tag:tracy.posthaven.com,2013:/posts Tracy writes 2023-01-21T09:25:06Z Tracy Young tag:tracy.posthaven.com,2013:Post/1928039 2023-01-12T16:06:43Z 2023-01-21T09:20:53Z Part II: The failure points from $5m to $100m in ARR

I had the privilege of leading PlanGrid to $100M in ARR before I stepped down as CEO and passed the baton to Autodesk Construction. I’ve had years to dissect the mistakes I have made in my first startup, and I’ve now taken my lessons learned to TigerEye.

Regardless of what industry you build for, or where you are at in your startup’s growth towards a $100M journey, there are many things that will likely fail. This post breaks down PlanGrid’s key failure points and what I’ve learned from them. If these reflections help even one founder make one less mistake, I would consider this post worthwhile. 

Our failure points: 

#1: Org structure and communication failure

As first-time founders we were too creative about organizational structure. We had a flat management hierarchy in the early years, and we bragged that we ran our startup like Star Trek — you were either in engineering or operations, and everyone reported to a founder. This was cute, until it quickly stopped working. People care about titles and career paths, and if you want to retain great people, you have to care about these things too. 

In Year Three, we tripled from 30 to 90 people, then doubled the team to 180 a year later. Those were the most painful years, because we went from a high-execution team to one that felt like it was stuck in molasses. We didn’t know how to hire giants, so we recruited several mediocre managers who in turn recruited more mediocre people. Meanwhile, communication gets a lot harder with more people, and I  did a poor job communicating the direction of the company. We had a first-mover advantage in a category we created but lost our position during these years of slow execution.

Takeaways: Be creative on how you’re solving problems for your customer — don’t be creative about org structures. Hire a great HR leader as a business partner to help recruit and retain the right team, and architect a good communication flow. And remember that A players can recruit other A players, but B players usually end up recruiting C players.

#2: Internal conflict

Our trickiest inflection point was hitting Dunbar’s number — at 150 people, everything went to chaos. Hierarchy is a factor. At 10, 20, or 30 people, everyone can report into a founder — at 150, just based on basic management ratios, there's now three to four degrees from the frontline team member to the founders.  

Not feeling like a unified team becomes dangerous when we don’t hit revenue targets or product milestones. When there is a mismatch on velocity and performance, it’s easy for those who feel like they’re performing to blame any slowdown on everyone else. There are natural tensions between sales and marketing, support and product, and product and engineering, and everything becomes magnified with more people simply because communication gets harder.

Another heartbreaking side effect with growth is that the people who helped get the company to its current success may not be the right people to grow it the next five years. 

Takeaways: Fight for your company's core values. If you don’t like the ones you’ve written, rewrite them so you can live by them. Hire and fire by these core values. Anything less will send the signal that it’s all bullshit.

#3: An executive not working out

My biggest mistake was hiring a big-public-company tech executive with a fancy resume who had never worked at a startup. And although everything in my gut told me that they were the wrong fit, I felt so underwater with work that I convinced myself that my life would suck less if they were just in the building. 

The big tech exec came from a sweet life with an established brand, big budgets, unlimited perks and fully built-out recruiting, engineering, marketing, sales and customer success teams. Being at a startup is hard in a way that is almost indescribable to anyone who hasn’t experienced it. The only way a big tech exec can be successful at a small startup is if they had been at one before, and they willingly volunteer to roll up their sleeves and get in the trenches again. 

As we grew to nearly 500 people, we would have several versions of the executive bench. The best indicator of an executive’s success is that they have already done the thing you want them to do at exactly the same stage that you are in and want to grow to. With that said, I do believe a first-time executive with raw talent and a growth mindset can be successful. In my case, at my first startup, it felt risky to be learning on the job as a CEO and be surrounded by other leaders who were learning on the job as well. Luckily it worked out for us. 

Another good indicator of how execs will be to work with is what their former colleagues, bosses and direct reports say about them. After hiring and firing several wrong VPs, I tripled the number of reference calls on any serious candidate. With over 10 references across the board — people who they have reported to, people who reported to them and their peers — you start to see a good picture of who they are and what it would be like to work with them.

Here is a brief list of red flags on an executive who isn’t working out:

1. They frequently use the wrong pronoun “I” followed by “[contribution to the company]”.
2. You dread having 1-1s with them.
3. They blame you or their peers.
4. They complain laterally and downwards.

There are certain decisions that only the CEO or founders can make.  When executive red flags show up, try to fix them quickly.

Takeaway: Always trust your gut on people.  

#4: Losing product market fit

Construction people used our software because they loved us.  If construction folks were using our competitors' software it was because they were told to. In enterprise software, the best product doesn’t necessarily win, and there is a long trail of great enterprise software under tombstones.

Although we skipped the corporate buyer completely in the early years of PlanGrid to much success ($50M in ARR), in order to get to $100M in ARR, we needed to go upstream toward the enterprise segment and build products for the corporate buyers who would never touch our core product. 

Selling to the enterprise requires a series of features and products that have nothing to do with making the end-user happy. There is security red tape that the non-user buyer cares about: RBAC, SOC2 Type 2, ISO270002, Admin Consoles, SSO and more.

As more VCs came up with predictions around mobile technology disrupting the construction industry, hundreds of millions of dollars of venture capital was poured into our competitors. Copycats showed up around the world. Within a few years the category we created became a category that the corporate buyer cared about. Our product was not built for this buyer. They saw us as a point solution, which pushed us into a never-ending feature battle against platforms. 

Prior to PlanGrid’s acquisition, in my last years of leading the company, our growth slowed to high double percentage year-over-year growth while our competitor’s growth was rumored to be triple digits. We needed additional growth levers. We pushed towards internationalizing our product. We launched two new product lines with small scrum teams and slim budgets. Concurrently, we were knee-deep in technical debt and our Vice President of Engineering quit with no notice. These were rough years. But through hard work and great people who continued to pour their heart and soul into the company and customers, we hit almost all our milestones and secured the attention of Autodesk, our future acquirer. 

Takeaways: It is completely possible to have product-market fit one year and lose it the next because the world, the market and the competition shifts over time. Always go towards where it hurts the most and try to fix that problem because it’s not going away. Looking back, it was obvious that we needed to launch more products and build for the enterprise, but we were too slow at executing on that strategy. 

#5: Life happens

I’ve come to believe that a big part of our jobs as founders is to manage our own emotions. It doesn’t matter how well we were doing; it never got easier. Life doesn’t stop just because we’re doing the hardest thing we’ve ever done before.

I remember how excited we were to get accepted into YC’s Winter 2012 batch. As we were launching our product into the world, living the entrepreneurial dream and sleeping and working out of our Silicon Valley hacker house, we were also experiencing the cruelness of life. In between demos and code commits, we greeted hospice care at our doorsteps. We watched our cofounder battle, and ultimately succumb, to cancer at age 29.

As our team grew to hundreds of people worldwide, it felt like sad stuff was a constant: family getting cancer, partners and parents dying suddenly and children getting terribly sick. This is the human condition. It bleeds into our startup journey, because it's impossible to separate our personal lives from our professional ones. The best we can do is to be as generous as we can for our teammates.  And sometimes just being by their side and witnessing their loss is enough. 

Takeaways: Life is short and hard even for the most fortunate of us. And that’s why, whatever you have chosen to work on, it has to be worthy of your time here. Because if you have any success at all, it will take up at least a decade of your life. And if you’re really lucky, you get to work on it for multiple decades. 



This article was previously published in TechCrunch+  last week. It’s the second post of a three-part series focused on lessons learned from my days leading PlanGrid. Part one is here. The last post will be about what I discovered during the $100m ARR to acquisition period — stay tuned.

Writer's note, essay has been updated to "B players usually end up recruiting C players" after receiving good feedback from the community.




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Tracy Young
tag:tracy.posthaven.com,2013:Post/1892235 2022-10-18T15:26:57Z 2023-01-21T09:25:06Z Part I: Founder-Led Enterprise Sales, Zero to $5M in ARR

In 2014, I drove through Sand Hill Road pitching a profitable construction software startup with five million dollars in ARR and zero sales people. We received three generous term sheets within forty-eight hours and closed a Series A a half-day later. This post summarizes how we led sales as founders in the early stages of PlanGrid and shares tips that can be applied in this tough economic climate.

It is important to note that we built an easy-to-use product that solved a significant pain point. If you've already established and validated product-market fit, these tips will help you get closer to your customers and sell more effectively to them. But if you're not there yet, keep in mind that the advice I'm offering won't help you – without some semblance of product-market fit, not even the best sales leader in the world will be able to grow your company [1].

Here are five things we got right in sales:

#1: Understand how money flows.

We understood how money flowed through the companies and construction projects we were selling to.  We knew that although corporate headquarters technically had a budget for IT and software, it was already maxed out to pay for legacy solutions. Construction projects have their own independent accounting silos, so we could skip the buyers at the corporate office completely [2]. We were domain experts and had been responsible for construction budgets at our previous jobs. We knew exactly which line items we could tap into. For example, ten percent of many construction budgets was slated to “random allowances” and another ten percent to “contingencies.” We targeted our end users at the individual level, folks who have never purchased software in their lives but had jobsite buying power. Our end users regularly put $500+ charges on their credit cards for construction tools and materials to get the job done. No one would blink an eye at a $50 monthly charge for our software solution. When thinking about your customers, invest time in understanding who owns what budget and who has the power to approve purchases.

#2: Write the ten-second “wow” demo script.  

I’m borrowing from Apple here. PlanGrid was once a top-ten business app on iOS, and our software was preloaded on every demo iPad in Apple stores. We worked with Apple’s experts, who guided us in creating ten-second “wow” demo scripts to train their in-store sales reps on how to demo our software when a construction contractor, engineer or architect visited their stores. The most important thing we learned during this process was that there is a short window of time to secure someone’s attention. Don’t waste it. Everything you say and show during these few seconds needs to be high-value for your prospects or you will lose them. These ten-second scripts would become the foundation of our sales rep training program.

#3: Show up where your potential customers are.

We knew that construction folks would spend most of their waking hours on jobsites. And because they were working long hours at physical jobs, we knew they would also be hungry. We would put on hard hats and safety vests and walk straight into a construction jobsite to drop off a big box of fresh local donuts and a stack of our business cards, offering to bring better food for the whole field office team if they invited us back for a thirty-minute lunch-and-learn demo.  Another place we walked into were construction trade conferences. But in 2012, we were a poor startup with founders who weren’t even taking a salary at the time. We couldn’t afford to rent the conference booths [3]. So instead we purchased a few attendance tickets and crashed the conference. My cofounder and I would physically bump into people at the conference and ask, “Do you want to see something cool?” and proceed to demo our software. A third of these impromptu demos would result in a business card and the request for us to follow up, but that behavior can also get you removed from the event (a lesson we also learned). Crashing a conference is not for the faint of heart. It was both scary and embarrassing, but we were hustlers. Founders often have to do things that we don’t want to so the startup can survive.

When we finally earned enough money to afford renting booths at conferences, we got creative in order to secure attention. One example was Greenbuild in 2013. We commissioned a fashion student to make a dress and a suit out of blueprints, and our colleagues volunteered to wear it [4]. They walked the conference and looked like they were part of the event. People would stop and ask to take pictures with them, and in turn they would use these opportunities to demo our product.  

Field marketing was one of the most important lead generation campaigns for us. By the time I stepped down as PlanGrid’s CEO in 2019, we participated and organized over 300 events a year globally.  Obviously this was all pre-pandemic, but in-person events are starting to pick back up, so get creative if you go.

#4: Get prospects into the right swim lanes.  

Time is the only resource we will never get more of, so we cannot let anyone — especially not a random prospect — waste our time. The average contract value of PlanGrid in the early years was $5,000. We had a highly transactional, small-deal-size business in 2014. To protect time, it was crucial for us to identify which customers were at best $500 in ARR and which ones could grow to $100,000 in ARR. If it was a $200 deal, the prospect would get an email with a link to a demo, and maybe a ten-minute phone call at the end of month to nudge them to buy. If it was a 6-figure potential deal, three co-founders would show up at their front door. We would personally train them on new features that they suggested, listen to their feedback and offer white-glove-service bug fixes on the spot. Prioritize defining the different swim lanes for prospects, and identify the right teammates that need to talk to them and when. It’s also important that swim lanes evolve as your company grows, but don’t change so rapidly that you’re constantly developing new messaging and targets. Signals and data points obtained over time will tell you what’s working and what’s not. 

#5: Always know the next steps, and ask prospects for their business.  

This one is simple. After you’ve shown prospects what you have to offer, ask them directly what needs to happen for them to make a decision. More likely than not, you are their lowest priority, so make the process easy for them. Lead the customer after a meeting and tell them what next steps are. Schedule the meetings for them. Write sample emails they can forward to their colleagues. If they tell you they have all the information they need to make a decision, ask if they will buy today. What is the worst that will happen? 

Selling to the enterprise is like a never-ending fist-to-fist combat — one that lasts for decades, if you are lucky. As a startup it is important to understand that the cost of selling to enterprises is high. A good frontline enterprise sales rep makes $200,000 per year on the low end, and you may not know if they are performing for you for a full year. They will also need a lot of support from departments that may not exist at your startup yet, such as business development, pre-sales, customer success, professional services, post-sales, demand generation, product and field marketing. Enterprise buyers love their red tape (for good reason) — security and compliance, SSO, RBAC, license management, on-prem support — the list could go on.  Unless you are prepared to invest in all of these products and people from Day One, founders need to get in the ring and figure out how to fight in a way that your competition cannot. An unbelievably great team and an unbelievably great product is a good start.

I’ll be writing more tips about the journey from $5 million to $100 million and $100 million to acquisition in the upcoming months. 


#entrepreneur #founder #startups #sales #selling #customers #b2b 


[1] The foundation of founder-led sales is to make sure you have a great product that solves a real pain point.  I’ve coached and advised hundreds of startups during my time as a visiting partner at YCombinator.  When founders lie to themselves it’s almost always over having product-market fit when they do not. Their product simply did not solve a big enough problem for people to care about. So a key question to ask yourself is: Does the problem you’ve chosen to solve hurt your user so badly that they’ll pay money to make it go away? Does that problem make their job suck so much that they’ll be a champion for you and convince their boss and colleagues to pay for it?

[2] Although we skipped the corporate buyer completely in the early years of PlanGrid to much success ($50M in ARR), we would build products for the same corporate buyers in the later years because they became the sole decision-maker for construction field software. Within a few years the category we created became a category that the corporate buyer cared about. It is completely possible to have a product-market fit one year, and lose it the next because the world, the market and the competition shifts over time.  

[3] There are a bunch of add-ons from renting booths at conferences. You can get the smallest bare-bones booth for $5k, then rent the carpet for the booth for another $1k, and rent an electrical outlet for another $1k — and a table and tablecloth might cost another $1k. 

[4] The original blueprint suit and dress in 2013 worn by my former PlanGrid teammates and good friends Alexei and Leslie.

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Tracy Young
tag:tracy.posthaven.com,2013:Post/1877476 2022-09-08T12:27:14Z 2022-09-09T13:53:41Z Why I Started TigerEye

I started a new company called TigerEye. We’re building a sales solution that will help companies make better strategic decisions. It all sounds vague because we’re in stealth.

I want to share why I am building a new company.

After I ended my watch at PlanGrid and Autodesk in 2020, I got to work at Y Combinator for two batches. Founders would ask me questions about a problem they were experiencing, and I would answer them by sharing PlanGrid stories, expanding on the things we did right, things we got wrong and things I would do differently if given a second chance. 

Everyday I spoke to smart and hungry founders and learned about industries I never even considered. I was energized by the small population of female founders disrupting consumer and health tech, but female founders building enterprise technology were scarce.

During this time, millions of women would exit the workforce to care for their families as the COVID-19 pandemic forced schools and day cares to close, driving an increase in gender disparities in the U.S. workforce. I thought about the father chasing his career while the mother was left chasing dirty diapers. I thought about the families who need to juggle jobs while caring for vulnerable or senior family members. I grieved over how a virus exacerbated our non-existent support structure for women in the workforce. I thought about how mentally and physically challenging child care and elder care is and how rarely it is openly discussed. All of it made me livid.

I took that anger and focused on building again.

Normalize women in (enterprise) CEO roles.

I’ll buy you a beer if you can name from memory female CEOs in tech on all your fingers. The people who have defied the odds and paved the way for women in enterprise today include leaders such as Carol Bartz, Ginni Rometty, Meg Whitman, Shellye Archambeau, Therese Tucker and Ursula Burns. There are a few B2B female CEOs today doing incredible work and inspiring us to build, but females in top executive positions still remain few and far between. The first step to change is acknowledgement, so let us acknowledge that in 2021 female founders secured only 2% of venture capital in the U.S.  

Magic occurs when something that we previously believed to be impossible happens. 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.”

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.

And 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.

Businesses need to run better.

We’re in the middle of multiple irreversible world crises. All businesses need to figure out how to build better and faster, with fewer resources and more compassion towards people and our planet.

After stepping down as PlanGrid’s CEO in June 2019, I helped with integration efforts into Autodesk. We replaced PlanGrid’s business point solutions to deploy the “winners” in enterprise software. I saw firsthand what using these business solutions did to our team — it slowed us down.

The most surprising lesson I learned from building PlanGrid was that the best product doesn’t necessarily win in enterprise, but those with the largest sales team will. Even with a meaningful outcome, we 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.  

There is low-hanging fruit across the board in business software. And since we’re experts in building mobile enterprise software, why not help other businesses eliminate some of the bullshit so they can focus on building a better company for their team, their customers and the world.

Every day, I get to work with — and learn from — colleagues and customers from all walks of life, from Boomers to Gen Z. I refuse to believe that the TikTok generation and future leaders will still be deploying legacy solutions two decades from now. There is simply no way they’ll stand for it. 

If you’re in sales and want early access to TigerEye, join our waitlist


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Tracy Young
tag:tracy.posthaven.com,2013:Post/1622273 2020-11-28T20:43:30Z 2023-01-15T16:00:37Z The Truth About Starting a Startup

(I wrote this for YC’s Future Founders Conference for Women. I’ll add the recording when it becomes available. The actual talk I gave on November 18th should include bonus streams of unconscious thoughts and cursing, in case someone is into that.)

My parents were refugees of Communism. Wherever the line was between being poor and being homeless, my mom and dad lived just right above that line for many decades. Growing up, I watched them work seven days a week without ever complaining so my siblings and I would live a better life than they did. We didn’t have much, but there was a lot of love. All I wanted to do was make them proud to honor their sacrifice for us. 

I’m rarely the smartest person in any room. I went to a state school. I liked math and architecture, so I studied to be a construction engineer. My work uniform was a hard hat, orange safety vest, and muddy boots. While I worked in construction, I saw firsthand why projects are so often behind schedule and over budget. We built PlanGrid to solve the problem that we experienced in the field.  

I grew up at PlanGrid. It was the most beautiful thing to me. I loved it completely with all my heart, to an unreasonable and unhealthy degree, and I think it has to be that way for startups to work.  

When I look back at our almost decade journey, however inspiring our technology was, or how impressive our growth was, the happiest memories in my heart, the only ones I’ll remember 20 years from now, are always with people. It’s an incredible feeling, building something people want, seeing their jaw drop from awe at something you’ve made for them. One of our early users told us, “after 30 years in construction.. this is the best tool ever given to me.” And nothing compares to working hard with people you trust, running at full speed towards the same mission together.

We had a reputation for being good people building good software for the construction industry.  Some construction publications would refer to PlanGrid as the “Darling” of construction technology, and I remember I didn’t know how to feel about it at the time. I think I wanted to be associated with a noun that was less lovable and more fierce. But I now realize it was their way of rooting for us.

A big part of our reputation came from how we interacted with people. And it was so simple and true to who we were. We just treated others the way we wanted to be treated. We were normal, decent people who loved building things. If this is your vibe also, please don’t be afraid to show it because even in business, it resonates with people. I’m proud of the culture we built at PlanGrid. 

But as high as the high moments were, there were a lot of unhappy and hard ones. And that’s just how business is — When it feels really good, it probably means something terrible is about to happen. And conversely, if it is feeling awful, it will get better. That, or it’ll feel bad a little longer, but it always vacillates back to good. I’ve come to believe that a big part of our jobs as founders is to manage our own emotions through the emotional rollercoaster called building a startup.

And I think that’s why company building isn’t for the faint of heart. It doesn’t matter how well we were doing; it never got easier. Because as we’re trying to find product-market fit, as we’re trying to get people to part with money for our product, life continues. Meanwhile, life doesn’t stop just because you're stressed out doing the hardest thing you’ve ever done before.

I remember how excited we were to get accepted into YC’s Winter 2012 batch. As we were launching our product into the world, living the entrepreneurial dream, sleeping and working out of our Silicon Valley hacker house, we were also experiencing the cruelness of life. We watched our cofounder die at 29 years old. We watched cancer eat him alive, and there was nothing we could do to help him. We felt heartbroken, angry, and confused. I remember on so many occasions; I would turn the corner in our house to find one of my co-founders, who are all tall, strong men, sobbing in a corner, mourning our best friend.

And this is the journey. 

Because we weren’t unique snowflakes with this terrible thing that happened to just us. As our team grew bigger to hundreds of people worldwide, it felt like sad stuff was a constant: parents and partners dying suddenly, children getting sick, deeply tragic stories of life.

And it’s why, whatever you have chosen to work on, it has to be worthy of your time here. Because if you have any success at all, it will be at least a decade of your life. A decade of life where you are doing nothing but working on the problem you have chosen, obsessing over it and neglecting friends and family, a decade of barely taking care of yourself because there isn’t enough time to do anything but build.

We always had excellent health and dental insurance for our team. But I rarely used it. Not because I was so healthy or had great teeth, I just couldn’t find the time. So when I wasn’t CEO anymore, I finally went in to get a bunch of things checked out, including my long aching teeth I had been ignoring. My dentist found six cracked teeth, all from grinding at night. When he learned that I was a founder, he said, “that makes sense, cracked teeth from stress.” Stress messes up your body — and starting a startup will bring you to a new level of stress.

I often get asked about work-life balance.

I never figured it out. Work-life balance is such a beautiful concept in theory. You get to have your cake and eat it too. Let me give you a few examples of why it was so hard for us to find work-life balance:

When we only had months of runway left in the bank, there was no work-life balance. We had to work around the clock so that our company could survive. When we were behind on our big product launch, when we’re behind on our revenue goals, when we released nasty bugs to our users, or when our servers were down, there was no work-life balance. 

And then there are unforeseen conditions. What startup included Covid19 into their new fiscal year plan. Shit seems to happen often while building a startup.

And by the way, it doesn’t matter how big your company is and how fast you’re growing. There are never enough resources. Even when we got to $100m in recurring revenue, we still didn't have enough people to build and support our customers, not enough money to invest in our business’s growth.

And then there are competitors. 

Some competitors had way more of everything we did. And if they didn’t have more resources than we did, we had to assume they were working their hardest to eat our lunch and dinner. So the only thing we could do to compete was to make ourselves into multiple people, 10x if we could.  An easy way to 10x ourselves was by not having a personal life and not taking care of ourselves.

It might surprise you to learn that I’m not trying to convince you not to start a startup. I only want to properly warn you about the commitment of building a startup, so you can better prepare yourself than I did.

But I lucked out. We had picked a problem to solve that we cared about. And it turns out; it is much easier to do a good job at something that we love. I loved building tools for people who take showers at night because they reminded me of my immigrant parents and how hard they worked. I believed that if our software helped them get home to their kids, even 10 minutes earlier, it was all worth it.

I think there is a balance to everything in life. I believe that for every terrible thing that happens, there is also a good side; Even tragic things like a friend who didn’t have enough time. Of course, I would much rather my friend be alive, but the good side of this incredibly tragic thing that happened was that we got a front-row view of how short life is. I remember thinking: “How lucky I am to be alive and still have time here?” A big part of me realized then that I wanted to build something beautiful for myself and in memory of my friend. 

The only reason PlanGrid worked — was that we loved it, and we poured our hearts and souls into it. 

If you’re thinking about starting a startup and pursuing something you love, do it! I’m so proud of you. I know how hard it can be, in particular, to feel judged for how I looked, to feel judged for being a woman. And whether sexism was something I encountered or whether it was mostly my insecurity — what I felt was real, and it was hard and painful.

But I want you to look at me as an example and trust that it is possible to overcome all of that.  I’m not trying to downplay discrimination because it happens. There have been people who have said crazy things to me like: “but you’re too small to found a company”, “you’re not tall enough to be CEO”, “you’re too young”, “well you’re not too young, but you look too young”. Another CEO had advised me to “hire a professional CEO who can do my job better.”

The fact is, for every person who has ever doubted me, there were hundreds more who believed in me. They could have cared less about my gender and only judged me by my work ethics and output. I promise you there are many more good people in this world, and they have been waiting to work with you.

Building PlanGrid was one of the most rewarding, most challenging, most meaningful experiences in my life. The greatest privilege of this entire journey is the deep connections made by working in the trenches with people. Something magical happens when we trust and believe in each other on a startup journey that is impossible to do alone. It took me too many years to learn to raise my hand and ask for help, but when I finally learned to, a village of people came to my support.

I’ll close with the last conversation I had with Antoine, our co-founder and Chief Mad Scientist. I still think about it every day, and I hope it’ll be helpful for you too.

“Life is short.  Take care of the ones you love.  Don’t be afraid to try new things.  Never do anything that makes you unhappy.”


This post is dedicated to my co-founders: Ryan Sutton-Gee, Ralph Gootee, Antoine Hersen, Kenny Stone <3


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Tracy Young
tag:tracy.posthaven.com,2013:Post/1561957 2020-06-22T16:22:36Z 2022-09-12T08:42:35Z Reflections on Being a Female Founder

Not a lot is written about being a female founder and CEO. I used to believe that my journey as a startup founder was the same as any other founder's experience, regardless of gender, in that it is lonely and hard. I believed the same when I worked in construction. At the time, any questions about there being a difference felt deeply unnecessary to me. 

For example, here is my snarky answer in 2015 at TechCrunch Disrupt: “When Tracy wakes up every morning, Tracy doesn’t think ‘Oh, I am a female.’ When I wake up in the morning I think ‘Wow, I’ve got a lot of work to do. I better get showered, caffeined up, and get my ass to work.’”

For context, I am the daughter of refugees, first to be born in America. The minority part of my identity I understood well, having witnessed my immigrant parents grinding their nose to the stone without ever complaining, so their children could have a better life. I was proud to be their child. The female part of my identity, however, was hidden under plain masculine clothes and behind a stoic demeanor. I was afraid that I wouldn’t be taken seriously as a CEO and I perceived any attention to my gender as bad.

Then, when I became pregnant in 2017, my opinion changed. Women have different lived experiences than men, and not acknowledging this would be a disservice to humanity.

On the same day I learned I was pregnant, I also learned that one of our tech executives left his laptop on his desk, and would not be coming back to work. I remember the highest level of excitement I have ever felt, finally pregnant after trying for almost a year, and within a few hours, I swung to one of my lowest moments as a CEO.

I thought that I must be the worst leader for someone to just leave me like this. That night, I vomited into my sink and cried sloppily in the dark. Someone I trusted had snuck out of responsibility in the most selfish way imaginable, and my body responded with intense physical reactions. I wondered if male CEOs would have reacted this way. I wish I knew. By morning, I kicked off an executive search, filled in as leader for the department, and announced my decision to the team. One thing I learned during this time was to not waste turbulence. As part of the shocking announcement of our executive’s sudden departure, I also made a bunch of decisions that I previously lacked the courage to make and rolled everything out at once. There were major people and product roadmap changes, budget and schedule cuts all in the span of a few weeks. Our team had many questions, followed by many emotions and opinions about our new R&D direction. Some team members, including great engineers, quit.

Emotional roller coasters seem to be law in startups, and I believe managing our own emotions is a big part of the job. What I have found is that I cannot stop myself from being human, but I can practice dialing down the duration of negative feelings like anger, fear, and sadness.

When my baby belly began to show, I told my leadership team we were expecting, and by the end of day most at the company knew too. There are no secrets in a startup. One colleague told me the next day that she knew I was pregnant because she saw me eat two bagels. That conversation made me realize that team members are always keeping an eye on their founders and leaders. In some cases, I do believe my coworkers genuinely cared for me. In most cases, I believe they were evaluating how well the company was doing based on my actions throughout the day and that factored into whether or not they should answer all the recruiters’ calls.

Three months before I was due to give birth, I got a message from the CEO of a large competitor who had enough cash to acquire us. There was M&A activity in our industry, and, I too, wanted the option for our startup to become acquired. I was to give a presentation to several of their CxOs (a strong indicator that they were not just kicking the tires). In my own office, it never bothered me that my team’s eyes would sometimes wander to my basketball shaped belly during conversation, but it did get under my skin when these strangers, who I was negotiating with, looked at my stomach during this presentation. But that was mostly my own insecurities, something I would learn to deal with.

Two months prior to giving birth, we received a disappointing M&A term sheet, so we declined. There were more problems in the company that I could no longer ignore, and because there was a baby in my belly, I could not use social drugs to escape from my stress, and was stone cold sober through all of it. I needed to make another leadership change. Some of our board directors told me: “We support your decision, but let’s wait until you come back from maternity leave”, to which I obliged. Although I understood the rationality of their advice, I felt trembling anger for not being supported in that moment. I’ve also come to hate the phrase- “bad breath is better than no breath”, because it is terrible advice. My biggest regrets in business involve keeping the wrong person in the company for too long. I knew in my stomach that it was not going to work every time, I would even dread having unproductive 1-1s with them, but I would come up with excuses like- “I know they can’t stay, but I’m so stressed out right now.” The fact is, I hired the wrong person, I failed to help them grow as a leader and I owed it to my team and company to fix my mistakes.

I went into labor the same night of our first user conference. The weeks leading up to the conference, watching our whole company burn late night candles in preparation for our new product unveiling, I wondered how many male CEOs would skip their conference for the birth of their child? I assume most would. I kept reasoning with myself that if I wasn’t pregnant, there would be no question whether I’d be there or not, so I must be there. Forcing myself to parade my 9-month pregnancy, deliver the keynote, support our team, and work the halls as the host, was my way of feeling like a superwoman, which was mostly about rubbing my own ego. I arrived home around 8pm that evening, and my water broke immediately. I would hear my son’s first cry 32-hours later.

No one told me how hard breastfeeding would be. Like clockwork, every 2-3 hours a tiny mouth latched onto me for 20 minutes, resulting in raw and bloody nipples. The amount of time and effort it requires to breastfeed doesn't stop there. You'll also need to make time to eat an extra 500 calories each day, time to pump and wait for milk to slowly drain out of each breast, and then time to clean each pumping piece thoroughly.

After the M&A deal fell through, I was concerned that two of our largest competitors were coming together. I was determined to get back to work as soon as possible and fundraise a war chest to fight back. However, being only 4 weeks postpartum, I was still healing. And by healing I mean I was still bleeding from several tears in my vagina from pushing out a baby. Even something as natural as emptying my bladder felt debilitating. When my son was 6 weeks old, I handed him over to his nanny (a vetted stranger, really) and went back to work. I wiped tears from my eyes as I drove away, convincing myself that the company needed me more than my son. In reality, waiting a few more weeks for my return would not have made a difference. 

To this day, I ask myself why I rushed back to work when I wasn’t ready. And I think I was scared. Not because our business was in trouble. We had two years of runway in the bank and our interim CEO (our CFO) and the team were running the business just fine. I think I was scared of what others might think of me as a new mother and CEO, maybe because of my own insecurities, maybe because of the societal norms ingrained in me. I pressured myself into proving that I was as dedicated to PlanGrid as I always have been.

I would spend the next two months driving to VC’s offices, and down to Sand Hill Road, to secure our war chest. Despite this full schedule and constant traveling, I needed to pump milk. But I never asked to use any investor’s Mother’s Room. On some days, I would park my car on a sleepy street in Palo Alto and pump milk with a silicone hand pump in front of someone’s nice house, reading profiles of the investors in my next meeting from my iPhone. Occasionally someone would drive up, or a jogger would run by, and I would feel completely humiliated.

I’ve always hated fundraising. It's putting our hearts and souls on a platter for money and for smiling strangers to poke holes in us. However, PlanGrid could not have fueled growth the way we did without selling pieces of it to investors who took a chance on us. I often get asked about how it was to fundraise as a woman. I’ve heard awful stories firsthand from friends. Horrific stories like being offered a term sheet if sex was involved. Thankfully, that was not my experience. I believe I am in the minority.

I think there are bad apples in every industry, but it is especially prevalent in those that control so much money and power. We tried to time all of our fundraising for when we were in a position of strength with attractive revenue growth and enough money in the bank to walk away from any or no deal. I also fundraised with my co-founders, and in later rounds with my CFO. I think it is easier for predators to target their prey when they are alone. I was never alone. 

After half a dozen no’s to our Series-C fundraising, and a few weeks before we planned on stopping fundraising all together, we secured a round. We then received a revised M&A offer to purchase our company at a much higher price.  

Our job as founders and CEOs is to maximize all options for the company and choose the best path forward for our team and customers. A part of me wanted to stay CEO of PlanGrid forever. I grew up at PlanGrid. I watched one of my co-founders die of cancer during PlanGrid. I married another one of my co-founders and we became parents together. My self worth was completely tied to the company. PlanGrid gave me purpose and fulfillment. However, in fall of 2018, the best option for our company given the competitive and market risks, and our own internal challenges, was to sell our company to an incumbent with obvious technical synergies, for over 10x multiple on revenue. So we did. The day we announced the sale to our team was the most frightened I have ever felt in my life. I was afraid that I had let our team down by selling, but they didn’t see it that way. That night, we celebrated together.

My contract with our acquirers was set to last 18 months. The plan included 12 months to run PlanGrid as a standalone company (or try to), and 6 months to fully integrate into the mothership. Everything that made me a good founder, made me a terrible employee at a public company. I was used to having complete autonomy in leading PlanGrid. As a startup, we would make changes quickly. We could take dozens of small bets and risks every quarter. Depending on those results, we would abandon or make larger bets in the direction that was working. Risk taking is much more limited at a public company, in part because they must report to Wall Street every 3 months. At a larger company there are also more dependencies, it felt like I couldn’t sneeze without asking permission from the heads of five other departments. New leadership took good care of our team and products, and people were nice to me, but it was obvious I was unhappy there.

A few months after the acquisition, I became pregnant for the second time. And shortly after I found out, I also had a miscarriage. While with my team, I felt it slip out of me. I went to the bathroom and I knew exactly what it was. I walked back out to the group pretending as if nothing happened. For the next few months, I grieved, fighting back tears almost every hour.

The women's experience can be really hard - I went through infertility, pregnancy, birth, miscarriage all the while trying to balance being a good leader, good mother and good partner. To top it all off, I felt I had to be a version of what I thought a good male CEO was, so that I wouldn’t be judged or treated differently. It would take me years before I realized how delusional I was. I became a better and happier leader by being honest in who I was, even if it meant feeling raw heart pounding discomfort most days. And it turns out, my female identity was much more important to me than I realized going in.

The tech industry has a long way to go toward gender equality in the workplace. The first step to change is acknowledging that things need to change.

I am no longer employed by the company that acquired us. I posted on LinkedIn that my watch has ended. I have much more time to read about the world we live in and who is controlling it. When I look at leadership across companies, and leadership across countries, it looks predominantly male. And that means our world is missing out on a lot of hardworking, self-identifying women who can improve it. The problems of our time are overwhelming and massive. In the midst of a pandemic and too many crises, our women leaders are proving they are great at leading and getting things done.

I want to see a world where men and women, who make up equal halves of humanity, also make up equal halves of leadership. When that happens, I wholeheartedly believe that the entire world will benefit. We owe it to our sons and daughters to work hard to get there.


Thank you to Nina Achadjian, Maria Alegre, Andrea Barrica, Ralph Gootee, Kat Manalac, Madison McKay, Kristina Milian, Sarah Moon, and Strat Sherman for reading drafts of this.


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Tracy Young