The Path to CRO with TigerEye's CEO and the CROs of CircleCi, Lattice, and Notion

Hi everyone. Welcome to the panel, Path to CRO. My name is Tracy Young and I am the CEO and co-founder of TigerEye. Today's talk aims to equip everyone with practical advice to navigate their journey to the CRO role. So please join me in welcoming Erica, CRO at Notion, Elabee, former CRO at Front, currently president at Lattice, And Jane Kim, former CRO at CircleCI.

Woo-hoo!

And yes, can we just take a moment also? This is 3 badass women executives who have created meaningful outcomes at their company. And I'm just gonna speak for them. I know, I don't even know your stories, but I know it was frickin' hard for all 3 of you guys. Let's take a moment and celebrate these women with me.

Thank you. Yeah! Woo!

So all of you guys took very different paths to becoming a CRO, and you obviously bring with you a ton of experience. What is a key decision or event you made that shaped your career? And we'll start with Jane.

Wow. I like to think that there were many sort of twists and turns along the way, but one key decision for me actually was, so I actually worked in finance before I transitioned to tech, and when I was in finance, I did the biggest deals as an individual contributor. You know, every deal I did was a year-long, 18-month cycle, millions of dollars. But then when I decided to transition into technology sales, I started actually as an SMB sales leader. So never been a manager, never did SMB sales. And that probably was the most important decision in terms of giving me, well, one, the management experience, but two, just trying to have a better appreciation of the different types of deals, the different types of segments, the different types of salespeople that you would work with along that. And getting that level of exposure was really great. It was also sort of starting a little bit at the bottom and working my way up. Was also a great learning experience of how to make that work. So, so that's what I would say.

What about you, LD?

Yeah, I might share two kind of pivotal moments, if you will. So the first one occurred when I was at LinkedIn. So I was an account executive back in 2009. So LinkedIn was a very different company at that period of time. And I'd always imagined getting into sales leadership. And I thought that that would come in the form of running like an SMB or mid-market AE team, and I'd sort of work up from there. And I was approached by the gentleman Brian Frank, who ran the sales operations team at LinkedIn. And he came and tapped me and said, "Hey, would you be interested in building out our first SDR/BDR organization?" And my first reaction was like, "No." 'Cause I imagined jumping into leadership in sort of a full cycle capacity, and I had just always understood that to be my path. And I ended up eventually saying yes, and, It was an incredible experience. It allowed me to immediately get into leadership. It allowed me to get my feet wet managing and coaching folks who were hungry for coaching and development, and probably a slightly safer space than with more tenured, experienced folks. It gave me great exposure to kind of cross-functional partnership and operational excellence. And I also met my husband, who happened to be my co-manager, and we're happily married with two kids. So it was a great experience personally and professionally. And then I would say my second one was, making the decision to leave a fairly scaled role leading 200+ AEs at LinkedIn to join a smaller stage startup. And it was sort of that moment of, hey, do I wanna continue to build a career with tons of learning and opportunity at, at this point it was 2016, and LinkedIn had grown substantially, and stay in a more kind of structured, at-scale role, large-scale, larger corporation environment, or do I wanna make the bet, jump into a tech startup, and kind of take all that's there? And I made the jump to becoming VP of Sales and Success at Intercom, and really enhanced my learning curve, tons of rich experience, but also just a pivotal move. And I think one you wanna be decisive of and go in eyes wide open around.

Erika.

Amazing. For me, I'll share one. I would say the most defining moment on the journey to where I am today was getting the opportunity to make the leap from— I was leading sales operations at GitHub, and I was approached for the opportunity to make the transition to leading the global sales organization. It was not something I think that was expected for me or planned. And, you know, took a beat for me to recognize kind of the magnitude of the opportunity and shift the mindset of I had long been an operator. I loved operations, I loved anything with data and numbers, and I thought I was just gonna be in operations my whole career and was presented with this really unique opportunity back 5+ years ago, which was rather unique. Now it's more of a trend, I would say, to see operations folks making a leap into sales leadership and revenue leadership. And, you know, it took a leap of faith on my part to invest in kind of new skill sets, learn new areas, take over a team that was pretty established, had a beloved leader, and kind of carve my own path in terms of who am I as a revenue leader. And, you know, I learned the greatest lessons in those first couple of years about myself and who I eventually became now, that I'm at Notion as a CRO as well.

So let's double-click in there. I mean, very different muscles being on the sales ops side to being a quota-carrying sales leader. What was the hardest part about making that transition?

The hardest part was just the mindset, like kind of reshifting, developing that empathy for— I was so used to operating in like the science, you know, as an operations person, especially sales operations. I thought very much that like everything could be solved always with like process and numbers. And I think I really had to lean into being empathetic to there is always art that exists no matter what. And there is a lot of art in sales. I believe a lot of it can be data-driven and science-oriented, but I would say that was, you know, one of the critical things I had to challenge myself with is to develop that empathy for the art. I had to get out there and learn what it meant to be a quota carrier and kind of prove that I could understand that since it was unique that I had not, you know, grown up in my career with that experience. I leaned on— I had a great, you know, surrounding set of leaders and peers that were very helpful and kind of helping me make that shift, go learn about what it means to be a quota carrier and kind of, you know, leave behind some of the ideas that I had around that.

Yeah. Thank you, Jane. Talk to us about the importance of mentorship. None of us would be here without help from others. So who is one person that comes to mind that's helped you along the way?

Yeah, that's a great question. I do believe so much in mentorship. I think absolutely there's no way that I'd like to be able to stand here in front of all of you and tell you that I got to where I am entirely on my own, but that absolutely isn't true. But mentorship can be tough, you know, especially if you come from a non-traditional, maybe a non-traditional background or an underrepresented background. You know, as a Korean American woman, you know, starting out in finance and then, you know, technology sales about 15 years ago, there weren't a lot of people that looked like me. So finding mentors that I felt really understood my experience was a little bit tough. But that's one thing I'd say about, and I, I have somebody, absolutely, I'll talk about that made a huge impact. But I think one of the key things about mentorship is that it shouldn't actually be one person. I think the best ways to build mentorship is building a community, a network of people that can support you in different ways, right? That can help you, support you in the moment that you're at now or the situation that you're in or the transition you're trying to make. And getting sort of that level of perspective is really important. And it kind of takes the pressure off of that one person that's going to be your, you know, your guide through all of this. So, you know, so I'd say mentorship is more about, you know, what you're looking for mentor in terms of mentorship and, you know, what are the challenges, what are the things, types of insights that can help you and using that as your guide to seek you out. But there is definitely one person I can think of. She was at the time the general counsel of the company I was at and wasn't really necessarily a fit from the first viewpoint you think of. It's not like I was trying to climb the corporate legal path, but, you know, she was a woman, a gay woman, and from her I learned just how to be able to, you know, see the unique strengths that my personal background and my personal set of experiences, right, coming from finance, coming more from an operations perspective, you know, into a quota-carrying role and how I could start to gain more confidence and, um, in my unique background, my unique skillset, um, that it can really bring to the table. And so, um, having a mentor that was helping me sort of find that authentic voice was, um, is something that I will always honestly will always think about and treasure as part of my career.

Mm-hmm.

LB, you have had the classic sales leader career path. You know, you were like frontline salesperson, ran the SDR team, frontline, second line, third line, CRO. Did you always know you wanted to be head of sales? Like, this is what you wanna do in life?

I think kind of, yes. I mean, so when I was, my parents are both attorneys, so when I was young, I wanted to be an attorney, and then briefly in college, thought about the finance path. But once I got into sales, I loved the competitiveness of it. I loved the meritocracy element of it. I loved the strategic element of it, the ups and downs. So, you know, for me, there was sort of like a, it was a good early match. And I also always knew I wanted to lead. And so I think pretty quickly I knew that that was the path I wanted to take. I will say, you know, going back to the concept of mentors, I was lucky enough to have a mentor at LinkedIn. A gentleman by the name of Mike Gamson, who ran sales and success at LinkedIn. And so he and I were able to meet and talk through what that path could look like and some of the experiences that I'd want to get along the way. And I think that was immensely helpful.

Mm-hmm.

There's folks in this audience who also want to be the leader. What's your advice for them?

So a couple things I wish I had done more of. So as you mentioned, I had a classic path and then I went like IC into manager and various sort of levels of leadership. I think I could have been more prepared to be a VP of sales or even a CRO and beyond if I'd actually had a little bit more intellectual curiosity outside of my core role. So I was always really focused on making sure that I was a good manager, leader, set vision. Held a high bar of performance, wasn't afraid to make the tough calls, made sure the team was rowing the same direction, hit numbers. Always helpful in sales. And, you know, like stepping back, especially at my time at LinkedIn, there's more I could have done. I always worked with sales ops closely, but I kind of, I could have pulled up beyond some of the core capacity modeling to better understand and get more financially fluent earlier. That's something I had to kind of learn on the job at Intercom and then Front. I wish I had partnered even more closely with PMM and really understood and been a bigger part of crafting messaging and positioning. Because in this type of role, that's huge. So my advice would be, if you do take a classic path, which I'm an advocate of, take the time to kind of pull your head up and around And when you're in a position that you feel like you're operating well in, take the time to go out and learn some of the other components around you, 'cause it'll make you a better holistic leader.

Mm-hmm. McKinsey recently put out a report that startups today are hiring CROs earlier than before, which makes sense because there's all this pressure for growth, so why not hire the person and make them responsible for it? But this is, it's a hard job, as you guys know. There's lots of natural tensions in place, which is why you're suggesting that build relationships, understand other folks' roles. There's just natural tensions, I think, with sales and marketing and sales and engineering and sales and product. And so this is a question for all of you guys. We'll start with Erica. Describe your worst day as CRO.

Worst day. Yeah. I mean, often I would say the highs and lows always have to come For me, it's usually involving the people, the people on your team. I definitely have had some bad days of like, wow, we're not executing as we need to, and I'm disappointed in myself, or we're not achieving the growth we want. But I think often the worst day is when people I really care about are either leaving the business, or they're struggling, or they don't feel like they have what they need. It's usually those moments when I come home and I'm really upset and I'm talking about it. At the dinner table with my husband. It's usually about the people, and it's about usually probably someone leaving the team or someone not feeling like they can be successful within the organization is like my worst, worst day.

Yeah, hitting here. Jane, what about you?

I would absolutely echo that. I think in this last 12 months at least, there's been a lot more disruption in our industry than we would like. So anytime that you are You know, I think the worst day absolutely is any day that you have to face a layoff. Um, you know, making those hard decisions about the, the future of the company versus just these amazing people that have invested in the company's success and where you've invested in their success. And that is always extremely hard. And I've been on both sides of it. I've been on the side where you're making the hard decisions and I've been on the side where I was being to let go. And so I think that's really, really tough. I think, you know, the ability to make kind of the tough decisions, you know, even if they may affect people that you admire, that you respect, and that you love is always really difficult. I think another tough moment, so it's hard to say which day, but tough moment is when you realize that you've made a mistake, that you've made a decision, right? Sometimes being a leader means making those tough calls. And saying, we're going to go in this direction, not that one. We're going to go after that segment, not this one. We're going to go into this market, not that one. And if those decisions don't pay off, customers are all affected by that. And as a leader, how do you get past the, oh my God, this is the thing that I did, to, okay, how do we continue to build the business? How do we continue to keep the ship moving in the right direction and learn from those mistakes along the way?

Mm-hmm.

Elvie?

Yeah, I would plus one to Erica and Jane, but maybe just to add two other kind of tough moments, 'cause it's hard to isolate to like the worst day. I mean, I think I've had some bad days and I've had some awesome days, and you have to live for the awesome days. The two kind of categories that to me create bad days are one, and I think this is explicit in their, implicit in this role, any time where you really have a lot of optimism around the numbers, and you just really feel good about getting to that forecast or that plan, and then you get surprised and you have to take down the number. It's just a shitty feeling. And there's great learnings that come from it. And I think in this type of role, if you're working at early-stage tech startups, you tend to take on ambitious numbers and go for growth, especially across the last decade. So it shouldn't be foreign that you're not always going to get to that target. I still think it never feels great, especially in those moments where it felt like you were headed in a different direction and then, you know, conversion rates take a downturn or, you know, whatever circumstances happen, happen. And then the second is I take pride and love having a really strong sense of team, particularly within my direct reports. And I've had the opportunity to work with some of the folks that are currently on my team in previous lives, and I take that relationship really seriously. And so any time where I feel like there's big discord amongst my leadership team, and I would say like any executive team I've sat on, that isn't resolved pretty quickly, those are crappy days as well that like I take home with me, if you will.

All right, let's sell this role here a bit for the audience. Why CRO? Like, why would you try to convince this crew here to go after this career, right? Like, how does a good day look like as a CRO? Or the best day as a CRO, how does it look like? Erica?

Oh, okay.

But back to the people. I mean, there's a lot of like good celebrating you get to do. We were talking earlier, like, if your company has a president's club, like recognizing high performance, is like, that's amazing, right? To celebrate other people. You know, I like even I'll have an awesome day when it's like a rep is closed, like a really complex, hard deal. And there were 40 people at the company that actually got it over the line. And you get to go like talk about that or you put it in Slack and you call people and you get on Zoom. And I don't know, that just feels, that feels great. Like you did something really complex across many, many functions, like It's never just one person that's getting things done for customers. And I don't know, I really like that when you see 40 people that literally make it happen across 10 functions and you get to go celebrate that. That's a great day. I also like when you're setting strategy for the period of time that you may be aiming for in the future. I think providing a lot of clarity and setting a vision and setting some goals, to me, that's really gratifying. I think that's a good day as a CRO. To align people, put a good goal out there, make it ambitious, and create some excitement around what that means if you accomplish that.

Yeah.

Jane, what about you? Best part about being a CRO?

Oh gosh. I talk about this. I sometimes think that being CRO is the most humbling of jobs because yes, you might think that you're at the top, but I carry no number, right? I don't own any accounts. I don't close any deals. And so my success literally is predicated on the success of my team. Which is actually really clarifying of what my job is. My job is to make sure that my teams are as successful as they can. And so I absolutely echo Erica. Any opportunity I have to celebrate, you know, the great customers that we've supported, the great deals that we've closed, and just the great performance from the team. The best moment absolutely is when you're on that stage and you're announcing President's Club winners and you see the excitement on their faces and The thing that always kills me is they always thank me, that, you know, the winners always come up and they thank me afterwards for the honor. And I'm like, it's absolutely the opposite. I'm the one thanking you for all of the amazing work, the amazing contributions, the ways that you've elevated the rest of the team. And so this is the smallest way that I can think of to thank these top performers. So yeah, those are absolutely the best moments.

I'll be your president, but really you still lead sales. So like, what's the best part?

100%. Well, so I think nothing beats a great global revenue kickoff. And I'll say, CRO, anything in revenue I think is incredibly difficult, but I would also not choose any other role around the table. It's incredibly gratifying and fun, and you just have to be signed up for the ride. But a global revenue kickoff to me is this magical moment where everyone's in a room. There's so much energy. I mean, I think go-to-market teams are the heartbeat of, of the company, especially energy and kind of vibes-wise. And there's something really cool about getting folks excited about the year to come, feeling all the potential and having that moment of alignment and clarity on what you're collectively setting out to achieve for the year. That's, is incredibly, I think, intoxicating.

So let's talk about automation. What part of your job should be automated? To rephrase this question, this is like a request for startups question. What do you wish someone was building for you? And we'll start with Jane and go down.

Oh my gosh. Number one, absolutely, is insights. The amount of time, and I say this as somebody who has been deep in operations in the past, but the amount of time that I spend, you know, trying to, to get the right set of data, the right reports, the right view of what I need, um, versus the amount of time that we're actually gleaning the right insights from that, that, that absolutely should be, um, should be better automated and something that, um, is necessary because, you know, what I tell my team all the time, like, you know, lead an organization, I've led organizations of 200, 300 people, but I'm still only one person. I have only one set of eyes, one set of ears, And, um, there's only so much that I can see for myself. And so I need to be able to rely on my entire network. I need to rely on the billions of data points that we now all sit on, right? You know, this is great in terms of data, but also the challenge. And, um, and so I can only make the decisions, right? That's my job is to make decisions. I can only make the decisions with the best information that I can possibly have. And so the, it puts the imperative on making sure that we get that. I need the feedback. I need to know what's I need to understand what's happening out in the field. I need to understand customers' sentiment about, you know, our product or, you know, the, the market that we're going after. And so the ability to be able to gather that in a way that is in not just gathering it, but gathering in a way that's insightful, I think is so hard. And absolutely would be something that would, I'm sure, give any of us a major leg up as we, you know, have to make those those tough calls.

I'll be—

I think the really short answer is I, um, in, in my role, I have really clearly, uh, asked my head of revenue operations to own the tech stack and think deeply about places where there's, you know, um, room for automation or great synergy. So I'll be honest, I don't spend a ton of time thinking through sort of tech stack. It's not my natural inclination, but having come from Intercom and Front, which are both technologies that include, you know, automation as part of your strategy on how you talk to customers, I believe there's still big opportunity on whether it's customer support teams or BDR and SDR teams to automate some of the places where we have intelligent, expensive people answering very foundational, fundamental questions. I think there's some really good technologies out there tackling this, but still room to run.

Erica?

Yeah, I mean, for me personally, similar to Jean, I would say wrangling the data and understanding what's happening in the business, especially connecting the dots across marketing and sales and CS and the support organization. I feel like I look at sets of data and I think there are probably like 10 to 20 questions I probably always ask. And I would love that to get automated out of my brain into the things that come to me where instead of looking at, you know, a set of data and trying to understand what's happening, it already answers the next 10 questions that I inevitably ask. Because I always feel like you look at something and you're like, wow, if I could just, understand this piece of it. So I'd like to automate that. The 10 to 20 things I always think about and ask and just have it appear.

Yeah.

And help me understand that connected journey across, you know, the end-to-end for what customers are experiencing and like where we have the opportunity to optimize.

So I know you guys have seen Glen Gary Glen Ross. Be interesting to see the age of this group here. Okay. A lot of people have seen Glen Gary Glen Ross.

Great.

So there's a certain stereotype in sales that I believe can be true, but I hope that it's outdated and wrong. So what impressions of sales do you think is just like totally not correct? I'll start with Jane.

Oh, this is a great one. So I started my, you know, I started my career, you know, many years ago, decades ago now. And, you know, sales was very, very different. And the one myth that I absolutely think can be busted is the myth of the rainmaker. Um, yes, there are some people who have magical skills on, at the negotiation table that just know exactly where to push and pull to get the final deal closed. But, um, but sales is something that absolutely can be demystified. Um, it doesn't take somebody who has these mythical skills to do well. Sales is, uh, sales can be a science. It is an art for sure, but it can be a science. There are stages and processes that go from an early introduction and generating interest to ultimately getting to a close. And so the thing that I think is really exciting about that is that anybody can be good at sales. And I think that's the other big myth, is that it's an industry that is still very much, has changed a lot in the last 25 years, but, you know, it's still dominated by men, by white men. And that doesn't have to be the case. Sales is something that, you know, every person can learn to do and can be good at because it takes data, it takes being empathetic, it takes communication skills, it takes, you know, getting savvy with presentations, with data. And I think all of that is really exciting because Those are all things that you can break down and learn to become, you know, that ultimate, you know, top performer, you know, that ultimate closer. And it's not this mythical set of skills that you're innately born with.

Mm-hmm. Elby. I think the one that always really gets me is that sales folks, or specifically sales leaders, are like independent operators out there for their own best interests. I think that the vast majority of individual contributors are there, especially I feel like in this current workforce generation, are there, yes, to do really well and certainly make great money and earn the President's Club ticket, et cetera. But I do really believe that a lot of them are also motivated to see the company be successful, to see their peers be successful, And I think you can also cultivate that culture. And then as a sales leader, one of the things that was really instilled in me at LinkedIn is you actually don't wanna show up as a sales leader, which also tells you about some of the pejorative connotations of a sales leader. You wanna show up as a business leader. And so I think the most successful sales managers, leaders are always showing up not, to the table thinking about like their own team's interests or how they blow past their number, but really always in service of building the best, most sustainable, efficient business possible. And to me, that's always been really important, how I show up as a leader. I really wanna be known as a holistic revenue or business leader, not as someone who's gonna be protecting my interest or my team's interest. Ahead of the company.

Mm-hmm.

Erica?

Yeah, I would say, you know, sales is very strategic. And I think, like, sometimes I hear people talk about sales in not that way. And to me, you know, the best reps and the best teams, you know, they're really kind of like the CEO of their territory. They're like running a business. They're thinking about their customers and their accounts in a very strategic way. And they're doing that by engaging in a team sport. As I mentioned earlier, like, none of this happens with one person. It's everybody at a company across many different functions that gets things done for your customers. And that's very strategic. You have to connect a lot of dots, the right dots. You have to influence. You have to collaborate well. You have to actually identify, you know, what's going to get you over the line for customers. And that's very, very strategic. And so— That's what I would say that I think gets underestimated.

I guess one other quick— I've never given out a set of knives for second place.

All right, last question, and then we're going to open it up to the audience. What's a piece of advice that you would give yourself 10 years ago? Anyone can take this one first. I'd love for all of you guys to answer.

I'd say the biggest piece of advice I would, would give is kind of going back to what I was saying before. Like there's part of being a sales leader that you think it's just about the number. And don't get me wrong, hitting the number is pretty important. But what I found to be more important as a CRO is how do I build and develop a team? And more importantly, how do I build and develop leaders? You know, I want all of my teams to achieve the goals that they want in their career. And for me, you know, sort of shifting my focus from just the deals and the number to then shifting focus on the organization and the leaders that we're building and the skills that we were developing within the team as being more important for the future success of the business and frankly more important for the future success of those individuals. And so that's really something I feel like I wish I knew that earlier because then I could really kind of focus on, you know, the areas that we're gonna make the most, that we're gonna have the highest amount of leverage and the most amount of impact is sort of understanding the people aspect and cultivating that.

I'd share two things. So one, just to reinforce, I think, Taking the opportunity to have intellectual curiosity on what does an overall healthy, financially sustainable business look like. Better understanding marketing in and out 10 years ago. Learning the differences of how EPD teams communicate and work and the language that's innate to those teams and how to be an effective partner. At bringing product feedback at scale and in quantified ways to those teams. So really having more intellectual curiosity around the cross-functional elements would be one. And then the second, I, I think so much of this job comes down to how effectively you can communicate at different altitudes and really knowing how to resonate whether you're in a board meeting or a senior leadership or exec team meeting, or with your directs or the broader organization or the broader company. And so just really continuing to be intentional about developing those skills and thinking through how to tell the right stories and the right narratives across the right audiences.

Yeah, mine, like thinking back on the careers, maybe more broad, I would say early in my career, I feel like it was often said like, you'll work hard and you'll get recognized. And, you know, 20-plus years ago, you know, I kind of took that to mean like, be quiet and be patient and your time will come. And I think, you know, how I've ended up where I am today is because there have been points in time where I couldn't do that and didn't do that. And I had to ask for something, ask for an opportunity because I could see where I could have impact. And that changed my trajectory. And I have a friend, like a very wise person I worked with for a long time, that she has a really good analogy for it. It's sometimes there's not a seat at the table, but you need to pull up a chair. And I think it's just like recognizing you can do that and picking those opportunities, you know, can change your career trajectory. And, you know, did for me, you know, to end up to where I am today.

I love that image of just like, oh, I don't have a seat at the table.

My kids know how to do this.

They're just like, drag chair across and like sit themselves down where their parents are. Look, these are 3 growth stage sales leaders, um, who have created incredibly meaningful outcomes for the companies I've worked for. I'm gonna open up the questions to the audience now. This is your chance to get to ask them anything. Got one, one brave person walking up.

Oh, 2 brave people.

First of all, thank you for all of that. My question is, where do you go to continue your own personal and professional development?

Are there certain podcasts, books, things you are really interested in?

Because I find for myself it's hard to keep up with all the martech, all the changing patterns, trends, and it's sometimes like information overload.

And so just curious where you guys go to kind of continue your professional development.

For me, I'm a— I love podcasts. So like, I will consume a lot of podcasts and I try to pick things that like are relevant for that particular time. Like, oh, I'm struggling with this piece. Like, how do I think about these benchmarks or, you know, whatever it may be? And so I consume a lot of podcasts and then It's been great. I've met two other fabulous, three fabulous women leaders. You know, I lean on my network a lot of just like picking the brain and like having a few of those thought partners that when I've got something meaty on the docket that I can go to that just have a different set of experiences or have lived through it. So those are my two podcasts and then my, my network.

I was going to say, I think there's a couple of thought leaders in the space. That I try to follow and kind of intentionally seek out. I mean, whether I agree with all of their thoughts and theories or not, it's a great way to kind of challenge myself on my own philosophical beliefs and how they play out. I'm also a big believer in networks. Actually, Jane and I met through a networking group for kind of women revenue leaders. And then I also am a big believer that learning comes from all different directions in the role that you're in. I often feel like I get these inspirational moments with like my directs or people on my team, cross-functional partners. And so I think sometimes there's a misperception that you can only kind of learn top down. And I have been a big beneficiary of learning from a ton of different people at all different levels that I've worked with and finding inspiration moments. Across all different levels as well.

I'll put a plug. There's a great podcast called Grit, and it comes from Kleiner Perkins, and they do a great job of interviewing different sales and business leaders, CEOs, and it's really all about talking about their tough moments. So in a lot of ways, I feel like that those are the best learning moments, not through their successes, but through the mistakes and the things that they've learned.

Next question. Come on up. Hi.

My question is about CRO compensation structure. Are there any best practices between base salary and—

How much do you guys all make?

Thanks. So maybe I'd answer this in a few different ways. I think variable versus base really will depend on stage of company. How you and your leader talk about the job and what's important in the job and kind of, you know, set up that structure. And probably also vary on, you know, CRO can be wide ranging in terms of, you know, whether you're running sales or whether you have broader, you know, functional remit. I would say traditionally it's going to be anywhere between 50/50 to, you know, 80/20. Depending on all of those different factors. I would definitely advise figuring out how to get benchmarking so that you can show up as a credible partner in an interviewing process. And be a thought partner to whoever the hiring manager is and advocate for yourself in a very data-driven way. That's something I started doing the last couple of years and have benefited from.

As CEO, I wouldn't want my head of sales to have anything less than, let's say, half a point of equity, right? Ideally, I want them to have like a whole point of equity or more. Next question.

Hi, founder of Marketrix. So my name is Hirosha. So basically, I have seen throughout in terms of sales teams joining in, the point where they close the first deal, right? That's the point where they get the most of confidence, right? And then where they start driving things forward, right? So as sales leaders, like, you know, what sort of advice would you have so that we can push the teams to get to that point as soon as possible? Thanks. Honestly, my advice is in a lot of ways, honestly, just do what you can to get them to that first point. I think that they're— that getting to a new hire or new sales team, I mean, for a new company, like, getting your first win is— there's— it's not just important for the revenue, but it's important psychologically. It's important for their confidence. And there's a lot of ways in— actually, whenever I build onboarding programs, we get time to first deal as being one of the key data points that we track. Um, and for me, it's about just getting to the first deal. So I don't care if the discount rate is double what it should be, or if, you know, it's, it's a really small deal, but what matters is that you get that first win because that will be the watershed moment for all the other great wins that come behind it. So my advice is whatever it takes to get your team to getting that person to their first deal. I mean, within reason, but I would really push that to, uh, to try to get that.

The only thing I might add there is there's a fine balance between protecting your brand by having someone ramped enough to be able to well represent your company, whether they're doing discovery or a demo, etc. But then there's an onboarding program that's just like too long where you're not getting someone like out there in the water learning how to swim. And so really spending time with your leaders, thinking through that right balance because you don't want to like throw someone on the phones day one and create a bunch of like really crunchy moments from a brand perspective, but you— and create like a bad customer experience. But I think if you wait too long, you can actually inhibit that confidence building moment. And I also believe some of the best learning just comes from making some small mistakes and learning on the job, getting those tough questions, and then, you know, committing to like, I'm going to go find that out and never have to circle back to a prospect or customer again.

I'm so tickled that Jack is standing there waiting to ask this question.

I've got a question.

Yeah, yeah, go ahead.

Hi, and hi Tracy. Um, hi everyone. I'm curious to hear about, um, how you think about your role as like the first team sort of as part of the exec team versus your role as like a revenue leader. And, um, in general there's like a lot of points where you're going to be in these decision-making rooms when you're sitting there with like the CEO, the head of product, head of people, where you're going to realize that a decision is going a direction that's not maybe helpful to sales this quarter or even this year. And I'm curious what your mentality is in those situations when you're in the company leadership seat, sort of like a generic, general C-level leader relative to just being a sales leader. And maybe was there a moment in your career when you flipped from, I'm a director VP to now I'm actually really a company steward? Is it always a balance? Do you always take the side of like, I'm just going to speak for sales? How do you balance it?

Wow, that's a good one. Yeah, I mean, I guess for me, like, I really do think about that executive team as the first team. And I feel like I really internalized that over the last few years. I don't know that there was a moment, but I think a series of moments where I realized, you know, only having my sales hat on leads you astray. Like, you make a product decision, an EPD decision, you know, to fast-track something that you really shouldn't have if I had my sales-only hat on, right? And I was putting pressure, like, we need this thing, we need this thing to come out, and it's not the right decision for the business or for EPD. Yeah, so for me, I think it's like, I really think of the exec team as the first team. I think my responsibility to my revenue leaders is creating an environment in which they are their first team. And that enables them when something goes against sales or something they maybe don't like, that they can help each other figuring out what do we have to shift in whatever that direction may be and how do we all band together to, you know, figure out our new path.

I think it is absolutely imperative that in any of these roles, you're part of your executive team first, and that is your first team. And I think this plays into a lot of what I believe philosophically, which is you actually don't want to show up as a quote unquote sales leader. You want to show up as a business and make sure that everything that you're doing is very clearly in the service of building a strong, sustainable, unified business. And I think, you know, as a sales leader or revenue leader, Go-to-market leader, you should care as much about efficiency as the CFO, and they should care as much about growth and culture as, as you do. Um, and that to me, that's a sign of a really effective executive team. And I also think there are moments where because of your heritage, your history, your background, you are also obligated to make sure that the executive team lands in the right place by bringing forward your knowledge, which may look like advocacy, but You're simply bringing forward information or perspective that actually may help the company land in the right place. So I think it's a balance. I think you want to show up as exec team first, business leader. And you also don't want to go so go with the flow that you're not actually bringing those moments of truth on those friction points. So it's a balance.

Erica, LB, Jane, you guys are awesome. Thank you so much for being here today with all of us, and thank you for the audience for joining us today too.

Thanks.

Thank you.