Women Of The C-Suite: Tracy Young of TigerEye On The Five Things You Need To Succeed As A Senior Executive

An Interview With Candice Georgiadis

Make the money work and always have runway. You need to create so much value that people are willing to pay you every year for the products your company creates.

As a part of our interview series called “Women Of The C-Suite”, we had the pleasure of interviewing Tracy Young, CEO of TigerEye.

Tracy Young is the co-founder and CEO of TigerEye. Tracy is an experienced company leader with a successful track record in scaling private enterprise technology companies. Previously, she co-founded and served as CEO of PlanGrid, the leader in construction productivity software that Autodesk acquired for $875 million in 2018. During this time, Tracy led the company through years of massive growth — from inception to product-market fit, and from $0 to $100 million in annual recurring revenue (ARR) — and drove teams to execute on strategic business initiatives.

Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I am the co-founder and CEO of TigerEye, a sales software company currently in stealth. Previously, I was the co-founder and CEO of PlanGrid, a leader in construction productivity software, which Autodesk acquired in 2018 for $875 million.

I studied construction engineering management at California State University, Sacramento. I cut my teeth in the construction industry as an assistant to a foreman, then worked for a chief estimator bidding jobs, and spent another four years in the field managing construction of large hospital projects. From these experiences, I saw firsthand how complex construction projects are — they require sophisticated coordination between many different organizations. And yet, data was shackled in legacy, paper blueprints. PlanGrid got everyone on the same page across any device.

In between PlanGrid and starting TigerEye, I served as a visiting partner at Y Combinator (Winter 2020, 2021).

Can you share the most interesting story that happened to you since you began leading your company?

I’ve enjoyed bringing some of the best former PlanGrid people back to help build my new company, TigerEye. We are the sum of everyone we surround ourselves with. At TigerEye, everyone understands we are all excellent at something, and amateurs at most things. We are humble, approachable teammates, and we walk it like we talk it.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful to who helped get you to where you are? Can you share a story about that?

I would have never become a construction engineer and I would have never become a founder had I not had role models like Karen Hansen (a builder) and Julia Hartz (a founder). I looked at them and thought, “I’d like to do that too.” Magic occurs when something that we previously believed to be impossible happens.

As you know, the United States is facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

In 2021, female founders secured only two percent of venture capital in the U.S. Founding TigerEye is activism for me. Being a great founder and a great leader is not dependent on gender. But when the leadership of an entire industry is predominantly male, the world is simply missing out. As someone who often thinks about what kind of world my children will grow up in, I wholeheartedly believe that a world where at least 50 percent of the decision-makers are women would be a better world than it is today.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example.

The only way I can be successful as a co-founder, CEO and mother of three is having a partner who shares 50 percent of the child care duties with me. I cannot stress enough how important equality is in the workforce and in the household. We’ll all be impacted by sickness and aging, and we’ll need to care for loved ones at some point in our lives, which is why we embrace time flexibility at TigerEye. We devote our most energetic hours to the most intellectually demanding work tasks and take care of family as needed. We share core hours so we can be available to each other and work as a team. We only have a handful of standing recurring meetings, and we believe a five-minute phone call can resolve most problems.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

I see the CEO job as having four key responsibilities:

1. Define the vision (northstar) and mission for the company. Running a startup can be very chaotic, so having a vision and mission helps anchor us.
2. Right people on the bus at the company. I like the way author and teacher Jim Collins puts it, “If we get the right people on the bus, the right people in the right seats, and the wrong people off the bus, then we’ll figure out how to take it someplace great.”
3. Sales. So much of the executive role is selling to people they want to recruit and retain at the company, selling the product to customers and selling the vision and a chance at high return to venture capitalists.
4. Make the money work and always have runway. You need to create so much value that people are willing to pay you every year for the products your company creates.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

You do not need to know it all. But you have to have a growth mindset. I believe in kaizen, a Japanese term meaning change for the better or continuous improvement. I’m a construction engineer by trade. I knew more about HVAC systems and the tensile strength of rebar than business. The most challenging part of being the CEO of PlanGrid was that every single day I was in the biggest job I had ever held before. I constantly worried that I was letting everyone down. At times, I knew I was completely out of my depth. But I surrounded myself with leaders who were smarter, more talented and more experienced than me. I asked for help and I grew professionally and personally.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

On top of commanding daily operations, fundraising and fielding multiple M&A offers, I went through two pregnancies at PlanGrid, childbirth and a miscarriage. No male executive knows what it is like to try to navigate your business while going through these highly personal and traumatic events happening in your own body and mind.

What is the most striking difference between your actual job and how you thought the job would be?

I was an engineer by trade and I thought that company building would be a big engineering problem. But unlike engineers, the CEO’s job requires a lot more talking and selling. It became apparent early on that I needed to get good at sales.

What are your “5 Things I Wish Someone Told Me Before I Started” and why?

1. First and foremost, your team matters most. It’s crucial for you to prioritize and protect your company’s culture. You do not need to tolerate oversized egos, arrogance or cynicism.
2. Focus on solving a real problem that is worthy of decades of your life (if you’re lucky). I’ve said in past interviews, “Keep an eye out for things that are so painful it makes you wince — you want to build software to solve it right that minute.” It takes years to build a lasting company. Focus on solving a real problem that carries significant value for you and will make a huge difference for customers.
3. The best product doesn’t necessarily win in enterprise, but those with the largest sales team will. Even with a meaningful outcome, PlanGrid lost in the market. A big reason why we’re building TigerEye is to build sales software to help companies with the best products win.
4. If you find yourself at a job where you do not have the opportunity to be at the leadership level, it’s your responsibility to let management know how they’re failing you. That might be scary, but there is little to lose. Feedback is vital. If that doesn’t work, remember that time is a fixed resource, and you need to go find a company that values you. If you can’t find any company that values you, start your own company. Be your own boss.
5. Lastmover advantage is an opportunity. Leverage tech that’s only possible thanks to innovations made in recent years, and learn from the mistakes of the pioneers.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? (You never know what your idea can trigger.)

I want to see a movement of generosity and care. Our time here is very short. I believe the best we can do is be as generous as we can.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why?

Jane Goodall, because we’d have a good conversation.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.