SaaS Breakthrough – Featuring Shawn Winters

demio saas breakthrough featuring shawn wintersAbout Shawn Winters:

Shawn Winters is a Strategic Acceleration Manager at GitLab, a leading collaboration tool for DevOps.

Shawn is a SaaS and Technology Startup Sales & Business Development expert with experience at Seed, Series A, Series C, Series D and Publicly Traded Organizations.

His specialties are Remote work, Mindset consulting & SaaS Sales Development & Marketing.

meetdemio · How GitLab Has Hit Hyperscale By Empowering Next-Generation SDRs


Show Notes:
03:00
A Complete DevOps Platform Delivered As A Single Application
05:45
Leveraging LinkedIn To Really Hone In On Your Ideal Customers
09:20
Joining In And Adapting To Working Fully Remotely
12:40
The Concept Of A Next-Generation SDR
"So what we set out to do was build out this framework where we could empower the individual SDRs to work with program marketing to field marketing, digital marketing and run their individual specifically focus, account based marketing kind of campaigns that they could deliver more specific messaging. They could be empowered to do things outside of that normal role, which you know, kind of gets a bad rap at the end of the day, like an SDR comes in and they make a ton of dials and that's what they're good for. Right, and so we're empowering. These SDRs to do more of what is going to be good for the customer at the end of the day and I think that's where we've gone at this point is we're rolling this out to our entire companies. We call it an acceleration SDR, so leveraging and becoming aligned and kind of individual pods essentially to deliver that, that account base kind of marketing, that account based selling."
15:45
Baselines And Empowering SDRs
18:55
Hyper-Personalization Is Too Much
" (...) business decision makers that we're trying to get in touch with, they're getting hammered, right? They're getting hammered with even hyper-personalized messaging and all of that. So how can you stand out when everybody's doing the same thing. So we figured out from a tactical level that it's not about being hyper-personalized, it's about being focusing on them and what we can do for them.(...) aligning what we're doing and being very casual, being very human about it. (...) We need human interaction at the end of the day, more than ever. And so it's not about being a generic spray and pray kind of organization, but it's also not about being a hyper-personalized organization. So what we've found is if we can kind of hit that middle ground and you know, catch somebody at the right time and looking for change agents in organizations, that's the most important thing"
"Because timing is the most important thing when we're trying to get into a deal or trying to build awareness or educate different customers, we need to find the change agents within the organization that are going to help drive those, so it's about not being so hyper-personalized that I spend, you know, an hour trying to, to write the perfect email or the perfect LinkedIn message, but not going so fast that they understand that I'm just blasting them with generic messages."
21:40
Using LinkedIn For Personal Branding And Social Selling
28:30
How Companies Can Overcome The Challenges Of Working Remotely
"It's always evolving. That's one thing that GitLab is fantastic about and I would recommend any organization that is moving to all remote workforce is adopt this mentality of minimal viable product or process. Meaning, Hey, like it doesn't need to be perfect for me to document it and push it into action, but it needs, we need to do it. We need to start, start doing this particular thing, test it out iterate on it and improve on it. "
35:05
Mental Conditioning And Mental Health Practices For Remote Workers
"The other thing that I've been experimenting with as well and I definitely want to touch on this is , I don't, I call it a mental workout of the day or a mindset workout of the day where it incorporates, it's like a 15-minute break throughout the day where the first five minutes are, are about meditation and becoming still. So, you know, you have all these things that are going on in your mind all day, all day, every day. Let's get still for five minutes, then we move into a five-minute I am statement. So like, Hey, you know, I'm doing a good job today. Like affirming ourselves at the end of the day. Like I am healthy, I'm happy. All of these things that are power driven. And then, and then finally which is my favorite part is visualization. So walkthrough visualization of like, Hey, like what is the rest of my day look like? I'm going to visualize seeing, using my imagination to see myself doing really great work. You know, virtually high-five in my, my coworkers or hearing my, my bosses or my manager's voice inside my head saying, Hey, you're doing a great job today, Shawn."
39:00
Lessons Learned From Things That Didn't Work Out As Planned
45:10
Next: More Overal Efficiency And The Next Wave Of Field Marketing
49:30
Lightning Questions
Transcript:

DA (02:51):
Hey Shawn, thanks for joining me today on the SaaS breakthrough Podcast. How are you doing today?

SW (02:55):
Doing fantastic. Thanks for having me, David. I appreciate you taking the time today.

DA (03:01):
Yeah, it's a real privilege, real honor to have you on. I think we've got a lot to talk about, interesting time in the world and a lot of cool topics to talk about that stuff from what you guys are doing. But for our listeners who don't know, GitLab, let's just start off there. Let's talk a little bit about what GitLab is, when it was founded. Who your customers are and what you doing uniquely in the marketplace.

SW (03:22):
Yeah. So the GitLab was founded in 2011. We started out as a on prem version of what most people kind of confuse us with is GitHub. Right? So we, our CEO Sid, he created GitLab because he didn't want his code living in the cloud, which was what GitHub was doing at the time. So back in 2011, that was our focus. Since then, what we've been doing is actually building out a entire dev sec ops life cycle delivered as a single application. So if you think about how software is delivered nowadays and the software development life cycle, there's a bunch of different tools that are used strung together, integrated together, maintain to try to deliver software better, faster, more secure. And what we've come in to do is we've realized that organizations are actually moving slower because of those different tools.

SW (04:26):
And we call that the tool chain complexity or Daisy chain or any, any kind of like tool chain where it's slowing teams down and we believe that GitLab, keeping things simple and making it, delivering software through that one single user interface allows companies to be a lot faster and respond to the market and deliver better products faster. We serve literally every organization that is out there, right? We believe at GitLab that, you know, software is eating the world. And so organizations going through digital transformations and essentially trying to compete today are going to have to end up developing software. So that's why we've had a lot of success is we can appeal to so many different industries not just technology, technology in SaaS startups or technology in SaaS companies, but everything from transportation, oil and gas you know, health care, all of these different areas. We serve those customers. So we, we believe that when we're implemented right you know, companies are gonna be able to respond to that market respond to their customers and, and deliver that better product faster.

DA (05:46):
One of the questions I ask on here often is when you appeal to a wide audience like that, pretty much anyone using software online, all of these different industries and niches and verticals, how do you find, or how do you build ideal customer profiles? Do you have those, do you just do you know, value systems or software builds? Like how did you guys actually come up with like what your marketing customer profile was?

SW (06:12):
Yeah, you know, it's a good question. Because what I think happened at GitLab, at least from my perspective was, I think we can predict, we can always start out with an idea of like who our ideal customer is going to be based on our current customers. Right? That's a pretty basic kind of a thought process when we're going out trying to find that ideal customer profile. What, and you know, me being, you know, on the ground floor when I first started and, and trying to figure out who those people are, which organizations to kind of market and sell into initially, I would always look at it from a perspective of like, Hey, like I imagine this company is going to be good based on that ideal customer profile we already had.

SW (06:57):
And so crazy because, you know, even organizations where I felt like, yeah, this company is going to be a software company. You know, they're going to be delivering products, they're going to want to deliver it faster. I'm so often wrong that those are the right people to engage with right away, right? And so what I, what we use to help identify and what I've seen over say, I spread out a hundred counts in that particular territory. What I do is I look for specific titles, right? We look for specific titles that that can like raise a red flag or give us an alert that this company is mature enough to talk about this particular value proposition, right? And so I think that's where we've seen the most success is. Really doing the account based research and seeing what the titles are at the end of the day.

SW (07:50):
Because you know, we can, we can use these you know, databases that we buy and everything and, you know, it's hit or miss, you know, 60% or so. The data is, is good enough, but the titles aren't there, you know. So leveraging LinkedIn to really hone in on who are those ideal customers, whether it's like a tire company that you would never expect to be leveraging some of these new technologies like Kubernetes or you know, some of the stuff that we look at to identify those ideal customers. You know, that would not have been available if we're just using a database. Right. So I think the ground for looking at companies trying to decide, Hey, what are the key titles that we're looking for? And being able to take a step back from a holistic kind of of view of it and say, Hey, there's a, there's, you know, 50, 60 of these types of titles at this company, I think this would be an ideal company to start using this particular messaging. So that's what I believe has been successful at GitLab. Kind of erasing our original assumptions. After, you know, I mean, it's always good to make goals and kind of go based on our ideal customer profile, but taking a step back, erasing those assumptions and being like, Hey, here, here are the titles that we know. Here are the initiatives that we know fit what we're trying to do value wise and going after those companies and bucketing in that way.

DA (09:20):
I like that. Yeah. That makes a ton of sense. And we've been hearing a lot of marketers and people on this podcast have really talk about LinkedIn and in the power that you have there for searching for those titles, whether organically or, you know, reach out or advertising. So kind of cool validation there. When did you actually join the GitLab team?

SW (09:41):
It will be two years ago in September. So yeah, it's basically, you know, GitLab is such a fast growing company. When I started, I think I was around employee 350. And since then we've scaled to upwards of 1200 up until up until recently, you know, there's been the slowdown and even, you know, GitLab being very strategic in our hiring process. We are, we are ramping so fast. It seemed like we were having 20 new colleagues a week that we're onboarding. So that's obviously slowed down a little bit. But we've been, we've been growing fast, so I'm pretty much a veteran in GitLab years we call it,

DA (10:27):
It's like, every year is about 10 years in a hyperscale like that. That's awesome. And I want to talk about workforce. I want to talk about what it's like to be in like kind of a hyperscale company like that. But when you're coming in employee, you said 350, I think. What are you focusing on first when you're coming into marketing? Obviously you have a lot of stuff built out. What are you coming into the team to look at?

SW (10:49):
You know, I mean, at least for me early on it was, it was just such a unique situation to be working all remote. I know the whole world is working all remote now. But for me personally, my, my thing was I wanted to, I wanted to learn from who's doing good work within the organization early on, and become best friends with them essentially so that I can learn how to, how to operate in a remote environment because it's different how to really be successful in my role. And so something that I did early on was engaged with my colleagues that, you know, were doing, that I had heard from other people, my managers, et cetera, that were doing really good work. And so that was something that I would set up with. I'm sure a lot of people already know now, it's called a coffee chat, right?

SW (11:38):
Where you just get to know somebody on the other end of the, of a computer screen, which, you know, previously, if we're in an office setting, you know, that's, that's a little bit different. But it, that's what helped me early on really start to focus and hone in on the, on the key areas where I could be my very best and add to the organization. But the two high level, not very tactical, I know you'll want to talk about tactical, but very high level was like I just wanted to come in, be the best that I can be. Really focus on what I can control and then also be a team member, like collaborate with teams and encourage people because being in a remote environment we're isolated, we need that human element at the end of the day, that social element and it's really challenging in a remote environment.

SW (12:26):
And I think doing that early on, building these relationships with people that are already doing a really great job in their role in marketing, sales, whatever. I think that helped me succeed early on and get that.

DA (12:38):
I think this is such a good conversation for this time in the world of people going remote learning how to manage remote teams. And quite honestly a lot of teams may stay remote now into the future. I was just reading an article about, you know, like Twitter and Google kind of pushing it forward for like basically a year. People may never go back to the office. So really kind of like this interesting transition in the world and I think this is very, very valuable for people. But from a tactical marketing perspective and then getting into that conversation, you know, we really started to hear more and more about this kind of concept of a next generation SDR. In your experience being in kind of a hyper growth company, being with GitLab, what have you seen in this evolution of SaaS marketing and what do you think that SaaS marketers need to know more than ever? Now that things are kind of changing here on the landscape.

SW (13:30):
Yeah. What we're doing, what we've seen you know, as SDRs fall under marketing at GitLab, what we've seen as something that is, SDRs have been kind of stale, right? And in the last five to 10 years it doesn't really seem like much has changed or evolved with the role. So our, our organizations from the top down, our chief marketing officer, Tod Barr and all the way down to our ground level SDRs. We've set out about eight months ago to create that next generation SDR. And what that means to us at a, at a tactical level is to be aligned, right?

SW (14:14):
And empower the individual SDR to leverage and work with field marketing, program marketing, digital marketing, all these areas which were previously siloed, which, you know, GitLab as a, as a product is looking to break down silos within organizations. And we do that through our actual application. And if we're going to practice what we preach at the end of the day, we need to do that with our organization and our SDRs and just across the entire company, right. So what we set out to do was build out this framework where we could empower the individual SDRs to work with program marketing to field marketing, digital marketing and run their individual specifically focus, account based marketing kind of campaigns that they could deliver more specific messaging. They could be empowered to do things outside of that normal role, which you know, kind of gets a bad rap at the end of the day, like an SDR comes in and they make a ton of dials and that's what they're good for. Right, and so we're empowering. These SDRs to do more of what is going to be good for the customer at the end of the day and I think that's where we've gone at this point is we're rolling this out to our entire companies. We call it an acceleration SDR, so leveraging and becoming aligned and kind of individual pods essentially to deliver that, that account base kind of marketing, that account based selling.

DA (15:46):
I think alignment is a conversation that we've had a lot on this podcast, sales, marketing alignment, SDR alignment. It's a great concept to talk about, but I guess from the tactical level for me to understand a little bit better. When you're saying you're creating this alignment for your SDRs able to go to these different departments, all of that. Fantastic. It sounds like it comes from a base level of value system that you guys have built in the company. So that's like a lesson by itself, you know, you build off your values and you build them into everything. But are you guys basically giving your SDRs you know, marketing budget, you're giving them time, you're more than anything giving them like the results are in approach. Instead of making X amount of dials, we want you to make X amount of you know, sales that come through. And basically to do that you have open range to talk to all of these different teams. You can do these different initiatives and we don't care like how you actually do it. What we just want is the result? Is that kind of the approach to it?

SW (16:41):
Yeah, I think we're getting to a point, it's still, I think most organizations, even the very progressive organizations are still struggling and we struggle with it as well, is really given that budget to the individual SDR. I mean, some of them are people we just hired, you know, and so it's kind of, it's a transition that we're going into where, you know, some of the acceleration team that I was on previously. And now moving in more to an ABM leading, executing on that. It was a smaller pod of six of us that were testing this out that we're building this next generation SDR. And yes, we did have budget to do, you know, different, different stuff like direct mail digital campaigns. You know in email, sponsored email, just stuff outside the normal organization that the SDRs were doing that we were testing out. So it was like we were a POC type of group that could test out all these different functionalities and these different PR advertising kind of campaigns and marketing campaigns in order to see if we can get those results.

SW (17:47):
And what we figured out over time is there's at a minimum, there's a baseline level of what works. Right. and that's everything from, we developed a new prioritization kind of model for who are, who are the right people to target, what are the, what are the right personas, the right customer profiles, all those types of things. And we've embedded that in what previously was undefined for SDRs and the organization. So we're getting them more ramped up quickly like that. We're providing best practices for leveraging tools like, you know sales navigator and how to, how to use that tool to get to the right people, how to use the advertising on that level. Right? So we're empowering the SDRs to work alongside with, you know, like I said, those field digital and program marketing to develop these mini campaigns. And I think as we progress down this road, that's where SDRs are heading across the organization. Which as you know, change in any organization is challenging. So it's rolling out and I think we're, we're moving fast, but you know, it's always kind of a little bit of friction there.

DA (18:56):
Yeah, change is always tough, especially when you're at 1200 people remote. I can imagine that's a tough machine to turn at some level. From a tactical level, did you find any specific experiments, initiatives worked really well for you while you were in that kind of accelerated SDR role? Were you seeing, you know, maybe direct mail working for certain industries and others? Or was it kind of just, you know, each like ABM customer was just handled differently and it was just about being in the trenches and just trying things?

SW (19:26):
I think our experimentation is important. What I think in previous organizations and what you know, SDRs have been doing for a long time as a, there's that idea of like being very hyper-personalized and what a conclusion that we've made and my team has made over time is it's, it's hyper-personalization is too much. You're not going to get to the right people at the right time doing too much. You know, these, all of these really important, you know, people that business decision makers that we're trying to get in touch with, they're getting hammered, right? They're getting hammered with even hyper-personalized messaging and all of that. Right? So how can you stand out when everybody's doing the same thing. So we figured out from a tactical level that it's not about being hyper-personalized, it's about being focusing on them and what we can do for them. And so, yes, Hey, what are, what's their role? What are they focused on? And aligning our, our in a quick and easy way, aligning what we're doing and being very casual, being very human about it. I think at the end of the day especially now with everybody being remote and you know, everybody's talking about practicing social distancing. We need human interaction at the end of the day, more than ever. And so it's not about being a generic spray and pray kind of organization, but it's also not about being a hyper-personalized organization. So what we've found is if we can kind of hit that middle ground and you know, catch somebody at the right time and looking for change agents in organizations, that's the most important thing, right? Because timing is the most important thing when we're trying to get into a deal or trying to build awareness or educate different customers, we need to find the change agents within the organization that are going to help drive those, so it's about not being so hyper-personalized that I spend, you know, an hour trying to, to write the perfect email or the perfect LinkedIn message, but not going so fast that they understand that I'm just blasting them with generic messages.

DA (21:37):
That was super valuable. Yeah, I think that's very, very helpful. I love that. Now moving on, we talk sometimes here on the podcast about leveraging personal branding. That's a conversation piece that we've had multiple times. I know you've been using social selling to build a personal brand as well. Can you take us behind the scenes and and kind of talk about your approach and process to doing something like this, building that kind of personal brand?

SW (22:00):
Yeah, so pretty early on I realized, and I think we all probably do this at some level is working harder versus working smarter. And for me, I realized if I could, any amount of goal, whether it was being an SDR or you know, being in my strategic acceleration role I needed to change the way that I was going to operate on a day to day basis in order to make that goal more attainable because I don't come from a position where I want to just be average or you know, best or like, you know, a top performer. I want to be the best that I can be. And so what I, what that drove me to do was really looking to this social selling. I had gotten introduced to it back in must've been 2016.

SW (22:57):
I was working at a company called Pantheon and I just didn't grasp the gravity and the power of social selling. And so once I was at GitLab, I was like, I'm going to check out this social selling thing. And it was really cool. I took a little class on LinkedIn learning and within like a minute or two, I realized, wow. Like I had to pause the video, I had to go back on my LinkedIn and just change everything about it because I was not doing a good job of being an individual, being an individual that's also part of GitLab and wants to engage with people. So when it comes to personal branding, I think that's the power of it is when we build our personal brand, we're also much more appealing to the prospects that we're reaching out to because they know that we're not somebody that's just sitting there trying to get something from them.

SW (23:51):
We're actually looking to build strategic relationships at the day, at the end of the day, like this isn't just a fly by night kind of encounter. I want to engage with you. You see my profile, it's the first interaction that we can get with each other. You know, you might not even accept my, my connection request. So I want to portray out to myself and, and show this prospect, show this potential business partner, whoever it is, who I am on that first interaction. And I think that's what our LinkedIn social selling can be for ourselves and our personal brand. And how that plays into it is like what are you passionate about? At the end of the day we're all passionate about something and we all want to talk about it. And what if I'm passionate about something that this prospect or this customer, this business partner is passionate about?

SW (24:44):
Like how much more of a lasting relationship are we going to be able to have when that's the basis for our relationship, not, Hey, I'm going to sell you this software solution and then two years down the road I'm gonna be somewhere else and you know that's, you know, I'll try to sell you something else. Right? So that's what I've been focused on is like how building my personal brand on LinkedIn and, and stepping into my own voice can actually help me as an individual at GitLab and help GitLab in general. Because that's just, it makes it so much more valuable. It makes it so much more fun for me.

DA (25:20):
I love that. And I think what you're saying is absolutely true. It's about being like a real human and that value expansion and that value addition to someone else and just not about just like throwing out a software down their throat. But I guess from like the detail's perspective, have you found any specific, you know, description, title, you know question additions to your LinkedIn profile have kind of helped that, that better? Like is it just about the languaging and how you're approaching what you're writing on your LinkedIn profile or is it, you know, also things like creating kind of a fun new title and like the way you're describing your job position? Like how does that actually work from that tactical level?

SW (26:00):
Yeah. From, from everything about like what's your, what you, if you're writing about yourself, right? Like about what you're passionate and about as an individual and then at the company, like what are you trying to do? Like give these prospects, give these people who are going to get engaged with you on LinkedIn. Give them a like a little day in the life of who you are and like what you actually bring to potential customers.

SW (26:22):
You know, one thing I put in my LinkedIn profiles is I'm typically talking to, you know, these types of people about, you know, GitLabs, CGI and CD function and what that means for organizations and they really get excited about XYZ. And so it's not just like, Hey, Shawn Winters is a quota crusher. He meets all his KPIs and, it's not geared towards like recruiters to come after me and like sweep me away. It's geared towards the customer. What does the customer want to see? What is it, what are the people that are coming to my LinkedIn profile wanting to see at the end of the day? And I think that actually brings people's guards down. They see realness in my profile. They see somebody who is getting what they, what they see on my profile. So when I interact with them, it's very what's the right word?

SW (27:14):
It's very natural. And I think above and beyond that, there's just little things that, that you can do to, that I did to help ease that transition. Cause maybe people don't want to engage with you right away. And that's totally okay. But adding little pieces of content on there that, that kind of, they can do their own self serving kind of research into your organization. Understanding that our personal brands also can be that first engagement with our company too. Right? So, you know, I think, I don't know if the, if the, right, if it's seven pieces of content or whatever that they used to say before a customer's ready to engage or potential customer ready to engage with the sales person or whatever. But if you, if you were to have three or four pieces of content on, on your LinkedIn page that are, you know, your organization focused on what you're doing, that can be, that can spark that conversation, that could spark that project and maybe you were previously unknown to them. So I think it's so powerful to add pieces of content about not only your company, but who you are as an individual on, on your bio. What do you care about? And what do you do on a day to day basis.

DA (28:26):
Yeah, that clarification was fantastic. Thank you for that kind of explanation. I think that really paints a great picture in my mind and be super helpful for our listeners. I want to swap back to that conversation about remote work. We started there and I think it's a really great conversation piece for where we are in the world right now. Very relevant for a lot of companies that are kind of either transitioning there or me maybe thinking about, you know, staying there and ping maybe their marketing teams and stuff like that remote. We've been lucky enough to be remote since day one. And that's been, you know, a big reason why it's been such an easy transition here during this time. And you guys have a lot of experience. You've been a part of this, you've seen this huge growth happen as well in a remote company, which you guys are at insane scale compared to us and I can't even imagine what that must be like. What would you say some of the top challenges that you guys have had to work through from an all remote environment and what recommendations would you give to other companies to help you know, solve them moving forward.

SW (29:23):
Oh man, that's a, that's a loaded question there, David. A lot. There's a lot, there's a lot there. I think. I think for me, what I believe if a company is really going to go remote and it's such a challenging question because if you're, if moving from an office situation to remote, you already have so many procedures and strategies in place that are geared towards being in an office, right. And, and although a lot of the things that GitLab does seems like common sense, there's so much thought and really like just being strategic in the background that that comes, or that really preempted all of the things that we do at GitLab. Obviously organizations need to have the right tooling in place. If you don't have good video conferencing tools like zoom or, I don't know, maybe a webEx or whatever it is that...

DA (30:20):
Demio.

SW (30:21):
Or Demio. Ah, there we go. I mean, there you go. Right. I think that's super important. I think living by values at the end of the day is going to help organizations make the right decisions when it comes to moving remotely. It's, it's just hiring people too that, that are self motivators and able to think outside the box and communicate in a remote organization. Right? Those are, those are stuff that questions that should be really thought out and methodical when hiring people because if you're going to hire people and they're not going to be able to work remotely, you're going to know through certain questions like, you know, Hey, tell me how you would communicate with somebody that via email. Right? Like what, what is your strategy on how to communicate with somebody internally via email?

SW (31:11):
I remember I got asked that in my, in my interview question when I was like, kinda like thrown back a little bit. I was like, why does that matter? But it does, you know, it's like communication asynchronously or you know, when when we're not face to face is different in a remote organizations and organizations need to be aware of that because if organizations can't communicate clearly, , there's gonna be a lot of silos, there's going to be a lot of efficiency losses overall. And then if they, if, if you're an organization that's saying, Hey, like we're going to transition and be, you know, completely remote instead of just, you know, starting out as a SaaS startup and being remote, I think that's a more of a challenging task. But good news is, is I'll plug GitLab. We, we have, we're an open source company, so we have like the most, we're the most transparent.

SW (32:04):
It's, it's almost ridiculous. You, you, you'll see we have a remote work playbook. We have this great head of remote Dan Murph that's got a lot of content out there on, on how like we do everything from hiring and onboarding to stuff like force functions, which is, you know like say we delete our Slack messages every 90 days. So what does that do for an organization and actually creates this, this, this mental idea that, Hey, like any important information shouldn't live in Slack that's pertinent to the business. It needs to live in our project management software. So that's just one example of, you know, the all the thought and the thoughtful strategies that go on when transitioning to remote workforce. It's not easy but I think it's the future, honestly. I really do.

DA (33:00):
I feel the same way. I, you know, we made that bet on, on remote work early and especially now with this kind of accelerant of the COVID-19 era. It's just that, you know, this is going to be the future. I think there's a lot of work. We can still do a question. Do you guys have all 1200 plus people in Slack?

SW (33:17):
Yeah.

DA (33:18):
How crazy is that?

SW (33:20):
You know, we do. I think we're. It's always evolving. That's one thing that GitLab is fantastic about and I would recommend any organization that is moving to all remote workforce is adopt this mentality of minimal viable product or process. Meaning, Hey, like it doesn't need to be perfect for me to document it and push it into action, but it needs, we need to do it. We need to start, start doing this particular thing, test it out iterate on it and improve on it. And so, you know, we have things like we have a channel inside GitLab that's like, Hey company, FYI, where only leadership can, can post on this, on this particular channel. And it's really for your information, high level announcements from the company. We can use emojis to like it or do whatever like that, but it's a very cool way to, Hey, like, here's an announcement for the company.

SW (34:13):
And then we have those all the way down to, you know, marketing FYI, SDR FYI, et cetera. So I think there's just like all these little nuances that kind of come become clear. And if your organization, if you empower your individuals at your organization to, which what GitLab does, which is everyone can contribute. That's one of our, our mission. That's our mission essentially. Even if, if it's somebody that's, you know, an operations or maybe they're an SDR, they can add, you know, they can make an improvement on something and they have that freedom to, you know, Hey, like, here's what I, I think we need to do you know, a new channel to talk about you know, marketing operations or whatever it is. That's, that's something that I think organizations as they move remote are gonna make things more powerful and empower the individual at their organization as well.

DA (35:06):
Love that. Yeah, that's super helpful. And we were kind of talking before the show a little bit about, you know, the mental stress that's going on right now in, in kind of this you know COVI- 19 era and what it does to the freedom and ability that you get from remote work. You know, knowing that you're an expert in like mental conditioning and you've been remote for so long. What about, you know, routines or add ons that you know, marketers listening that are going remote, that are dealing with this now can use to navigate these challenging times and kind of just keep that mindset, that performance as high as possible because it is sometimes lonely to work remote. It is a different feeling than being in office.

DA (35:46):
Yeah. 100%. You're, you're a hundred percent correct there David. For me, one of the advice that I would give people for mental conditioning and mental health overall is to have as much routine as possible early on in the day. And do the things like we all know that, Hey, like journaling is something that's good. Meditation is something that's good. Exercising is something good. So you know what works for you as an individual and if you're unfamiliar of on what works, you know what the top people in your industry, top marketers top, you know, business people over all are doing to like make themselves operate at a high level on a day to day basis.

SW (36:28):
Do a little research, check out what you know, like what, what are the top people in my industry doing in their morning routines and sticking to those and what works for you is super important. I believe that shifting our mindset from working that eight to five hours 8:00 AM to 5:00 PM at the end of the day is, is something that we need to take, take a step back and go, that doesn't, that's not where we need to be focusing our time. Right? I don't have to sit at my desk from eight to five now that I work remotely. So building in time throughout the day to do, you know, go on a walk if you can get outside wherever you're particularly at or just even move locations, right? Like I'm looking at my living room right now. I'm going to take a little break in a little while and just go sit on my couch or you know, sit outside for a little bit.

SW (37:18):
Stuff that we can do to detach from our workspace because when they simultaneously become one is when we're going to have problems. That's when we're going to have burnout. That's when we're going to have lack of motivation is when we're constantly feeling like we're in our, our work environment and we're not detached from it. The other thing I would, I would recommend is being really methodical about your calendar. How, what does your ideal day look like? Plan it out the night, the night before. Say, Hey, like if I do X, Y, and Z, if I get these, you know, issues done or you know, make these, send out these emails or work on this project, I'm going to go reward myself with, you know, a little break throughout the day. So planning those breaks, planning time for exercise, planning time for family. All those things that previously you weren't able to do in an office setting, you now have the flexibility and the freedom to do those things.

SW (38:16):
But at the end of the day, we also have this appreciate or we have to do what we need to do for the organization who's trusting us to work. So it's that balance between freedom and getting work done for my organization. And once, once individuals can build that into their day to day and kind of build that habit of that balance and feeling that out, what does that, what does that look like? For me personally, the remote work is just so exciting. It's the flexibility, like we talked about the freedom to go wherever, whenever. I know that doesn't pertain so much to right now with COVID, but that's what I believe can help organizations and individuals really succeed in working remotely and maintaining a good, a healthy mindset. The other thing that I've been experimenting with as well and I definitely want to touch on this is , I don't, I call it a mental workout of the day or a mindset workout of the day where it incorporates, it's like a 15-minute break throughout the day where the first five minutes are, are about meditation and becoming still.

SW (39:23):
So, you know, you have all these things that are going on in your mind all day, all day, every day. Let's get still for five minutes, then we move into a five-minute I am statement. So like, Hey, you know, I'm doing a good job today. Like affirming ourselves at the end of the day. Like I am healthy, I'm happy. All of these things that are power driven. And then, and then finally which is my favorite part is visualization. So walkthrough visualization of like, Hey, like what is the rest of my day look like? I'm going to visualize seeing, using my imagination to see myself doing really great work. You know, virtually high-five in my, my coworkers or hearing my, my bosses or my manager's voice inside my head saying, Hey, you're doing a great job today, Shawn. I think taking those and implementing those are going to be very foundational for organizations as they move forward to help eliminate or help flatten a lot of the mental breakdowns and burnout and depression and motivation, lack of motivation that that can occur from being by yourself all day.

DA (40:29):
Wow. This was just such an amazing block. You know, I'm a big fan of remote work. We do a lot of these things ourselves. And just to hear you say all of these and validate so many of them. Fantastic. Go back and listen to this guys, if you're, you know, in that remote position. I think one thing for me that's been very helpful is exactly what you said is just like using your calendar. I block time in my calendar, I put time in for breaks. So I do have like reminders, take a break, take the time away. And I don't feel pressure that I have to keep working all day, which can happen so often. And I also try to do like the really important things earlier in the day when I have the most energy. And that's for me. Not everyone has that same kind of schedule, but that's what works for me. And you know, kind of looking back over the past, I guess, you know, you've been here for two years, but looking back maybe over the past year, any lessons you've learned from maybe experiments you've done or marketing initiatives you've done that, that didn't work out as expected?

SW (41:23):
Yeah, I think, I think one of the direct mail campaigns that we, that we did weren't very didn't, weren't received very well. You know, I think when it comes to a lot of the paid kind of advertising that we've done on LinkedIn, although we get good open rates like on, on sales navigator and so on, it just hasn't yielded the results that we've looked for. Additionally the one, it's really hard to measure the impact of building your personal brand and how that pertains to getting results for your individual job. So I'm always looking for new ways on how to measure that. I think it's been, you know, overall I've done well as an individual and, and that I believe that that building, that personal brand, putting out content has helped that. But at the end of the day, it's really hard for me to measure the overall success.

SW (42:25):
So it's like I can't spend all my day, every day just building my personal brand and thinking that that's going to drive all the results that I need for GitLab. Right. And so I think it's a balance between doing that and then doing the things that we know really actually work. And then additionally, I think something that hasn't worked for me just as in regards to just being a remote employee overall is just keeping, keeping myself in a little silo, right. Focusing on what I know and like sales and marketing, only attending those types of meetings, it's really hard as a remote organization, as a remote employee to feel like you're a part of the company if you're not attending, you know, like AMAs or ask me anything. So, or you know, group conversation updates where it's the engineering team and knowing what they're doing.

SW (43:19):
So GitLab and allows us to go to any meeting minus, you know, really high level meetings with, you know, maybe our executives or our C-levels et cetera. But they empower us to go to these meetings and stay up to date on like, Hey, what's going on in customer success? And so what I realized was a mistake for me early on was just focusing on, on marketing and sales and what's allowed me to feel more and more involved in the organization is attending as many of these meetings that I can fit into my calendar and also continue to do my job because I think it helps me overall stay in the loop, stay ingrained in the company culture. To add that, one thing we've done that's been really well received was we do this thing called like basically this week in Demio and it breaks down like overall, like, I guess just like vision for the month and kind of what's going on, like a running update and then it's each department broken down who's doing what, what the goals are in each department. So like, even if you don't go to those meetings, you still get like an update of like what's happening in all the different areas of the company. Which to your point is exactly what you're kind of talking about. It's like you're not feeling too siloed in that remote workplace.

SW (44:26):
Yeah, that's, that's super important. And, and, and I think, you know, we'll, we'll, we'll probably touch base on values in a little while, but transparency is huge. And if you're, if you're used to being in an office setting where there's a marketing meeting going on and you're not in it, are you going to get any of that information? You're not. Right. So empowering organizations to, while we're working remotely record those meetings and if we're not all in the same time zone, that person who wasn't able to attend that marketing meeting can go back and relisten to it working asynchronously. So there's so many added values to that as well.

DA (45:09):
Really good point. Yeah. Excellent point. I love that. And looking forward in 2020, there's a lot of unknowns. It's going to be a different year than we ever experienced before. What are challenges or opportunities that you see for GitLab? You know, maybe for just the industry as a whole or any marketing ideas or things that are going to be easier or harder, (inaudible) moving forward.

SW (45:31):
I know that for GitLab, one of the main things that we're trying to do in 2020 is to be more efficient overall. So we have a lot of high level initiatives that are, are trying to focus on how we can create efficiencies because especially if we're scaling, which we like we did from, you know, 300, 300 two years ago to 1200 plus employees and even more. We're going to have to, there's going to be some inefficiencies that happen when we're scaling that fast. So I think it's something that's really cool by GitLab and from the top down is, is everybody being involved on this efficiency, these efficiency projects to improve some of the levels of efficiency within the organization. And it, and it kind of is an opportunity right now, especially with, you know, COVID-19 going on and you know, maybe we don't have the highest level of engagement that we've had in the past or things aren't moving as fast as they were. So it's like the perfect time to find those little efficiencies or big efficiencies within the organization that we can improve. When it comes to marketing, obviously field marketing isn't happening anymore. So I think what we've done at GitLab is really transitioned field marketing into something different, right?

SW (46:49):
Like how can we use, and just asking ourselves the questions, right? We're still trying to figure out what that looks like, but asking ourselves the question, like, how can we use these talented individuals that are in field marketing in other areas of the business? Or how can we even transform what field marketing looks, right? Like, I know a lot of organizations are doing virtual field marketing events and stuff like that. We're, we're, we're dealing with that, we're doing those types of things, but even thinking, taking a step further, like, there's no better time right now than to look into the future and like create the next wave of field marketing or, or just overall the entire marketing organization. Like, Hey, what's the next, what does a marketing organization in 2025 look like? What is, what is that next generation of the marketing organization look like?

SW (47:33):
And how does it align with sales? And, you know, how, how does that affect program, digital field marketing? And I think that's something that organizations should do and, and look at that as a strategic opportunity moving forward. And then additionally, I think, you know, the opportunities are, are endless when it comes to resetting communication habits. Not only with prospects and ideal customers, but internally. We're now, if you're an organization that's moving from working in the office to working at home, if you're in an office, there's a lot of like social let's call them challenges that go on, right? There's politics, there's not being able to give direct feedback in the way that you want it. Or there's all these like built up kind of like calcified bad habits when it comes to communicating. And I think that for us moving into a situation where we're going, we're going all remote and now we have this even more intimate setting of being on a video call with people, we have that opportunity to actually reset our communication habits and build stronger relationships, not only internally but externally with clients. So and customers. So I think that's just a tremendous opportunity because if we can't communicate as human beings, you know, are we going to be successful? I would think not.

DA (49:01):
I think the key kind of message I'm getting now is that from you at least is that it's taking the time to just rethink some things. Getting out of those comfort zones. Sometimes when we're going so fast, it's hard to take a reflection of where you are and what you can do to improve. So you said efficiency, you know, communication and kind of moving forward. What new things, optimizations and changes and growth things can you predict and jump on now. So to your point about meditation before, it's kind of similar to that practice, right? A little bit of stillness, a little bit of thinking through it and then moving forward, which I love. Well what I want to do now is I want to flip over to our lightning round questions. Just five quick questions that you can answer with the first best thought that comes to mind. You want to get started?

SW (49:45):
Yeah, I'm excited.

DA (49:46):
All right. You got this again, first best thought that comes to mind. What advice would you give for early stage SaaS companies starting marketing today?

SW (49:57):
Values. Align all your decision making with your values. You know, if you, if you plan that out and if you do that right, I think you can be, I think anybody can be a successful organization.

DA (50:08):
I love that. I couldn't agree more. It's all about taking those times to build those values at the beginning of your company life cycle. I love that. What skill do you think is vital for marketing teams to improve and build on today?

SW (50:20):
Two things. I would say hiring, right, like hiring the right talent, not, not the you know, what's, I think there's a lot of pressure to hire people in general, especially at, you know, GitLab growing so fast. So hiring the right people. And then additionally account based marketing. Like how can we leverage ,how can you leverage account based marketing to really cater your content to, to the people that you're reaching out to, the accounts you're working.

DA (50:48):
And I think you shared a lot of great information on some of those ABM kind of tactics, ideas, things you've kind of figured out over the past few years as well on this episode. That was fantastic. What about a best educational resource you'd recommend for learning about marketing or growth?

SW (51:01):
Oh man. This podcast, the SaaS breakthrough podcast I would say is a good one. And additionally, you know, I think finding who speaks to you at the end of the day as an individual, I think there's so many great marketers and you know, people who are doing marketing out there today that are going to give you great information. It's all similar. It's just find that person that resonates, their messaging resonates with you and, and, and roll with them and you know, really kind of dive into what they have to offer.

DA (51:35):
Yeah. I love that. That's awesome. How about a favorite tool you can't live without?

SW (51:40):
I can't live without sales navigator. It's just so powerful. The, the segmenting and, and understanding these accounts that, that are prioritize and how to prioritize them and using Boolean and it's just amazing. I love it.

DA (51:57):
Yeah. That's awesome. What about a brand business or a team that you admire today?

SW (52:03):
I'm going to have to toot our own horn here at GitLab. I'm obsessed with our leadership at GitLab. I think the transparency that they, that they emulate on a day to day basis. And their unceasing cool of just being better every single day really inspires us. Our our CEO Sid is just amazing. He just is, is someone so important that I look up to. So I, I gotta I gotta holler at them and, and if anybody wants to look into more than that, again, we're a super transparent company, so if you just search, GitLab and plus anything on Google, you're going to find what you're looking for. So I definitely recommend that.

DA (52:46):
Yeah. And we'll definitely link to the site and all that stuff with the show notes, the resources. We're a big company built around transparency too, so I absolutely love that value. And it's, it's really something to be said when you're thinking about a whole landscape of great companies and you're willing to say your own because it means you're really inspired by it, by who you work for and the company that you work for. And so congratulations to you. Congratulations to GitLab. It sounds like you're, you're just absolutely in a great place. I mean, 350 to 1200 employees over two years is incredible. So congratulations to you guys.

SW (53:20):
Thank you. I appreciate it.

DA (53:23):
Awesome. Shawn, thank you so much for your time. It was a real pleasure. You shared so much knowledge and wisdom. Again, really appreciate your time and we wish you all the best.

SW (53:32):
Thank you David. I appreciate you.

DA (53:34):
Talk to you soon. Have a great day. (...)

Resources:
Download GitLab Remote Work Playbook:
https://about.gitlab.com/company/culture/all-remote/
Learn More About GitLab:
https://about.gitlab.com/
Connect With Shawn:
https://www.linkedin.com/in/shawnwinters1/
Follow along on Our Journey to $100k MRR
A shaky start? No doubt. Yet, three years later, we've got our eyes set on $100k MRR. We'll be sharing everything along the way.