The business of growing and monetizing an open source product | Ashley Kramer (GitLab CMO/CSO)
Episode 109

The business of growing and monetizing an open source product | Ashley Kramer (GitLab CMO/CSO)

Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer.

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Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b.

In today’s episode we discuss:

Where to find Brett Berson:

Where to find Ashley Kramer:

Where to find First Round Capital:

Referenced:

Timestamps:

(00:00) Intro

(02:34) Marketing in closed vs open source companies

(07:40) The role of marketing at GitLab

(09:23) The tensions of being a commercial, open source company

(12:36) Advice for nurturing community and dealing with disagreements

(15:02) GitLab's main marketing metrics

(20:26) The thinking behind GitLab’s org structure, in and around marketing

(28:19) Selling to enterprise as an open core company

(29:53) The difference between open core and open source

(30:39) Serving many different customer segments

(35:10) GitLab's planning process

(39:22) An example of GitLab’s marketing in practice

(42:12) How marketing collaborates with product

(45:55) Marketing lessons from working in an open core company

(49:46) Examples of GitLab's focus on transparency

(52:22) Why GitLab is transparent about their marketing

(54:59) 2 examples of GitLab's uniquely transparent culture

(58:35) The downsides of being a transparent company

(60:13) GitLab's meeting structure and cadence

(62:04) Benefits of having an engineering and product background as CMO

(71:09) People who made an outsized impact on Ashley's career

Brett: Well, let's do it. Thank you so much for joining us.

Ashley: Thanks for having me today.

Brett: So I thought maybe we could kick off and talk a little bit about marketing and distribution in the context of sort of a developer led open source, sort of open core model. And maybe kind of a jumping off point would be, I think for most of your career, you worked in more traditional closed source software. And so now that you've sort of immersed yourself in what GitLab is doing, I'm really interested in, like, what are the big ideas or the things that matter most when you compare and contrast marketing in the context of an open source company versus marketing in the context of a closed source company?

Ashley: Yeah. I think the, the interesting thing while, while you're right, all of the companies that I've been a part of leading up to this, uh, were closed, um, closed core closed source. But when I think back to my time, I worked at Tableau software, few, uh, careers back. And what was interesting about their customer bases, they wanted to do more with Tableau's product and we did have a way to do that you could crack open, they called it the viz, and you could customize it. We saw these large enterprise customers being very successful doing it. Now the downside to that is customer A is making all these changes and doing these powerful things.

Customer B wasn't benefiting from it at all, and they might have to go do it again on their own. And so when I joined GitLab and I started understanding the true value of being an open core, started as an open source, now open core public company, that value is repeatable. So as customers our contributing code to our platform, we are able to share that as part of our platform with the entire world.

So it's sort of opens up all the contributors in the world to be part of our team and part of our development and innovation and really helps with our speed of innovation.

Brett: And so how does that then impact the way that you think about your role in marketing?

Ashley: Oh, it's super exciting because I'm not just marketing all the time, what our plans are and our R&D team is working on, I have the whole world as my incubator to speak to and to drive further value and to put value in the platform that of course, we're going to go speak about features, capabilities being added. And in a true open core company is very transparent in how they operate because they want people offer. They want people contributing and so we have policies online and all of these different ways we think about it that our direction is very clear. In our handbook, I'm sure we'll talk about that at some point, that's a unique value of GitLab too. So people can go see the direction we're going so they know what they're contributing. You know, we'll get accepted as part of where we want to go. But it also, all of the things we're working on, the issues we're working on as we call them, the things under development, everybody can go see. So one, they're not going to work on something we're already working on, but two, they can understand what's coming. And that's something that customers really love is something we believe in very deeply at our core at GitLab, which is transparency.

Brett: So, if there's a company 7 years behind you, but are sort of spiritually aligned with the way that you think about open core and sort of the commercials parts of their business, are there things that you've done exceptionally well as a company specifically as it relates to marketing? That you think they might find inspiration from or their specific ideas that they can implement. Sort of at a company that's 20 people getting off the ground has a million in revenue sort of scale business. So there's sort of some product and some pull, but they don't really, marketing is not a function that they have. It's not something they've done explicitly.

Ashley: So it really, the community becomes your marketing at that point in the journey. And so if we look back to the beginning of time of why, so just a brief, brief story of how GitLab got started. Dmitriy, who was the first founder was at another company and wanted to have a collaborative development tool and did not get approval to buy any of the options out there.

So he started building an open source one on his own. Sid, our other co founder and CEO to this day, found it via Twitter post or one of the projects that were out there that was marketing. And he started contributing. He reached out to Dimitri. And of course there's a long story of where they went from there that we'll talk about more.

And so if you think about when you have this open source model as part of how you're building your product and your company, open source as a company mindset as well, but the entire community becomes your marketing driver. And so, you know, you can do very, very tactical things like reward them top contributor, gets something sent to them or, people love badges these days, gets a badge. You can have hackathons where everybody comes together and the coolest idea coolest piece of innovation capability that is built gets some sort of again recognition or reward. And so you don't necessarily need a CMO or anybody in marketing to really drive this when you start as that, as that as your route as open source is your route, you open it up for the the people that are contributing to the product that clearly believe in it because they're contributing to this to actually be your marketing engine.

Brett: And so what does that look like now that you're at at scale in terms of like key programs? When you think about the role of marketing at GitLab?

Ashley: Yes, it's still a core part of our role. Obviously, we're a public company now. So we also do all of the core marketing that you would do even as a closed core company, but we still have a group and it reports directly to me. That is um, developer relations and community. And so we run specific products through that, like our code contributor program, where we still do those exact same things.

We still have hackathons, where we bring people together. We still have top contributors, we call them GitLab heroes, and so we still run those programs. Now what I've been working on with a person in seat that runs that group, is bringing the two together. So we have core marketing that's focused on paying customers and getting more prospects that will pay because you do that as a public company.

We have the community team that's working on making sure the community is happy and continue, continuing to contribute. So now, how do we bring those together? How do we get the community to speak up to their bosses at the companies they work at? And understand the value that GitLab could drive to the company in the companies that are using us at large scale, how do we train them to have code contributors sitting within seat at the company? So you have a company that's using our platform really widely. They want a few more capabilities. Don't wait on us. We'll empower you and teach you how to have some code contributors in seat so you can move faster. And then, of course, we get the value from that as well since it's an open core platform.

So that's the step that we're at right now is bringing those two together. But what we had back in the day when we were just a million revenue company still exists as part of where we are today as a public company.

Brett: What have you noticed in terms of if there are any tensions between sort of the roots as an open source company, as you've layered on sort of the economic engine of the business?

Ashley: It's, it's always, you know, I'll be transparent in that it's, it's always something we have to think about. So we still, as a good open source steward, we still provide our product. The core means feature limited way. It has a set of features that individuals would use to be successful. But when it comes to enterprises and companies being successful, things like integrated security, then we start charging for those.

Of course, that's part of our commercial model. And so we have to be really, really thoughtful and careful about how we think feature by feature that's being built both by us in the community. Do we put this in our free version, which, which we will, we will always have as a good open source steward, or is this something that falls as part of our paid for package. And the, the framework we use for that is, is documented in our GitLab handbook.

It's all about explaining to the community and our customers what our business model is. We have promises. So we have 11 promises listed out there on what we will follow to make sure that we're continuing to serve the community that helped us get where we are today, but also understanding that we're a commercial product now and then help them differentiate how we think about, okay, this feature is coming into the product, will it be in free or it will be part of, we have two different tiers, we have three tiers, but one's free, so two tiers of how we actually charge, and so we just try to be as open and honest and transparent about that and list it out. And, and that's how we move forward.

There will always be a few people that disagree. Um, and, and we, we deal with that and we, we appreciate the feedback. It's, it's a core value of ours is collaboration and contribution. Um, but that's the model that we've built around it.

Brett: Can you talk a little bit more about the promises and maybe how you landed on the specific framework that you all use?

Ashley: So this is, this is something that you know, our CEO and, and all of the, all of the executives in the company worked on together. I mean, Sid very much so believes in open source. He's, he's built a company with Dmitriy on top of it. But it's all about helping people understand for us the why behind we're doing things that we're doing.

So, so one example is we try to stay true to our core that when a feature is open source, we won't wake up one day and just change it to be part of a free tier. That, that's one of the promises we have. Um, another one we have is that we'll always release an open source, the tests that we have for an open source feature, we'll share that with the world. And so those are two examples like I said, we have 11 of them. I'm happy to to go through more of them, but it's going through and it was speaking with the community, understanding the community on what's really, really important so we can continue to bring them along, while we also become a commercially available product. And this, this all happened um, of course, before we went public, the team did a bunch of work together. So, so we made sure we weren't underserving the community because now we're this public fast growing company.

Brett: Could you go sort of a few levels deeper when you think about engaging with the community and, developer relations function. I'm interested because, you know, you mentioned this a second ago, I think it's kind of the same with an employee base team members, community members, et cetera, that no matter what you do, you're going to bother certain people.

Certain people are going to like it. Certain people aren't going to like it. Certain people are going to understand that you need to have a high quality economic engine and that actually will benefit them because you're able to invest in the product and so on and so forth. Given, unlike other companies, you have this very specific, powerful constituent that is developers that, you know, are contributing to the product and evangelizing it. Are there things that you think you figure out in terms of working with that community, bringing them along that others that are engaging and nurturing a developer community might sort of find inspiration from?

Ashley: First and foremost, it is being transparent with them. You just have to do that as a business like this. Helping them understand, hearing their feedback. I think too often companies that, you know, don't even respond to this kind of feedback. So hearing their feedback, at times you are asking them to disagree and commit, just like at times we all do in our jobs, but explaining to them, helping them understand the why behind it, which is why we have the framework around what we do feature by feature and code check, check in by code check in to help them understand. You, you're, you're absolutely right that there will always be people, um, whether it's in the community, whether it's within the company that don't agree, but for me, our transparency first, like we will not, I'm a product manager and, as my background, and often people would talk to you and say, I want this feature. And you talk to them in this giant circle that makes them feel really loved, but is also kind of telling them no, whether they get that or not.

And so we like to be a little bit more direct and transparent here at GitLab and say, we understand. This is not going to go in the free version. It's going to go in the paid version because of this and help explain it to them. Just, I think that's where we gain the respect that we're not hiding anything and we're not trying to move away from our promise to support the community, but we have to make these decisions now as a company that also sells this as a platform. There's no smoking gun for us behind it. It's just making sure we stay open, transparent, continue to run these community events, continue to elevate the people that we call GitLab heroes that are contributing, not part necessarily of their company, but as the projects they're doing as well.

Brett: When you think about the marketing function at GitLab, what are the different metrics that you care most about that you sort of end up being the governing metrics for the part of the business that you own?

Ashley: So we have five core ways that we look at our metrics. Um, it's, it goes along what we would consider the buyer's journey. So the first is awareness. We do have a big competitor in the market that has a very, very similar name to us. Um, And then there's others as well. And so for us, it's all about understanding our awareness in the market.

So that could be aided awareness where you start to limp them along. And hey, when you think of a DevSecOps platform, who do you think of? And then unaided awareness in that, what is DevOps, what is DevSecOps? And so it's, it's trying to get surveys out there, get an understanding out there of who knows who we are and what we do and what more awareness do we need to do.

So that's the first one. The second one is consideration. So now we have prospects that have entered into our funnel in some way, and they're starting, there's always considerations, sometimes people say, I want to stay with status quo, challenge me on why, some people say, I'm also looking at a competitor, and some also say um, you know what we're going to build it ourselves. We don't actually hear that one as much. And so for, from a consideration standpoint, we look at metrics of how they came into the funnel, but also in general, overall, uh, our win loss rate and the analysis on win loss rate.

So we want to really get in front of what we think they're going to be hearing from competitors and how we can differentiate with our value and make them make the decision to move further in the funnel. and have that deal be closed. So that's the second one. The third one is conversion. So I also run, as part of marketing at GitLab, I also run our sales development team, which brings in which is SDR sales development reps and business development reps. So what they focus on is inbounding and outbounding, of course, in coordination with our demand gen team. And so for them, it's all about something we called sales accepted opportunities.

So whether it's a current account or a net new account. They're getting all of these prospects lined up, and the minute it gets over to the AE, and he or she says, yep, this is a good, this is a good option. I'm going to go set up a meeting. So we measure a metric on that. We measure the first order sales accepted opportunity metric for that one.

And so now, now are the good ones. Now, now is the fun time. Now they're customers. So now we're getting into expansion. And we measure at GitLab, the day that we get the customer in the funnel, we know what our opportunity is there, and we know a lot of customers don't come in and say, I want to buy your platform right now today for all 10, 000 of my developers, and they're probably going to start with a team or two, or they're going to start with the department.

And so we very, very careful, carefully measure the expansion opportunity there. And then from an expansion standpoint, we look at how can we um, how can we really get that expansion pipeline going? And that's via ways like having other powerful customer stories. That's the number one thing I've learned in my time here is customers really, really want to hear how other customers have been successful and often customers that are close in their industry. The best one that we've released so far this year was Lockheed Martin. So you have this really um, big, giant $26 billion in revenue. I think company that's been around forever that was having problems with their transformation.

And, you know, I'm going around the world right now, speaking at a tour that we have. And the minute I tell that story, I have people come up to me and say, I can't believe that Lockheed Martin was able to transform their software development practices with GitLab and we have exact ways that they did it.

They're like, if they can do it, we can do it. And so that's one, that's one of the ways we're leaning into expansion is trying to understand how do we get people to understand they can do it too. And the value, they almost get, they almost get FOMO at that point, which is kind of funny. Um, and then the other thing that really, really works, particularly in upper mid market to enterprise, uh field events, field events have been back for about a year, and they're almost even more popular now because for two years, we all sat in our houses and stare at each other on Zoom and try to make these deep personal connections with peers at other companies or with the vendors that are providing a software.

And so we found that throwing really powerful field events is really helping with, with our growth pipeline and getting expansion within these accounts. We also do that within customers too. So we'll go in and bring all the different teams using GitLab together and run a fun hackathon. And we've, we've actually heard feedback from some of them that that's the first time they've met their, their such giant companies.

It's the first time that they've actually met some of the people at their company. And that was because GitLab brought them together. And now they're starting to see us as a partner and a trusted advisor versus just this vendor that's throwing software at them and, and taking off and going to the next.

And then the fifth one is evangelism. And this is partly the community piece. This is partly tied to field events. But what we really look at here is, who is contributing code both within the wider community and how many people within the wider community and also within the enterprises that we already sell to. And as I mentioned earlier, now we're trying to marry those together and bring them more closely together.

How do we bring community closer together? There's probably a lot of the community sitting in seated customer sites right now, and maybe they're not using it necessarily for their job, but maybe for a project they're working on. And so a metric we're measuring is how we can bring those two worlds more closely together.

Brett: When you think about the areas of ownership for marketing in the context of GitLab, you know, the demand gen, SDR, BDR function, and the expansion function, I think those are examples of functions that can sit in various parts of the business. And I'm curious at how you sort of landed on, on ownership there inside of marketing?

Ashley: So that was a, that was a decision that predated me. But from my standpoint you have the demand gen engine that is very typically within marketing, you know, sourcing all of these things. And so to have, to have the sales development that's going to take those and convert them to something or going to take those lists they're producing and go make some calls. Having that close partnership, I've seen it in both places too, makes a lot of sense, but it also drives that cohesion with the sales team because the sales team has, you know, the pre sales team and, and AEs that will go build the relationships and the post sales technical team that will make it successful.

And so we just had a new CRO join about a quarter ago. And it was one of the first things we talked about is I said, do you think this makes sense here? And he said, he loves it there for that reason. Like that cohesion is there within marketing to, to drive all of these leads. And now my team can focus on what to do them, how to progress them through the stages, and how to close it.

And so it can sit anywhere. But I also don't like walls being between like, I don't want MQLs coming in and being thrown over a wall and then the team picking it up and throwing it back over. So it's, it's, it's actually not by design, but ended up happening this way. My VP of Integrated Marketing lives in the exact same town as my VP of sales development.

And so, so what, what better way, they're on the same time zone., They can go get coffee if they need to talk about something to, to drive that cohesion on what's working and what's not. So we can get the sales team everything they need as far as leads.

Brett: What about the expansion sort of component that that's the one that seems maybe most counterintuitive relative to maybe traditional enterprise software, where either it's sort of its own CS org that sits outside of the sort of office of the CMO, or in some cases you have the CRO that sort of owns expansion in that way.

Ashley: So Sarah and I jointly own expansion. So we're driving the pipeline for expansion, and of course, he owns the overall number, which can be a mix of, is a mix of net new and growth. And so from that perspective, we're running all of the things I talked about, like getting all those customer stories.

Obviously, we own ABM and helping them there as well in the field events, because then we're doing what we call measuring influenced pipe. The marketing events, things we're doing, campaigns we're running, is bringing an interest and then that's influenced pipe that then they go and close. And there is a CS team that reports directly to the CRO and is responsible for um, we have the customer success managers, we have our services team, of course, and then we have our more technical um, solutions architects in field CXOs, there's field CTO, field CISOs um, and so they, they are part of that process and they're very often at our events and they're very often contributing the content that we're building to send out to the world to make sure what they're hearing is, is integrated in what we're producing to help build that influence pipe.

So it's a jointly owned goal by the whole company, really. But I, my specific focus is building that pipeline. Our CROs focus would be closing it and producing that net ARR number.

Brett: Does that sort of joint ownership generally feel easy and clear? Or they're sort of things you've had to pick apart in terms of making that type of joint goal work really well in the context of the business?

Ashley: So the number one thing we actually focus on every year going into next year's planning, we're talking about it right now, is what split should marketing be focused on? So we're building, there's, there's three ways to build pipe. The sales team can do it directly. The AEs can do it directly. And they always should be doing a measurement of that.

Marketing, of course, is a large part of that. And then partners as well, our channel partners. And so when we think about where we need to discuss, obviously, what's, if our pipeline's behind, there's obviously needs to be a conversation um, or it's not progressing. Um, and we can help where we really need to revisit every year is should marketing be focused more on getting net new logos in, or should it be focused more on expansion, or a very healthy mix of both.

And so in the past, as we were growing as a company at GitLab, marketing, you would say they're more focused on net new because we want to bring it in now so we can close quarters and quarters ahead. Since we're starting to really move up marketing, get these larger enterprise deals where we've done a lot of things like GitLab Dedicated, which is a single tenet SaaS server that will manage for the customer. We've had a lot of interest in highly regular- from highly regulated companies and we really differentiate there.

Now, maybe going into next year, we need to start thinking about should we be a little bit tilted more toward helping on the growth because it's a, it's a really known fact that it's much easier to get more revenue out of current customers, particularly if you do the right thing and make them successful, expand their capabilities, bring in more teams and people to buy more licenses than it is to set up a brand new customer. But we can't forget about that either.

Brett: In terms of the way that you design your org, is each one of those sort of 5 areas of marketing owned by, like, a single threaded leader? Or is there some other sort of way that you configure the team and why?

Ashley: We actually when we came up with the framework when I first started, we went back and forth on this a lot. And so I get lab. We really believe on having a DRI for everything a Directly Responsible Individual. And then, of course, there's a ton of contributors. And so there will be several of my VPs that contribute to each of them. Awareness is an example. Pretty much everybody on the team is working in some way for more awareness. But I would say that's the number one tracking mechanism that I give for my Vice President of Corporate Communications, because that person is responsible for getting the message out to the world, doing the thought leadership, getting that awareness out there.

But you could argue our VP of Products Marketing has a big hand in that, our VP of Community and DevRel for the DevMindShare. So, so each of them has a directly responsible indiv uh, individual assigned, but their job, it's not a, I don't see it as a journey, as a line, it's a circle, because we keep selling to the accounts over and over.

So for, for me, It's everybody contributes to all of it, some more heavily to others, and one leads each of them.

Brett: And then if something's sort of ahead or behind, there's a single person who's on top of that in, in the org?

Ashley: There's a single person that should be raising the flag. We do OKRs quarterly at GitLab, and they're transparent to the company, and we understand. So CEO level OKRs is where we start, then CMO, CRO. We all have them, and then those teams have them. And so we do check ins on these. Some teams weekly. For me, I check in about monthly to see where we are.

And we do the status red, yellow, green. And so obviously if something pops up green, I'm not going to ask as many questions. If I see some red pop up, we should start asking some questions. Um, something that was in red for a while when I started was, um, our evangelism. And we have a great team on that, but we just didn't have the right focus.

We needed to help drive their focus toward what was really moving the needle for the community and for the business. And so that's an area that, you know, the VP of DevRel and Community came in and really started focusing on and would be the one anytime he sees anything going off track that raises that flag to all of us.

Brett: When you think about enterprise customers, specifically, large accounts, fortune 500 companies, is the open source open core community led strategy, a big part of how you go after that specific customer base? Or if I were to look at that part of the business, it maybe looks more like traditional closed source enterprise software?

Ashley: We're transparent in I think it depends, it depends company by company. So we're transparent in that we're open core. However, they can have a completely air gapped you know, owned version of their own, we sell in all the different deployment models. And so I wouldn't say we always go in and lead with hey, we're, we're open core outside of some, you know, I, I visit with a lot of customers in PubSec and that is actually for a lot of the agencies, a requirement.

And so, so there we probably lean into it a little bit more. But for some of the other industries we lean into more of where we are one single platform where you can plug in other tools so you don't have to kick out all of your tools. But over time, if you want to standardize, use this as the foundation, everything from the idea that the product manager comes up with all the way through building, checking, securing, and making sure the code is of quality and getting it out to the world, you can consolidate on that. And so we really lean into the single DevSecOps platform for these enterprises and then an underpinning of that is, and if you want to move faster, build capabilities. You are able to do that because of our open core model.

Brett: For those folks that aren't as familiar with open core versus open source, what does it sort of mean to you?

Ashley: So it means that we will always have a product that they are able to download and it's a, it's a core feature, limited is how I would call it, version of the product that is everything a developer or a team of, of uh, a small team of developers would be able to use to be successful without having to pay.

And then again, through that transparency and helping them understand we have the commercially available version, which is on is on top of that core feature free version, which now has add ons and deeper security type features that then you move and you pay for.

Brett: How do you think about sort of balancing all the different segments and stakeholders when you think about the role of marketing? One of the things that I've noticed is even if you take sort of the OpenCore model out of it and sort of the engagement in the developer community and so on, it's often very hard for a company to do an excellent job at enterprise and mid market or an excellent job nailing enterprise and SMB and most companies tend to have a dominant hand, which is sort of their power alley.

And then they don't do the other things as well as a company that's only mid market focused or whatnot. And I feel like you have an even more complicated sort of challenge and that you have different customer segments and customer sizes and verticals from enterprise to government. And then you sort of have this open core open source model.

And you're marketing and engaging and evangelizing with that group. And are, are there ways that you operate in your role as sort of leading marketing that helps you sort of balance all of those or figure out kind of where you're going to over invest or over- or under invest in any given period of time?

Ashley: Yeah, I mean, it's a, it's a constant balance that we talk about as a, as an entire team and not just marketing the entire E group. Product has to think about do you build features for SMB to be successful and get started? Or do you build these FedRAMP type um, large enterprise features? And so it is holistically as a company, something we have to have a viewpoint on.

And so, we do cater to and focus on all of them. Um, obviously building enterprise features and doing enterprise time type marketing is often a bigger lift and, and takes a little bit more thoughts. So what we, but we don't want to forget about never the community, never SMB, because I always like to say, you know, the SMB that we sell to today in five years can be the next public company.

And now we have this giant footprint and have built with them and grown with them. And so what we try to do for SMB specifically is understand the personas of SMB. They're not going to have, you know, as many requirements and regulations they need to follow. They probably have a large, skew more toward the actual developers writing code versus the people that need to sign off and the heads of and the C levels.

So we try to, we try to have great content for them. We try to target them where they're hanging out, you know, send ads to Reddit, um, where they hang- in fact, my CEO just just raised one to me that he saw this morning on there. And so, which is great, we want to target somebody like him. So we're, we're really trying to have this more automated approach to get in front of them.

And, and that's probably lower mid market and down to SMB. And so some of the companies that are still growing, we want to try to get in front of them and get them into the trial as quickly as possible to make them successful, they're more hands on when it comes to enterprise. Some of the things we talked about before you mentioned verticalization.

Biggest thing we have in verticalization is other customers, banks want to talk to other banks that have been successful. And if I can get a public story out of that even better because one public story can kind of be sent to and communicated to the much larger enterprise group. And so, so while I would say we love all of our children equally and, and we put a focus on all of them, they're always, as you move into this enterprise, there's always a little bit more time and effort and thought that needs to go in, how to target them, how to get them to a field event, and what will bring them there. And we also sell to different personas. So, CTO is obvious. They're running the engineering team or head of engineering.

CISOs now have become really big with us because we're a very secure platform. Um, and so, and, and one of the questions I asked the CISO that we, uh, welcomed a little over a quarter ago, I said, actually, in his interview, what, like, how can I target you? Like, let's, let's say you weren't coming to, to GitLab, how can I target you and make sure you know that were a great solution that you should want your teams and actually the development teams to, to be using? And he said, please don't send me any marketing content. We get so much our LinkedIn feed like LinkedIn feed messages and he is like, but when another reputable company or CISO specifically says, Hey, why don't you come to this round table with me or let's go do dinner? It's, it's kind of like a more of a networking is what he said. And so it's those kinds of insights you have to know and understand. We probably wouldn't have to take that approach with the SMB segment.

SMB probably we can send out some messages where they're hanging out or, or target them where they are online. When I say where they are.

Brett: Maybe you could talk a little bit about, and you're sort of already touching on this a little bit, how the executive team sort of plans and organizes what you're going to do on a quarterly or an annual basis. And I'm interested in it because it hits on sort of the complexity of your business with so many different type of customer stakeholders.

And so like, what does the overall process look like today?

Ashley: So today we have actually a really great framework about it- around it. We have a vision, which is 30 years it's huge, um, and then we go down to what is the, what is the sort of goal in 10 years? Like, what's the strategy of where to be in 10 years? do we need to get to get, do to get there in three?

And then this year specifically, what do we focus on? Those are called, those are called the yearlies. And so we work as a team to help the company, we just did this presentation a few weeks ago, this is our three year strategy, and this is why, and we had everybody contribute in some way as part of this so it wasn't a top down, hey, a bunch of people at the C level got in a room. Um, it was a very collaborative multi month process with a framework, and it's not just looking at product. I think too often people think like strategy means product. It does, but it also means our operations strategy are go to market strategy, which is sales, marketing and products together.

And so we have, we look at it in those three buckets and we decide, all right, this is where we want to be in three years. And this is why telling them the internal team as many customer anecdotes, things we're hearing, things we're seeing in the market, the competitive landscape, helping them understand the why behind three year.

And these are the yearlies we need to focus on. And we like to have three to five. I think right now we have five, these, these are the, the five big yearlies. And then every quarter, those yearlies stay the same. And we have OKRs to hit under each of those yearlies, some of them end up being multi quarter, but a lot of them we're able to achieve.

So that helps us measure what we're doing quarter over quarter, is aligning to what we said we needed to do by this year to get to that three year strategy, to get to everything else.

Brett: So can you give an example of like, what's the level of detail in what you're talking about at the three year level versus when you talk to the, talk about the three to five sort of yearly goals or yearly themes?

Ashley: Yeah, so, so an example of, an example of the three year. would be, we really want to, we, we've continued to be known and stand out as a DevSecOps platform. However, the world is still talking about a DevOps platform. Gartner just released an MQ, Forrester just released a Wave. We placed really great in them. We're proud of that. We created that category. They've proven we own it, but they're missing the Sec in there. So we want to start driving people toward understanding the value of having security. As part of this DevOps, a DevSecOps platform. And so that's not something that happens overnight. That's something that will take about three years probably for Gartner to say, No, GitLab was right.

It is a DevSecOps platform MQ that we're going to do. So then if we back that back to a yearly goal and we're establishing those actively right now, we have to understand. Okay, great. What do we need to get there? What are we still missing that people might come and say? And we can again, say, say in all areas and product like what everybody say that we have best in class.

I won't give an exact tactical example, but something in security. And if not, we should probably drive toward that. And then there could be KRs under that. From a go to market standpoint, obviously a very real yearly is everybody's pitching the platform. We're not pitching features anymore. We're pitching, pitching the value in the outcome of the platform, which then tells marketing that's how we need to be messaging, positioning, enabling the sales team.

And so it's In three years, we'll be able to measure is everybody just saying DevSecOps platform. It's not just a word that GitLab has created because we believe that's where the market should be. And that's where we are. And then go back to the year. This is what we need to do to get people moving further in that journey.

And every quarter, this is how we should be measuring that.

Brett: thought it would be interesting to maybe bring some of the marketing work you've been doing recently to life by talking about a sort of a new feature or product that maybe you launched in the last handful of months where like, when you looked at the body of work that your marketing team did you were like that was excellent end to end. And maybe you can kind of take us on, like, the trajectory of actually what that looks like sort of end to end, and sort of the interplay in this case between sales and marketing and product to give a sense of, like, how you think in practice, specifically marketing around a feature or product might work.

Ashley: So I'm going to give you the buzziest buzzword of the year, AI, you knew it, you beat me to it. So it is a great example. So we have a competitor out there that went really, really hard on having a feature around completing code for developers. It's very valuable and we have something in beta as well.

Um, and we already had something we were working on. The easy button would have been to say, let's talk about this more. Let's get louder about it. Let's announce it instead. We stepped back and said the value of AI on our platform is along every step in the software delivery life cycle. So that will be one piece of it.

And customers absolutely need to know we have it in prospects, but we should be telling an end to end story of AI throughout the entire process and it took a little bit longer. It meant we didn't have an answer the next day, but it meant that we had the time to go deeply understand what product was working on and the timelines of um, what they were planning to release.

It meant that we started with an initial pitch around that and then everybody from myself to our CRO to the entire field started pitching this and we created a really, really great framework around feedback, hey, this is working, this didn't really work. Customers are really concerned about their privacy, and we have a really great approach to that.

So we should be talking about that more. So this was the best example I've seen in my time here, which granted has only been a little over a year and a half. So I'm sure they've done this really great in other areas, too. But I was really proud of watching the team just come together together. And solve this giant, you know, next step and what we needed to do to stand out in AI because there was a lot of buzz around this one feature of code completion. And then um, really understand what was resonating with customers. We named it like everybody else did GitLab Duo, which is the suite of AI capabilities, and now we're starting to release. We already had some in product, now we're starting to release more and more.

And so, uh, that's the fun part where we can actually sort of have the launches and talk about the things that are coming out of beta that customers have contributed to and we know are ready to be um, released in production.

Brett: What are the key marketing rituals across the life cycle of shipping a new important feature or product? I think maybe in the context of, of some companies, people feel like product sort of drives some new feature and then it's thrown over to marketing to market. But my sense is that you have sort of, um, a more sort of integrated process.

Ashley: We do, and I, I'm, I'm really happy about that and, and proud of our collaboration with product. Um, what, when I first started, that was one of the core things Sid, our CEO, asked me to focus on, as he said, " I want to make sure that exactly that is not happening, and I also want to make sure that we're measuring the need in the market and the value of what we're producing as the product team is building these features".

And so for us, it's again, it's a it's a core value for us. It's collaboration, but it's also fostering that open communication of, if you think of the Venn diagram of it, how all of go to market works, marketing is kind of in the middle there. We need to understand what's happening in product and have that collaboration and also gather the feedback from the sales.

Give them what they need, but then gather it. Make sure we're actually producing things that customers are getting excited about or driving and solving deep pain points. And so the number one thing I think as far as what I'm driving the team to do, I've been a product leader, and so I understand how marketing can be perceived sometimes, right?

Oh, it's marketing, they're going to take our stuff and put some fun words around it and get it out to market. So we've built a product marketing team that is getting deeper and deeper. They're matched with product managers, and they're getting deeper and deeper into how our product works and understanding the value of it to really want the product managers to come together and have that brainstorm session of, Hey, we're thinking about building this and this, what do you think will be more valuable?

And of course, the sales team actually contributes to this too, so we can properly prioritize. So we made it just this collaborative process. But I think tactically on the marketing team, again, because I've had the background of having the marketing team that didn't know anything about the product. I think it's really important that we deeply understand the pain points it's solving for customers, the value we're providing and also what more they're asking for. So we can be a core contributor into that overall process.

Brett: How do you go about doing that as a marketing team?

Ashley: The Chief Product Officer and myself, you know, we found ourselves probably in my first six months in seat solving a lot together, but way too much. And what we realized was it was because we were meeting every week, probably more, I probably talked to him every day. But we weren't actually pushing down to the teams and it was the same thing was happening at times for marketing and sales and so we sort of pushed down to the team.

We'll solve the big things. We'll remove the rocks from them. We'll ,when there's you know disagreements and, and need, need another party to come in. We'll get involved but we really push down to our teams. Like, Hey, VP of Product Marketing, you're meeting with the VPs of product weekly, right? And you're bouncing ideas off each other.

And you're building that natural collaboration where David, our CPO, will just randomly text me something in the middle of the day and like get a response immediately because we have that relationship. Do you all have that with your counterparts? And also, do you have that with your counterparts in sales?

Because thinking it always needs to go up to get solved to come back down. Um, first of all, it's not efficient. Slows things down. And it's not an effective way for those relationships to be fostered and move forward. So that, it's, I would say it's really us pushing down and saying, why don't you know, why don't you two work on that and let us know if you can't come to a conclusion on, it is, it's worked really, really well and it's also freed David and myself up to get on the road and go talk to more customers and provide value for the field team, which is a core part of both of our jobs.

Brett: Maybe kind of zooming back out and switching gears um, slightly, I'm interested if you in the future were to join sort of a more traditional closed source enterprise software company again, are there important ideas that you've learned in the context of GitLab that will sort of change the way that you work or think about marketing, even if there isn't an open course or in a part of the business.

Ashley: Yeah, there's several. First and foremost is, because of how open source works just as a model in the market, transparency has to be front and center. Um, everybody has to understand what, what's being contributed. Everybody has to understand why things are going the way they are. And so, um, for me, and that, that's translated to us as a business, we are as transparent as a we possibly can be as a public company, both internally and externally. And I think internally what that gives is, is a sense of being part of the mission and part of the team versus just somebody working at a company that's, that's taking a bunch of orders. 

Really, a real example there that I absolutely love, so I've, I've been reporting to a CEO for several, different companies now, and this is the first company where I actually know everything, after we do an earnings call and our windows open and our CFO goes on the road show, I understand what they're saying. And not just me, he sends out a Slack to the entire company of the sentiment, the overall themes and sentiment from investors.

And like, how cool is that to be an engineer first time in your career and understanding from the CFO, what people investing in our company and under and really putting, putting their hope behind are thinking about what we're doing. And so I feel like that engineer might go to another company and be, really upset to find out that's actually not normal.

And so the first thing I would push culturally is as much transparency. It makes people, even when uncomfortable things happen, it gives them more comfort knowing we know this is happening. This is why, this is what we're going to do about it. Instead of just sitting there wondering. And so, um, and so that's the, that's kind of from a company perspective.

The second one, I did learn at past companies as closed core companies, but it is, it is the value of other people marketing and evangelizing you that starts with community, but that can be, you know, champions within customers too. And when I, I did work at Tableau software, they have a Zen master group that were the best marketers, the most enthusiastic users.

So it can exist in closed core I don't think it always does. But GitLab has just opened my eyes even more to how much more reach you can get by other people talking about, we can talk, we're paid to talk about our company, but we want other people to sort of foster that excitement and, and bring it, bring it to life.

And so from, from the perspective of going to a company that isn't open source, I think those are the two. And then I, and then I also understand more deeply now the value of, you know, open source is giving things, giving your product or a piece of it away for free. And a lot of the companies I've been at, they have a free trial and it like caps at like 15 days.

And how many people can find value outside of small tactical tools in 15 days. And so the other thing I think, I, I, I'm never going to go to a closed core company, and be like, we should open source all of this. And it's going to solve everything because that could be a very big misstep depending on what kind of company it was. But getting more creative around how you make them successful with a product without just nickel and diming and making sure that they have this period of getting comfortable with what the product is a giant conversion for us is from trial, but it's also from people that were using our product for free, and they're like, you know, what I do want to integrate security now. I do want some of your services to help me with adoption and then they become a paying customer. So you can take that mindset even to close core companies.

Brett: On the first point about transparency, I think a lot of folks know about GitLab's open source employee handbook. And you gave a great example about the CFO sort of sharing investor sentiment internally, and so transparency, as you mentioned, is both external and internal in the context of GitLab. What are some other examples that maybe most people might have not heard of that kind of brings the idea of substantial transparency or as close to sort of complete transparency as possible?

Ashley: Yeah, I mean, from a, from an external standpoint, I get feedback on the handbook in two realms. One is our customers understand what's happening. They don't sit around and wait for our product managers to go get on a call and sign an NDA and say, Hey, here's the roadmap. Like it is transparent on our, and when things change, we'll put why they changed.

And so from what I've heard from customers is they can really trust us because we're being open and honest, even about the things that, that maybe we are going to make a change on. What's been interesting to me, and I didn't realize was going to happen, was we each have our own sections too. So I have a marketing section to the handbook of very, you know, very many amount of pages product has one engineering.

I actually had a CMO at a really well known company see me at a conference and she said, my team is using your handbook all the time. And it was kind of a wake up call to me. I had just started here to go back to the team and say, are we keeping the handbook up to date? Cause it's, it's kind of hard.

You change things all the way, all the time. And so we have to keep front and center and Sid, our CEO, is really, really good about reminding us that as we make decisions and changes, make sure you're changing that in the handbook. And it's, it's probably easier in some things like product because they have a process that, okay, we're going to do this feature, we'll put it in the handbook and in the issue.

For us in marketing, when we're like, Hey, we're going to change the way we measure this. It's not always top of mind for marketers to say, Hey, we should go, and it is GitLab, we use GitLab and we actually write a merge request and merge it in. And so that's been the interesting one to me is a lot of people have come to me and said, yeah, I use your marketing handbook to help me understand, like I wanted to improve, this part of my org and it was really helpful. It's been, uh, that's been kinda interesting. 

And then during the pandemic we did a remote playbook on how we run as a remote company. We've been remote since the moment we were founded. And so, you know, we have over 10 plus years of being a remote company. We had that all documented and so we actually put together a remote handbook that we sent out to customers and allowed them to download to help them understand how to run as an all remote company, because everybody was an all remote company, almost, during the pandemic.

Brett: Maybe talk a little bit more about what's in the marketing section of the handbook and other than maybe helping other people in their marketing departments, why the transparency there is actually useful, because it's, it, I think it's a bit counterintuitive. Being transparent about product roadmap, for example it, it makes sense why that would be valuable to what you're, what you're trying to do at GitLab. But like why being ultra transparent about what you're doing in marketing, why is that useful for the business?

Ashley: It's more about how we operate, it's less about, and a public handbook is also used by the internal company, and so it's more about how we operate. So, as I mentioned, when I came in the very first thing, you'll see if you go to GitLab marketing handbook, you'll see that framework I walked you through earlier about awareness being one consideration and through how we measure it.

And so, um, like I said, that, that was helpful for that CMO I talked to his team, but it also aligns my team. You know, I could say it in an all hands, then it's a one and done. But as new people enter the company and on board, um, as people are trying to get up to speed on where we're going. They have one place to go, and then we break off each section.

Okay, so product and brand marketing. This is how we're thinking about it. This is, this is how we're working. So from the perspective um, Sid, our CEO, doesn't like to think about, to him, it's transparency internally and externally in one place. One place to update, one place to keep everybody aligned. Now, having said that, we became a public company, and so we had to introduce something our legal team, uh, noted as a SAFE framework.

Please don't ask me what it stands for. You can Google it cause I don't remember, but it's basically understanding if this is financial information, it can't be on the public handbook. If this is anything about pipe metrics, it's so we also have a version of the internal handbook where we put those things that need to stay company confidential.

But my team is still trained to go to one place there. They go to the handbook and then sometimes you click on a link and it takes you into the internal handbook if you're logged into our single sign on.

Brett: You must have a very tired legal team in general.

Ashley: We have an amazing, amazing legal team. That was one of the first things I told our chief legal officer when I started because we had just IPO'd. And I think that was most of the heavy lift is trying to understand and, and that's where they came up with the SAFE framework. We do constant education. We have a, we have a channel where, and we have a very, very responsive legal team.

And so like if anybody has any kind of question, ask first, right? And then they'll tell you, yep, you could put that in the external. No, you can't do this and do this instead. And so that is really, really helpful, but yes, they are a very hardworking team.

Brett: When you look at the way the company internally operates outside of the handbook, what are some of kind of the interesting things that you do in the spirit of transparency?

Ashley: So we do several things. We never have a meeting without a meeting agenda. And it's, it's by default. We always make it open to the company if possible. Again, sometimes things can't be possible. And we keep calendars open so people can go and sort of understand what meetings are happening, what's happening in the meeting.

If you don't want to be in it or you can't be in it because you're on a different time zone, we have people in 60 plus countries, it's hard to get all time zones on one meeting, we document everything that happens. So there's always a clear agenda attached to each meeting. And then there's, there's kind of like the, the context of the meeting, the agenda we want to follow.

And then somebody takes, it's actually kind of everybody contributes, but somebody takes notes to the conversation as it's happening. So if you can't be live in that meeting, which honestly happens to me quite a bit, we have an E-group meeting. So all of the direct reports to the CEO once a week. And I feel like more so lately, I'm always on an airplane for that meeting.

And to me, that's one of the most important meetings of the week. It's when we all get together and, you know, solve things and talk about things. And then I'm in the air. I can't join. But I can actually usually real time follow on WiFi what's happening and they can see me typing. But even if I was, happen to be in another country and asleep, I can go back and look and I can even pre enter stuff.

So we have a section called Customer Insights. So I can go and say Ashley and then I put in parentheses async. And then I say, I met with this customer found this blah, blah, blah, and they'll read it out loud, even though I'm not there. So so that's one that I think, is just, really speaks to our transparency.

A cool one that our CEO started a while back that a few of the other C levels have, have thought through that has been a really big hit, is something called a shadow program. And so, did uh, last year had the CE, in prior years too, had the CEO shadow program where anybody at the company, I think you have to be here for a certain amount of time, um, can can apply to shadow him for two weeks And when you shadow Sid you go to one on ones so they would come to a one on one with me.

It's kind of funny It's like me and him talking but another person just kind of like watching. And anything except probably a few very highly confidential, you know, if it's like an HR or something like that, they go to every single meeting and they understand what it's like to be a CEO of, of the company, uh, for two weeks.

And what I think is even more awesome, because Sid leads by example here, is he has been known after meetings to ask them, how did that go? What could I have done differently? And then asks them at the end to write their insights. Some of them have turned them into public blogs of like what they learned and what it was like.

And so that's another example of if, if the CEO can do that, we can all be pretty transparent. If somebody can, somebody or two people can follow the CEO through all of this stuff, that, that's the biggest message in the world. And so those are, those are two other examples of how we really try to promote this transparency.

And then from an efficiency standpoint, we don't really like to present. And so we really try to pre send materials to make the most effective meetings, not sit there and present slide after slide in a meeting, we assume everybody has pre read. Then we can just jump into rich conversation.

There are often things that require voice overlay. So we're encouraged to put those on video and send like a five minute clip, which we know everybody watches in 2x and so it's two and a half minutes. Um, and so some of those things I think just speak to our transparency and our efficiency values at the company.

Brett: What do you think of the downsides of being so transparent? Like it can't all be, it can't be like a free lunch, I would assume.

Ashley: Well, I run crisis um, for the company. So for those of you that don't know what crisis is, it's control of the narrative. When we've all seen companies have like an email screenshot leak, and this happens to like Salesforce every week, it feels like right now, or, or a clip from an all hands that somebody gave.

And so, we have a lot of pride in the company in what we're doing and a lot of trust. But you are always going to have a bad actor at some point, you know, not agree with something, go speak out. And because everything is so open for us, that can be, that can be a risk. And we have to understand that.

And so what we do is we, we, again, we just try to be open and honest about when we can communicate things and the why behind why we can't. And then when things happen, we, we have, the team that can help understand how to do it better next time. And the thing we stand really true to is, I never have wanted, and I know the team would agree with me, just one bad instance, one bad actor to spoil it for everybody else. 

So while we have had these things happen and every company has, it's not like we're like, all right, we're changing everything. We're just going to completely become a closed- and so that's the other, and that that gives the team a sense of, okay, I never want to be that person.

I'm mad that there was a person that did that. And how can we help everybody understand why we have to be better next time? That one's really important is you can't just change everything because one bad thing happened, but it is something that my team watches very, very closely because marketing brand usually owns, um, crisis for companies.

Brett: Something you mentioned a minute ago is this weekly sort of core marketing meeting. Could you talk a little bit about sort of how you structure that and maybe why you landed on the format that you have now?

Ashley: Yeah, so I mean, we have several different meetings. So all of the CEO's direct reports meet once a week. And I think we all model that. So we all model getting our teams together once a week and our direct reports. And so the way that that we run our meeting is It's kind of open agenda. Everybody knows it's going to happen on Tuesdays at a certain time, unless I'm on a plane or something, and everybody just sort of freely goes in throughout the week and puts in things that we need to talk about.

And that includes people like my people partner. And so she joins and sometimes my executive assistant has things that she needs to raise that are coming up that we might not be aware of that are like on the calendar. And so I bring our CRO in sometimes to, to give updates. I actually joined the CROs every single week because he believes that his finance partner and his marketing partner should be part of that.

And so everybody at the company runs them differently. I tend to run mine looser because I feel like as executives, including my team, we're structured in a lot of what we do. So I try to keep it loose if we don't have time to get through everything, fine, let's prioritize what we need to talk to, but let's not, let's not stop something because we're going to run out of time.

Let's have that healthy, rich conversation. And as marketers, other orgs might answer this differently for you, we need to have a lot of time to brainstorm together, and we don't have an office to go get in front of a whiteboard. So we use a lot of that time to just collaborate and I always like an action to happen out of it.

I don't just want these thought processes. That's why we have DRIs. But I really like to foster an environment of let's just, let's be loose about this. Let's not robotically go through each because in marketing, I think that creativity and that flow and brainstorming is really important.

Brett: One of the things, and you mentioned this when we started the conversation, that's unique about your path into the role of the CMO is you started out as a software engineer and then did a lot of product work and sort of more recently have done marketing. What ways do you think that has positively impacted your role as a marketer, maybe other than in this case, you're actually marketing to engineers so you really understand the customer. I'm curious kind of what, what's been valuable about that in, is there anything that's been valuable that a CMO peer of yours that doesn't have an engineering background, like, there are things that they can learn from that or might be useful for them?

Ashley: I think it can be if they come to a DevSecOps company like I did. But I think for me, when you are in any kind of technical product company, which of course GitLab is, to be CMO and to, you have to really understand who you're selling to. And so, yes, I was a developer. I wasn't really a great one. And maybe that's because I didn't have something like GitLab, but I understood how hard it was.

I really understood how hard it was. And, and so having that sense of this is, that, I have the empathy for who one of the personas that we're selling to, and I also understand what they want to hear and what they don't want to hear, you know, what, what kinds of things will resonate? Because I've been there and a lot of the people on my team have. Now on the flip side you know if you fast forward from when I was an engineer developer, um, after college and for the first few years of my career, you know I, I end up at a company where now i'm running product and part of engineering and I had some really, really big problems with quality of software, getting it out, competitive, getting out on time, competitors were coming in. And I actually, um, was a buyer of GitLab. And so I actually brought GitLab in with my director of engineering, who was the first one to pitch it to me. And then I saw firsthand. So now I understand the empathy and what's going on in the developers lives. And now I understand what I was trying to solve to prove to my CEO and my board, like, no, this is, this is a problem with tooling.

I'm not sure about teams yet. So I'm going to need to bring a platform in to measure it. And also, we just have a lot of disjointed processes. And so that's the second piece is I was a customer and a few companies ago when I was at Tableau, some of the first executives there was the same thing. They were a customer.

And so they just really understood you have that extra level of confidence and passion that this, it didn't, GitLab did solve problems for me back then. So I mean, I would encourage other CMOs, if you're not technical by design to try to get there, but also if you're outside of, you know, there's, there's other CMOs, CMOs sell MarTech, right?

And so then they're probably the best seller at the company because they're, they're able to do that. But I also don't want to think just because I bought this five years ago that, that I know everything. And because I was a developer longer that I know everything. And so that's why the second part of my title is Chief Strategy Officer.

So what we do is we use me as an executive sponsor, just like our CPO, just like our CRO on accounts. And I can then go hear from the customers firsthand too, as a, as a former buyer, what do buyers need now? As a former developer, what do they need now? And so a lot of people ask me, why do you have two titles?

I mean, what CTO wants to talk to the CMO of a DevSecOps like my platform, but they definitely want to talk to somebody that is working on understanding their needs that was a former customer and that wants to come back with a team and understand are we strategically going in the right direction.

Brett: And why is it important for you to do that versus the Chief Product Officer or CTO or VPEng or other people that may be at peer companies would be doing that work?

Ashley: Well we have over 7, 000 customers, um, and we plan to keep going and all of those people you just described absolutely do that, but they can only do so much of it. And also, you know, a lot of times I think what the product officer is going to hear about is features that we want in the platform. And CTO as well, like, we need this to change in infrastructure. CRO, we need a better deal. We want to negotiate this. And he can do a lot of this too, but I'm just going in on a listening tour and saying, like, how are things going for you? Like, and not, not like, is that feature broken, but, you know, have we been providing value?

What more can we be doing? Where do you want to be in three years as far as your software development practices? So I can make sure GitLab's going on that journey with them. So it's, and then we all, as I mentioned on our E-group call every week, we have a customer insights line and all of us come in and put in what we're hearing.

And you'll see that pattern of like the different things. And then we can all look at it and make sure that we're all aligned strategically for where the company is going.

Brett: Can you share a little bit more when you're doing these sort of listening tour style conversations? What are you asking for looking for in, with those customer interactions?

Ashley: So I'm looking for different things. What one I'm looking to understand is our messaging landing. So I'm we these meetings are not usually about me getting there with a PowerPoint, but I'm sort of talking to them about pitching to them about whether it's, the last year it's been mostly how are you differentiating an AI?

Is it secure? What's your, what's your approach to that? But also just in general understanding the problems that they're still having within their, their R&D teams or, or they're measuring efficiency of how their teams are performing is just two examples. We, we can accomplish all of that, but are we properly positioning that? 

The big one that I learned this year, there's two pieces to it, so I've been to, um, our AMEA region, our APAC region. And of course, I live in the United States. So I've done the Ameritour. And they're all slightly different journeys, regionally. I'll be in Japan probably early next year for the same reason, as far as maturity, and so that also is an interesting thing to learn because we can't have a one and done messaging and positioning one and done pitch deck because, um, while we're leaning into something really heavily, heavily In the AMER they might not quite be there in Australia yet they might still be trying to figure out how to solve, you know, step one on their journey versus a lot of a lot of the companies here are in the wild expansion phase, we're ready to do more. 

So that, that's one. Two is, is the vertical or industry, however you want to position it. So I've told this story to the team a ton. I went um, and I'm going again in two weeks and met with our PubSec team, and they took me on a big tour of all of our PubSec customers, awesome customers in the agency.

And it was, they, like, they were speaking a different, they love GitLab, but they were using all these different words that we don't use in our messaging because that's not what we generally use outside of PubSec. So I came back to my team and I gave them this list of like, this is what I was Googling the whole time that I was on that because I didn't know some of them.

But I said, we're actually not really speaking to them, which tells me the team is probably taking our stuff and making it more fit. And I don't, I don't want our sales team wasting time on that. I want that us producing content that speaks to the people that they are selling to. And so that was the big one I came back with is financials saying something a little bit different than PubSec saying a little different than software.

And tech and we need to take more of that approach in how we're helping and enabling the team with assets with content with whatever it is in, in how we're telling our story to them.

Brett: Are there sort of questions you keep going back to over and over again, as you're having these conversations?

Ashley: Yeah, so, I mean, I, I'm asking them first and foremost, and I just asked, we have an executive advisory board and I just asked them these questions the other day because it's a, it's a mix of industries is well, first and foremost, I always ask them to explain GitLab to me, tell me what GitLab does instead of telling them, tell me, and they all say something slightly different.

What is the value it provides? And this was a big eye opener for my team because they were all in this executive advisory board meeting we did a few weeks ago. We had from three different customers in three different industries say three different things because the person in finance, cared, of course, a lot about security.

The person that works at a car company cared a lot about the competitive landscape and getting ahead and moving faster. Um, and then there was another customer, I forget which industry that was, that really cared about efficiency and wanted to understand how efficient processes were.

And so, those are kind of the three that I start with. And it's, it's been fascinating that, and it's okay that they're not repeating the same thing. It'd be, it'd be really bad if they just all said like one feature in our product, because that means our expansion opportunity is really low there. But that's, that's really the first three that I dig into to try to understand.

Um, and then and then we take it in whatever direction they want, because I'm going to learn something regardless. But those are, those are the three that I really want to understand on a first meeting with these executives, champions, sometimes individual contributors within the companies, depending on who I'm meeting with.

Brett: Maybe we could wrap up with sort of one of my favorite questions, which is when you think about your role of CMO, are there folks that have had sort of an outsized impact on how you think about the work? 

Ashley: Yeah, I mean, I've had a lot of people throughout my career. I've taken career pivots. You can, you had mentioned it earlier. And, you know, first and foremost, those people letting me know that's okay, is I think people get a degree and then really try and realize maybe it wasn't the right thing, but then keep like, I need to be passionate about what I'm doing and I need to understand where my strengths are because I don't really like to not be good at things and there's plenty I'm not good at even in marketing still. Um, and so, so that's first is just being okay with saying okay, this isn't working maybe I should, maybe I should make a change and having the right network of people around you to do that.

Um, the other thing is a board member actually told me this when I was interviewing and I was just being transparent, it's a transparent company, and he asked me something like what, what would be your marketing weakness and I was like Demand Gen.

Like, I didn't even have to, I didn't have to pause. I was like, you know, messaging, positioning, communication, community, DevRel, all of that fits into my background. I've had Demand Gen under my umbrella before, including my past company, but it's not something I dive deep into. Or ever had and I loved his answer.

He kind of waved his hand and he said, great, you're going to bring in a fantastic VP to do that. And that's exactly what I did. And she knows every single day. I'm asking her questions because I want to learn that and the next time somebody asked me in the next role what is your weakness? It'll be something different.

Because she is going to teach me what I need to know at my level about demand gen already has, but it's not something that if I had to operate as that, as the, you know, I had to operate for a while as different core, like DevRel and community. I was the leader of that with a great director for a while.

The Demand Gen one was one where I was like, I don't know how much I'd be able to flag- numbers or numbers, but I don't know how much I'd be able to flag. And she, she, and I um, I interviewed her on my very first day at the company. So I took that very seriously. And so, yeah, that's, and then for me, the other thing, which seems obvious, but isn't always the case um, for some people is um, I want to be in lockstep with our chief product officer.

Like, I want him to feel comfortable calling me and saying, like, what is your team messaging? And I want him to be comfortable with me calling and being like, what's going on over here? Like, why is this moving so slow? And not have it feel like we're attacking each other. And of course, the same with CMO and CRO.

Those partnerships are so, it's just like a product leader and engineering leader, are so important that you can really solve together, not finger point. Because that's the thing that's going to progress the company forward. And that's the thing the teams feel to if they're seeing you model that behavior.

Guess what? They're going to do it too, because they understand that's how we operate.

Brett: Thank you so much for spending the time with us.

Ashley: Yeah. Thanks for inviting me. I enjoyed it.