TigerEye and PlanGrid's CEO: Lessons learned on the path to $100m ARR (Workshop Wednesday LIVE)

excited to have you week after week. As you may know, this is every Wednesday at 10 AM Pacific. We want to make this as interactive as possible. Tracy has already mentioned that she would love if you put your camera on because it is so much easier to talk, communicate, network, etc. if your camera is on. So please join me in putting your camera on, getting your questions ready, and making this as interactive as possible for the next 30 minutes or so. All right, this week we will hear from Tracy Young, CEO and co-founder at TigerEye. We will be discussing founder-led sales, lessons learned on the path to $100 million ARR. Again, get your questions ready. We are going to make this as interactive as possible. And with that, Tracy, welcome.

Hey, thanks for having me.

Of course. We are going to get things started with a few different warm-up questions. Are you ready, Tracy?

Mm-hmm.

All right, so our first question: how would you define what you do in your day-to-day role?

So, um, I am one of the co-founders and CEO of a stealth company called TigerEye. Um, in my day-to-day role, I make money work. And then I also make sure that the team is all pushing towards the same direction so that we're working together.

Great. I love that answer. What a good one-liner. What project are you working on today you're most excited about?

I'm super excited about TigerEye. TigerEye is in stealth, but we're launching this summer, and so that's going to be a big moment for us.

Great. Okay, very exciting. And in the last 12 months, what is the hardest thing you've worked on?

Being mom. I have 3 young kids. Every single day they test me. They test my patience. All the parents are like giving a thumbs up. I feel you too. Happy International Women's Day, by the way. I see a lot of women on the line. And for the men on the line, please celebrate the women in your life. Thank them for all the hard work, all the care that they give you. And it's a great day to be able to honor 50% of our population.

Agreed. OK. Could not be a better way to kick things off. And agreed, motherhood is the hardest job. Thank you to all the amazing moms and women out there. With that, though, Tracy, I will let you take it away.

Great. Hello, my name is Tracy. I was co-founder and CEO of a company called PlanGrid, which I ran for almost 10 years. I'm currently working on my new startup, but I got to, I got to lead this startup for 10 years, and we got to sell to Autodesk, and I got the company from nothing to $100 million in ARR. Before I passed the baton over to the Autodesk construction team. And what's really funny is I retired from Autodesk in March 2020. I thought I was going to take this big trip, and I retired into freaking shelter-in-place and COVID lockdown, into a worldwide health pandemic. And what that gave me was a lot of time to reflect on all the mistakes that we made. PlanGrid. And now we're taking all our lessons learned over to TigerEye. So for this talk, I'm trying to think of, as I was trying to think of what would be helpful for you, and I have no context here, right? I don't know where you are on your startup journey. I don't know what you're building. I don't know where your revenue targets are this year. But I do know that if you are on this path to building your startup, there are a handful of things that are gonna fail. If it's already failed, it's coming if it hasn't already. So let's talk about that. Number 1, your org structure and communication failure. For us early on at Plangrid, we tried to be so creative about organizational structure. We didn't give anyone titles. You were either in operation or engineering, and we even bragged that we're like, we run our company like Star Trek, except that people really care about titles and people really care about career paths for the obvious reasons. And so if you want to care about your team at all, these things have to matter for you. And, um, as our team grew from just a couple of people to 30 people, then we tripled one year from 30 to 90 people. People. Then we doubled the next year, 90 to 180. These were such hard years for us, especially as first-time founders and young founders at that. Like, no one great wanted to work for some punk kids. And so we hired pretty mediocre managers to start, who in turn hired more mediocre people. And, you know, we had to blow up the team at some point. Um, everything fell apart. We were this high-functioning fast-moving startup, and suddenly we had more people and it didn't get easier and it didn't get faster. We were stuck in molasses and it was unbelievable to me. Huge lessons learned for me. And it was one, a factor of hierarchy. When you're only 10, 20, 30 people, everyone can report to a founder. So communication is really easy as long as the founders are lockstep. But when you're, when you're at 150 people, you know, when we hit Dunbar's number, everything went to chaos. And I think again, hierarchy is a factor because now we're talking about 2, 3 to 4 levels away from the frontline to the CEO and founder. And that means everyone has to be lockstep in the way. And we didn't have a cleanly architected communication structure. Um, and we didn't understand that we have to repeat things. We can't just say it once and think the whole team. Is on board with it. We have to explain and bring the team along with our thought process and our journey. So, um, my takeaway here for you is we have to be creative on how we're solving problems for our customers. We cannot be creative with org structures as we did in the early days of PlanGrid. This is where we need to spend all our creative— creativity is for the customer and not for the team. In fact, it's very simple with the team. We just have to have clear vision and clear direction on where we're going, and then everything needs to fall in line with it. Second thing that's gonna fail, internal conflict. This one sucks so much when you have a team that is not cohesive and working well together. I think there's natural tendencies, or sorry, there's natural tensions that are always part of every startup. Sales and marketing, natural tension there. One is generating leads, the other is supposed to close it. Product and engineering, national, natural tension there as well. Maybe product design and engineering because you've got people speccing out what the other side is supposed to be building. Then there's engineering and sales. Feels like we're never getting enough products to sell. And these tensions get magnified when things go wrong, when things aren't going as we wish they were, when we're not hitting our revenue targets, when we're behind on our milestones and delivering product to our customers. And when there is a discrepancy and difference in how people's people's expectations are, or if they feel like they are performing better than their other teammates, the natural thing that happens next is just a bunch of finger-pointing. I did my job, but this team did not. I've been working my ass off and these pe— this team is failing. And this is so massively damaging for a startup or any team. And so My takeaway here is fight for your company's core values. Unfortunately, you know, I liked our core values from PlanGrid, but we didn't live by them. I mean, just to give you an example, we had a core value that says like, we won't hire jerks, except that I kept jerks around. And the signal that that sent to the team was, if you just perform for Tracy, you can get away with murder. You can totally be an asshole and she is not gonna fire you. And so this is what we're doing differently at my company TigerEye is the core values are defined and not only are they defined, we have this other doc that really clarifies in black and white what these core values mean. It's our commitment to each other. It includes something very simple. Um, 10, 10 commitments. One of them's like, I will walk it like I talk it. I will not speak destructively behind someone's back, et cetera, et cetera. And we've hired by these core values, we've fired by these core values, we've made strategic decisions by these core values, we've made product decisions by these core values. I'm talking to you guys right now, but I want my team, if they're trying to make a decision right now, which at a startup is like decisions across the board and our ability to make decision quickly and execute is what separates us from these big companies because they can't move as fast as us. They can't touch us on this front, and that is our competitive advantage. I'm talking to you right now, and I hope my team is bringing up the core values right now and making decisions with it. Executives not working out, or managers not working out, and, um, I think with high-level team members that have a team under them, their blast radius is much larger than like an IC or frontline person. If I have, if I hired an executive at Plygrim, just by stats, I would assume that there's a 33% chance of it working out in year 1. So let's talk about why this, it's just really hard, you know, at the executive level, they're so good at selling themselves, especially if they're in sales and marketing, like this is their job. Marketing. This, like, they are excellent at marketing themselves. And then execution is a completely different thing. So you interview a bunch of people, you finally select one, they're gonna be, you know, they're gonna help you save this department, they're going to help you achieve all your goals and ambitions. Well, there's some red flags, and I made sure to write them down so that I can go through them with you. Number 1 red flag. They use the pronoun I frequently. I'll give you some examples. I did this for the company. If it wasn't for me, we wouldn't be here. Your real leaders are going to be giving all the credit to their team. They're not gonna be using the word I that often. 2, you dread having one-on-ones with them. Your best executives, you can't wait to be in on a one-on-one and catch up on how much work both of you guys have done and the team has done. You can't wait to talk about strategy and what we're gonna do and accomplish together in the next 3 months. You should not dread having one-on-ones with your exec because they are leading such a big and crucial part of your team. If you feel that, that is like the biggest red flag. You've got to do something about it. 3, they blame their peers. Things aren't going right, and things don't go right at startup often, and they don't own up to it. They're not about the problem, about solving the problem. They're just literally blaming everyone else. That's a really bad sign. And then 4, you catch wind that they've been complaining downwards and laterally. Like, it should be like the military. You complain up, man. You don't get to complain and smear your shit all over everyone else in the team. That's, that's like really bad leadership. And, um, if you see these, there are certain decisions like firing executive that only CEOs and founders can make. No one else can make these decisions. And I think by the time the CEO finds out or the founder finds out, it's already too late. You're usually the last one to find out anything. The frontline team knows first, then their peer, peers know, and then somehow the founders know. So, and the team is looking towards you to make the right decisions, them to make the hard decisions for the company. Takeaway here is always trust your gut on people, that your gut is actually highly, highly intelligent. And our minds will come up with a million excuses on why you can't fire them, but it's never as bad as you think it's going to be. I made up every single excuse, right? I'm just like, oh, but like, I'm so stressed out right now. And like, if there's no leader here, it's gonna fucking blow up. But that was never the case. It was always the right decision, and I never made the decision soon enough. Losing product market fit. We nailed product market fit with PlanGrid. We basically digitized the construction record set. So instead of looking at like thousands of pages of paper, which we all know paper sucks, and this is 2011, you open up your mobile device and there's like all the paper and here's all the version control. You can see which one's current. You can see which ones are outdated. And you can push your notes to everyone else. Like, we totally nailed product market fit with a very simple product for its time. And then we hit $50 million in ARR, and we hit a wall. And it was crazy to feel it because we were growing so fast before that. We sort of hit a wall in terms of TAM and SMB and lower mid-market, which was our sweet spot. And we needed a quantum leap up to the enterprise, except that our product, although amazing for the end user, for the carpenters and superintendents and project engineers and project managers on the front lines in the field, the corporate buyer couldn't have cared less about our product because it wasn't for them. But they were the buyers. They were the decision makers. And we couldn't get to them. And it was very obvious what we need to do. The enterprise B2B SaaS playbook is like very well defined for all industries. You've gotta have SSO, you've gotta have role-based access control, you've got to take care of SOC 2 Type 2, you've got to have ISO 27002, GDPR, the compliance list goes on and on and on. It is a well-defined checklist. That you just have to get done, an admin console so people can control the accounts. Well, we took too long to do that. And we ended up selling our company. And we have a competitor that is a public company today because they were so good at building products for the enterprise. My takeaway here is we just kicked the can down the road because it was hard to build for the enterprise. And we didn't want to because it was boring. We wanted to build software for the construction workers in the field. We didn't want to build software for the people who take showers in the morning. We wanted to build software for people who take showers at night after they've done a hard day's work because we believe they deserved good software also. And we didn't do this. We didn't go towards where it hurt the most. And building towards for the enterprise was where it hurt. And we took too many years to get there. And it is completely possible to have product market fit one year and then to lose it completely because the world changes, the market changes, your customer changes. Number 5, life happens. This one is hard and it affects all of us. As we were launching Plangrid into the world, my co-founder Antoine died of cancer. He was 29 years old. I didn't even know it was possible. I was 20-something years old at the time. I'd never seen anyone die in my life, and my really good friend and co-founder just dies. And I will never be able to have— it is so heartbreaking to not be able to have a conversation with someone you love again. But this was not unique to me. I'm sure you have had people who have passed in your life and you've experienced that type of loss. And as our company— as our company grew to 500 people, it felt like sad stuff was happening all the time. This is just life. I mean, parents dying, grandparents dying, children getting really sick. I had a couple of team members where this happened and their kids were in and out of the hospital. Really, really sad. I had a coworker whose husband didn't come home on a Friday night because he had died in a car accident, leaving her with 2 young kids. And life continues. And, um, it doesn't stop just because we're doing the hardest thing we've ever done before. And so my takeaway here is that life is short for all of us, even if we get to live the entire span, the entire spans of our life. And so we have to choose a problem that is worthy of our time, and we have to be present every single day, every single minute, because there's so much— there, of course, is so much highs and lows with building a startup, but there's also a lot of in-betweens that are completely boring and mundane and hard and tough. And we've got to find presence in those moments because that is where happiness comes from. That is where a life worthwhile and worth living comes from. Thank you for letting me cry in front of you and mourn my good friend. And I'm done. That's the talk.

Thank you, Tracy. Um, feel free to stop sharing your screen. Um, and thank you so much for sharing both your like vulnerability and candor in all aspects of that presentation. I think it was really powerful from a lot of different angles, and we really appreciate that. We are going to move on to the Q&A portion of this presentation. But just to point out, you are getting a ton of love in the chat, so you should definitely take a peek there because you have a ton of wonderful messages coming through.

Thank you.

All right, are we ready to move on to Q&A?

Yeah.

Okay, perfect. So first question, um, you mentioned that you were a really young founder. What type of tips or tricks do you have for young founders in the space?

Surround yourself with people who know way more than you, and you'll learn from them. And the best people will go out of their way to teach you and just have this growth mindset and have this ruthless humility where you look yourself in the mirror and ask yourself how you fucked up that day and then learn from it and grow from it.

Agreed.

Awesome.

Thank you for sharing. Um, What do you recommend, or what strategies do you have to align internal communications between traditionally combative teams? You listed a few different teams that traditionally don't get along in times of stress, and what are some recommendations you have to align them internally?

Be ruthless about documentation and communication. In that you don't want 5 different strategy docs from different teams. There is one. There's our strategy right here, clear and simple. It's written like a real human writ— wrote it, right? Like you talk. And then there should be just a couple initiatives that are driving your vision and everyone should be pushing those along. What you don't want is Yeah, just like a bunch of different strategies and everyone pushing the company in different directions. That's where the tension gets damaging to the company, I guess. Because you can't actually get anything done.

Great. We have a question in chat from John Williams. Do you want to mute yourself and ask, John?

So I actually asked a couple, and this has been great, Tracy. Thank you so much. I know you're kind of catching up on the text that's in there. So in the early part, you mentioned that, you know, it's easier when the team is smaller and everyone can kind of get together to communicate with you and share what's really happening. And that, that gets diluted a little bit as you grow larger. I was just curious. What was the most effective approach that you guys had? Did you just have a meeting once weekly when it was a smaller team and then just meeting with the heads of the business units after that? I'm just curious so that, you know, we can get out here and do the best practice really.

Yeah.

So, um, what's really interesting at my new startup, we're only 16, 17 people right now. And so we are a small team and I'll tell you what we're doing right now. Um, we have a coffee meeting every Monday. It's for 45 minutes. It's with me and my co-founder and the rest of the team. Are all hands essentially. And there's no prepared presentations or anything like that. We just speak openly about what's in our brains. These are the things that we have to do. Hell or high water, we've got to find product market fit. We are launching the product in the world. We've got a few more months to build this out. Where are we weak on? Where do we need help? Where do we need more user interviews? Where do we need more customer input? And feedback. These are the areas that Tracy's worried about. Let's talk about it. These are the things that I'm doing about it. Do you guys see anything wrong? Should I be doing anything else? Because it's a smart team here. Okay, great. So you guys are supportive of what my focus is on. Then it's just like open. It's just like, all right, you know, questions. We all have questions. We're remote team. So it's really important that we use this time to communicate. And I think we have to lead by example. And show that it's okay to have the hard conversations. And I know I won't get judgment. I know no one's, you know, I expect our team to have the hard conversations and I expect all of us to be respectful as well. And so I think that's something we're doing well at. We have this other meeting later in the day on Mondays called whiteboarding, and this is where we— everyone is part of the product process. We every— I'm making, not making, everyone's optional, but everyone's pretty much attending all of them is all the user interviews. The whole team is attending. I want them to hear firsthand from the users what the pain points are so that they understand why it's important, why our solution is important and valuable. Whiteboarding is just our, our head of design leads it and we throw a bunch of stuff on FigJam and then we talk through it. Something as simple as let's talk through the filtering of our system. Or we have a bunch of words that are in our product and it's like, let's wordsmith this together 'cause we don't like it right now. How can, let's dump like 5 versions of the same sentence and like, let's just vote on it. Which one is the most simple that our customers can understand? Maybe there's like a portion of our product that has graphs and like we all throw different types of visualizations that we like for inspiration. Later on in the week, we have something called show and tell. This is really, really exciting for us because the team shows off what they've done that week. And for the operations team who hasn't maybe sometimes built something, they can do a tell. So we want, the point is we want everyone to participate and we want everyone to feel the movement and progress and trajectory of the company. So those are the things that have worked for us.

Great.

And did that answer all of your questions, John?

Oh yeah, and more. Thank you, Tracy.

Okay, moving on to our next question from Clark.

Hey Clark.

Hi Tracy. You mentioned a couple times about product market fit and you just mentioned it again. When you were in that journey, what portion of your personal time as CEO and founder was spent on that versus the you know, spreading yourself across multiple team members going through that process and like what role did you play in that? I'd love to hear a little more about that.

Yeah, I don't program and so I spend, my, my, my co-founder does, although now he's really leading the engineering team. Um, I spend all my time on customer success and sales. Uh, I think YC's model is very simple and it's, it's effective. Talk to users and write code. There's nothing more to that. You keep doing this and you're honest to yourself about the problem that you're solving and the way you're solving it for your customers, you're gonna find product market fit, or you'll find out, you'll invalidate what you're working on and then pivot and work on something better. Talk to users and write code or build whatever it is you're building. Maybe it's not software. Great.

We have a question in the chat. You mentioned firing is needed. What decision process do you use to draw a line between give a chance to change versus fire? How does the answer change depending on the stage of the company?

Oh, okay. So I think the advice I've heard from every single founder leading impressive companies is you can't fire fast enough. Maybe we focus this answer on how to fire. You have a team member that's not working out, and there is a chance that it could work out, but they deserve the feedback first. So you'll say something like, these are the expectations of this role. You were hired to do this. Um, or Things have changed in the company and these are now the new expectations for this role. You are not meeting these expectations for XYZ reason. I think that you can meet the expectations by doing 1, 2, 3, whatever it is. And by the way, we have a business to build. We have shit to do. So if you are not meeting these expectations by this date, we have to talk about parting ways. We'll make sure to do it compassionately and, um, you know, with respect to you because you're a— you're a great person. This is why you're here, but it's just not working out. There is, I'm going to say, only a 25% chance of it working out after this. You'll see people— some people will just completely check out because they're now interviewing somewhere else. Because they have— they don't fucking care if they meet your expectations or not, or they don't believe in themselves. They just need to go. And you'll see it. You'll see their performance just drop. Then for that 25%, you'll just see them rise to the top. They'll take your feedback and they will run with it. And those are the people you want to keep.

That is it. Answer. Um, We have another question in the chat. Any advice on how to generate leads when trying to sell to big organizations?

Oh, it really just depends. I don't have enough context on this business here. If you can surround them, so I don't know who your, your buyer is, I don't know who your user is, I don't know who's going to deploy your thing at that company. But if it's an enterprise company, there's a lot of people. So you wanna make sure, and I think this is true for all products, but I just like, not enough context here. You wanna surround them. You wanna make sure several people are talking about you and your solution because more likely than not, there's more than one buyer here and more, definitely more than one stakeholder and more than one decision maker. And I think maybe the best advice I could give you Um, without knowing enough is always know what is needed to make for them to make a decision. Just ask them. You give your demo or whatever, and it's like, who are the decision makers? What do I need to do for you to make a decision? You should then find out who the stakeholders are, who you need to demo to, who you need to teach about your thing. And then you go do it. And then the other advice I have is always know the next steps because these enterprise sales can, can go on for years. And so you wanna make sure you know exactly what is supposed to happen next and try to lead your customer in every way.

Great. And if there's any follow-up or more specifics to that question, um, feel free to follow up in the chat. What framework did you use to create vision and strategy?

I use a framework, um, I drafted it up with my co-founder. It should be a, a big lofty vision. Anything less is just not worth your time. You should feel it in your heart that this is how you want the world to function, whatever it is you're trying to solve, that if you realize this vision, the world is gonna be a better place. So it's less about framework and it's more about passion and your ability to communicate why this matters to your customers, to your team, to people you're trying to recruit, to investors. And then you break that vision down. To very simple initiatives that would drive it. And then you sell the team on it. You sell your ass off. Like, if we get these initiatives done, then we get further along on our vision.

Great. We also got feedback in the chat that your answer to generate leads when trying to sell to big organizations, you absolutely nailed. For their organization. So thank you. Um, our next question— also, please hop in if you would like to ask these questions yourself. Um, I have messaged you privately, and so if you do want to answer these questions, please just respond— or ask these questions, please just respond back to me. Um, but how did you figure out the problem that PlanGrid solves for, and how did you validate it?

Oh, the paper problem in construction is obvious to everyone. No one likes lugging thousands of sheets of outdated paper around on a job site. We were just the first ones to do something about it, and we lucked out on timing. How did we validate it? We just built it. We built it the most simple version possible, and then we showed people, and we said, said, do you want to use it? And then we got a bunch of people to use it. And then eventually, we got a bunch of people to pay for it. And then it was— I probably didn't realize how validating it was until we made our first million in ARR. And it was like, OK, this is like, we can probably build a business out of this. I mean, it was a fun project before that. And then we made $10 million in ARR. And I think that was the first time I realized that we could build a big business off of this problem.

Sorry. Hey, Tracy, I asked this question. My name is Ahan. Hey, I just had a follow-up question for that, if that's cool with you. In terms of like now going from Plantbird to TigerEye, what are some things in validating a problem and going about it that you would do differently?

I have this strong opinion that you should, like everyone has a better chance of building something valuable if you're solving a problem that you experienced, because then you feel it in every cell of your body that this is wrong, this sucks, this is painful. And then you go and solve it for yourself. And then hopefully it's a big enough problem that a bunch of people want to pay for it, for your solution. I think that it does, it does work. I've seen a lot of successful companies where they saw, they saw this problem from somewhere else adjacent to them and they saw the pain and they're like, I think that's a big market and I'm gonna go solve that. I do, I have seen it work out, but I just think it's much harder because now you've got to go and go into learning mode and learn other people's pain points versus just experiencing it firsthand.

Got it.

Thanks. Great. Our next question comes from Long Pen.

Hi, Jason. Thank you very much for sharing. Very authentic. I also led a company of similar scale and could really feel that heartfelt, the, the problem that you're facing. I have two questions. The first question that you answered previously, it's about hiring quickly and firing quickly, so I'll skip that one. So I'll switch to another question is what, when you're transitioning from SMB to enterprise, what are the steps you take? What are some of the, the learnings that you take away from that? Because the salespeople, the sales team is probably very different from selling to SMB and selling to large enterprise. How do you build out that capability and how do you manage that transition?

So one, it has to be, the product has to be enterprise ready. And then two, your go-to-market team has to be enterprise ready. I think hiring, it sounds like your company is big enough where you can hire enterprise salespeople. If you were a startup of only 30 people, I would say don't waste your money on enterprise salesperson. Like, the founder has to do it. Then it's about figuring out the list, the universe of people you can sell to. Where they're located, what their phone numbers are. It's basic sales operations. What is the universe of people who can buy our thing? And then writing that list down or buying that list, shoving it in your CRM, and then strategically going after them. 'Cause you want them to be talking about you. You want them even better. You want them to be thinking about you when they're not supposed to be thinking about you. They're driving in their car. They're taking a shower and like, oh, maybe I need to go deploy that product. Maybe I should evaluate it again. So how do you do that? It's, it's making a lot of noise without coming off annoying, which is more art than science. I don't know if I have any silver bullets here, but you want to get their attention. And it's hard because they're either you're taking wallet share away for someone or or you're going to be making them create new budget for your thing. And that is massively hard to do. So then it just, it does go back to the product. If your product is enterprise ready and it solves a real pain point, you're just gonna, like, that's half the battle. Then the other half is getting their attention and caring enough about you.

And second question is, how do you balance the demand from your sales team and your product team? So the problem that I constantly face is a product manager or operations team will come in and say, hey, our competitor just launched this new product. We need to develop it, get it onto the pipeline. Well, and the engineering team doesn't have enough bandwidth. This is tug of war that constantly flow up to the CEO level. And problems like these probably happen every day. And inevitably, you get mired into the details. In practice, how do you balance that, that leading the company without getting too deep so that you don't have the bandwidth to think about strategy, goals, customers, etc., and not playing favors between you and team and sales and operations team?

Your questions are so good and hard.

Based on experience.

So, so PlanGrid, we got into what you described here a feature-to-feature-based battle with several incumbents who have been around for like 15 years longer than us. So the question and conversation became a constant, well, these guys have XYZ features, so we like your thing, but we also need you to build XYZ feature. So we were just forever in catch-up mode. And with my new company TigerEye, I promised myself and the team that we're We're not gonna go into feature by feature battle, fist fight with anyone. We're gonna come over here and our architecture is just gonna be smarter. I'm gonna go into an architectural battle where they can't even come into the conversation. But that's very hard to, I mean, it's much easier building from the ground up that way than trying to, I'm trying to think of like how we would've pivot Plangrid that way. It would've been very hard. And it is a slog. With that said, with enterprise sales, I do think it's just this forever fist-to-fist combat. So you just slog it for another 10 years and you just keep doing your thing and then you wake up and you're a much bigger company 10 years later. Again, no silver bullets here, but those are just my thoughts.

That's the fun of building startups. No easy problems. Thank you.

Thank you. Our next question comes from Vishal.

Hey, Vishal.

Um, hi, hi Tracy. Um, uh, my question is about the enterprise sales. Um, you mentioned about, uh, the difficulties of getting into enterprise sales and getting the attention of the buyers. Um, I've had some experience doing this, including going to events and you know, really, or being in the same conference room or, you know, attending the same type of events and getting their attention. And so far I've had success mostly with, you know, meeting people at these events. And so I actually don't do any outbound on email. I, I just take a lot of time to craft these personalized, pain point-specific emails or LinkedIn messages, um, and I don't really spam anybody. And so, um, we're able to get success with this, but it's not at scale because it's just with a very few selected set of clients. So we have a very high hit ratio, but the effort that goes into it is just too much. So having said that, I wanted to ask you if there's anything that we could do better, or maybe we're doing it incorrectly, or, you know, because at this scale, at this— if we, if we continue to do this, I don't know how long is it going to take for us to scale.

So There's no silver bullets in marketing either. There's only a series of things you try out that work okay. It sounds like to me you're doing all the right things. I aspire to do the things that you said with TigerEye. I mean, free and meet, like marketing emails suck. Having cookies on your website suck. Like I don't wanna have that. I don't wanna give people that experience. I hate it myself. I love personalized emails, right? Right. And I aspire to do exactly what you're doing for my current startup. I will say that it's important as you think about scaling and, you know, 'cause you know, you are thinking about scaling to have tests because you need more levers for growth, you need more pipeline and that's a constant forever. So at any given quarter you've got to, just test out something else. I'm trying to think of what might be helpful from PlanGrid. And it might not work for your industry. But all of our customers were either at construction conferences or trade shows, a good, great place to be. And then the rest of the time they're on job sites. Well, construction people are working on their feet all the time, so they're hungry. So our— we bought these boxes. These boxes, these like donut boxes that said it was like blue boxes with the word PlanGrid on it. And our sales reps would, and marketers would go to local donut shop, fill it up with fresh donuts instead of the pink box, and then just walk into a job site and drop it off. And it said PlanGrid, fresh donuts, and they leave their card and it's like, hey, if I can show you guys PlanGrid, it'll only take 30 minutes, I'll buy pizza and burritos next time. And it was an incredibly effective campaign because again, everyone is hungry on a job site. There's— you cannot have enough free food on a job site. And they go in and they just show off Plangrid for 30 minutes for a lunch and learn. Other things we did, we would, we would swag bomb a city, a new market that we wanted to go into. So we'd drop off like t-shirts and swags at these job sites that we very much wanted people to talk about. So like, even though our product wasn't on these projects, you'd see Plangrid everywhere on t-shirts. People were wearing it because you're also sweating all the time and like you're getting dirty. So it's nice to have a clean shirt to wear. Let's see, what else did we do? Oh, we had these events called— so field marketing events were really important to our marketing strategy. In fact, by the time I left in 2020, well, no, It was pre-pandemic. I think we were doing over 300 events a year, which is like, there's only 365 days in the year. So what that meant was we had like a dozen to 20, um, national events or international events. These are big conferences. And then we had hundreds of regional small events, um, breakfast events for the contractors. And then we had something called Beers for Builders. Construction people also really like drinking beers after work. So you really need to get in the heads of your customers and what they're doing and what they like. Construction people like drinking beer. So we're gonna sponsor— it was so cheap for us. We would sponsor at the local brewery across the country just for a few hours. And it was, you know, strategically located near a bunch of construction projects we wanted. And so it's just like, come over for beers. It's on PlanGrid. And we would just mingle with construction people and it'd be like a $500 tab and that's it. And then we would get a bunch of cards and then a bunch of people we could follow up with.

Yeah.

Okay.

Thanks so much, Tracy. But, but so that's the bottom-up approach, right? And then, and, and I'm sure that works great in certain industries, but how would you distribute that between the, let's say, a top-down approach versus a bottom-up approach? Or is there—

You have to become a thought leader. You can definitely pay to be on the Gartner where there's like the classic really expensive playbook. You probably need to get into email blasts at some point and like cast the nets wide and there's a playbook for that.

Okay, gotcha. Thanks.

It's expensive and it's not fun and I don't like it.

Thank you.

I know donuts and beer definitely sway me. Um, Jessica, would you like to ask our next question?

And free swag.

Yeah.

My question is around scaling kind of at the higher end of the range of zero to 1 million. So you talked about the nuggets around scaling from zero to 1 million, 1 to 10 million. What about once you're at around 50 million and now you're really starting to think about scaling big and planning making sure you've got kind of the plan, um, and infrastructure and the pace to get to, uh, to exit. What are the kinds of things that you think about in the $50 to $100 million space?

Um, and I have a limited view of just PlanGrid and then my new company. Um, I think that if you're serving downstream like us, SMB and mid-market at PlanGrid, you need to start thinking about upstream towards enterprise. If you're servicing enterprise only, you've got to think about going downstream. If you're selling to only one vertical, you've got to think about expanding to other markets. It could be international. That's what we thought heavily. And that's where a lot of our efforts were with bringing PlanGrid to international markets to increase— it's all about increasing TAM, right? To just like increase the potential pool of people who could use our thing and pay for our thing. International is really important. We went, we went from being used by mostly general contractors, and we had this big effort to get it down to the subcontractors. So then there's also thinking about your, like, the industries within your vertical, if you service a vertical. And but if you have a horizontal business, I would imagine you'd want to get really crisp on verticalizing the different, you know, if you have a horizontal business, you think about verticalizing your efforts. Healthcare became a big, another big vertical for us. It's all about slicing your business in more ways and then strategically going after those markets. And there's investment involved. You don't know if what's gonna work. So it's really important that we are testing out 3 things. We're testing out the APAC region, we're testing out the civil construction market, we're targeting electricians as well. We don't know which one's gonna hit, but we've got to go after several because that's our protection.

Super helpful.

Thank you.

Our next question comes from Anthony.

Hi, Tracy. Thanks for your talk. Really appreciate you being so raw and authentic.

Yes.

My—

there's some feedback there. My question— yeah, my question revolves around a point you made earlier on about what happened on PlanGrid of getting out of market fit, right, with not being enterprise ready. So for early stage companies like where we're at on the dot, we're an early stage company and we have a product that's kind of that can work across many segments and we're focused on one right now, which is more kind of nonprofit, SMB, size, but I do see a great opportunity in the enterprise space. And the challenge that we're facing, that I'm sure all, you know, all of us startups are facing, is you have the constant demand of trying to manage your, your roadmap to address current customer needs and so on. But you, you know, I'm trying to figure out, well, at what point do I put the energy on being enterprise ready and kind of juggling the the decisions on the trade-offs of working on that versus not working on, you know, any product enhancement that will help me drive more business in our current market segment?

Oh man, you have just asked the hardest question for every company. It's like, how do you prioritize? Because you only have so much resources, you only have so much money, or you have like no resources, money and it's like, how do you focus your energy and efforts? Okay. There should be a really simple matrix that you can just draw on a piece of paper. It's like on the Y-axis, it's level of effort. On the X-axis, it's impact to the business, to your customers. And hopefully that's correlated. If it's a big impact for your customers, they're gonna buy a bunch of your thing and then it all also is high impact for revenue in your business. So level of effort versus impact. You should be able to map everything you're thinking about working on, on that cross-section. And if it is low effort, it's not that hard to do, and it's high value for the customers, like, go freaking build all of that chunk of work. If it is super high impact, super highly valuable for the customer, but it's super high level of effort, you can only take on one a quarter if you can build that fast. You can only take on one a year. And so you better choose the best one, and you've got to think about it strategically in your role. Then there's everything else, and so it has to be an honest discussion when you're going to do it. Is it on icebox? We have this term called icebox. It's like, yeah, that'd be nice, but like we're never going to do it, but we're going to track it because it's going to come back to life at some point. You know, we, we have our own dev tools and dev processes that help us prioritize everything in between, but I'm sure you do too. So again, work on the stuff that's high impact and low level of effort first, and then you'll to get 1 or 2 gorillas that you're going to take on for the year or for that quarter.

Thank you.

Our next question comes from Simon Letchford. If you'd like to unmute yourself.

Hey guys, thanks everyone. Tracy, thank you. This is so raw and so honest. I've loved every minute.

Thank you.

We have a B2B SaaS solution that runs on Salesforce. So we are forced to be top-down. We couldn't possibly sell this bottom-up. My question is, when do we start? What would you suggest I should be looking for as an indication that it's time to move away from founder-led sales to start hiring, you know, professional marketing, lead gen, SDRs, AEs? I'm just interested in your—

Yeah. If you bring on an enterprise sales rep for B2B enterprise SaaS product in the CRM sales ecosystem, their profile is probably such that they're currently an AE or even sales manager with at least, let's say, a $600K to a, you know, $1 point something million quota.

Yeah.

So if you are at that revenue target, if you are there in terms of revenue, it means you've sold enough to meet someone's quota, which means you can pass that on to one other person. Hmm. So maybe I'd use a number in between like $800,000 in ARR.

Hmm.

You get to $800,000 in ARR, you can probably hire someone else train them up, take over those accounts or go after, you know, new accounts and then expect them— you're a founder, right? So like you're really good at selling. So my question maybe to you is how much would the average salesperson be able to sell if you were to personally train them up? Could they sell that much, what you've done to date, or would it be a little less? And whatever that number is.

I thought it would be less because we know the market so well. We've been, you know, I think it's funny the company is called Swagger Sales. So yes, we should know how to do this. I feel like I can write a playbook pretty easily. The biggest gap we've got right now is meetings. You know, every time we get a meeting with the right person, they look at it and go, wow, I've not seen that. So I feel like the playbook piece isn't the hard bit. It's just getting the meetings and then financially managing the transition to, you know, prioritizing lead gen or, or SDR or AE. So we're just trying to juggle sequencing at the moment.

I think I would think that if you're, if you were at $1 million ARR, I think it would be safe to hire at least 1 or 2 salespeople, if not more, especially if you think you can train them up and maybe they won't perform as well as you, it'll be a little bit less, but you should be able to dump your problem knowledge in them and also teach them. It'll take 3 months, 6 months to ramp them up.

And would you start lead gen or AE in terms of outside hires first?

Oh, I would, I would sell your vision, sell your opportunity and let those reps know they are also going to be in charge of generating leads. Yeah, maybe it's 60, like, you know, the basic marketing we're doing, we can probably get you 40% of the way there, but you're also going to have to roll up your sleeves and lead gen yourself. And that's not crazy to ask of a sales rep.

Very helpful. Thank you so much. Really great session.

Thank you. All right, I think we have time for one more question. Catherine, if you want to unmute yourself. And to everyone else who we did not get to their questions, my apologies. There were an unprecedented amount of questions in the chat. We really appreciate your participation. But Catherine, if you want to close us out.

Hey, Catherine.

Sure.

Thank you, Tracy. Hi there. The question was also concerning the sales organization. So at what point you start differentiating between the roles of an SDR and account executive. So How do you see it? At what stage? Roughly 20, 30 people company or by revenue? So I think of SDRs as just more entry-level salespeople. They should be more junior. Some people are naturally good at it, like they just want to be on the phones all day. That should probably be your inside inside salesperson where they're closing deals over the phone. But I think of an SDR/BDR team as just like more junior. Then your AEs are more— they're more experienced. They know how to take a lead and then get it to the finish line. I think it's less about how big it is and it's just about your needs as a company. Do you need more outbound efforts to generate pipeline? I mean, is how— like, how much pipeline do you have right now? That should be a factor in your decision, then you're gonna need— if it's not enough, then you probably need a bunch of people to make phone calls and cold call people. If you have a bunch of inbound leads, you probably need a bunch of people to get on the phone and, and do discovery calls with them. And then, then there's a ratio of like how many people do you need to close those deals and how long your sales cycles are. Um, so this is a much longer conversation. It's, it's a balance between that you want a clean funnel where everyone is constantly working. Phone calls are constantly being made. Demos are constantly being, being given.

Yeah.

Um, AEs are constantly working deals and building relationships. And then at the end of the funnel, of course, you want revenue to come out of it and renewals to come out of it. Got it. Thank you.

All right. Thank you so much, Tracy. That was by far one of our most interactive, candid, and, uh, just overall insightful conversations. We really appreciate, um, all of your insights, and thank you so much for joining us. We really appreciate it. Um, if you have not already, please check out those messages in the chat. They are so, so nice, um, and it definitely makes my day, so I'm sure it'll make yours as well. But we will be back next week with selling— the 7 things all founders should know about Sales. Uh, so please join us again next week, and again, thank you, Tracy.

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