Episode 05

Normalizing women & mothers in leadership

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Women make up 42% of the workforce, yet only 32% of senior leadership positions are held by women.

The representation of women gets even smaller when you look at the C-suite: As of this year, 10% of Fortune 500 CEOs are women.

This data doesn’t take into account how many of these women are parents, but anecdotally we know it’s even lower when looking at mothers in leadership as a subset of all women.

To be blunt: these numbers are bad. We need to - and can - do better.

And while the lack of female leaders is disheartening, there are many women who have prevailed against the odds. Sharing their stories is a small but important step to continue to advocate for women and mothers in leadership.

In today’s episode, we welcomed Tracy Young - a female founder and mom of three - to the podcast to share her story.

Tracy successfully reached $100M annual recurring revenue before selling her first company for $875M in 2018, and has since raised $35M in funding for her second company while she was 8-months pregnant.

She shared her experience with motherhood, being a successful businessperson and her take on why we need more women and mothers in leadership - as well as what we can do to normalize it.


Disclaimer: This podcast transcript is autogenerated and may contain minor errors or discrepancies. 

Allison: Hi Tracy, I am so excited to have you with me here today. For many, many selfish reasons, I saw a lot of my story in your story as I was looking through your history.

And I should say what I hope is my story since you have accomplished so much more and done so many wonderful things while also building your family.

And I've also read a lot about how incredibly vocal you have been about supporting mothers, parents, women in management and in leadership in general, and especially as entrepreneurs.

We know that you started PlanGrid in 2011, so you built the business almost to the sale before becoming a mother.

Can you tell me a little bit more about what that experience was like once you began that family building process as you were trying to negotiate funding slash a sale to Autodesk and then sort of walk through what that experience was like?

Because I personally cannot fathom selling a business going through late stage fundraisers while also becoming a parent for the first time.

Tracy: So I think I was in my early 30s. I'm running Plangrid. It's the first company I founded. I was a construction engineer by trade. And every day I was in the biggest job I had ever done before. And I came up with all these excuses of why this is not the year where I'm gonna get pregnant and become a mom, because there's just too much work to do.

And I remember having this conversation with my friend, Maria, and I was like, you know, I think I'm gonna go freeze my eggs. And Maria, at the time, was also a founder and CEO and a mom.

And her advice to me was, look, if you want to be mom, go be mom. Why delay it? It's never the right time. You think I was ready for these two kids? Like just go, just go get knocked up. Go try it's going to take time. She was right because it took me a year to get pregnant.

And you know, it's like month over month when my period came was like, ah, what's wrong with me? Why can't I get pregnant? What's wrong with, you know, I started to blame my husband.  What's wrong with you? Nothing was wrong with us.

I think we were just way too stressed out for that to happen, but it eventually happened. And this is, this must have been 2017. And PlanGrid's at the stage where at our board meetings, we were looking at, you know, how is the company gonna look like in the next three years? Are we gonna take this company public? And around the same time, Autodesk called us and said they were interested in acquiring us.

And so around this time, we're entertaining conversations with Autodesk. Fast forward a year, it would take a year for negotiations to get through. And the deal would fall through for various reasons several times. And we knew we needed to maximize all options for the company.

And so after I had my son in 2018, we're still negotiating with Autodesk, the conversation's still continuing. We made a decision to also fundraise a Series C. Leo was like six weeks old and I went down to Sand Hill Road and I was so scared, I'm so petite so I’m wearing a baggy sweater and like it's really hard to see that I had just had a baby.

But I was breastfeeding at the time and I was so scared to tell these VCs I have this newborn at home and I need to pump milk between these meetings. So I’d sit in front of someone's super nice home in Palo Alto, and I would just use a silicone hand pump and pump milk. I was so sleep deprived and forgot to bring the refrigeration kit.

And we secured a series C term sheet, and then a few months later, Autodesk, we came to a deal that we could sign with Autodesk.

Allison: Wow. And so you started to try to get pregnant. Was there a moment when you found out you were pregnant where you thought this is bad timing or at that point had you just said, we're doing it?

Tracy: You know when it rains, it pours. The day I found out I was pregnant with Leo, and again, this has taken a year. I was so happy. Best day of my life. And I go into work and I got an email from my VP Engineer who said, my laptop is in my desk, my keys are in my desk, I'm not coming back.

And I remember calling him immediately and saying like, have you heard of a two weeks notice? Like we had a one-on-one yesterday. Why? Why are you doing this? Am I that bad of a leader that you just have to bow out like this?

And so you can imagine the emotion swinging to a very low moment in my career and having to clean that up and keep the team together in a time where I think a lot of us felt, especially the engineering team, felt like they were abandoned. I mean, their leader just left without any reason. Lots of reasons, of course, but didn't have the courtesy to talk about it or have the courage to talk about it.

Allison: Yeah. So after you then signed with Autodesk, I imagine you stayed on for a certain period of time with Autodesk after that. Was it more, and now I'm projecting my own experience with motherhood, but…, I also have three children, and I’ve found when I've had my children in moments of really extreme stuff happening at work, I almost find that I like to delay dealing with the motherhood changes.

Like I just can't imagine going through all of this and welcoming a child for the first time. Was there a moment after you sold where you felt like you could take a deep breath and focus a little bit more? Or is that not at all your experience? Is that me totally projecting what I felt?

Tracy: There's just new problems that come up. There was, there was these, this deep feeling of malaise in the company. And partially it was because we're now being jammed into a completely different culture. Partially there's a lot of unknowns about, okay, well, you know, Autodesk just acquired three startups and jamming them into this other startup they had bought a few years ago. So with four marketing leaders, who's gonna be the leader for this new construction curve? So there are just a lot of unknowns and we just had a set of new problems they hadn't seen before.

And the goal was obviously retention of the team, but 40% of the team would leave within 18 months. And that's how much turnover we saw. It's very depressing.

Allison: And then you ended up going on to Y Combinator and eventually starting your current company, TigerEye. Can you walk through a little bit when you added in the second and third children in the mix there? And did you think, we're just doing it, this is what we want. And when they come, they come.

Tracy: Yeah, yeah. So after the acquisitionI was actually supposed to lead PlanGrid's product line as CEO for a year, but it became very obvious within the first quarter that it just didn't make sense. We needed to integrate ASAP and integrate our teams so that customers wouldn't get calls from four separate people from different product lines.

And so within six months, I found myself really without a job. I mean, they very much wanted me to be this cultural leader, but I wasn't responsible for anything. I mean, it was like, I think my official title was VP of strategy. And so I tried to tell my general manager, like, this isn't a real job. Y Combinator is asking me to help out. Can I work? And she said yes, just stay here, go work with her. So I had two jobs and then I got pregnant with my second child, which was great.

And I eventually left Audodesk and worked at Y Combinator, very pregnant, then COVID hits. And so everything went into lockdown and remote. And then I had a COVID baby. Yeah. You know, I had the full birthing with the mask and my husband had a mask.

Allison: Same.

Tracy: There was this moment where my husband's like…are you sure you don't want the doula in the hospital with you? And I was like, no, man, you're going to be there with me. You're not getting out of this.

Allison: I know. That was, I mean, even thinking back about giving birth, wearing a mask, it was so scary because nobody knew how dangerous it was or was not for pregnant women, for the baby, etc.

Why then? I'm curious to hear more about how you ended up starting TigerEye. I also have a particular passion around women in sales. So I want to talk a little bit about that as well, but maybe share a little bit about TigerEye and how you came up with the idea and what that looked like to transition.

Like, were you just itching like crazy to become a founder again and you just could not wait? Or how did that come about in the midst of all of everything else that was happening in your life?

Tracy: You nailed it. So…I just have to work. It's part of my personality, very intense that my family doesn't need 24/7 and driving everyone crazy. And I think startups reward the founders who are this intense and obsessing. And no one would ever question why a founder is arguing over pixels or arguing over words. Startups allow for that. So it's a place where I feel very comfortable being myself. And I just like working.

When I left Y Combinator to basically go into maternity leave and be with my second child - and also, I guess, Leo was home too. So being with both of them - I'm also married to my co-founder. We just ended up spending a lot of time dissecting every mistake we had made at PlanGrid.

And what happens with that is you just start wondering if you could do it better next time. Have I actually learned anything, especially going back to Y Combinator after my second was born and my husband was working for Y Combinator too? There's a couple of things at play.

One, we were very much itching to start another company, just out of curiosity. Did we learn anything? Can we build a better company? Did we get really lucky or is luck correlated to hard work?

Allison: Right.

Tracy: The second thing at play was funding hundreds of companies, getting to meet thousands of founders who are incredibly bright and smart and ambitious. And over and over again, Ralph and I wondered where all the women were.

Millions of women had left the workforce because of COVID to take care of their children, to take care of their families, and many of them still have not returned back. And it was, you know, maybe the feminists in us really felt strongly that we can talk about diversity issues all day long, but the one thing that we can change is ourselves and us starting a company with a female CEO and a female founder. Just one more unit to the statistics in the positive direction.

Allison: Yeah, which is interesting because TigerEye is sales enablement, right? And sales is also a space that, I don't know what the stats are at entry-level sales, but as sales reps get more experienced, more senior, there is a very low percentage of representation of women in sales, which is something that I've become very passionate about because I think a lot of that does come back to parental leave and how we don't pay sales reps their comp, which is oftentimes 50% of their salary or their take home pay when they go out on parental leave.

Have you learned more or gotten more into the weeds of women in sales or are you more focused on women in leadership, management, entrepreneurs?

Tracy: Yes, it has, naturally just because of the bad statistics, right? And it's so interesting because anyone can be good in sales and it's a great career for those who are willing to do the hard work and willing to just every single day get better at what they do. And it pays well and it gives a certain type of flexibility that a desk job doesn't get, right?

I knew sales reps, men and women who would, you know, some of them would wait till like the last month of the quarter and how to make it to their number. I knew people who would front load all their work, get to their number and sort of take a break and a vacation the last week.

And the flexibility for those who can get the work done in a small amount of time is incredible. I don't think any other job allows for this. And it pays well, especially as you move up into the management positions.

But as you look at the leadership and even front line, second line, third line management, there are very few women. And it's crazy to me because if I was a sales rep, I would want to report to a frontline manager who's a woman. I just feel like they would be able to be a more compassionate leader.

Allison: There are also some stats and I almost hesitate to say this because I don't know them off the top of my head, but I've read that overall, female sales reps do outperform male sales reps. Like there have been actual studies on this and yet there just aren't that many women in sales. What do you think the problem is?

Tracy: You just don't know what's available to you. It's very, you know, traditionally, you think about salespeople, you think about Glengarry Glen Ross, and that is a culture that no talented women would ever want to work for.

And I believe that is still true, but it's sort of this dying culture today. Yeah. Gen Z coming into the workforce, millennials are in the workforce, and I just don't think these generations are going to stand for anything less than a good culture.

We need it to be diverse. We need it to have more perspective, we need it to be smarter. So I care about getting more women into sales because I think these are great jobs where they can not only contribute to our economy, pay taxes, but it's such a good job that they might be able to also take care of their family in a way other positions might not be able to.

I feel deeply passionate about seeing more women in leadership, mostly because of our world events today. What if half of our leaders were women. Would it be good for the world? I'm going to bet it would be, and I would like to see that in my lifetime.

And then more than anything, I want to see a strong economy in the U.S. And the only way to see a strong economy is if 50% of the population is contributing. Because when we have a strong economy, it means people are doing well. Their livelihoods are doing well, right?

Allison: Yeah. Yeah, and I oftentimes get asked like, what is the biggest thing that would help more women, especially continue to thrive in the workplace? I personally think it comes down to childcare. If I could figure out an answer to that, I would probably be a billionaire. I think it's a really complicated problem that probably has to be dealt with at a political level, unfortunately.

Tracy: Oh my, I would love to see universal quality childcare and like…let's invest in the parents, let's invest in the next generation. Because  if you don't have childcare figured out, you can't work. And most of the childcare duties ends up falling upon mom, which means we are taking women out of the workforce.

Allison: Yeah, I think it is like the number one thing that if we could figure that out and it's not gonna be a startup that comes up with something that solves this problem, I think it has to be, yeah, universal childcare or something, you know?

Why does everyone celebrate when their child gets to the age of kindergarten and it's free? We  shouldn't have to wait five to six years to feel like finally, finally, we can, you know, focus on ourselves and not spend so much of our income on childcare.

I wanna shift a little bit. You fundraised for TigerEye while pregnant, I think actually quite pregnant later in your pregnancy. I read a piece that you wrote about how you, I think got the term sheet and then told them that you were pregnant. You also told your board when you were around 20 weeks pregnant.

I also fundraised and told my board for Parentaly when I was pregnant. So I'm curious to hear your perspective on the sequence of events, how you decided when to disclose and what that felt like?

Because this is actually one of the biggest questions we get, not from obviously entrepreneurs, but from, I would say, pretty much every woman who is pregnant working. They struggle with when do I disclose that I'm expecting a child.

Tracy: Yeah. I was very fortunate. I was an employee of YC for a year. And they asked me to stay after. And it's just like, you know, I don't think VC is for me. I think I want to found another company. And Ralph, you know, same thing with Ralph at the time. And Michael Stiebel came back and said, well, can I learn more about what you guys are building?

And then we told him in like a 20-minute phone call, he was like, okay, well, can YC invest? And I remember thinking, has he forgotten that we're pregnant? Like I'm eight months pregnant right now. He hasn't forgotten, of course not. And so many of our meetings are remote and through Zoom that you're like, maybe they just have forgotten and they, you know, it's because they can't see my big belly through the screen.

Yeah. But no, they knew and they were totally fine with that. They're like, you know, we have kids too. And I was very grateful for the partnership there for trusting us.

Allison: I think it's really interesting because our business is about going on parental leave. And so one would hope and expect that our investors would very much embrace this. But I also struggled with a lot of infertility throughout my childbearing years. And we really wanted a third kid. We thought it would take us forever to get pregnant. So we started, got pregnant the first month. I mean, we were just absolutely shocked. We had used fertility for the first two. So it was like, what is going on here?

And that was right as I was starting to raise my seed round. And so it was also really early. So I almost felt like, okay, good. I don't have to tell them because, you know, based on societal expectations, you don't have to tell in the early days. And then I think I signed the term sheet when I was 12 weeks pregnant. And then I told them, and of course they were fine, happy, but it was something that I, even though my company deals with parental leave, I was still nervous.

And so I'm like, are there people out there that aren't nervous, you know, when they're disclosing this fact to folks? But I also think it sets a really good example to be able to see someone like that go through, and that's why I love your story. You went through so many major career milestones while navigating something that, let's be honest, is very physically challenging and emotionally challenging as well.

Tracy: It's so funny because I'm trying to channel my male founder friends who are also dads now. Yeah. And I'm not sure if any of these topics hit their mind. No. And it's different, right, because of course it is very hard to welcome a newborn into the home and take care of your partner and  take care of yourself and be sleep deprived for the first six months of the child's life.

But it's very different growing the baby in your body and then going into the world, there's C-section and having to heal after that. Okay. But we are women and we are strong and we've been doing it for generations and we survived as a species because of it.

Allison: How did you handle your parental leave, your third one? Cause you were, you know, in an early stage business. You know, how did you, how many weeks did you take?

Tracy: I think we had like one or two contractors. So the startup basically stopped, everything stopped. And it was early enough where it didn't matter. We didn't have customers yet. We didn't beta customers yet. But yeah, it did, it did stop.

But you know, as soon as I was healed and as soon as the Baby was old enough for his grandparents, her grandparents to help out and nannies to help out. We were in full swing back at work.

But I do think remotely helps. Like I don't lose my time sitting in traffic going to an office. And we have flexible work hours at TigerEye. So we have six shared core hours. And then the last two, you work when it's your most energetic hours in your day. You know your life more than I do. Some people like to work at midnight until 3AM. That's when they're the most awake apparently and I like working at five o’clock in the morning.

Allison: Yeah, no that's great. What is it like starting a company working so closely with your husband?

Tracy: It’s non-stop projects. It is non-stop communication about the kids. We're raising kids together. And then we end up talking about work a lot as you can imagine. I very much like it. And we have experience with it.

It is very hard when founders come to me and they come to me with some statement, like I'm thinking about starting a company with my partner. What advice do you have for me? And my advice to them is don't do it.

Allison: Yeah, that terrifies me.

Tracy: As you know, relationships are really hard. Marriage is hard and it takes constant work forever. So why complicate it with something like a startup that's also incredibly hard?

But with that said, we are also an example that it can work. We have a great relationship. It takes work. It's hard. And I think we are really good founders together, mostly because whatever our skill sets are, there's very little overlap, which means between the two of us, we can take care of a lot of stuff.

Allison: Yeah, that's great. I wanted to touch a little bit on when you think about what your best case scenario is for TigerEye. And this doesn't need to be just, you know, the ultimate exit or monetization, but you've been really successful.

You obviously have this itch to go back and do it again. What does success mean to you now, this time around?

Tracy: I want to build a product that people like to use for their jobs. I want to hear them say, just as they did in PlanGrid, I don't know what I was doing before this product. And then I want to build a culture that people like working for.

And I think another lens of success is 10 years from now, if so many of our teammates at this company end up starting their own company, we would find it incredibly meaningful and rewarding.

Allison: I love that. Well, thank you so much for being here today. I find you incredibly impressive. I think we don't see enough stories from women or even parents that have been so successful in a B2B world, especially.

And so I really appreciate you sharing this and sharing some details around your family building years in tandem with building your career. So thank you so much.

Tracy: And thank you for what you do too. I think it's incredibly important.