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Awaken* newsletter

June 13, 2024

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Tracy Young is a founder who has been on my radar for a long time. Beyond the fact that she is a successful exited founder, having sold PlanGrid to Autodesk for just under $900 million, Tracy’s family–like my own father–immigrated to the United States following the Vietnam war. With one major success under her belt, Tracy is going for a second, having recently founded a new startup named TigerEye, which focuses on AI-powered strategic planning. I sat down with Tracy to chat about lessons from PlanGrid, what she’s currently working on at TigerEye, and her identity as an Asian woman.

On Identity

I wasn’t the only one with a newsletter on the call! Tracy also recently started a LinkedIn newsletter titled Predictable Growth, a monthly Q&A with women leaders generating revenue for their businesses. I asked Tracy what the motivation behind starting it was, and what she hoped to see it accomplish:

Representation matters. In sales and go-to-market functions, women are underrepresented at the leadership level. However, many impressive, talented, and hardworking women have achieved the CRO/CMO level, and I wanted to hear their stories. So, it’s a way for us to showcase women and give them a platform to tell their stories and how they got to where they are. There are many great jobs in sales, but many women don’t realize that they’re available to them. Anyone can be good at sales, it’s not just men. Reaching the highest levels in sales gives women a lot of power to help out their families, help the economy, etc.

In previous interviews, Tracy has pointed out how women are especially underrepresented in enterprise SaaS. I asked Tracy if she had any ideas why this is the case, and how we can increase representation:

I’m not sure why that’s the case. But you can see it if you look at the stats or walk into any enterprise company. I would guess it’s systemic. I think it starts with the words we use for boys and girls, the way we treat them, and what is expected of them. This is part of our cultural history. One way to change that is to show what is possible. What Predictable Growth aims to achieve is to showcase all these women who are leaders at their companies. There’s no decision that the CEO is making without running it by them. We want to say: “This could be your future, if you want it”, for anyone reading, and hopefully, it’s a young woman reader.

Next, I wanted to get Tracy’s thoughts on how being an Asian woman has affected her experience as a founder:

My PlanGrid co-founder, Ryan, and I met in college. He’s been trying to convince me to start a company with him since I was 18. Being an Asian woman, I didn’t think it was possible. I brushed him off for many years. I thought, “I’m not a founder,” because I looked at all these other founders, and they didn’t look like me. That kept me from starting a company for a long time. Around 2007-2009, I remember Ryan really wanted me to apply for Y Combinator with him. And again, I told him, “I just don’t think it’s going to work.” I didn’t think other people would accept me, and I didn’t want to put myself through it. It wasn’t until Y Combinator put out a request for startups working on the exact problem we were working on that I felt comfortable applying. That request for startups almost gave me permission to apply to YC. But even when we got in, and we were making real revenue, and we fundraised, and we had real customers, and our product was getting better… even then, I still felt that founders should look a certain way. I don’t know how many years in we were before I finally realized how wrong I was.

In an interview eight years ago with Ron Miller at Techcrunch Disrupt, Tracy responded to a similar question very differently. I asked her what motivated her shift in perspective since then:

Back then, I really tried to separate myself from being a woman. I felt like that was not part of the equation. And again, it’s such a big part of me, I am a strong woman. For many years, I pretended that I wasn’t, down to how I dressed. What really woke me up was becoming a mom. Going through pregnancy and birth and postpartum recovery, and taking care of a baby, I think it was really at that point when I realized how strong women are, how strong our mothers and grandmothers are, and how strong my colleagues are. It was a disservice not to acknowledge that our journey is different. It’s not better or worse. It’s just different.

TigerEye

I asked Tracy how she came up with the idea for her new startup, TigerEye:

There’s no shortage of problems to solve in business software. If you talk to anyone who works for a public company, you’ll find a lot of outdated software still in use. After selling my last startup, I worked for a public company and got to use these expensive products that our company was paying for every year. I saw firsthand how they made us less productive and frustrated our team. Many areas need improvement, such as HR software, finance software, sales software, and everything in between, including development tools. 

A common strategy I hear from founders is that they want to start by selling to other startups, and then grow into an enterprise software company alongside their clients. I asked Tracy how she decided to skip that and go straight for enterprise customers:

I like to solve problems that I have experienced. TigerEye comes from my experience running a fast growth company for ten years. When we reflected on our PlanGrid journey, we asked ourselves a few questions: What would have accelerated growth? What would have made the difference between us still running PlanGrid today versus needing to sell? TigerEye is that product. This is a scientific tool that would have helped us grow more efficiently, be more profitable, and would’ve enabled us to be more courageous in our decision-making by providing extra validation. It’s an AI-powered business simulator. You can test out your plans before you make your team execute it. You can test out as many plans as you want and as many scenarios as you want before you bring it to the board for sign-off. Back at PlanGrid, we had a bunch of very smart people trying to generate the same thing that took months that TigerEye is outputting instantaneously now. This is the product that I wish I had to help grow PlanGrid. And this is why we are building for the enterprise. All I know to do is build things to help me with problems I’ve faced.

Starting a Company as a Second-time Founder

I asked Tracy what she thought about distribution at PlanGrid, and how that has changed for TigerEye:

PlanGrid was always mobile first. We really benefited from timing. Steve Jobs announced the first generation iPad, and we decided to start building construction software for that device soon after. We were one of the first enterprise apps to launch on all of the app stores. 

Let’s say you’re a construction person and you’ve got your new iPad or other tablet. You search for construction because that is your profession, and PlanGrid pops up as the top result. If it looks interesting, you might download it, and we had a freemium model so users could try us out. As a mobile-first company, having great SEO on the app stores was crucial for our inbound growth. That’s how we thought about distribution for PlanGrid, but that is totally irrelevant for TigerEye (although we do have a mobile version of our software). TigerEye is an enterprise-grade product, and you can’t just try it out as an individual. It is being deployed to whole departments, and that is a completely different distribution model. For many years, PlanGrid was sold on a per-seat basis. At TigerEye, we have an unlimited seat model, and it’s deployed to several teams at once, and the starting fee is five figures. It’s an enterprise-grade product. And so for us to get deployed and adopted usually takes a field sales team two or three conversations with the company, because it’s not just sales, it’s revenue operations, it’s strategic finance, and then it’s a champion at the C-suite level. It’s very different from PlanGrid’s model, where anyone with a credit card in a job site could swipe their credit card and buy PlanGrid today.

Next, I asked if she felt that being a second-time founder came with any benefits:

There are definitely benefits. For example, the first 15 people we recruited were people we had handpicked and worked with before. As a result, we were able to recruit a talented team with a strong track record and a strong work ethic. It’s difficult for first-time founders in their early 20s to attract talented individuals. The people who worked for us were our friends or recent college graduates. From our decade of experience, we’ve also seen what works and what doesn’t in terms of core values. This time, we made sure to have a set of values that we live by personally and professionally. These core values are non-negotiable and we share them with candidates we’re trying to recruit during our first phone call. We’re serious about it. Everyone says they care about their core values, but we actually hire and fire by them. 

Tracy’s emphasis on core values stood out because this was the first time I had heard a founder emphasize them to this degree. I asked Tracy why this mattered so much to her:

Through my experience growing PlanGrid to 450 employees and scaling the team to 1,300 employees post-acquisition, I got to see what slows down a team. I got to see how infighting can destroy a company. There are minor things that you can put in place to mitigate this, such as basic rules of engagement. We have a document called “Our commitments to working with each other,” which outlines how we work together at TigerEye. The document clarifies our five core values. It’s very simple, you cannot misinterpret what the core values mean. I’ll give you a couple of examples: 1) I will walk it like I talk it. 2) I will never speak destructively behind my teammate’s back. 3) If I have a problem, I will go to you and talk it out because we’re professionals and I can trust that we can have the hard conversations. If everyone follows these rules, then we’re in a really good place. That means that when there are problems, we can speak openly as a team and get through it together. We were very deliberate about the culture and work environment we were creating, especially as a remote company. I think our culture is especially important because we aren’t together every single day.  

Fostering a Culture of Authenticity

Throughout my research, a consistent theme Tracy touched on was being authentic as a leader. I asked her if she felt there are boundaries to authenticity and if it’s fine for CEOs to express fear or lack of confidence to their team.

There is definitely a line in terms of vulnerability and authenticity. It’s never acceptable to be disrespectful. Some might argue that they’re just being direct, but there’s a difference between being direct and being rude. It’s okay to question things and suggest new approaches. When I’m concerned about something related to the company, I share it with the team. I either present a potential solution or let them know that I’m working on one. This approach makes it easier to lead and get the team on board with the direction we’re heading. They may not always agree, but at least they understand why I’ve made certain decisions. If they understand, it’s easier for them to commit to the decision, even if they initially had reservations. 

To your second question, I think it is completely okay for a leader or anyone in the company to show that they are human, and as humans we experience fear and insecurity–they are natural emotions. As a leader and a productive teammate, it isn’t beneficial to dwell on these negative emotions. It’s challenging, if not impossible, to suppress these feelings because they will eventually surface. My approach is to allow myself to experience these emotions when things are tough, but also to take control and not let them linger. For instance, I might allow myself a day to experience these feelings, but the next day, it’s time to put on a game face and figure things out together. As long as there’s movement and progress, then it’s okay. Feelings like anger, insecurity, and sadness, when prolonged, are completely useless. They don’t serve anyone any good. They’re just there making everyone feel bad and that is absolutely not okay.

I asked Tracy what actions she takes to make sure everyone on her team is comfortable being authentic and vulnerable with each other:

We do this fun activity. We all take the Enneagram test. New teammates will take the test and present their enneagram results sometime within the first few weeks. The presentations are basically: “This is when I’m at my best. This is how I am at my worst. This is how I want to get feedback.” This helps us understand who we are as people because there are all kinds of different personalities, and conflict comes from two personalities at their worst coming together. If we can acknowledge and understand that might happen, it’s easier to get through it together. Essentially, it’s having self-awareness and giving your team a blueprint of being aware of who you are. 

For those who don’t know, Enneagram is a popular personality test that emphasizes how you interact with other personality types, making it a popular choice for teams. I am normally skeptical of these kinds of tests, but even I am a big fan of Enneagram, and I think it has helped me better understand myself and my interactions with others. For those curious, Tracy is Enneagram type 1, “The Reformer”. A fitting type for a person with such ambition and vision.

Shoutouts

If you are a leader in sales, RevOps, finance, or marketing, TigerEye has built a go-to-market planning tool to help you track, plan, and predict your go-to-market performance. The tool analyzes every change in your CRM using artificial intelligence to guide decisions and show you where you’re headed.

If you are interested in checking out what Tracy and TigerEye. have built, please drop her a note on LinkedIn or on X (f.k.a. Twitter) @Tracy_Young. Thank you Tracy for the interview!

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