The Twenty Minute VC20Sales: How to Scale a Career While Scaling a Family; Work-Life Balance; Parental Leave | E1012
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140 min read · 27,892 words- 0:00 – 4:25
20Sales Guest Introductions
- HSHarry Stebbings
Team, I am so excited for this. It's been 3,000 shows. I've never done a show like this. We have the most incredible lineup of people today. So we're gonna start with the question, very simply, who are you and what's the best part about being a working mother? Jess, we're gonna go to you first. Who are you and what's the best part?
- JAJessica Arnold
Hi. Jessica Arnold, VP of Amplitude, um, in Sales Development. And I am the mom of two kids, six and three. And I think the best part about being a working mom is just having an independent life outside of my normal life, um, and then also being able to just show that's okay for my kids and just model that.
- HSHarry Stebbings
Lauren, I'm gonna hand over to you. Best part and who are you?
- LSLauren Schwarz
Yeah, great to see you again, Hari. I'm Lauren Schwarz, VP of Enterprise Sales at Fivetran. I'm the mom of a two-year-old girl. And I think the best part of being a working mother is the empathy it has built in me for working caregivers and the trade-offs that parents need to make. It really has inspired me to build a more inclusive work environment for our team.
- HSHarry Stebbings
Stevie, we said before the show, as I said, um, you know, my mother is, uh, going to learn gaming after hearing your episode. Still waiting, um, but I live in hope. Um, over to you. Best part and who are you? (laughs)
- SCStevie Case
I love it. You gotta hook me up with your mom. We'll do a Zoom session. I'll get her started. It'll be awesome, and I think she'll love it. Uh, Stevie Case, I'm the Chief Revenue Officer at Manta, and I'm also single mom to an 18-year-old daughter. And she is amazing. She's a senior in high school, so I'm definitely at the far end of the parenting spectrum in this group. And for me, the best part is really what started as the worst part, which was the forced intentionality and the focus that you have to have as a parent. I was forced to develop it as a, a single mom when she was very young, and now I think it's probably, uh, really truly one of the superpowers that I've developed because I'm a mom.
- HSHarry Stebbings
I mean, we're gonna get into that. That is a great and a meaty topic for the intro. Thanks for just dropping that one in, Stevie.
- SCStevie Case
(laughs)
- HSHarry Stebbings
Uh, Renu, your turn.
- RGRenu Gupta
Thanks, Hari. Renu Gupta, I'm currently consulting and advising for multiple early stage companies. I am a mom of a nine-year-old boy and a five-and-a-half-year-old girl. Uh, the best part about being a working mom is showing my son and my daughter what an equal partnership looks like at home. I'm two parents who love their careers but love their children even more.
- HSHarry Stebbings
I love that. Maggie, it's so good to see you again. I mean, w- e- we do message, uh, very frequently, so you've probably had enough of me by now. Uh, but, uh, tell me, who are you and what's the best part of being a working mom?
- MHMaggie Hott
Hi, Hari. Great to see you again. I'm Maggie Hott. I recently joined OpenAI, and previously before that, I was leading sales over at Webflow and as well as at Slack for... Spent about six and a half years there. Um, the s- so I'm a mom to a one-year-old and a three-year-old. And the single best part about being a working parent is being an inspiration to my daughters and really showing them that you can do whatever it is that you put your mind to. It's just been really awesome to kind of see how they've adjusted their mindset over the past couple years of their lives and that they have really no fears and go after whatever they want.
- HSHarry Stebbings
I love that. Julie, your turn. Best part and who are you?
- JMJulie Maresca
Hi, Hari. Hi, everyone. So good to be here. I'm Julie Maresca. Uh, I lead Global Accounts and Strategic Verticals at Atlassian. Prior to that, I spent, uh, six years at Slack in a variety of leadership roles. Um, I am a mother of three. I have three boys. I have qu- twins who will be nine, and a two-year-old boy who, um, is potty training, so that's- that's fun.
- MHMaggie Hott
(laughs)
- JMJulie Maresca
Um, the best part (laughs) of being, uh, a working mom, I think, is just inspiring other women who are earlier in their careers and thinking about whether they can do this or not. I mean, there's a lot of, uh, women right now that are questioning whether this is possible. So, I love that we're all here talking about, uh, how we make it work. Um, I also love that being a boy mom, I'm sort of modeling that a working mom is normal and it normalizes that for them. And Mom and Dad both work and both help out at home.
- HSHarry Stebbings
I mean, three boys and then the first like, "Hey, honey, it's twins." Ooh.
- JMJulie Maresca
(laughs)
- NANarrator
(laughs)
- HSHarry Stebbings
Ooh.
- JMJulie Maresca
Yeah.
- HSHarry Stebbings
And I thought sales quotas were nerve-wracking in 2023.
- JMJulie Maresca
Yeah. (laughs)
- HSHarry Stebbings
(laughs) That's another thing. Uh, we'll get into that. That's fascinating. Well
- 4:25 – 13:29
Balancing Career and Family: Tips and Strategies
- HSHarry Stebbings
done, Julie.
- JMJulie Maresca
(laughs)
- HSHarry Stebbings
Um, S- Stevie, we're gonna start with you on a really tough question, which is, how have you navigated your growing career while also growing your family?
- SCStevie Case
Well, the honest answer to this is, is very poorly at first. And it was really painful in the early days. You know, my daughter is 18 now. Uh, when I had her, I was in product, so I was still on the product side of the house. And I made the transition to sales when she was around two. And at that point, I got out on the road with her, and one year later when she was three, I became a single mom with full custody. So I was navigating trying to be an AE and figure out how to parent this kid at the same time, and it was ugly. Like I have distinct memories of doing a demo while I was driving her to daycare and she was crying in the backseat. And I'm trying to like explain features, and I'm in the- the tr- the, uh, driveway at Wendy's (laughs) trying to get her a Frosty and like muting in between explaining features. Like it was ugly. I did not have resources at that point in my career. I couldn't outsource stuff. I didn't have a lot of help. And that brings me back to the highlight, which is, I was forced to get super focused. So, when I was at work, I was 100% at work. And when I was at home with her, I was 100% with her. And I used to think about it as almost just looking at the- the road right under my feet. And I would only focus about two feet out in front of that. That's all I could do. And it's gotten a lot easier over time, thank goodness. Uh, life has definitely become a little bit less complex. But that focus and the intentionality that I bring to both home and work has really continued to serve me well, because the truth is...It's gonna be gnarly at times, especially when you're ambitious and you're growing your career. There are hard moments, and there are no really clean solutions. I think the women on this call navigated much better than I did.
- GUGuest
(laughs)
- SCStevie Case
Um, but you really just have to manage it day-to-day and be thoughtful and be in the moment. And if you do that and trust your instincts, ultimately I find that the balance finds you.
- HSHarry Stebbings
Well, how do you think about that, managing that balance? And also kind of when to lean in and, and when to lean out?
- GUGuest
Yeah. I do think balance is an ongoing focused effort, and you need to be intentional with it because if you're not planning ahead and not focused, your, your life or work can definitely tip the scale, um, quite significantly. Uh, so it's a practice. And, um, I like to give myself a little leeway. Um, you know, I may not balance every day or balance even a week, but, you know, this month maybe I'm traveling for the first two weeks, but I'm gonna take off, you know, a few days the last two weeks. So, I try to look at the long view that, you know, balance ebbs and flows over time. But I do think planning and setting expectations is really important. I have a global team, uh, so I don't mind getting on meetings at 8:00 PM. My kids are sleeping. But from 5:00 to 7:00, or 5:30 to 7:30, I really need to help out with dinner and getting them to bed. So, I, I set those expectations up front and, um, I feel that when I'm setting expectations and not having to make game time decisions, uh, I don't have regrets. If I'm, if I need to make a game time decision, I'm usually regretting, "Oh, I wish I could be there for my kids," or, "Oh, I wish I could be there for my team or my boss or, or my company." And then you're just distracted and not focused about whatever decision you made. So, try my best to plan and organize the week and break time out where I am gonna step away for myself, for my family. Of course, you can't always do that, so, um, it's great to have a support system. I have, you know, a, a husband that I can hand off the kids to when I need to, or just friends and neighbors and, and, um, setting that up. And then, and then, you know, making sure you find that, like, what fulfills you and what you enjoy doing. You know, I know that I may not... I'm gonna choose not to do the yoga class with, with the team after work. Uh, but I, I will make sure to get one-on-one coffees with those folks and build relationships with them. But I know for myself, that's not on the priority to... and what's gonna make me successful and fulfilled, uh, with my family and, uh, at h- at home.
- HSHarry Stebbings
Julie, you mentioned kind of game time decisions there. Maggie, if there's anyone who can absolutely crystallize, like, the plan, I know it's you-
- GUGuest
(laughs)
- HSHarry Stebbings
... uh, with your kind of strategic thoughts, which you've outlined to me many times before. Um, (laughs) -
- GUGuest
(laughs)
- HSHarry Stebbings
... tell me, when we think about, like, strategies or tools specifically to help maintain that balance to allow for those game time decisions, what advice would you have there?
- GUGuest
Yeah. My biggest advice is that nothing is more valuable than your time. So, work and life these days, especially with so much of a shift to remote work from home, they're so intertwined. I think probably most of us on this call work some variety of hours from 7:00 AM to 11:00 PM, but this is really flip-flopping between work and personal life, back and forth, just like how Julie was saying. So, there's been two big tips that have worked really well for me that I've kind of had to figure out over the last few years. The first one, again, going back to nothing is more valuable than your time, it's ask for help. It's ask help from your friends, your family, your neighbors. Uh, whether that's something of, "Hey, can you watch the kids for half an hour?" Or asking for help from your partner. Um, it's also if you are, if you have the means and are able to afford it, spending some money on things maybe like grocery deliveries. So, rather than going and spending two hours back and forth in the grocery store, bringing the kids back and forth to it, just have Amazon Prime, spend that 9.99, and get it delivered to your house. And all of a sudden, you've got two hours back in your day. Or cleaner, same thing. Rather than, you know, spending hours cleaning, if you have the means to do it, maybe once a month have those cleaners come, and then you all of a sudden start getting hours back. The other strategy has been more of a mental shift for me, candidly. It's realizing that not everything has to be perfect. I think, you know, when I became a new mom, I was like, "I have to be that perfect mom. I have to make the cupcakes for that birthday party. I have to have them dressed in all of the greatest things." No, that is not the case whatsoever. The only thing that our kids are going to remember is how much you love them and how you treated them and how you cared about them. So, my learning has been go buy that store-bought cake for my daughters. They have two birthdays within four days of each other. Just go buy that cake and don't spend those hours trying to make everything perfect. Rather, spend those hours having dance parties, reading them books, and just spending one-on-one time with them, and that's gonna mean so much more to them.
- HSHarry Stebbings
I love the way I'm, like, nodding my head like, "Ah, yes, getting the two hours back for grocery deliveries. Ah, yes." And like, I haven't been to a grocery shop in years. Uh, but... (laughs)
- GUGuest
(laughs)
- HSHarry Stebbings
I don't feel your pain, but I sympathize.
- GUGuest
(laughs)
- HSHarry Stebbings
Uh, Lauren, I have to ask, how do you prioritize your mental health and well-being, being the best version of yourself, while also juggling responsibilities both work and then at home?
- GUGuest
Yeah. It's really hard is the answer. Uh, one thing is you have to find your outlet. So, for me, it's singing. I love singing. I sing with a group of women, some of whom I've been singing with for 30 years, and we rehearse three hours a week. And I show up every week, not because I have the free time, but because it feeds my soul. It's really hard to match the feeling of 15 treble voices coming together in harmony for me, creating something bigger than what you can do by yourself. So, that's my super nerdy investment in my own mental health and well-being. But-
- LSLauren Schwarz
My advice to working mothers is find an activity that's just yours, a creative outlet that fills your cup and doesn't require you to take care of anyone else, even for just three hours a week because we spend the rest of our lives caring for our families, caring for our teams. And, uh, the only way you can do it is to fill up your cup.
- HSHarry Stebbings
Can I ask, do you ever miss it? It's so easy to be like, "Oh, I have my gym or I have my this, my singing," and then like it's a busy week, something's missed at work and oh, the first thing to go is that outlet. Do you ever miss it and how do you protect against that?
- LSLauren Schwarz
Well, in my role it requires travel so I sometimes am traveling for a client meeting on a Tuesday, which is ... rehearse and what we've done to be inclusive to folks who have that kind of commitment is, uh, we have a Zoom access to rehearsals so I can actually listen in while I'm traveling so that I can accomplish both what's expected of me in my job and also continuing to learn music, uh, for our upcoming concerts.
- HSHarry Stebbings
This is like the most productive and efficient singing group I've ever heard.
- LSLauren Schwarz
(laughs)
- HSHarry Stebbings
To have like an attendance by Zoom if you're traveling, my word, I'm so impressed.
- LSLauren Schwarz
(laughs)
- HSHarry Stebbings
I think
- 13:29 – 17:55
Jessica Arnold - Coping with Feelings of Guilt as a Working Mother
- HSHarry Stebbings
the, I think the hard thing is here like, you know, often there's a lot of guilt tied to kind of whether you're spending time at home with the kids, which is great, but then you feel like it should be spent at work or the other way around. Jess, I'm, I'm intrigued, how do you think about handling the guilt that many mothers have when they have to focus on their career?
- JAJessica Arnold
Well, it's nice that you really shot off an easy question, Harry.
- HSHarry Stebbings
(laughs)
- JAJessica Arnold
It's not complicated, it's, uh, it's pretty surface, um.
- HSHarry Stebbings
I mean, it was teed up for me, Jess. I didn't-
- JAJessica Arnold
(laughs)
- HSHarry Stebbings
Try to be real. Hollywood is fake, right? (laughs)
- JAJessica Arnold
Um, so a little story about me. My mom actually left corporate America and started her own business as a sales trainer and motivational speaker, so my childhood car rides were actually filled with books on tape, The Seven Spiritual Laws of Deepak Chopra or Brian Tracy Affirmations, um, but one thing that she actually put in practice with our family was this seven quick question questionnaire, um, that centered around core value identification and goal setting. And so we did this every year as a family and as an adult it's actually, I've continued doing it and it's forced me to be intentional on what I want to accomplish that year and then also knowing what I'm not willing to sacrifice. And so when I became a mom, I had this feeling that I, I just went from going, uh, giving 100% to everything in my life to basically 70% on a good day and I hated that feeling. I just felt like nothing was enough and it was just constantly chasing nothing, and so I, I felt guilty, um, and so then I started being like, "What, like what actually is guilt?" I started to do readings on it, trying to see like what people are saying about it, and I found out it's an emotion and, and it's an emotion that, that comes from when a person actually believes that they compromised their own standards of conduct. And so when I read this I was like, "Wait a sec, I know my standards of conduct. I have been talking about my standards of conduct my whole life," (laughs) like as from my mom, um, and it just kind of clicked that I, because I already knew this, I, I knew that guilt was always gonna slip in. Like you can't avoid that. It's going to, you know, be a cloud on some days, but I also tried to practice looking at it, trying to understand where it was coming from and then choosing to let it pass me by, just like roll off my shoulders. It's not perfect. I have great days, I have not-so-great days, um, but I have boiled it down to three things that I think work for me. And it's not really unique advice but it's writing down your goals for the year, knowing what your five core values are, and then sharing them. So I share them with my family, my husband, my support system, and I think that sharing them actually makes it real, it allows me to be reflective through the years and understand like what needs to change, and it also gives other people in my network a, a way to support me if... or celebrate me if I'm doing something that I wanted to accomplish.
- HSHarry Stebbings
Uh, someone said earlier that it's important to ask for help. Um, Jess, if you were to give me advice, I'm a, a young guy, uh, with no kids, but I have, you know, people in different teams that have kids. I would hate for them to feel guilt that they are spending time with their children. I, I love kids and I would be terribly upset if they felt that. How can I try and help alleviate that as much as possible with my team members? What can I say, what can I do to try and make it better for them in that way?
- JAJessica Arnold
We're all salespeople. I would just get curious. Start doing a discovery call. (laughs) I mean, in all seriousness though, it's asking what they need. When do you do drop off and pick up? Are you going on any trips? When's your kids' spring break? My boss just asked me that recently, "When's your kids' spring break? Are you taking time off?" And I hadn't even thought about that. (laughs) Um, so I think it's just about knowing the people that you're working with and being curious about their lives.
- HSHarry Stebbings
We mentioned kind of what, what leaders can do. In terms of leadership, I do want to talk about kind of the aspect of sales leadership and combining the two.
- 17:55 – 23:20
Challenges and Advantages of Being a Mother in Sales
- HSHarry Stebbings
Uh, let's start, you know, Rainer, with you. If we think about the big challenges, but then also advantages of being a mother in a sales leadership role, what do you think they are?
- RGRenu Gupta
Um, no it's a good question, Harry. So look women are already a minority in sales, um, women of color are even a bigger minority and then if you add on them being a parent, it's even a tinier percentage. So I see less people that look like me in executive meetings, board meetings, um, off-sites, team meetings, and even customers are not expecting to be negotiating deals with someone like me. But I do look at this as a huge advantage, right? I believe that working parents, working moms, we're all very, very efficient with our time and we're very good at qualifying out, which is obviously a- a huge, um, uh, you know, pro as being a salesperson. So, um, we do honestly need to work a bit harder sometimes to prove what we're capable of, but this usually means that we're more prepared, we, you know, we respect people's times, we know how to show value, we know how to present value. So, um, you know, my hope is that by doing panels like this, we're paying it forward to tell other women who are thinking of growing their families or debating whether to stay in sales as a working parent, to stay, right? There are many people out there to support you, find your community, find your tribe, be vocal, be transparent. Um, and frankly if you're working with someone who you don't feel comfortable sharing that you're looking to grow your family or you're pregnant 'cause you're worried that, you know, you might lose that b- great territory or lose that promotion, you're probably working for the wrong person or organization.
- HSHarry Stebbings
I totally agree with that. Um, Jess, I'd love your thoughts on this. Challenges but then also advantages of being a mother in a sales leadership role.
- JAJessica Arnold
Yeah, similar to what Raina was talking about, I used to feel like I had to assimilate all the time, so I had to speak in a different language or, you know, like figure out what the rules of golf were, still don't know. Um, I think the Masters is going on, uh, (laughs) but-
- HSHarry Stebbings
Or something.
- JAJessica Arnold
... in all seriousness like I just always felt like I had to kind of put on this, like, mask to make sure that I could be with the other mostly male leadership members, um, in the room, and it's, it like just feels fake. And so when I finally started sharing more about myself and I just found I could sh- share more about my life, people responded really positively and I felt like all of a sudden what was my challenge, which was trying to be this fake person of myself, was when I, when I identified that challenge and changed it and was just like, "Hey, why don't I just be me? I think I'm pretty great," um, I found that people liked me too. (laughs) And, um, so then I, then I started, like, leaning more into that and understanding s- I think Stevie actually mentioned this earlier, is what is your superpower? And so I think being different is our superpower, and so being able to, like, lean into that, not n- now we're just not assimilating into a group of people that are all acting a certain way, but because we're different, we can kind of meet people differently, and I think that that's something that I've really found to be an advantage.
- HSHarry Stebbings
I totally agree. I remember when I first became a VC, I bought a Patagonia gilet.
- JAJessica Arnold
(laughs)
- HSHarry Stebbings
It was terribly uncomfortable. I've still got it. It's, like, brand new, you know, I've still got it, but it-
- JAJessica Arnold
(laughs)
- HSHarry Stebbings
... is very strange. H- like a cardigan, um, bizarre. I was about 18 as well, so I looked strange.
- JAJessica Arnold
(laughs)
- HSHarry Stebbings
Um, anyway, um, Lauren, I want, I want to move to you. We mentioned that kind of, you know, challenges and advantages of being in sales leadership. How has your experience as a mother actually influenced how you think about decision-making and style of leadership?
- LSLauren Schwarz
Yeah, it's, I, I, it's honestly expanded the scope of how I engage with the world because it's forced me to seek to include and understand folks with different experiences and responsibilities outside of work like parenting, um, and that truly came from having the experience of being a- a mom myself. And I have, th- a couple of us have said this already, but there aren't a ton of moms at least leading enterprise sales in tech, for example. So whenever I feel like I'm bringing an underrepresented perspective to the table, I feel frankly emboldened by the women and, and the allies who ha- fought to make it possible for me, for us to have a seat at that table. So you asked about how I think it's influenced my leadership style. I, I try to create paths for folks who don't see anyone who looks like them in their dream job, and so tactically what that looks like is leading groups for women in enterprise sales leadership, seeking out opportunities to mentor folks with diverse backgrounds and doing something like this, participating in a public speaking engagement where I
- HSHarry Stebbings
(laughs)
- LSLauren Schwarz
... can and spread the word that women and moms can and will achieve more than what they've been told is possible. And I think that I'm inspired to do this, to drive change for women and mothers in leadership from my own mother who was the first female VP at Morgan Stanley when I was born and she was fearless. She even picketed outside her office when her leadership meetings were held at the men's club and so she couldn't attend, um, and unfortunately I lost her when I was nine years old, but her memory has been such a powerful motivation for me and I really try and carry forth that legacy every day as a mother fighting to raise a daughter in a more inclusive world.
- HSHarry Stebbings
Can I, can I ask one? And, and
- 23:20 – 27:01
Julie Moresca - Motherhood and Leadership: Insights and Perspectives
- HSHarry Stebbings
I can throw it out a little bit to everyone, but when I think about, like, how children impact leadership, one thing I think about is, uh, feedback and then also kind of goal setting. It's such an important part of parenting as well. How has being a mother impacted how you think about feedback to your team and also goal setting and expectation setting with them? And I think probably best if someone raises their hand given the incredible line-up we have.
- LSLauren Schwarz
Julie, you should take this.
- JMJulie Maresca
Go ahead. N- yeah, well, I mean, I feel like being a mother and just how incredible mothers are in balancing making their children feel invincible and maybe at the same time... pushing them to places they don't want to go and they, you know, they know they don't wanna eat broccoli but it's good for them. You know, you, you have to give that tough love. I, I feel like those innate sort of qualities of, of being a mother actually really can be great leadership qualities, especially, Harry, in what you're speaking about in giving feedback. If your team knows that you care about them and your people know that you care about them, then everything you say, you know, they know that it's because you really want them to succeed and it is in their best interests. So I think you have to break down the walls, you have to be vulnerable. You know, people get scared of talking about teams at work being like families. To me, the best performing teams I've had were when they feel like they're family. Like, you can be so honest with them and be like, "Look, that was crap, but you are amazing, but you need to do it this way." And, uh, and also m- make them know that you know that they can run through walls and they can do it. Um, so I do think that that sort of, what we learn instinctually as mothers does make it a little bit easier to give that feedback if you really embrace it like, like Jessica said. Like, you're, being a mom is a superpower when it comes to sales leadership.
- HSHarry Stebbings
Oh, my mother's an incredible, uh, superhuman. Uh, can I ask you, Judy, a really hard question? Which is, do you think we're really at a stage... So you mentioned that really tough feedback. Do you think we're really at a stage where incredible female sales leaders, who are mothers or fathers actually, that's unfair of me, who are mothers or fathers, can go to their seniors or their superiors or CEOs and say, "You know, I just, I don't feel like I'm on top of it. I feel like I'm at 70% of my game"? Do you feel like we are at a stage yet where we can have that directness with, with that honesty?
- JMJulie Maresca
I think it's, I think it's a good, uh, it's a good question, a fair point. I do think we're making progress. And I do think that there's probably some that are modeling it a little bit better than others. I mean, um, Renu mentioned, you know, if you're not in a place where you have a voice or you can't say what you feel, then you're not at the, the right place. So I also believe it's about earning the right. Like, you can earn the right to have those, uh, conversations. Maybe you've shown up really well somewhere else and it gives you the platform to say that, "Hey, I'm not at my best right now." But you do need the rest of, um, the company and the culture to be there and, um, be open to it. And, you know, that's why I think it's on us to either choose places that we know really value that or, um, you know, drive that change. But I, I do agree, we probably still have a ways to go.
- HSHarry Stebbings
I wanna touch on some inspirational
- 27:01 – 33:04
Stevie Case - Overcoming Challenges of Motherhood
- HSHarry Stebbings
stories, some anecdotes. Let's bring this to life. Stevie, there's no one better than an amazing story. I, I loved our episode so much.
- SCStevie Case
(laughs)
- HSHarry Stebbings
Uh, but I, I wanted to move to you. When we think about inspiring stories or personal experiences of, like, overcoming challenges related to balancing motherhood and your career, what's one or two that come to mind for you?
- SCStevie Case
Yeah. You know, it's so interesting because Jess really touched on this idea of that feeling of being fake at times and having to put on a mask. And I really deeply struggled with that for years when my daughter was younger. I started this sales career and I already felt so completely out of my element. I had this weird gaming background (laughs) and, like, all this backstory that I was trying to push as far away as possible. And then, but not only was I a mom, I was a single mom, and I just was do- honestly doing everything in my power to hide it. And I would, like, do anything at work. I set no boundaries. If there was, like, a trip or an opportunity or something coming up, my answer was always yes. I never even hinted that I might have an obligation that could get in the way because I was so scared of the idea that I had a commitment at home and I was working with all men. And I was like, it felt so unfamiliar, and even though some of them were parents, I just felt like a total outsider. But I doubled down on that myself by pretending it wasn't there. So I would literally... Like, if I had to go on a trip and I was single mom, I would, like, fly people in from all over the country (laughs) to watch my daughter. At one point, I flew her mother-in-law in from Canada to stay with her. And like, I would never mention these things to, to the people I worked with. And it was so hard and so isolating and so painful to do that, and that continued for a long time. And, you know, I went to Twilio, um, where I was before Vanta, and at Twilio I started as an enterprise AE and I started on my same thing, like, "I'm gonna pretend." Um, but I had this incredible sales leader, shout out Alison Welch, who is also now a CRO over at Neo4j. Alison was amazing and she really championed my career there. And the first time she promoted me at Twilio, you know, I had been crushing it as an AE and she wrote this incredible note. She said, "You know, I wanna tell more of your story, like, about who you are." And she wanted to include in there that I'm a mom, and she just, like, gave me permission. And from that point forward, everything felt different because I felt seen as a full human. And like Jess said, I embraced it and I ran with it and I felt empowered in a very different way. And from that point forward, I have never stopped doing that because it actually brings me back to the very beginning of my sales career. I had this amazing mentor, Matt Golden, and Matt...He really-- he was so hard on me and he taught me so many lessons, and the most valuable one was that when you're selling to people, you're selling to humans. And if you are vulnerable and you show your weaknesses and you show all aspects of your humanity, you actually give the other person permission to also not be perfect. And that has stuck with me 20 years on, and I think it's what people who aren't parents can do for parents in the workplace, is be real. Just be human and everybody's got commitments. Like be real about what your commitments are, be real about not feeling great, and in doing that, you will give permission to everybody around you to also be real.
- HSHarry Stebbings
Can I just ask one question? Do you think vulnerability is a luxury of being successful? Like, I look at me in this light, you know, alcoholic, bulimic, depressive. I would never have been that honest. (laughs) Um, I wonder why I'm single.
- SCStevie Case
(laughs)
- HSHarry Stebbings
Uh, I would never have been that honest, um, when I was not so successful-
- SCStevie Case
(laughs)
- HSHarry Stebbings
... earlier in my career. Now, I'm like, "Oh, fuck it if you like me or not." Um, you're a rockstar CRO, you're a leader of your profession. Is it a luxury of being successful that we can be and it's seen as a strength almost?
- SCStevie Case
Yes. It's a luxury and it's a privilege, and I think there are a couple of things I would call out in there. One is I-- you never really feel like you've made it. I think, uh, there's a certain sense you can always look at other people and see, "Oh, they've made it more than I've made it," or, "I haven't really made it. (laughs) I'm still climbing." So part of that is the perception you have of your own success. You can give yourself permission to be more real earlier rather than holding the bar for some, like, ridiculous accomplishment that you have to achieve before you're able to be real. And I think it's incumbent on those folks who have reached that point in their career and have the luxury and privilege to give everybody around them that permission because you can actually open it up for other people. You can open up an environment where people are allowed to be human and make mistakes and be real, and I think that that's what leadership really looks like in the workplace now. Like, that is the bar for being a great leader. It's not just leading your team to victory. It's doing that and respecting the humanity of the team you've built and allowing them to be real and human. Uh, you know, you list off those things which it sounds like you think are deficiencies about you, Harry, but we all have those things. Like, I told my story in Vanity Fair this year. I had a lot of those things, and we're not alone. And the more you say it, you give other people permission. So that's where I try to focus now, is just creating a safe space around me for people to be human.
- HSHarry Stebbings
I view it as supporting the economy. My therapist has unwavering demands on his time-
- SCStevie Case
(laughs)
- HSHarry Stebbings
... so, uh, I'm really
- 33:04 – 36:09
Maggie Hott - Asking for Promotion while Pregnant
- HSHarry Stebbings
a net additive to GDP. Uh, Maggie, uh, I wanna move to you on an inspirational story. Hit me. What is the first that comes to mind for you?
- MHMaggie Hott
Yeah. First off, Stevie, thank you for always just being so real. There's, like, fewer people I know that are just more real and out there than Stevie, and I believe as leaders-
- SCStevie Case
(laughs)
- MHMaggie Hott
... and, and really anyone, we have a duty for those out there to set this kind of standard and set the stage of how we wanna show up. And we're gonna be setting this mirror in those who potentially look up to us or all of us who are leading orgs, um, are going to mirror what it is that we're putting out there. And we're gonna show that it is okay to act and kind of behave and share these stories. So thank you, Stevie, for always being so open and honest. Um-
- SCStevie Case
Thank you.
- MHMaggie Hott
We're... Yeah. Working parents are just some of the toughest that are, that are out there, and I think it's really important for me to never hide that I'm a parent. So obviously, I realize it's kind of coming from a place of privilege, but for my teams, I want them to know that I am a working parent, I am a working mother, when I am pregnant that I, you know, am not having the best days and sometimes (laughs) I just need to cancel that meeting or go off camera. And actually, speaking of being pregnant, one of the, um, biggest things that happened in my career was actually when I was eight and a half months pregnant. There was a role that opened up, uh, at Slack for an enterprise leader, and at that point in time, I was a senior manager of mid-market and there was this new role to help lead enterprise for our West Coast team. And I thought there's absolutely no way I should put my hand up for this role because I'm literally eight and a half months pregnant, I can't hide this whatsoever that I'm about to give birth, um, and who's gonna want someone who's gonna get the role and then go out on leave, you know, for the next five months? And I actually had two male allies, um, our VP of sales as well as our head of enterprise encouraged me to go for the role, um, in addition to, you know, many others within the company. But that was something that really stood out is that they told me that, "The company's invested in this person in a long term. You know, this isn't something that we're just thinking about short term, three months, five months. It's really important that we get the right leader in place, so you should absolutely go for the role." So I decided to put my hand up for it. I went for it, uh, again, literally interviewed eight and a half months pregnant. I stood the entire interview. (laughs) I was so uncomfortable, but I, like, felt like I had to stand and be there, and I really celebrated that I had been, you know, pregnant while also leading very successful teams in the past and why I was the right person for this. I ultimately ended up getting the job and I can very confidently say my career would not be where it is today if I hadn't gone for this job and if I hadn't gotten that job. And I was so close to just not going for it because I was in my own head. And so that's really kind of my story there and some encouragement for anyone who's listening is to don't be afraid to go for something, don't feel that, like, sense of shame or sense of guilt or sense of not being good enough because you are a working parent or a working mother or pregnant or planning a family. Um, that you should just really just go for it and, and see what happens.
- HSHarry Stebbings
Maggie, I love that story in terms of just going for it. And I didn't actually know that, but also, like eight and a half months pregnant going for a role?
- 36:09 – 43:30
Taking Parental Leave: Advice and Considerations
- HSHarry Stebbings
You go. That's fucking awesome. In terms of parental leave, how do we think about, um, parental leave? So let's, let's think, like, specifically, how have you navigated this? 'Cause it is a challenging topic. Also knowing that you're inevitably behind due to-... kind of, I feel bad saying it, but, like, your career being on pause while everyone else does progress.
- MHMaggie Hott
Yeah. So career pause, (sighs) I think, sadly, can be a very real thing. You essentially step out of the business for four to six months and the business is still moving forward without you. And that's why I actually think, and, and this is a bit counterintuitive, but it's so important for companies to have equitable parental leave for both parents, for the birthing parent and the non-birthing parent. So it shouldn't just be the female that is getting the bulk of the parental leave and, you know, typically the male or the other partner. Um, it really needs to be both need to have pretty darn near-equitable leave, uh, because if you don't do that, it actually puts women at a disadvantage both financially as well as in their career if they're taking far longer than their non-birthing counterparts. And this is gonna happen multiple times if they have multiple kids. So in my case, I've now gone out on leave twice in the last two years. And then, actually speaking on the home front, studies show that with a, a non-birthing parent or a partner's increased involvement in baby care can mitigate maternal postpartum depression. And actually, one in seven women get postpartum depression, which is something that is not talked about enough publicly and enough out there. It can be really, really hard to come back to work and to focus on your career if you're also battling postpartum depression at the same time. So if you're now able, if this, if, like, your company is able to increase the leave for the other parent, it's going to be associated to greater relationship stability. And this is actually largely because when partners take leave, it's going to signal a greater investment in family life, so it's gonna reduce the burden on mothers. It's gonna strengthen the parental relationships. It's really less about, you know, dividing those household tasks, and it's more about providing emotional support and being present during those early months. I think all of us on (laughs) on the call can attest those early months of a baby's life are some of the hardest, most tiring, most challenging. You're trying to heal, you know, from a major, major life event. Your body has just completely reorganized itself. You know, some of us have, have had major, huge abdominal surgeries to get these kids out, and it's really important for that other partner to be present during those earlier months. And then that's actually in turn gonna help the birthing parent or the birthing mother get back into the swing of things with their career because they've now had the support over the last few months. Whereas there's so many companies out there that think about this in kind of the old traditional way. I was actually just speaking to an investor at a different firm recently where they told me that in their firm, the male gets two weeks whereas the, the female gets a ton of time. But that's actually not setting that female up for success to have a very good entry into the first few months of their child's life.
- HSHarry Stebbings
I just have to ask these questions. Should we force then men to have the same time off? Like, you could put it in place, but, like, respectfully, I'd probably wanna get back (laughs) to work as soon as possible. Um, uh, should we force it? Because it, it is important for so many different reasons. Is that right?
- MHMaggie Hott
I believe so, but I think that also comes to, um, to making sure that men are also, you know, paid, that, that you're getting... And, and part of the problem with America is there's no set parental leave policy. We actually have one of the worst policies in the entire world. Uh, most coun- countries out there have far better leave policies than we do because we have pretty much zero guaranteed time. And so by doing that, in addition to potentially forcing or requiring for the partner or strongly, strongly encouraging the partner to take the time off, but it's also making sure that they're not gonna be missing out on compensation when the, they, when they are on that time. And sadly, a lot of policies that are out there is, like, a job will be guaranteed, but you won't be getting the full pay for it. So we also need to make sure there's the other policies that are out there to help support the non-birthing parent to go on leave.
- HSHarry Stebbings
Lauren, I'm intrigued. How did you think about this kind of potential career pause and that aspect of parental leave?
- LSLauren Schwarz
Yeah, I think it's, um... And it's critical, uh, and what Maggie just said at the end there, um, the non-birthing parent and the birthing parent, right? We wanna expand the scope of policy design to any type of family unit that's bringing a child into the world. And so, uh, it, it, frankly, it's critical to be inclusive of every approach to whether it's adoption, whether it's same-sex couples, wha- the whatever it is, um, we, we need to create an environment that doesn't treat people differently, uh, because they, um, um, because it's not... it's outside of their control. Um, so what I thought about... You know, I didn't think of it about as putting my career on pause. Really what I thought was, "Well, how do I continue the momentum while I'm out?" Uh, so for me, it was critical to invite folks on our team to step up, create opportunity for them to step up, put leaders in place who can keep the momentum going, and really that requires setting clear expectations for what will be accomplished before you get back. So, that's a lot of work and I, I don't wanna make light of it because you really have to take responsibility to make sure, you know, while a leader is on leave, how can a team be successful and what are the expectations and what kind of accountability are you gonna put in place? Um, because the business continues whether you're there or not. So it's, it's your choice, uh, whether you wanna put a blueprint in place to en- ensure your team has what they need while you're investing your energy into keeping a tiny human alive.
- HSHarry Stebbings
Can I ask, is it tough to be fully out? And what I mean by that is it's so easy to just, like, pop on Slack or pop on email just quickly, oh, it was just half an hour a day, but then you're kind of in and you're kind of out and it's kind of tough for your team then, and is that right or is that wrong? How do you think about that? Like, fully in, fully out, uh, checking in, not checking in, what's the right answer there?
- LSLauren Schwarz
Yeah. I, I think it's, uh, choose your own adventure for everyone, what makes them most comfortable. Uh, so I'd say for me, I really tried to honor the fact that it was, uh, a once-in-a-lifetime experience to s- or multiple times, depending on, on your family structure, but, um, to experience that time with my newborn and really just expand the scope of what life means. And every time I thought about it with that level of gravity, it was, um, really easy for me to say to Slack and wait.... or, uh, you know, empower someone else on the team to make a decision. Ideally, what I've done is create a team that can function in my absence. And so, um, yes, of course, always tempted to engage and, you know, folks reach out sometimes, uh, and that's really, really hard to- to- to create that boundary. But, um, for me it was, you know, setting out times where I was like, "Okay, I'm going to devote this hour to thinking about what's going on in the business. And then after that, I'm gonna sign off." No guilt. I assigned myself a schedule, I'm following the schedule, and I'm gonna refocus on this, again, really magical, once-in-a-lifetime, exhausting experience.
- HSHarry Stebbings
You clearly never saw Cheaper by the Dozen, but I- I'm thrilled that I managed to get in a plug for Slack there. Maggie, you should be so proud of me. Uh, you mentioned, Maggie, that America's worst
- 43:30 – 47:20
Fighting for Parental Leave in America: Current Landscape
- HSHarry Stebbings
at parental leave policy. Tell me, how can you advocate for parental leave if the existing policy isn't up to par? Like, what can we actually do to change things?
- MHMaggie Hott
Yeah, absolutely. Great question. I think about it in a four s- kind of four-step structure or framework. So, first I'll start off with, the number one thing that's important to do is to educate your company. And I've found that oftentimes, policies just haven't been formed, they're outdated, they haven't been reviewed in years. It wasn't actually a bunch of folks up at the top being like, "Let's make some really bad policies," it was just something that maybe was never worked on or maybe was really never thought through. So, it's a great time to really come together, and I'll walk you through the steps, but to really educate those at kind of the top who are the key decision makers on why it matters to go change these policies. So, the first thing that you should really think about doing is pull together data and research of comparable companies and comparable, you know, kind of companies within your industry. So, you know, if we are Webflow, who are kind of the, maybe top different fun companies that we can really compare ourselves to as we think about top talent. And then really go and look at, what are their policies? How are they treating this? Is there anything that we can learn from them? The second thing that's really important to do is to meet with leaders and peers from the company. Ideally, parents or people who want to be parents, or people who are really kind of like allies to families. So, really get together a group, form a group of people that advocate for the change in parental leave policy together and work on gathering that data across your network. Uh, the third thing then to do, and we actually, a group of us right here on this call, we did this at Slack, where we found an ally and a sponsor who was willing to champion this discussion at the executive level. So, really, you know, you've got this whole group of people, maybe some are- some are more junior in their career, m- some are more senior, but it's really important to have this executive that's going to be the sponsor for this. So, work with them and take y- these findings to the executive team and have a productive conversation. That's actually one of the most key things here, is don't go in combative, don't go in blaming, don't go in telling them what they need to do, but be very clear in your asks, in your education of what a good parental leave policy should look like. And then finally, be a bit selfish and advocate for yourself, and don't be ashamed and don't feel any guilt. Sales in particular has a ton of nuances, um, on parental leave. I think probably more so than any other role that's out there, because you're thinking about things like your quota, your book of business, who's gonna cover your accounts when you're out? What happens if an opportunity closes when you're out that you've been working on for years? Or what happens if an opportunity starts in one of your accounts and now all of a sudden you've come back, do you take it? Does the former rep take it? So, there's a lot of nuances within sales that are really important to think through with your leader and with that sales leadership team. So, make those asks, make the asks for things like a ramped quota when you're coming back into work, make the asks for protection over your accounts or deals that might close when you're out, and all- honestly, one of the most important things that you can do is ensure that you have an adequate leave coverage plan. Very similar to what Lauren was saying, um, when I went out on my last, uh, leave, I put together this behemoth of a coverage plan, and I made it very clear of here's when I want to be contacted and here's when I don't want to be contacted. You know, key hirings, final round interviews, firings, terminations. I made it, like, very black and white of like, "Here's what my needs are and here's when I expect to still be brought in." And then even different cycles. First month, I don't want to be talked to at all. Months two and three, totally okay to reach out to me. So, I would also say for ICs, for sales reps, for really anyone, be very clear with what your
- 47:20 – 50:25
Lauren Schwartz - Parental Leave Plans: What to Consider
- MHMaggie Hott
asks are and what your needs are for when you go out.
- HSHarry Stebbings
You mentioned those, like, gotcha elements there and those intricacies. Lauren, I'd love to hear your thoughts on this.
- LSLauren Schwarz
Yeah, I'll just share my story. I was pregnant when I started at Fivetran, and I'd done the high level due diligence of confirming that there was in fact a parental leave plan at all at this tech startup. It seemed like a market appropriate length of time, and that was frankly about as much as I was willing to ask about as a candidate. Uh, it's sort of a- a- a gentle subject to- to brief when you're not yet employed. Uh, and when I arrived, it actually turned out that you could only qualify for parental leave if you had been an employee for nine months, which was physically impossible for me given I was due seven months into the new gig. And actually, California doesn't guarantee job protection until you've been in state for 12 months. So, although that tenure cliff seemed outrageous to me, it was actually a step up from, uh, what's been provided to us by the government. So, there are a few other gotchas in there that just needed to be revisited, so I followed a lot of the steps that Maggie just outlined, um, to rewrite the policy. In particular, what I think was most effective into my approach was that we focused on their DEI implications of the policy. So, if you're- if you're, as a business, committed to recruiting diverse top talent, you have to be able to hire that talent regardless of where they are in their family planning journey, so it makes the decision for the business more about aligning with our values as a company and less about...... the ticky-tacky start date qualification minutiae. Um, and, you know, Maggie also mentioned on the sales side, it's, it's pretty unique. Another thing to look out for in parental leave policies is whether they pay you commission while you're out. So in sales, we're in somewhat of a unique position because so much of our income is variable. But it's totally reasonable to advocate that just like any other role, a salesperson should be paid our on hard earnings, which includes variable, while we're on leave. It's the only way to prevent penalizing birthing parents for taking leave that they physically require.
- HSHarry Stebbings
Can I ask this? Is there internal politics around the commissions? As you said, if it starts when you're away and you close it, or you start it and then it closes when you're away, is there politics? I haven't actually ever thought about the kind of internal politics and dynamics between, bluntly, the cash cycle and who gets it.
- LSLauren Schwarz
Absolutely, and there are nuances to it. Every deal is structured a little bit differently and also depends on the size of the company. When I was at Google, there was a double comp policy, so everyone wins and everyone's incentivized around the same thing. When you're at a startup that's looking for, uh, profitable growth, uh, that, that's not always an option. So you start to get creative developing splits and creating the most equitable opportunity that ultimately keeps the customer at the forefront of the experience so that, um, you know, we're not... It's, we're all making my problem their problem.
- HSHarry Stebbings
I don't think I've ever seen a profitable startup, uh, Lauren, but, uh, I'm, I'm more than welcome to. If you ever (overlapping)
- LSLauren Schwarz
We're making a profit.
- HSHarry Stebbings
If I want one, let me kn- let me know. I'm an investor. Um, uh, we, we mentioned kind of some tough elements
- 50:25 – 55:44
Renu Gupta - How to Ask for Help: Practical Tips
- HSHarry Stebbings
there and that actually finding the community of people we can talk to. Renu, I'd love to speak to you about this, which is like, how can we think about speaking up effectively and getting help versus bluntly sitting with all of the stress and struggles on our own? How do we do that effectively?
- RGRenu Gupta
Yeah, absolutely. I know Julie and Laura and the team kind of covered this earlier as well, but, um, so my oldest is nine. He was born in 2014. His name is Roman. And, um, nine years ago, as you can imagine, being in office was the trend. And so, um, you know, when you leave your, the floor of the office you're sitting in, um, everyone can see you. It's very visible. And, um, you know, s- for the last nine years, um, I've been the parent who had to pick up their child at least 50% of the time. And so this meant I would take my laptop and my bag and, uh, leave the sales floor by sometimes, you know, as early as 4:00, even 4:30, depending on, you know, where he was, in daycare or preschool or with our nanny. Um, but honestly, I never felt guilty. And, um, trust me, leaving the sales floor at 4:00, 4:30 is, uh, you know, this is when s- some of the folks that don't have kids, they're, um, there's really good energy. There's, you know, deals being closed, end of quarter. You can imagine, like, what it was like in, on, um, at, at this time. But... And I sat right next to, um, our VP of sales at Slack for, for three years and he would see me, you know, the days I was, uh, in charge of picking up my kids, he would see me get up at 4:00, 4:30, always with, "Have a good day, Renu. Awesome day today," or, you know, whatever it was. Um, and that helped me not feel guilty. That gave me the permission, uh, because he knew my family was a non-negotiable. I wanted to be there for pickup, I wanted to be there for the after-school activities, I wanted to be there for, like, the 9:00 AM, you know, first swim lessons that Roman had in a pool that was across the city. And, uh, my team, the people that, you know, I reported into, the people that reported into me always knew that this was something that was very important to me. So, um, you know, how can you speak up? Like, as a leader, know what your team's non-negotiables are. Ask them. Uh, be curious, like Jess said. You know, give them p- the permission they need to go to their kid's first swim lessons or their spring musical that's always, like, at 1:00 PM or, you know, the, the parent-teacher coffees that are always at, like, 10:00 AM, right? Um, make sure that they, that, that you as a leader know what's important to your team and, um, support them. And if you're not a leader, let your leader know what your boundaries are, what your priorities are, what your non-negotiables are, um, and don't be afraid to tell them that you want to be at your child's swim lesson or, or at, or at pickup every day.
- HSHarry Stebbings
I love that in terms of sitting next to the VP of sales and him encouraging you and being supportive in that way. That's awesome to hear. It, it's-
- RGRenu Gupta
Yeah.
- HSHarry Stebbings
It's lovely to have that support. And when I think about that and I think about kind of mentorship, uh, Lauren, if we think about how mentorship or support from others has really impacted your, your journey as a working mother, uh, are there some points which really are central for you?
- LSLauren Schwarz
Yeah. I think it's critical to get creative in building your personal board of directors. So I'm part of an incredible women's circle made up of other alumni from Stanford Business School that span from their 30s to their 70s. And so there's something really magical about sharing the ups and downs of your journey with a multi-generational support group. And anyone can build a board like this. In fact, you're looking at another one. This is my go-to group of sales leaders whenever I'm facing a challenge at work or thinking about a career transition or want to celebrate something. We do this daily and it's, it's really, really important, but you have to take responsibility for designing that personal board of directors. It's not something that's going to be handed to you. So that's that spanned outside of your company, outside of your industry in other cases. Um, and for me, when I, when I started at my current company, I mentioned I, I was pregnant, and, um, my boss, current boss and the, and the guy who hired me, Jim Smittcamp, was really, really inclusive. And a lot of people think that this type of mentorship would traditionally come from women, but I just want to call out, men can be incredible allies and advocates. So, uh, when Jim gave me my verbal offer, I said, "Listen, you need to think critically about hiring me for our VP of sales role during a season of my life in which I'm working on growing a family." And he leaned right in, not only underscoring the company's whole person values, but also when it was time for me to go out on leave, he spoke publicly about his senior revenue leader going on parental leave and set the tone that not only is it tolerable, but it's celebrated.
- HSHarry Stebbings
I, I, I love that. Can I interest one, which is like, I, I said to someone the other day in the team, "I have, I have no idea what it's like being a parent, but I just want you to know that you can tell me whatever you need. You can come to me with anything and it's okay. We'll figure it out together." Is that lazy of me because I didn't take the time to really speak to lots of parents and figure out what it is? Or is that actually okay of me 'cause I was giving them the, the room and the space to kind of be what they needed to be?
- LSLauren Schwarz
I think someone earlier on the call said this well, which is be curious. Just be open-minded about people's different experience, whether they have responsibilities at work that include parenting or include caring for an elder in their lives or what have you. So, I think it's a great approach to be open-minded
- 55:44 – 1:02:22
Lessons from Mentors: Personal Growth and Development
- LSLauren Schwarz
and create a space for people to be, as Steve said, vulnerable and then
- JMJulie Maresca
Yeah. No, I... Phew. I was worried. Uh, Madi, you, Raina and Judy, you have the, uh, (laughs) mentor commonality, uh, of Kevin Eagan, who I actually spoke to, uh, before this. Wonderful man, we had a great chat. Um, but I'd love to hear, how was that impactful in terms of how you think about really your journey as a working mother? Uh, I'm happy to start. I still work for Kevin. Um, and yeah, I think, (sighs) I think it's just having a great mentor empowers you to, um, be who you are. I mean, um, it, it opens the door for you to, um, I guess work freely, live freely. And I think about what Raina said, like (sighs) we have to demystify that, like, being flexible and being successful are not mutually exclusive. They can happen at the same time. And at the end of the day, your work will speak for itself. And that's how Kevin was. Like, it didn't matter, and it still doesn't, how you get the work done, um, but it's that you, you know, do the work. And, uh, I find that when we give people the avenues to get, um, their work done and work in the way that best suits them, we all, we see people at their best. And I think Kevin was a great leader, and is a great leader, in showing, in showing that way. Um, the worst thing is when you have to go through your day and your career feeling guilt and having things sit on top of you when you are trying to do your job. So, um, I think having a mentor that recognizes that early on is critical, and recognizes that we need people to show up as their best selves. So, if it means altering how we lead or our expectations or time commitments, then, um, at the end of the day, we all wanna be successful. So, the sooner we can get to that mindset, uh, the more successful and happy you will be and you'll, your teams will be.
- HSHarry Stebbings
Jess, who's been really impactful for you in your career in enabling that feeling from you?
- JAJessica Arnold
Um, yeah. I, before I went out on leave the first time, I w- we had gone through this big reorg and I was reporting internally to our global BP of revenue, Thompson, uh, Thomas Hanson, and I didn't really know him that well. Um, but I always think about this Maya Angelou quote, which is, "People won't remember what you said or what you did, but they'll always remember how you make them feel." And I, I was... It was a random afternoon, I was walking down the hall and he stopped me, and he w- was so excited for me. And he was just like, "I, you know, you're gonna go out on leave." He encouraged me to take the entire time. He was like, "This is the most, one of the most important times in your life and I just want you to be able to, you know, spend that time with your family." And I remember being, "You didn't have to stop and tell me that." Like, he, he made me feel so confident in being able to do what I needed to do for my family and for me, and I, I'll never forget that feeling. And maybe for him, he doesn't even necessarily remember it, although I work with him now at Amplitude, and I, we've kind of commiserated over this story. But it's... I don't know. I, I just think work now, especially after COVID, it's blended with life. And so it's not, yes, we're all sales leaders so the number matters, but it, it's also about making people feel the, the way you make them feel. And if you're not doing that, then I don't think you're doing the right thing.
- HSHarry Stebbings
So funny, I said that Maya Angelou quote to one of our interns the other day in, in my fund, and I tried to pass it off as my own quote.
- JAJessica Arnold
(laughs)
- HSHarry Stebbings
And they told me that they were an English student and that it was Maya Angelou's, uh, and I told them, "Well, that's venture capital. We package other people's knowledge and sell it as our own, so that's lesson one." Nah, uh, (laughs) didn't go down so well. Um, anyway, uh, Stevie, uh, who, who was your shining light in terms of this mentor?
- JMJulie Maresca
I have been so lucky on this front. I mean, Matt Golden was the first. I would have never been in sales without his willingness to take me on and teach me how to sell. But really, the transformative moment for me was at Twilio. And Alison Welch was a big part of that, but it was also that I had an entire reporting chain that included, um, all parents. So, Alison reported to the CRO, Mark Broditzky, he had kids, he talked about them very openly. George Hu, our COO, had kids. Jeff Lawson, the CEO, would talk about his kids. So, there was this real commitment to talking about family, and that just became part of the practice. And Harry, you asked if that question you had asked in opening the door for your team was okay, and the answer is absolutely. But the key is turning it into a practice, and that's what happened with all those leaders for me at Twilio, is it was just part of the daily...
- MHMaggie Hott
... the daily everything was just like, "Oh, I'm picking up my kids now," or, "I'm taking off next week to go skiing with my daughter," or, you know, just celebrating life moments. And, you know, Ari, you may not realize this, but the way you include your mom in your story, the way you talk about your mom, it actually gives parents more comfort and permission to talk about their kids because it's this little signal. And we were talking earlier about that luxury or the privilege of being vulnerable. When you're early in career, you're looking for these signals in the people you work with to see, is it safe? Can I talk about this? Is it okay? And by talking about your mom, you make it more safe. Uh, it doesn't... You don't have to be a parent to create that environment of safety. And that's what those folks did for me at Twilio, all the way on down from the CEO, and that's part of what made it feel so safe to be real.
- HSHarry Stebbings
That's so kind of you. I just hosted my AGM for my LPs in my fund, and we have like the biggest institutions in the world. We've got, you know, Harvard and MIT. My mother organized everything. She was there for everything, CIOs of the biggest endowments in the world. She smashed it. (laughs)
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
The only thing is, I think they were like far more impressed when they were with her than they were with me, which is, you know, a challenge in and of itself.
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
But, uh, I-
- 1:02:22 – 1:06:37
Creating an Inclusive Environment for Working Mothers: Best Practices
- HSHarry Stebbings
I love that and I'm so grateful for that. Maggie, tell me, in terms of actually getting granular and improving situations, how can we create a more inclusive and, and supportive environment for working mothers in sales leadership roles?
- MHMaggie Hott
Totally. So, I think similar to what, to what everyone said, is to normalize having children. You know, back in the day, so, you know, it wasn't normal for, for children to be around, to be talked about. My mother-in-law was L- um, lieutenant governor of Colorado, and she went back to work, I think it was something like two weeks after having both of her sons. Um, a- and it just wasn't a normal thing back then. And we're so fortunate to be in a day and age now where it's perfectly acceptable to be a working parent and to be a mother and to have a career. So, first off is to normalize it, and some really easy ways to do it is bring your kids on calls. If your kids are running around in the background, pop them onto a call and have them say hi. Honestly, everyone's gonna love it 'cause it's so fun and it kinda breaks things up. Be honest when your kids are sick or when they have, you know, their preschool, or their daycare, or their school is closed. Don't try to hide it. Say, "Hey, there might be a visitor that's gonna jump into our call," or have them over in the background. Your companies and teams, again, are gonna look up and mirror what you do. And then the other thing you can do is create resources and kind of support an affinity group. So, something that, um, we had at Slack that I then brought over to Webflow and created was a pregnancy support channel, and this is where people who are trying to get pregnant, are pregnant, new moms, really anyone who has like been on their pregnancy journey and wants to help support, um, can jump in there. And this has always been one of my favorite channels because you can ask any real and raw question and get all the advice in the world, pretty much, from people who have done it before. Something that we also had at Slack that I absolutely loved is, every month, kind of earlier days, we would bring in a leader from whether it's the sales team, or across the company, or maybe even one of our investors or someone in our network that would come in and talk to us about their career journeys. And again, inevitably in their kind of career and family life journeys, um, things like kids and being a parent are gonna come up, so really being open to sharing these things. Other things too that I've seen, you know, for in-office type cultures, family days at work, bring your kids in for... At Slack we used to have a Halloween party every year. It's like all the families and all the kids would come, and it just continues to normalize that like, oh, my CEO has kids, my COO has kids, my CRO has kids, and here's that person's family, which just makes it, just brings it to a different level. Um, or if you're a virtual type, you know, company, and, and many of us are, I've seen companies do virtual family events really well. So like a magician come in, and then everyone brings their families around the screen for an hour. Um, so there's just a lot of things that you can do that don't necessarily cost a lot of money and can be free. All these different affinity groups, advice groups, support groups, journey sharing, can really go a long ways to really normalize having a family within a company.
- HSHarry Stebbings
A magician comes in. I think that's called a head of sales in 2023, Maggie, but sure. (laughs) Um, uh, I- I- I do just have to ask, final one before we do a kind of quick fire on advice, I made it like mandatory that we're all back in office again. Um, I just think we're so much more productive in office. We're all in London anyway, but is that bad of me? And like, is remote just so much better in terms of being the best in this balance?
- MHMaggie Hott
It's gonna be different to every single, um, company. I, uh, you know, I just went from Webflow, which is fully remote, and now to OpenAI, which is more of a hybrid model. Um, so it's gonna be every company's gonna have its different choices. The one thing I would say though is still always remember to be flexible. While in office may be a requirement, again, doctors, uh, preschool, or like different school events or outings, soccer games, parent-teacher conferences, in a remote world, it is so much easier to just kind of like slip off and go do those things. In a in-office world, it's really hard to do that. So just continue to normalize that the expectation is that you are in office when you can be in office, but if you need to miss being in office for some other reason, you know, family event, sick event, whatever it might be, it is totally okay.
- HSHarry Stebbings
Yeah. No, I totally
- 1:06:37 – 1:10:49
Quick-Fire Advice
- HSHarry Stebbings
agree with that. Okay. No, good. Oof. All right. We're gonna do a quick fire. So we're gonna do a quick fire on advice, uh, which is like a short snippet of wisdom from each. And I'm gonna direct the conversation here. So what advice would you give to other mothers who are considering a career in sales leadership or other demanding roles? Maggie, let's start with you. What advice?
- MHMaggie Hott
Yep. Absolutely. It's believe in yourself. So have the confidence and the swagger in your ability to have a career and gr- be a great parent, and a great partner, and a great friend. It's inevitable that you are going to feel guilt. We've talked about guilt a lot throughout this, but it is a very real thing. I've felt guilt so many different times. So it's inevitable that you're gonna feel it, but you also need to accept this guilt as normal, and normalize it, and move on.
- HSHarry Stebbings
Lauren, what do you think? What's the advice?
- LSLauren Schwarz
Yeah. My advice is to earn the right to ask for what you need to be successful and if that's a more flexible travel schedule or a milk store service while you're on the road, ask for it and set the bar high for yourself and for your team for what success looks like on your terms. Because you can't argue with the results. But ask for the help that you need. Don't try to do it alone.
- HSHarry Stebbings
Jess, what's your advice?
- JAJessica Arnold
Choose the right partner. I think being able to have the conversation before family around how you envision your career and where you want to go, and what you want to do, and what you want to accomplish. And making sure that your partner's on board and you should be on board with what your part- partner wants to do and, um, just envisioning life after kids and how you're gonna deal with it together.
- HSHarry Stebbings
Yeah. Sadly, Bumble Premium's not paying off for me.
- JAJessica Arnold
(laughs)
- HSHarry Stebbings
Ah, Stevie, you're (laughs) ... You're... Ah, sorry, Julie, your turn. Ah, what advice do we have? I was completely distracted there. That was great advice though, by the way. Pick Your Partner is absolutely a brilliant, brilliant piece. I think it's Warren Buffet's biggest piece of advice too. Julie, what advice do you have in terms-
- JMJulie Maresca
Yeah, I- I think it's also pick your company. At the end of the day, you want to be so excited to go to work and so excited to go home. And if you know that you're coming into, um, you know, a sort of time in your life or work where you have to make decisions and make compromises, you wanna make sure you love what you do. And I've been through many careers, made many mistakes. At the end of the day, you're spending so many- so much time with these people, make sure you love who you work with, make sure you love the culture, and make sure the journey is one that you can embrace. And then the sacrifices or the guilt, it feels a lot more manageable.
- HSHarry Stebbings
Stevie, your turn. Hit me with some wisdom. Come on, what advice-
- SCStevie Case
Oh my gosh. Mine is don't apologize for yourself because you're always gonna have other commitments, things you need to leave for. Your child is gonna show up on camera during Zoom calls. It's gonna happen. You really do not need to apologize for that. Part of normalizing it is just acknowledging it and moving forward without acting like the other person is doing you a favor by accepting it. They're not. It's just normal. So let go of the apologies and just embrace that everyone has commitments and that it's okay.
- HSHarry Stebbings
I love that. Renu, final one. Wisdom, what advice do you have?
- RGRenu Gupta
Yeah. Go for it. So you know, I- I tell my team this a lot. Put your head down and just do good work. Um, sales are the numbers dashboard game so let the numbers speak for themselves and fi- find your tribe. Tribe, right? Find your tribe. Um, it's no coincidence that we're all on the same panel together. This is my tribe, this is who I go to for career advice, for mom advice, for, you know, life advice. And so you- your tribe is out there. Go find them, go find your community and you'll be surprised about how many people want to support you on your journey.
- HSHarry Stebbings
I absolutely love that. This has been so much fun. I- I feel like I've kind of been ingratiiated into this, like, tribe. Which I probably currently haven't as I'm not a sales leader, not- not a parent, um, and as a young single guy. But I'm gonna take that moment anyway. I can't thank you enough for- for welcoming me into your tribe for an hour and 15 minutes. This has been so much fun and I've actually learnt a huge amount, bluntly. So I so appreciate it and this has been wonderful.
- JMJulie Maresca
Thank you so much.
- RGRenu Gupta
Thanks so much.
Episode duration: 1:10:49
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