people want to want to be managers, but then when they had to deal with their first one of those moments, it's like, oh yeah, this is actually really hard. And it is. And I think being thou…

AI assessment note: “Writing down your talking points in advance, making sure you're talking to your people team”

Q how you feel there. The other element was the fundraising. I guess my question to you is, a lot of founders ask me, how should I approach it given that I'm not in a core tech hub? Given your, you know, experience and massive success, what advice do you give to founders in terms of raising in hubs that are outside the valley in New York and traditional VC ecosystems?

A That is a very interesting contrast when I think about fundraising for Boomi and fundraising for Guru. I personally have the belief that that has shifted dramatically. I think it used to matter a ton that you essentially pitch locally. You go to Bay Area, you build your company, you pitch VCs in Bay Area. I think now it's shifted to there are as many, if not more VCs that actually like the fact that you're building a company, not in the tech hub, because with tech hubs, when they get to a certain size, there can be a feeling of saturation. There can be a feeling of massive talent, competitive talent wars going on. There can be a feeling of echo chambers where everyone's having the same conversation and using the same rhetoric. You get outside of that in the non-tech hub, and all of that is gone. And it brings a different set of challenges, but it's not those challenges, right? And so I completely disagree with the idea that if you want to get amazing investors, you know, you have to be in their backyard. I think that used to be the case very much, but now I think it's absolutely not anymore. And I always advise Philly founders. First thing I tell them is, Sure. There's local investors here and you should pitch them, but they're just in your list. Like any other investor, it doesn't really matter that they're in Philly or not go to New York, go to Bay area, pitch them. Because i…

AI assessment note: “go to New York, go to Bay area, pitch them.”

Q I'm so pleased you mentioned Anna. I've actually had her on the show before, and she is just fantastic. But I do want to start the show today on you, because when I spoke to investors, the overwhelming feedback on you as a person was your incredible leadership style. So if we dig in there, how would you describe your own leadership style, Rick?

A I think I operate with definitely a sense of enthusiasm and excitement and rallying folks around a vision and why we're all here. And I think just always try to Connect that with transparency of the ups and the downs of the startup and try to bring a bit of a normalcy to the fact that all startups go through lots of zigs and zags and don't get caught up in what you read in media and publications. That's not really what's going on inside any particular startup. I don't care how well that company's doing, you know, on the outside, right? And so the way transparency might manifest to give specific examples would be Like in our town halls, when we talk about things and we always include lowlights in our town halls, as well as our highlights. Right. And I think if you kind of take people on that rollercoaster ride with you, I think they just tend to feel more connected to the company. They tend to feel like, oh, cool. Like, you know, I'm not getting hand waving, you know, platitudes here. You know, I just tend to feel that humans are smart and like, don't bullshit them and, you know, speak authentically to them. And that means they have to be one ready to hear the Bad news if this part of the business could be going better than it is. And also the professional, like, you can't go talking outside of the company about the stuff we're sharing, right? Because it's more sensitive than ma…

AI assessment note: “I think I operate with definitely a sense of enthusiasm and excitement and rallying folks”

Q I think the kind of common strain, though, throughout the three is the theme of empathy in your leadership style. I guess my question, and actually one from Ryan at Thrive, was leadership style and empathetic leadership style is inherent to character? Is it inherent to character, or can it be learned as a leadership style?

A I think it can be learned. I think there is a bit of character, right? That resonates. I think one thing I would reflect on from, you know, I don't know that I would tell you it's part of my character or not. I honestly don't know. But what I would tell you is like part of how, how I got empathy as a person was, you know, spending a lot of time in front of customers earlier in my career. And as we were building Boomi in the early days, but still prioritize that with Guru and like customers keep you real, right? Like customers keep you out of the office and, The good and the bad of that, of testing something with a customer and it falling flat, or customers having not a great experience, and they tell you that, and you need to make it better, right? Like, that has ingrained empathy into me in understanding what it is really like for everyone from an ADR who's trying to get that stranger to want to get on a call with you, all the way through to a support person. I'm wanting to fix an issue, and the customer's caught in an emotional state, right? But the second part of your question there, like, can it be learned? Yeah, I mean, I've I've been spending a ton of time and the guru leadership team on conscious leadership, and there's a conscious leadership group, and there's 15 commitments, and I've really gotten into that, and that gets into a ton of what you're talking about of empa…

AI assessment note: “I think it can be learned. I think there is a bit of character, right?”

Q It's interesting. You mentioned the culture there. It was what both Rick and Jake said was really exceptional about Guru's day. So we're going to touch on that later. On the flip side though, what didn't work at Boomi that you're maybe not doing at Guru?

A The first chapter of Boomi, Boomi's always been focused on integration, but in the early days was focusing on an on-premise application integration problem. And we really didn't effectively Understand our market, how to position, how to differentiate, and ended up in a very unfortunate position of having to compete with big incumbents like IBM and Microsoft and Oracle and, you know, TIBCO and all these vendors. And, you know, I think ultimately completely shifted the business as the world was moving to cloud and took a big bet. But I think what that kind of burned into my, my brain was just the criticality of positioning and how to tell your story in a unique and It's still something I personally struggle with, but have worked hard to bring really talented folks over to Guru because I've just seen the consequence of not doing that well.

AI assessment note: “worked hard to bring really talented folks over to Guru because I've just seen the consequence”

Q of the prior meeting and kind of referring back to that. The other element that I was super interested by was you said there about kind of meeting all new employees and really going through the culture with them. That's like amazing and I love it, but it doesn't necessarily scale. How do you think about maybe break points in scaling and break points in culture scaling with company growth?

A I think that specific tactical example can actually scale decently for us because I don't mean to imply I'm doing those on like a one-on-one context. That might be a room where there's 10, 15 people because they're the cohort that joined in the, in the prior month. And so the cadence I try to do is once a month or every other month, depending on how many folks are joining when, I think that can scale to a decent size. I'll be the first to admit when we think about this at a thousand person company, I don't have the answers today. And I will certainly continue my personal learning path of like, how have folks done that and techniques they've done. But I think that tactical example could scale well. I think the other one that I do believe in, and I think is an important part of scale to your point is recognizing that I don't think that your values are etched in stone. Like, I don't think you want to change them weekly. But we've kind of taken on the path of doing them once a year, because I think you tend to evolve them based on what the company needs. I think there's company values that are like behavioral, like I use the don't take yourself too seriously like that. I will never change that whenever, but I think they're aspirational company values to aspirational might be a mindset that we want to make sure comes into guru where maybe we aren't seeing it today, but we need that …

AI assessment note: “I think that specific tactical example can actually scale decently for us”

Q I'm sorry, double clicking on that. I'm too interested. When you think about kind of positioning and really enhancing your level of thought around positioning, what do you think you've done to actively improve that with Guru in terms of bringing people on and what sort of hires are those people?

A For sure. Product marketing as a trade and a capability. I think is one. And then I think understanding the voice of the customer. So the first part of your question, at least how I tend to think about it and things I've learned from folks here now, and Ramondi, who's our chief customer officer, you know, it's like on one hand, you use the language your customers are using to talk about and describe your product. And then you marry that with the innovation and exciting things you're building in the product. And I think combining those two things together is a recipe for success. I think If you do only one of the two, right? Like if you're doing innovative, cool things with your product, but you're speaking in weird languages or using acronyms that people don't understand, then like it's tragic, right? Cause all that great innovation is getting just misunderstood by the market and people aren't getting it right. Conversely, if you're so focused on the voice of the customer that you actually aren't innovating the space and talking about what you're doing, right? You can find that you're getting pulled in directions that aren't necessarily striking that balance of, You know, how do I solve customers problems that they have today with what are truly game changing, innovative things that we can bring to the market over the next five, 10 years from kind of executing on your vision pe…

AI assessment note: “Product marketing as a trade and a capability. I think is one.”

Q I'm so pleased you mentioned Anna. I've actually had her on the show before, and she is just fantastic. But I do want to start the show today on you, because when I spoke to investors, the overwhelming feedback on you as a person was your incredible leadership style. So if we dig in there, how would you describe your own leadership style, Rick?

A I think I operate with definitely a sense of enthusiasm and excitement and rallying folks around a vision and why we're all here. And I think just always try to Connect that with transparency of the ups and the downs of the startup and try to bring a bit of a normalcy to the fact that all startups go through lots of zigs and zags and don't get caught up in what you read in media and publications. That's not really what's going on inside any particular startup. I don't care how well that company's doing, you know, on the outside, right? And so the way transparency might manifest to give specific examples would be Like in our town halls, when we talk about things and we always include lowlights in our town halls, as well as our highlights. Right. And I think if you kind of take people on that rollercoaster ride with you, I think they just tend to feel more connected to the company. They tend to feel like, oh, cool. Like, you know, I'm not getting hand waving, you know, platitudes here. You know, I just tend to feel that humans are smart and like, don't bullshit them and, you know, speak authentically to them. And that means they have to be one ready to hear the Bad news if this part of the business could be going better than it is. And also the professional, like, you can't go talking outside of the company about the stuff we're sharing, right? Because it's more sensitive than ma…

AI assessment note: “I think I operate with definitely a sense of enthusiasm and excitement”

Q now that I really would love to double-click on. The first is you mentioned sometimes when it's not a fit. I always really struggle with this, Rick. I'm inherently uncomfortable with conflict as a person. How do you feel with those moments and what would you advise me on kind of your lessons on the right way to maybe let someone go in an empathetic and kind of vulnerable way?

A I think the vast majority of situations when someone's being let go, it might not feel this way in the moment, but ultimately it is the best path for both. It is the best path for the company and it is the best path for you as the person separating from the company. Again, oftentimes it doesn't feel that way, but that's always the mindset I go with because look, If there's a cultural misfit, then you're experiencing it, right? Like if someone comes into a company, and they do take themselves seriously, and they're used to a company where everyone's showing up with the best debater wins mindset, like, I'm not going to say that's right or wrong. I'm just going to say that's not how we do it at Guru. So if that's what you like, right, then you're probably hitting walls all the time walking around here, right? And so it's not good for you. And it's not good for the company, right? That Mental shift going into the conversation. And I genuinely believe it when I have to have that hard conversation does change it a little bit and it does make that concept a little bit better. But look, it sucks. It's awful. No one likes doing it. It's the hardest part of the job, right? Like I think people, lots of people want to want to be managers, but then when they had to deal with their first one of those moments, it's like, oh yeah, this is actually really hard. And it is. And I think being thou…

AI assessment note: “ultimately it is the best path for both. It is the best path for the company”

Q One from Ryan. What were the biggest sacrifices you had to make from building the three companies?

A The biggest sacrifice, I think, has changed. I think I learned a lot about work-life balance at Boomi that now has informed a lot of that marathon mindset you heard me talk about. I think I probably put too much of my personal self. I think startups can easily consume you if you let them. And then you pick your head up and you're like, wow, I haven't spent time with my friends in the last X time. Never again. And I won't do that again. So I would say sacrifice of the personal side of yourself is one that I feel is like, I won't call it a regret because we should look forward, but something I hope to never do again.

AI assessment note: “sacrifice of the personal side of yourself is one that I feel is”

Q And then the final one, Rick, next five years for you and for Guru, what's that exciting roadmap ahead?

A For me, I think a lot about blind spots. I quickly alluded to it in the nine types of leadership book, but I'm constantly trying to see what they are because how can I be a more impactful team leader and co-worker with the employees here? So I would put that in the bucket of like coaching and personal development. And then also I think at sea and really excited about that opportunity for the team, really looking at any relationship with an employee as a long-term relationship and how can we build and develop them under the Context of it being a long-term relationship. And then I think for Guru, just so excited at what I think is a market category that we have tapped into. Completely locked, by the way. I'm not going to say we called this one, but I think, you know, the world of knowledge management is truly something that matters to companies. The impact of not having it is real and painful. And the impact on the other side, once you actually have that and it is working, is real and positively impactful to a company's ability to Scale and launch new products and grow. And I think the fact that we're in this category and the fact that we spend so much time building a product so focused here, it's just one of those market dynamics that has me so excited. So I think five years, we'll see this category just get bigger and bigger and more and more real and clear to companies about w…

AI assessment note: “five years, we'll see this category just get bigger and bigger”

Q Well, I would love to kick off those days with a little bit on you. So how did you make your way into the world of startups? And what was that founding moment and story for you with Guru?

A Guru actually was the second company I started and was very much born out of a pain that myself and my co-founder, Mitch, Which lived while we were working at Boomi and then magnified once we got acquired by Dell, which is, you know, how do you make sure that your fellow coworkers have the knowledge they need to do their job? And very specifically, that collaboration that happens between subject matter experts that know about your product, your market, your competitors, what you're releasing, and the customer facing teams that need that knowledge to have great customer conversations. And we just tried all different systems and tried setting up all different things. None of them stuck. And by stuck, I mean, people just weren't relying on them to get the knowledge they needed. They just revert back to asking the experts. And you see the burden that creates on the company around shoulder tapping experts and burning them out and, you know, stuff we just see over and over and over again with our customers today. But, you know, that was the moment to the essence of your question of like, man, this really feels like a problem that matters and needs a fresh take. And that sort of led us down the path of creating your room.

AI assessment note: “that was the moment to the essence of your question”

Q Well, I would love to kick off those days with a little bit on you. So how did you make your way into the world of startups? And what was that founding moment and story for you with Guru?

A Guru actually was the second company I started and was very much born out of a pain that myself and my co-founder, Mitch, Which lived while we were working at Boomi and then magnified once we got acquired by Dell, which is, you know, how do you make sure that your fellow coworkers have the knowledge they need to do their job? And very specifically, that collaboration that happens between subject matter experts that know about your product, your market, your competitors, what you're releasing, and the customer facing teams that need that knowledge to have great customer conversations. And we just tried all different systems and tried setting up all different things. None of them stuck. And by stuck, I mean, people just weren't relying on them to get the knowledge they needed. They just revert back to asking the experts. And you see the burden that creates on the company around shoulder tapping experts and burning them out and, you know, stuff we just see over and over and over again with our customers today. But, you know, that was the moment to the essence of your question of like, man, this really feels like a problem that matters and needs a fresh take. And that sort of led us down the path of creating your room.

AI assessment note: “Guru actually was the second company I started and was very much born out of”

Q I think the kind of common strain, though, throughout the three is the theme of empathy in your leadership style. I guess my question, and actually one from Ryan at Thrive, was leadership style and empathetic leadership style is inherent to character? Is it inherent to character, or can it be learned as a leadership style?

A I think it can be learned. I think there is a bit of character, right? That resonates. I think one thing I would reflect on from, you know, I don't know that I would tell you it's part of my character or not. I honestly don't know. But what I would tell you is like part of how, how I got empathy as a person was, you know, spending a lot of time in front of customers earlier in my career. And as we were building Boomi in the early days, but still prioritize that with Guru and like customers keep you real, right? Like customers keep you out of the office and, The good and the bad of that, of testing something with a customer and it falling flat, or customers having not a great experience, and they tell you that, and you need to make it better, right? Like, that has ingrained empathy into me in understanding what it is really like for everyone from an ADR who's trying to get that stranger to want to get on a call with you, all the way through to a support person. I'm wanting to fix an issue, and the customer's caught in an emotional state, right? But the second part of your question there, like, can it be learned? Yeah, I mean, I've I've been spending a ton of time and the guru leadership team on conscious leadership, and there's a conscious leadership group, and there's 15 commitments, and I've really gotten into that, and that gets into a ton of what you're talking about of empa…

AI assessment note: “I think it can be learned. I think there is a bit of character”

Q of the prior meeting and kind of referring back to that. The other element that I was super interested by was you said there about kind of meeting all new employees and really going through the culture with them. That's like amazing and I love it, but it doesn't necessarily scale. How do you think about maybe break points in scaling and break points in culture scaling with company growth?

A I think that specific tactical example can actually scale decently for us because I don't mean to imply I'm doing those on like a one-on-one context. That might be a room where there's 10, 15 people because they're the cohort that joined in the, in the prior month. And so the cadence I try to do is once a month or every other month, depending on how many folks are joining when, I think that can scale to a decent size. I'll be the first to admit when we think about this at a thousand person company, I don't have the answers today. And I will certainly continue my personal learning path of like, how have folks done that and techniques they've done. But I think that tactical example could scale well. I think the other one that I do believe in, and I think is an important part of scale to your point is recognizing that I don't think that your values are etched in stone. Like, I don't think you want to change them weekly. But we've kind of taken on the path of doing them once a year, because I think you tend to evolve them based on what the company needs. I think there's company values that are like behavioral, like I use the don't take yourself too seriously like that. I will never change that whenever, but I think they're aspirational company values to aspirational might be a mindset that we want to make sure comes into guru where maybe we aren't seeing it today, but we need that …

AI assessment note: “I think that specific tactical example can actually scale decently for us”

Q I'm sorry, double clicking on that. I'm too interested. When you think about kind of positioning and really enhancing your level of thought around positioning, what do you think you've done to actively improve that with Guru in terms of bringing people on and what sort of hires are those people?

A For sure. Product marketing as a trade and a capability. I think is one. And then I think understanding the voice of the customer. So the first part of your question, at least how I tend to think about it and things I've learned from folks here now, and Ramondi, who's our chief customer officer, you know, it's like on one hand, you use the language your customers are using to talk about and describe your product. And then you marry that with the innovation and exciting things you're building in the product. And I think combining those two things together is a recipe for success. I think If you do only one of the two, right? Like if you're doing innovative, cool things with your product, but you're speaking in weird languages or using acronyms that people don't understand, then like it's tragic, right? Cause all that great innovation is getting just misunderstood by the market and people aren't getting it right. Conversely, if you're so focused on the voice of the customer that you actually aren't innovating the space and talking about what you're doing, right? You can find that you're getting pulled in directions that aren't necessarily striking that balance of, You know, how do I solve customers problems that they have today with what are truly game changing, innovative things that we can bring to the market over the next five, 10 years from kind of executing on your vision pe…

AI assessment note: “tend to look for folks who think about messaging and in a pragmatic and practical sense”

Q One from Ryan. What were the biggest sacrifices you had to make from building the three companies?

A The biggest sacrifice, I think, has changed. I think I learned a lot about work-life balance at Boomi that now has informed a lot of that marathon mindset you heard me talk about. I think I probably put too much of my personal self. I think startups can easily consume you if you let them. And then you pick your head up and you're like, wow, I haven't spent time with my friends in the last X time. Never again. And I won't do that again. So I would say sacrifice of the personal side of yourself is one that I feel is like, I won't call it a regret because we should look forward, but something I hope to never do again.

AI assessment note: “sacrifice of the personal side of yourself is one that I feel”

Q And I mean, my word, the Guru product really is a fresh take. I do love the UI and the design specifically, but I do want to touch on a couple of things because you mentioned Boomi there, and it was an incredible journey. But I want to start with what worked at Boomi that you've taken with you to Guru?

A I often describe Boomi as an accidentally good culture. And what I mean by that is, I don't know that we were intentional around culture and company values, but I think we ended up in a really good place. And I think one of the things that taught me was What does good culture and good company values mean? And what does it mean to create awesome teams that work together and solve hard problems together in a functional and effective way? And I think that ultimately, when I look back, worked really well and inspired me to bring those learnings over to Guru, and I think has borne out in an exciting way. Like people talk about the like, oh, if you could, you know, go back to high school again and start over. Like that's kind of the feeling that I think about when I like Reflect back on then and now in a positive way.

AI assessment note: “inspired me to bring those learnings over to Guru”

Q And I mean, my word, the Guru product really is a fresh take. I do love the UI and the design specifically, but I do want to touch on a couple of things because you mentioned Boomi there, and it was an incredible journey. But I want to start with what worked at Boomi that you've taken with you to Guru?

A I often describe Boomi as an accidentally good culture. And what I mean by that is, I don't know that we were intentional around culture and company values, but I think we ended up in a really good place. And I think one of the things that taught me was What does good culture and good company values mean? And what does it mean to create awesome teams that work together and solve hard problems together in a functional and effective way? And I think that ultimately, when I look back, worked really well and inspired me to bring those learnings over to Guru, and I think has borne out in an exciting way. Like people talk about the like, oh, if you could, you know, go back to high school again and start over. Like that's kind of the feeling that I think about when I like Reflect back on then and now in a positive way.

AI assessment note: “inspired me to bring those learnings over to Guru”

Q I agree with you, but kind of aligned to the kind of empathetic leadership situation. The other kind of core trait is kind of vulnerability within leadership. I think many are concerned about vulnerability maybe being perceived as a sign of weakness. What would you say to them, and can you maybe tell me about a time that you've been truly vulnerable with the team, and how did they respond?

A Yeah, I think I would describe myself as demonstrating vulnerability with myself, and then I'll tell you my view on how I value it in others, because I think it's absolutely critical. In myself, I think one way I try to personally demonstrate vulnerability are in opportunities like Town hall when we're talking about things that are going well, but also things that aren't going well. And I will try to demonstrate vulnerability with my colleagues on the management team and share something that didn't go well and try to do it in a very, like laying my cards out. Here it is. Here's the situation, right? Taking ownership for something not going well, right? Like as I've been working to build out our leadership team and like certain functions where we didn't have that leader, you know, this would be a recent example to your point of like showing vulnerability, like I can see those parts of the business that I'm trying to help not be on the best path they could be. And it's because of me, right? And I'm not trying to be overly critical of myself in saying that, but I'm also trying to just speak plainly about like, this part of the business is about to get a huge upgrade. And it's not because I think poorly of myself, but I think it's okay to recognize that as you're building and scaling a team, you're by definition going to bring leaders in that are going to be way better in their fun…

AI assessment note: “one way I try to personally demonstrate vulnerability are in opportunities like Town hall”