MasterStroke with Monica Enand & Sejal Pietrzak

A MasterStroke Move: Choose Brave

• Monica Enand, Sejal Pietrzak • Season 1 • Episode 1

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Stepping into the tech arena, where the echo of male voices often drowns out the rest, Sejal Pietrzak and Monica Enand have carved out their own success stories that defy the status quo. Their conversation peels back the layers of their climb to the top in an industry where female CEOs are as rare as flawless code on the first try. Sejal, hailed as a top SaaS CEO, joins me to exchange tales from the trenches of tech leadership, from the adrenaline of startup life to the strategic moves behind boardroom doors. We get personal, revealing the struggles and triumphs of our journeys as women wielding gavels in high-growth firms.

This heart-to-heart isn't just a trip down memory lane—it's packed with the nitty-gritty of making 'masterstroke' decisions that can pivot a company from obscurity to industry buzzword. You'll get an insider's take on the audacity it takes to leap from a cushy job into the thrilling freefall of entrepreneurship. We dissect the critical role daily discipline plays alongside those bold choices that define a career. As we reminisce about the grit required to launch a business amidst financial crises, you'll find yourself nodding along, recognizing the universal dance of risk, resilience, and the relentless pursuit of that next breakthrough moment. Join us for a session that's as much about empowerment as it is about the hard-earned wisdom of two women who aren't afraid to lead the charge.

Georgianna Moreland - Creator, Executive Producer & Managing Editor;
Matt Stoker - Editor


Monica Enand:

You know, it's so complicated for women in the society because we are socialized as women to worry about more about being perfect than we are to worry about being brave.

Monica Enand :

Building, running and selling multi-billion dollar software tech companies is what they do. They are founders, board chairs and CEOs in the software and technology space, leveraging artificial intelligence. They are wives and mothers. They are immigrant daughters. Join us as they share their insights, strategies, experiences and explore important issues shaped in our world. Welcome to the Masterstroke podcast with Monica Inid and Sejal Pietrozak.

Monica Enand:

Thank you so much, Georgiana.

Monica Enand:

And I'm so excited to be here with you, sejal. When I look at your career, I think it's been amazing. You have climbed the corporate ranks and been part of public companies, private equity backed companies. You spent 13 years at active networks. I know where you climbed and rose up to be the chief administrative officer.

Monica Enand:

You then were asked to be the CEO of Dealer Socket, which Vista Equity had asked you to do that, and I also have to say that in those executive positions and in that career, I find it exciting and incredibly impressive that you have won so many awards in 2019 on the software reports list of top SaaS CEOs and not only were you on this list of who's who of the very best top SaaS CEOs, you were ranked number seven, which was the highest ranking woman on the list, which is incredible, and I know that after being a CEO and doing that for multiple turns, you decided to take on some board work and you're on three boards now, two of which you are the executive chair of, and someday we're going to have to dive into that. What is that executive chair? Because I'm looking forward to hearing about that, but I know that all of those companies are high growth, highly efficient operating companies, and I am sure there's so much to learn from all of the experiences you've had in all those places, so I'm really looking forward to it.

Sejal Pietrzak:

Well, thanks, monica. Yeah, this is a really a fun thing to do, which is to share some of our insights and so much about our backgrounds to maybe give those who are listening, you know, understanding of what we've been through, because many of them maybe going through some of the same things that we went through as they're thinking about their careers. And I'm excited to introduce you, monica. I've known you for a number of years and you've had such an incredible career very different from mine and yet incredibly successful in a very different way.

Sejal Pietrzak:

Graduated from Carnegie Mellon University in engineering computer engineering and then you went to work at places like Intel and IBM and then you gave all of that up from these big companies to start your own company, your own SAS, which is Software as a Service company and incredible successful company, where you've had three monetizations and over 15 years is approved, has grown and grown and grown, and you've worked with private equity investors, with angel investors and private equity investors and you've won a number of awards too, including being the tech executive of the year in Oregon, and it's so special and rare to find you know a founder who also is an incredibly successful CEO that can scale their business, and so it's really fun to be here with you, monica, and you on the very entrepreneurial side me having never started my own company, having gone through the corporate sort of corporate even though they were smaller companies in some cases and bigger companies and others latter and now you've sold your company and so you are doing this podcast with us and sitting on boards, and this is exciting.

Monica Enand:

We talked about doing a podcast. We didn't spend a lot of time talking about. We talked about what we wanted to achieve and I know we'll cover that with our listeners but we didn't talk a lot about the name. And then our executive producer sent us the show notes and it said Masterstroke. And I was kind of curious. You know we had some funny comments about that. What do you think about masterstroke?

Sejal Pietrzak:

Well, yeah, it's funny. I think you remember I told you that. You know, at first when I heard the words masterstroke, I think everyone's going to think of this podcast as one about older people swimming or something like that. But then, but then, to be fair, I did look up the definition of what does masterstroke mean, because she wouldn't have sent it to us that way. You know, she didn't think it was a great name for our podcast, and it is an action that is very clever and produces success. Yeah, an action that is very clever and produces success. So if you think about you making that very difficult decision and action to start your own company and produce success from there, maybe you can talk a little bit about what it's like to take a risk and like that and what did you learn from it. And you know such a big, big decision. Can you let us know a little bit?

Monica Enand:

about that, absolutely. You know, it's funny when you, when I hear you talk about a clever action that produces success, I have mixed feelings about it, because I do think there are these pivotal moments where you make decisions and it changes your life forever. And there are definitely moments that I can go back and go yep, I know exactly what, exactly when it was, I know where it was, I know what I was wearing, I know exactly what happened. I don't know if men always know what they were wearing, but I do. I remember what. I remember the moments. But I also think success is not just the pivotal moments, right, it's about. It comes in the in, the day to day habits and the day to day work. So I and I know that when I've talked with you about your success, I know you talk a lot about the different habits that you've accumulated over time, which set a discipline for you, that have taken you on your journey. So I'm excited to talk about that as well.

Monica Enand:

But yeah, I mean it was scary to going back to entrepreneurship. It was definitely scary leaving big companies and having a safe job that someone else is paying, worrying about payroll and deciding to kind of take money all out of your retirement fund and quit your job and not have any income and then take on employees where you feel like you really do have to think hard about their livelihood and their success and you feel responsible for them. The truth is, I had been around a lot of entrepreneurs I mean, it happens to be I had been a lot of around a lot of male entrepreneurs and seen them do it, and it had always been something I had admired. I just thought, wow, look at them just out there doing it. And I know that for years I thought to myself, gosh, they're just so smart and they just know so much.

Monica Enand:

And then I was working at a startup for a really successful CEO who had started his company, raised venture capital from very prestigious top tier venture capitalist and had had prior exit track record, and I thought, wow, he just must know so much. And then I got to be part of his executive team and I realized it was me that was not right about that. It wasn't that he knew things but he didn't know everything. But he was figuring it out with the right people, getting the right resources, getting people to join him, having conversations and figuring out along the way, and I think there was this moment, and I actually remember I got out of the shower I had a towel in my hair and I thought to myself wait a minute, what am I? What have I been waiting for all this time? Why do I think there's some moment at which I'm going to be ready to know everything? That moment is never going to come, and I just either I do it or I don't do it.

Monica Enand:

And if I say I'm going to do it, I'm going to do it now. And I kind of just decided and I actually, still with the towel in my hair, called him and said you know my time at this, you know, thank you so much for this opportunity and I've learned so much. But my time here is over. And I've always told you, I had always told him that someday I was going to start my own company and I said I need to start working on that right now, two weeks from now, a few weeks from now, but I tip with transition period, but I need to get on that immediately. And boy, it's been so exciting and I never look back and I'm so glad I did it.

Sejal Pietrzak:

It's hard to make those big decisions and it's funny, you remember exactly where you were when you make those big decisions in, in, in any big decision in life, and that's you know what we're talking about with master strokes.

Monica Enand:

right, just making those masterstroke moments and thinking about those you have a lot of success in corporate America and moving up the ladder. Do you feel like there were masterstroke moments or do you feel like it was accumulation of lots of little things that you did?

Sejal Pietrzak:

It is a lot of little things, but there are a number that I would say that are the similar aspect. It's about taking on similar to you something that I would look at a job description and if I really looked at that job description, I probably should never have applied for that job or I would take on a job without really understanding that I couldn't check all the boxes. But I think if you look too much into those things, rather than just saying I'm going to learn it, I'm going to do my best and I'll figure it out, that's similar to you. I was at companies.

Sejal Pietrzak:

I never started my own company, but it's still taking that chance and that risk and betting on yourself and saying, yeah, I can do it. I've never done it before, but I can do it. I think a lot of people don't take those chances and they don't say I'm going to bet on myself and I know I'm going to learn it as I get into it, I'm going to work really hard to be able to learn it. I think that's probably the biggest thing Building those opportunities for yourself, not just saying I'm not going to do it because I don't know how to do it.

Monica Enand:

I think it's so complicated for women in the society because we are socialized as women to worry about more about being perfect than we are to worry about being brave. I think that's something you and I have talked about is when we can lift up out of that perfection and not worry about the perfection and say look, we're not going to worry about people can criticize us, fine, we're not doing everything exactly perfectly. Fine, we're going to do it and we're going to be brave and we're going to try anyway.

Sejal Pietrzak:

Tell us the story and I'm putting you on the spot a little, because I know this story of when you were first raising money. You had young kids and you were going through this whole process. Talk a little bit about that and what your experiences were.

Monica Enand:

I was working for another startup and kind of realized it's like now or never, I don't know what I'm waiting for Transitioned out of that company and then spent a little time exploring and figuring out what is it I wanted to build. It was based on technology around software as a service and where software is going. I built a prototype and actually was intending to see if I could bootstrap the company. I don't know. I was pretty naive about what it was going to take to get the company off the ground. I was moving along there and then in 2008 we went to beta with a product called Zapproved in August of 2008, and then in September, lehman Brothers failed and the whole global financial crisis really started, and at that time if you kind of remember back to that time we had no idea what was happening and whether the entire financial system was going to collapse, and so it became very evident to me that we were going to have to pick one thing, be the best at it, and then we were going to have to make sure that we really nailed it and were able to communicate it. So we picked a legal application and I decided I have to start raising money because I could not.

Monica Enand:

You know, this was one of those moments where you think, okay, it's really. I had drained all of the savings that I had taken and more. Look, there were so many hard things about starting a company and I think in the beginning I really knew I had to use some of my own capital, and my husband is one of the most incredibly supportive human beings. I'm super grateful for him. I can't tell you, I wouldn't be anywhere without him. But we had agreed on a certain amount that we were going to take from our savings and our retirement and we were going to bet on me and bet on this venture and a certain amount of time where I was out of work and not getting paid and a certain amount of money. And you know, after the great recession started, the financial crisis in 2008 and it became clear that I was going to need more money, I ended up having to go back to him and basically say, I know we agreed on X, but I need more. And I did that three times and you know how was that?

Sejal Pietrzak:

how was that? I mean, I can't even imagine. I mean, first and foremost, for anybody who's listening, I think something Monica said earlier if you are young enough that you don't have a spouse, finding a fantastically supportive partner is such a key part of success at least I think so, and it sounds like Monica, you think so as well, and and I've been lucky to have that as well. But to go back to your question and still going back to your savings, you must have been so convicted that this was the idea. How was that? I mean, how do you do that? Go back I think you have three times and say I need more.

Monica Enand:

No, you have to be convicted that, like this is the thing, because you have to convince investors, you have to convince employees, you have to convince as customers that you're going to be successful, and so you do have to kind of really get embraced that like I am going to get there and that is going to happen. But that's not that there's not. I mean, that doesn't mean that there are moments. There are moments where I'm thinking, oh my gosh, I stopped working, I took my salary out of our income, I blowing through what we worked so hard, our nest egg that we worked so hard to put away. And also, because it was a great price choices, the stock market was falling and, like some of our savings, and you had two young kids exactly that I had not put through college or anything.

Monica Enand:

You know, I at that time you still don't know all your expenses are going to be, and it was critically hard. And and while I say you know, my husband was incredibly supportive he at one point had to say, like I know you feel like this you just need 25k more, and 25k more, and 25k more. But are you sure that's really right, that you just need 25k more, because maybe you're gonna have to solve this some other way. And that's the moment at which I thought he's right, I have to go out and I have to raise capital and I have to actually fund this company and do it. And that started me on the journey of raising capital, talking to angels, kissing a lot of frogs, to find my princess as a woman in 2008, 2009, raising capital, when I would go to these coffee meetings because I did have young kids I realized that three out of the four times I met with a man, most of the angel investors were men. Actually, I only had one female angel investor, two actually out of how many do you think?

Sejal Pietrzak:

how many meetings do you think?

Monica Enand:

I had easily 200. And you know most of the men asked me fairly early in the conversation who was taking care of my kids. And you know there were times that made me mad. There were times where I would make a joke and say like oh, was I not supposed to leave them in the car, like you know, or just try to try to kind of blow it off Like what a ridiculous question, like why are you asking me? Do you ask any men that? You know I never did that.

Monica Enand:

But it also kind of told me like who was going to see me the people that didn't ask me those questions and started asking me quickly about the business and what I was doing and what the opportunity was. And that's when I knew like you were the right investor for me and I was going to invest more time and energy. So in some ways, you know it was annoying for sure, and something that probably men don't have to deal with, but it really did help me in the end figure out who do I want to partner with and who do I want to be part of this growing company. How do you handle that? You mean where?

Sejal Pietrzak:

you know where you don't have the choices to pick someone that didn't ask you those questions.

Monica Enand:

No, I think it's really hard and I think when you're being an entrepreneur, you know you can kind of quickly say, all right, I'm not spending time with these people, I'm going to move on. But I do think and these might be one of those pivotal moments is the people that you spend time with at work. You know there's this old adage like you are the average of the five people you spend the most time around. But I actually think, like you have to keep high standards for all the people that you're around, because it's not necessarily an average. Like it might actually be the least common denominator of like who you spend time with that can bring you down, because one person who kind of has a negative attitude can bring you down.

Monica Enand:

I know it's happened to me, it's happened in teams that I've been a part of, and so I think it's being really careful. But you're right, there are lots of times where you don't have those choices and you can't curate exactly the list you can. You want, and I think you know the important thing there is to sort of role model and be the person that you want everyone and hope that, like you're having an influence on those people and calling out behaviors in, hopefully, the most humorous and delicate and gentle and kind way that you can, but calling out behaviors that are not I was going to say that are toxic but are sort of not productive for you or productive for the people around you. Yeah, I totally agree. I know you've probably been in a lot of situations where you couldn't curate the group and you had to deal with people. How did you deal with?

Sejal Pietrzak:

it. I think a lot of it goes back to just having confidence and knowing that you're good, You're going to work through it and the people that and I think it's true, you know, trying not to be around, the people that maybe don't understand or don't care to understand diversity and different types of decisions of. I remember hearing someone say it may not work for you, but that's what's worked for me in terms of how I've lived my life, in terms of the kids and, you know, working full time and all of the stuff that you and I have both done and the decisions we've made.

Monica Enand:

You know you said that we get asked, and I've been asked this in a number of speaking events. You said if there was one thing you could tell your younger self, what would it be, and I think, honestly, this is that thing. For me, it's who you spend time with and how you allocate your time. Who you give your time to matters a lot. You know, I realized that if you can spend time with people who are positive, excited, ambitious, want to talk about ideas as opposed to talking about I don't know people or TV or you know, they really want to talk about bigger ideas, because I think that is the key. Like, for me, the happiest moments of my journey in my career have been the feeling that I am with a group of people and doing something that is bigger and more important than just myself, and I like being around those people. I feel like we're working hard together and we're doing hard things and I look back and go, wow, look at what we accomplished those. That's the biggest amazing reward for me.

Sejal Pietrzak:

I mean, and what's interesting is that starts even from when you're a kid right, whether you're on teams or whether you're in band or if you're whatever it is that you do, and knowing that together you're building something. And then it goes on throughout your career as well. Why are we doing this? Why did we create Masterstroke to begin with? You were talking, we were talking about our childhoods a little bit and our growing up, and one of the things that at least I think many of us didn't have growing up was someone that we can see out there, who's been there, done that become a CEO as a woman, someone who has experienced some of these struggles, some of these failures and how they've picked themselves up.

Sejal Pietrzak:

We didn't really have a lot of that kind of mentorship growing up, and things are just changing now. You see a lot more women, you see a lot more minorities, a lot more women of color getting the opportunities and taking those challenges on, and now you and I have gone through lessons for business for the last 30 years and it's important in my mind to be able to have to give back to people who are looking at these, looking at their future, looking at their careers and thinking about. Well, I wanna see people who have done it, who look like me, who think like me, who are me, or I wanna look at how did they handle this struggle, because sometimes if you're having trouble getting out of bed or picking yourself off the floor, if you could just remember a little bit that, hey, I'm not the only one dealing with this. There are lots of other people have done it and guess what. They've moved on and they've been successful.

Monica Enand:

I'm just doing it for me, by the way, just my own. What do?

Sejal Pietrzak:

I do.

Monica Enand:

No, no, no. Actually, I think a big part of it is pay it forward. I absolutely know that I did not get here alone and that there were so many people who inspired me, advised me, guided me along the way, so I absolutely wanna pay it forward to anybody who can take any inspiration from the things we talk about. But, to be honest, I sold the company in February of this year and I have spent the last six months kind of reflecting and with a little bit of space and calmness, being able to kind of process the journey that I was on. And I'm looking forward to doing that with you and sort of getting real about what that journey really was and what did I really learn. I think it's gonna be, I hope, a benefit to other people, but I think it's gonna be a benefit to me as well, just kind of making sure that I'm kind of fully processing and understanding what I went through, and that's a big part of it. So I think these kind of real stories are very motivating for me to kind of share with you and share with our listeners. All right, well, until next time. Thank you all for joining us.

Monica Enand:

I'm Monica Inand.

Sejal Pietrzak:

And I'm Stagiel Pietrazak, and thank you to our executive producer, georgiana Moreland.