Contact
  • HOME
  • / MEDIA /
  • Tracy Young Returns to Lead TigerEye After $875 million PlanGrid Exit, Reflects on Innovation and Identity

Awaken* newsletter

June 13, 2024

SHARE:

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!

Related Articles

Collin Hall

Stories

Celebrating Individual Narratives and Multiracial Identities Through the Book ‘Mostly Me’

In a world where the narrative of identity often falls into predefined categories, Mostly Me by Collin Hall emerges as a refreshing beacon of self-discovery.

Released on September 18 by Gloo Books, this picture book takes readers on a captivating journey, skillfully illustrating the complexities of biracial identity.

Author and Illustrator

Written by Collin Hall and beautifully illustrated by Crystal Dawn Chaffee, both of whom share a biracial heritage, Mostly Me is a heartfelt project born from personal experiences. Collin embarked on this creative journey shortly after the birth of his first daughter, driven by a powerful desire to equip her with the tools to embrace her multiracial identity.

Collin Hall is a proud biracial Korean/American based in Austin, TX, offering a voice that resonates deeply with those navigating the intricate terrain of identity.

Diverse Representation

According to the *Cooperative Children’s Book Center’s 2022 Diversity Statistics database, only 0.7% of children’s books published in 2022 were authored by multiracial individuals and focused on multiracial characters.

Collin’s Personal Journey

Collin Hall shares, “The biggest hurdle for this project was the internal identity-wrestling before words were even on paper. Having to re-engage with a part of myself I had avoided for a long time was hard, and typically paired with a good dose of uncertainty and guilt. Finding my own footing was, and is, a process, but one that put me in a much better spot to discuss multiracial identity with my own kids in the future.”

He also shared how re-learning Korean nursery rhymes was also a challenge and that it took longer than he expected.

Embracing In-Between Spaces

Mostly Me may be short and whimsical, but it carries a profound message—it’s entirely acceptable to exist within the fluid spaces of identity. It encourages individuals to wholeheartedly embrace all aspects of their heritage, irrespective of societal expectations.

I’ve got some green, I’ve got some blue. 

Some have asked, “So what are you?” 

Not quite blue, not fully green. 

I’m something new. I’m in-between.

Affirmation and Unity

Mostly Me serves as an affirmation, resonating with Collin and Crystal’s own experiences and the experiences of every multiracial child navigating the intricate landscape of identity. It instills the confidence to boldly claim one’s space in the world, reminding us all that there is no universal guidebook for this journey. Instead, it offers the comfort of shared emotions, questions, and experiences.

Within the pages of Mostly Me, Collin Hall extends an invitation to readers to embark on a profound journey of self-discovery. This remarkable book celebrates the beauty of embracing multiracial identities, encourages us to revel in the uniqueness of our individual narratives, and, above all, empowers us to find the strength to assert our presence in a wonderfully diverse world.

As we eagerly anticipate its release, Mostly Me promises to inspire and resonate with readers of all backgrounds, young and old, seeking to understand the rich tapestry of identity that defines us all.

CONNECT WITH COLLIN HALL / MOSTLY ME

Instagram: @mistercollin

Order here: gloobooks.com/products/mostly-me

Gloo Books: @gloobooks

*Independent analysis of data accessed on 07/02/2023 by Gloo Books using the Cooperative Children’s Book Center (CCBC), School of Education, University of Wisconsin-Madison Diversity Statistics Book Search (https://ccbc.education.wisc.edu/diversity-statistics-book-search/). Permission to publish granted by the CCBC 07/13/2023.

  • 3 min read

News

Hmong Legacy Market: Bridging Cultures Through Food and Community

At Hmong Legacy Market, located on Madison’s South Side, you’ll discover a treasure trove of homemade Asian cuisine. From steaming bowls of beef pho to whole roasted tilapia seasoned with herbs and chili, and delightful sesame rice balls filled with mung beans and coconut, this independent Asian grocery store offers a culinary journey.

Ze Yang, one of the owners, can often be found expertly preparing dishes like squash curry. To her, food is more than sustenance; it’s a connector, a storyteller, and a unifying force that brings people together.

As a young child in the 1980s, Ze Yang lived in a refugee camp in Thailand with her family, having fled Laos during the aftermath of the Vietnam War. In 1991, Ze Yang’s family received the opportunity to immigrate to the United States, sponsored by a distant uncle who had settled in California. Their early days in the U.S. were marked by challenges—language barriers, cultural shock, and financial difficulties. However, their farming skills from Laos allowed them to grow crops like green beans, tomatoes, and peppers, which they sold to support their family.

After six years in California, Ze Yang’s family decided to move to Wisconsin, drawn by the promise of better public schools and economic opportunities. Ze Yang’s parents worked tirelessly, holding multiple jobs to make ends meet. This experience inspired Ze Yang to become a teacher, focusing on helping immigrant children adapt to the American education system.

Ze Yang’s family thrived. They bought a house, built a family, the kids went to school, but they also wanted to pursue their entrepreneurial dream. They longed to create a space where people from diverse backgrounds could gather, savor homemade dishes, and access pantry staples from across Asia. This is why they opened Hmong Legacy Market, offering an extensive array of products, from giant spring roll skins to bamboo shoot chili oil, and from mango mochi to traditional Hmong celebratory clothing.

More than just a grocery store, Hmong Legacy Market is committed to the well-being of the community. In 2021, it partnered with Public Health Madison and Dane County to serve as a mobile COVID vaccination clinic. Looking ahead, Ze Yang envisions the store’s legacy continuing to thrive, driven by the spirit of family and the desire to improve and grow.

Featured Image Source: Madison

  • 2 min read

News

Entrepreneur Avin Ong: From Selling Hangers to CEO of Macao Imperial Tea

Avin Ong, the visionary behind Macao Imperial Tea and CEO of The Fredley Group of Companies, has carved a remarkable path to success in the world of food and beverage. His journey, from humble beginnings to leading a multi-million-dollar empire, reflects his belief that opportunities are abundant for those willing to seize them.

Growing up in a blue-collar family with limited resources, Ong’s early life was far from extravagant. His family’s livelihood revolved around assembling hangers and selling them in the bustling streets of Divisoria, Metro Manila.

Today, Ong oversees a diverse portfolio of businesses, including New York Fries and Dips (NYFD), Nabe Japanese Izakaya and Hot Pot, Café Kitsuné, and the immensely popular Macao Imperial Tea. His recipe for entrepreneurial success is built on several key principles.

Firstly, Ong emphasizes the importance of seizing opportunities when they arise. Having experienced financial hardship in his past, he has become adept at embracing opportunities without hesitation, even if he feels unprepared.

Secondly, Ong stresses the significance of understanding your target market intimately. He recognizes that different consumer segments require tailored approaches. For instance, Café Kitsuné caters to a more upscale audience, while Macao Imperial Tea targets a younger demographic through social media influencers like TikTok. 

Furthermore, Ong emphasizes the scalability of his brands, which has allowed for rapid expansion. Starting with less capital-intensive concepts like NYFD and Macao Imperial Tea, he has achieved impressive milestones, such as opening 13 new stores in a single day.

Innovation and adaptability are also cornerstones of Ong’s success. During the pandemic, while some of his ventures struggled, Macao Imperial Tea’s sales surged by over 300 percent.

Lastly, Ong’s humility shines through in his readiness to admit failures and setbacks. While he had to close some branches, he prioritized retaining his loyal team members by reallocating them to more successful establishments. He shared with Tatler Asia how he acknowledges that surprises are inevitable in life, as exemplified by his initial failure to gain admission to De La Salle University. However, his determination led him to eventually fulfill his dream of attending the esteemed institution.

Featured Image Source: The CEO Magazine

  • 2 min read

News

How College Dropout Sanjith Konda House Became a Successful Entrepreneur

Sanjith Konda House, an 18-year-old from Bengaluru, India, set off on a conventional journey to Australia to pursue a Business Studies degree at La Trobe University in Melbourne. However, he made an unconventional turn, abandoning his studies in pursuit of an entrepreneurial dream that would later become a successful enterprise, ‘Dropout Chaiwala.’

Sanjith’s bold decision to step away from academia during his fifth semester in exchange for a tea business venture demonstrated exceptional courage, a trait deeply ingrained by his upbringing.

Supported by his parents—a father employed as a mechanical engineer at a Saudi Arabian oil company and a homemaker mother—Sanjith had always been instilled with the values of responsibility and independence beyond his years.

With an initial investment of $120,000, Sanjith, alongside his friends Asar Ahmed Syed, Preetam Akula, and Arun P. Singh, set up their first ‘Dropout Chaiwala’ outlet on Elizabeth Street. Their menu started simple, offering just five varieties of chai, but they gradually began to catch the attention of students and office-goers alike.

Despite facing initial obstacles, Sanjith’s unwavering determination was the driving force behind the business’s growth. By March, they had a mobile chai truck in operation, catering to university events, festivals, and weddings. Another significant milestone came in August with the opening of a third store on La Trobe Street.

Under Sanjith’s dynamic leadership and with the dedication of his team, which included Apoorva Singla overseeing the Elizabeth store, Dropout Chaiwala expanded its menu to include light snacks. Within a year, the business generated $600,000 in sales and provided employment to 40 individuals, turning Sanjith’s bold leap of faith into a thriving success.

Featured Image Source: India Times

  • 2 min read