20Sales: How to Scale a Career While Scaling a Family, Strategies and Specific Tools To Help Maintain Work-Life Balance, What Companies Can Do To Empower Parents To Be Their Best Selves & How to Prevent Parental Leave Being an Inhibitor To Your Career

Today's 20Sales is a special Mother's Day edition where we are joined by 6 of the best sales leaders who also happen to be rockstar mothers. The Profiles Maggie Hott is on the GTM Team (Go-To-Market) at OpenAI. Before OpenAI, Maggie was Director of Sales @ Webflow and before Webflow spent an incredible 6 years at Slack. Stevie Case is the CRO @ Vanta. Prior to Vanta, Stevie spent an immensely successful 6 years at Twilio as VP of Mid-Market Sales. Renu Gupta is an advisor and sales consultant to some of the fastest-growing SaaS companies today. Previously she has held sales leadership roles at Slack, Thrive and Dropbox. Lauren Schwartz is the VP Enterprise Sales @ Fivetran. Before Fivetran, Lauren spent 4 years at Segment as Senior Director of Enterprise Sales leading to their acquisition by Twilio. Julie Maresca is the Head of Global Accounts at Atlassian. Prior to Atlassian, Julie spent an immensely successful 6 years at Slack in numerous roles including Head of Enterprise Sales for North America. Jessica Arnold is the VP of Global Sales Development @ Amplitude. Before Amplitude, Jessica was the Senior Director for Inside Sales North America at Dropbox for close to 6 years. In Today's 20Sales Mothers Day Episode We Discuss: 1.) How have you navigated growing in your career at the same time, growing your family? 2.) How do you balance your career and being a mother - when do you lean in and out? 3.) What are some specific strategies or tools that have helped you maintain a work-life balance? 4.) How do you prioritize your mental health and wellbeing while juggling your responsibilities at work and at home? 5.) How do you handle the guilt that many working mothers experience when they have to focus on their career? 6.) What are the unique challenges and advantages of being a mother in a sales leadership role? 7.) How has your experience as a mother influenced your leadership style and decision-making? 8.) How have you navigated going out on maternity leave without it having an impact on your career? 9.) America has one of the worst parental leaves of any country in the world. How can you advocate for parental leave if the existing policy isn’t up to par? 10.) What are some ways that companies can create a more inclusive and supportive environment for working mothers in sales leadership roles?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  So I always say my mother is the light in every room that she enters. I wouldn't be able to do what I do without her, and I think this is so true for so many amazing mothers. And so with Mother's Day this weekend, I really wanted to commemorate some amazing mothers, but also rock star sales leaders in this 20 Sales Show. And so today, we're joined by an array of incredible sales leaders who are also rock star mothers. They work at firms including OpenAI, Atlassian, Amplitude, Vanta and Five Tran, and this is such a special episode. But before we move into the show today, you might remember in our amazing episode with Maggie Hot, she mentioned a tool she could not live without called Pocus. What is Pocus? Well, Pocus is a revenue data platform that makes it easy for go-to-market

• 0:41Harry Stebbings?

  teams to analyze, visualize and action data about their prospects and customers without needing engineers. Pocus helps companies like Miro, Webflow, Loom and Superhuman focus their sales and success teams on the highest priority opportunities by surfacing insights at the right moment so reps can take action quickly. Pocus gives you a 360 degree view into product usage, empowering you to act on insights and fill your funnel efficiently. Sales teams save 10-plus hours per week digging through data to surface millions of new revenue opportunities. Learn more about why top PLG businesses trust Pocus as their revenue data platform by visiting pocus.com/demo. And Salesloft is the leading sales engagement

• 1:25Harry Stebbings?

  platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify and Stripe all love a new Salesloft, and so can you. It's the new way to sell. Find out more at salesloft.com. And finally, finding your next customer is hard, but it really doesn't have to be. ZoomInfo is the answer. So ZoomInfo handles the full revenue pipeline from marketing to sales, even ops, all based on the number one ranked business data. It's the single best way for B2B professionals to find their next customer, close their next deal and stream

• 2:10Harry Stebbings?

  Streamline their operations and best of all, it's all in one place. So your revenue teams can collaborate easily and close deals faster. Customers include enterprises like Snowflake, Workday, PayPal, Dropbox, Unilever, and thousands of startup and growth companies. Thirty thousand customers and growing. ZoomInfo is making their go to market playbook available for free for anyone's try. So if you want to find out how you can use intent data to target key prospects, or how to revive a stalled deal by expanding your buying committee outreach, head on over to zoominfo.com/20vc to see for yourself and sign up for a free trial of the ZoomInfo platform.

• 2:53Speaker 01

  You have now arrived at your destination.

• 2:56Harry Stebbings?

  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 going to start with the question very simply. Who are you and what's the best part about being a working mother? Jess, we're going to go to you first. Who are you and what's the best part?

• 3:13Speaker 02

  Hi, Jessica Arnold, VP of Amplitude and Sales Development. I am the mom of two kids, six and three. I think the best part about being a working mom is just having an independent life outside of my normal life. And that also being able to just show that's okay for my kids and just model that.

• 3:29Harry Stebbings?

  Lauren, I'm going to hand over to you. Best part and who are you?

• 3:33Speaker 03

  Yeah, great to see you again, Harry. I'm Lauren Schwartz, VP of Enterprise Sales at Five Fan. 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. And the way it's inspired me to build a more inclusive work environment.

• 3:50Harry Stebbings?

  Stevie, we said before the show, as I said, my mother is going to learn gaming after hearing your episode. Still waiting, but I live in hope. Over to you, best part and who are you?

• 4:00Speaker 04

  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. Stevie Case, I'm the Chief Revenue Officer at Vanta and I'm also a 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. 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 single mom when she was very young and now I think it's probably really, truly one of the superpowers that I've developed because I'm a mom.

• 4:42Harry Stebbings?

  We're going to get into that. That is a great and a meaty topic for the intro. Thanks for just dropping that one in, Stevie. Rain, your turn.

• 4:49Speaker 05

  Thanks, Harry. Raina 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. The best part about being a working mom is showing my son and my daughter what an equal partnership looks like at home when two parents who love their careers but love their children even more.

• 5:07Harry Stebbings?

  Maggie, it's so good to see you again. We do message very frequently, so you've probably had enough of me by now. But tell me, who are you and what's the best part of being a working mom?

• 5:15Speaker 06

  Hi, Harry. 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 Slack4. Spent about six and a half years there. 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 see how they've adjusted their mindset over the past couple of years of their lives and that they have really no fears and go after whatever they want.

• 5:45Harry Stebbings?

  Julie, your turn. Best part and who are you?

• 5:48Speaker 07

  Hi, Harry. Hi, everyone. So good to be here. I'm Julie Maresca. I lead global accounts and strategic verticals at Atlassian. Prior to that, I spent six years at Slack in a variety of leadership roles. I am a mother of three. I have three boys. I have twins who will be nine and a two-year-old boy who is potty training, so that's fun. Part of being 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. There's a lot of women right now that are questioning whether this is possible. So I love that we're all here talking about how we make it work.

• 6:29Speaker 07

  I also love that being a boy mom, I'm modeling that working mom is normal and it normalizes that for them. And mom and dad both work and both help out at home.

• 6:40Harry Stebbings?

  Three boys and then the first, hey, honey, it's twins. And I thought the sales quotas were nerve wracking in 2023. That's another thing. We'll get into that. That was fascinating. Well done, Julie. Stevie, we're going to start with you on a really tough question, which is how have you navigated your growing career while also growing your family?

• 6:58Speaker 04

  Honest answer to this is very poorly at first. It was really painful in the early days. My daughter is 18 now. 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. 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. I'm trying to explain features and I'm in the driveway at Wendy's trying to get her a Frost. And like muting in between explaining features. Like, it was ugly.

• 7:42Speaker 04

  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 road right under my feet. And I would only focus about two feet out in front of that. That's all I could do. It's gotten a lot easier over time, thank goodness. 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 continue to serve me well because the truth is it's gonna be gnarly at times,

• 8:24Speaker 04

  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, 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.

• 8:46Harry Stebbings?

  Judy, how do you think about it? How do you think about managing that balance and also when to lean in, when to lean out?

• 8:52Speaker 07

  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 life or work can definitely tip the scale quite significantly. So it's a practice and I like to give myself a little leeway. I may not balance every day or balance even a week. This month, maybe I'm traveling for the first two weeks, but I'm gonna take off a few days the last two weeks. I try to look at the long view that balance ebbs and flows over time. But I do think planning and setting expectations is really important. I have a global team, so I don't mind getting on meetings at 8:00 PM.

• 9:34Speaker 07

  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 set those expectations upfront and I feel that when I'm setting expectations and not having to make game time decisions, I don't have regrets. 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 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 from myself or my family. Of course, you can't always do that. It's great to have a support system.

• 10:17Speaker 07

  I have a husband that I can hand off the kids to when I need to. And then making sure you find out like what fulfills you and what you enjoy doing. I'm gonna choose not to do the yoga class with the team afterward. But 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 in what's going to make me successful and fulfilled with my family.

• 10:43Harry Stebbings?

  Julie, you mentioned kind of game time decisions there. Maggie, if there's anyone who can absolutely crystallize like a plan, I know it's you with your kind of strategic thoughts, which you've outlined to me many times before. 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?

• 11:04Speaker 06

  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 7am to 11pm. 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 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. Whether that's something of, hey, can you watch the kids for half an hour? Or asking for help from your partner.

• 11:44Speaker 06

  It's also if you have the means and are able to afford it, spending some money on things maybe like grocery delivery. 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 cleaners, same thing, rather than 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 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.

• 12:27Speaker 06

  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 going to mean so much more to them.

• 12:55Harry Stebbings?

  I love the way I'm like nodding my head like, ah yes, getting those two hours back for grocery deliveries. Ah, yeah, I haven't been to a grocery shop in years, but I didn't feel your pain, but I sympathize. Lauren, I have to ask, how do you prioritize your mental health and wellbeing, being the best version of yourself, while also juggling responsibilities, both work and then at home?

• 13:15Speaker 03

  Yeah, it's really hard is the answer. My take 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 them I've been singing with for 30 years. 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 mash the feeling of 15 troubled 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 wellbeing. But 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

• 13:59Speaker 03

  for our teams. And the only way you can do it is to fill your cup.

• 14:02Harry 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 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?

• 14:15Speaker 03

  In my role, it requires travel. So I sometimes am traveling for a client meeting on a Tuesday, which is how I rehearse. And what we've done to be inclusive to folks who have that kind of commitment is 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 work on music for our upcoming concerts.

• 14:37Harry Stebbings?

  This is like the most productive and efficient singing group I've ever heard. Like an attendance by Zoom if you're traveling. My word, I'm so impressed. I think the hard thing is often there's a lot of guilt tied to 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 intrigued, how do you think about handling the guilt that many mothers have when they have to focus on that career?

• 15:02Speaker 02

  It's nice that you really shot up an easy question. Harry complicated, but it's free surface.

• 15:08Harry Stebbings?

  It was teed up for me, Jess.

• 15:11Harry Stebbings?

  Hollywood is fake, right?

• 15:13Speaker 02

  A little story about me. My mom actually launched corporate America and started her own business as a sales trainer, motivational speaker. So my childhood car rides were actually filled with books on tape with seven spiritual laws of Deepak Chopra or Brian and Tracy affirmations. But one thing that she actually put in practice with our family was this seven quick question questionnaire that centered around core value identification and goal setting. And so we did this every year as a family and as an adult, 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.

• 15:52Speaker 02

  And so when I became a mom, I had this feeling that I just went from 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. And so then I started being like, what actually is guilt? I started like doing readings on it, trying to see what people are saying about it. And I found out it's an emotion and it's an emotion that comes from when a person actually believes that they've 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 from my mom.

• 16:36Speaker 02

  And it just clicked that because I already knew this, I knew that guilt was always going to slip in. Like you can't avoid that. It's going to 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 roll off my shoulders. It's not perfect. I have great days. I have not so great days. 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 that actually makes it real.

• 17:18Speaker 02

  It allows me to be reflective through the years and understand what needs to change. And it also gives other people in my network a way to support me or celebrate me if I'm doing something that I wanted to accomplish.

• 17:29Harry Stebbings?

  Someone said earlier that it's important to ask for help. Jess, if you would have given me advice, I'm a young guy with no kids, but I have people in different teams that have kids. I would hate for them to feel guilt that they are spending time with their children. 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?

• 17:54Speaker 02

  We're all salespeople. I would just get curious, start doing a discovery call. In all seriousness, though, it's asking what they need. When do you do drop off and pickup? Are you going on any trips? When's your kid's spring break? My boss just asked me that recently. When's your kid's spring break? Are you taking time off? I hadn't even thought about that. So I think it's just about knowing the people that you're working with and being curious about their lives.

• 18:17Harry Stebbings?

  We mentioned what leaders can do in terms of leadership. I do want to talk about the aspect of sales leadership and combining the two. Let's start right now 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?

• 18:32Speaker 05

  No, it's a good question, Harry. So look, women are already a minority in sales. 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, 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 very efficient with our time and we're very good at qualifying out, which is obviously a huge pro as being a salesperson. 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 respect people's times. We know how to show value. We know how to present value.

• 19:16Speaker 05

  My hope is that by doing panels like this or 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. 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 because you're worried that you might lose that freight territory or lose that promotion, you're probably working for the wrong person or organization.

• 19:47Harry Stebbings?

  I totally agree with that. Jess, I'd love your thoughts on this. Challenges, but then also advantages of being a mother in a sales leadership role.

• 19:55Speaker 02

  Similar to what Rena was talking about, I used to feel like I had to assimilate all the time. So I had to speak in different language or figure out what the rules of golf were. Still don't know. I think the Masters is going on. But in all seriousness, I just always felt like I had to put on this mask to make sure that I could be with the other mostly male leadership members in the room. And it just feels fake. And so when I finally started sharing more about myself and I just found I could 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. When I identified that challenge and changed it and was just like, hey, why don't I just be me?

• 20:37Speaker 02

  I found out pretty great. I found that people liked me too. Then I started leaning more into that and understanding, I think Stevie actually mentioned this earlier, is what is your superpower? Being different is our superpower. And so being able to lean into that, 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 meet people differently. And I think that's something that I really found to be an advantage.

• 21:04Harry Stebbings?

  I remember when I first became a VC, I bought a Patagonia Gilet because it was terribly uncomfortable. I've still got it. It's like brand new. I've still got it, but it's just very strange. Like a cardigan. Lauren, I want to move to you. We mentioned that kind of challenges and advantages being sales leadership. How's your experience as a mother actually influenced how you think about decision-making and style of leadership?

• 21:26Speaker 03

  Yeah, 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. And that truly came from having the experience of being among myself. A couple of us have said this already, but there aren't a ton of moms 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 allies who have fought to make it possible for me, for us, to have a seat at that table. So you asked about how it influenced my leadership style. 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 is leading groups for women in enterprise sales leadership,

• 22:11Speaker 03

  seeking out opportunities to mentor folks with diverse backgrounds and doing them like this, participating in a public speaking engagement wherever I can to spread the word that women and moms can and will achieve more than what they've been told is possible. 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 a men's club and so she couldn't attend. 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.

• 22:51Harry Stebbings?

  I asked one and 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 feedback and then also goal setting. It's such an important part of parenting as well. How has being a mother impacted how you think about goal setting and expectation setting with them?

• 23:09Speaker 07

  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. They know they don't want to eat broccoli, but it's good for them. You have to give that tough love. I feel like those innate sort of qualities of being a mother actually really can be great leadership qualities, especially, Harriet, and what you're speaking about and giving feedback. If your team... Knows that you care about them and your people know that you care about them. Then everything you say, they know that it's because you really want them to succeed and it is in their best interest.

• 23:52Speaker 07

  I think you have to break down the walls. You have to be vulnerable. 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 also make them know that they can run through walls and they can do it. I do think what we learn instinctually as mothers does make it a little bit easier to give that feedback. If you really embrace it, like Jessica said, your being a mom is a superpower when it comes to sales leadership.

• 24:29Harry Stebbings?

  Oh, my mother's an incredible superhuman. Can I ask you the 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 like superiors or CEOs and say 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 that honesty?

• 24:59Speaker 07

  I think 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. Rainu mentioned, 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 right place. I also believe it's about earning the right. You can earn the right to have those 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 the company and the culture to be there and be open to it. And that's why I think it's on us to either choose places that we know really value that or drive that change. But I do agree, we probably still have a ways to go.

• 25:43Harry Stebbings?

  I want to touch on some inspirational stories, some anecdotes. Let's bring this to life. Stevie, there's no one better than an amazing story. I loved our episode so much. I wanted to move to you. When we think about inspiring stories or personal experiences of like overcoming challenges related to balancing motherhood in your career, what's one or two that come to mind for you?

• 26:02Speaker 04

  Yeah, 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. I really deeply struggled with that for years when my daughter was younger. I had started this sales career and I already felt so completely out of my element. I had this weird gaming background and all this backstory that I was trying to push as far away as possible. And then not only was I a mom, I was a single mom and I just was honestly doing everything in my power to hide it. And I would 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.

• 26:45Speaker 04

  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 if I had to go on a trip and I was a single mom, I would fly people in from all over the country 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 the people I worked with. It was so hard and so isolating and so painful to do that.

• 27:28Speaker 04

  That continued for a long time. And I went to Twilio where I was before Vanta. And at Twilio I started as an enterprise AE and I started on my same thing. I'm going to pretend. But I had this incredible sales leader, shout out Allison Welch, who is also now a CRO over at Neo4j. Allison was amazing and she really championed my career there. And the first time she promoted me at Twilio, I had been crushing it as an AE. And she wrote this incredible note. She said, I want to 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 gave me permission. And from that point forward, everything felt different because I felt seen as a full human. Like Jess said, I embraced it and

• 28:12Speaker 04

  I ran with it and I felt empowered in a very different way. 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. 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. 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.

• 28:56Speaker 04

  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.

• 29:04Harry Stebbings?

  One question, do you think vulnerability is a luxury of being successful? You're a rock star 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?

• 29:16Speaker 04

  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 you never really feel like you've made it. I think 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. I'm still climbing. 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.

• 29:58Speaker 04

  You can open up an environment where people are allowed to be human and make mistakes and be real. I think 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. We all have those things. 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.

• 30:35Harry Stebbings?

  I view it as supporting the economy. My therapist has unwavering demands on his time. I'm really a net additive to GDP. Maggie, I want to move to you on an inspirational story. What's the first that comes to mind?

• 30:48Speaker 06

  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 and really anyone, we have a duty for those out there to set this kind of standard and set the stage of how we want to show up. And we're going to be setting this mirror and those who potentially look up to us or all of us relating orgs are going to mirror what it is that we're putting out there. And we're going to show that it is okay to act and behave and share these stories. So thank you, Stevie, for always being so open and honest. Yeah, working parents are just some of the toughest that are they're 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 coming from a place of privilege, but for my teens, I want them to know that I am a working parent.

• 31:32Speaker 06

  I am a working mother when I am pregnant, that I'm not having the best days. And sometimes I just need to cancel that meeting or go off camera. And actually, speaking of being pregnant, one of the 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 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. And who's going to want someone who's going to get the role and then go out on leave for the next five months? And I actually had two male allies.

• 32:12Speaker 06

  Our VP of Sales, as well as our head of enterprise, encouraged me to go for the role in addition to many others within the company. But that was something that really stood out is that they told me the company is invested in this person in a long term. 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. Again, literally interviewed eight and a half months pregnant. I stood in the entire interview. I was so uncomfortable, but I like felt like I had to stand and be there. And I really celebrated that I had been 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

• 32:54Speaker 06

  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 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. You should just really just go for it and see what happens.

• 33:24Harry Stebbings?

  Maggie, I love that story in terms of just going for it. And I didn't actually know that, but also eight and a half months pregnant going for a role. You go. That's fucking awesome. Do you want to ask it? Cause you mentioned that the time off afterwards. I think us Europeans and particularly the Swedes, in terms of parental leave, how do we think about parental leave specifically? How have you navigated this? Cause it is a challenging topic, also knowing that you're inevitably behind due to, I feel bad saying it, but like your career being on pause while everyone else does progress.

• 33:52Speaker 06

  So career pause, 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 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. It really needs to be both need to have pretty darn near equitable leave. 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.

• 34:33Speaker 06

  And this is going to happen multiple times if they have multiple kids. So in my case, I've now gone out and leave twice in the last two years. And then actually speaking on the home front, studies show. That with a non-birthing parent or partners 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 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, your company is able to increase the leave for the other parent, it's going to be associated to greater relationship stability.

• 35:14Speaker 06

  And this is actually largely because when partners take leave, it's going to signal a greater investment in family life. So it's going to reduce the burden on mothers. It's going to strengthen the parental relationships. It's really less about 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 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 from a major life event. Your body is just completely reorganized itself. Some of us 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 going to help the birthing parent or the birthing mother get back into the swing of things with their career,

• 35:59Speaker 06

  because they've now had this 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 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.

• 36:23Harry 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 want to go back to work as soon as possible. Should we force it? Because it is important for so many different reasons.

• 36:37Speaker 06

  I believe so, but I think that also comes to making sure that men are also paid, that you're getting 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. Most 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, it's potentially forcing or requiring for the partner, strongly, strongly encouraging the partner to take the time off. But it's also making sure that they're not going to be missing out on compensation when they are on that time. And sadly, a lot of policies are out there as 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.

• 37:18Harry Stebbings?

  Lauren, I'm intrigued. How did you think about this kind of potential career pause and that aspect of parental leave?

• 37:24Speaker 03

  Yeah, I think it's critical of what Maggie just said at the end there, the non birthing parent and the birthing parent, right? We want to expand the scope of policy design to any type of family unit that's bringing a child into the world. I didn't think of it about as putting my career on pause. Really what I thought was how do I continue the momentum while I'm out? So for me, it was critical to invite folks on the team to step up. Great 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 don't want to make light of it because you really have to take responsibility to make sure while a leader is on leave, helping a team be successful and what are the expectations?

• 38:07Speaker 03

  And what type of accountability are you going to put in place? Because the business continues whether you're there or not. So it's your choice whether you want to put a blueprint in place to ensure your team has what they need while you're investing your energy into keeping a tiny human alive.

• 38:22Harry Stebbings?

  Can I ask, is it tough to be fully out? And what I mean by that is it's so easy to just pop on Slack or pop on email. Just quickly, it was just half an hour a day, but then you're in and you're about and it's tough for your team then. And is that right or is that wrong? How do you think about that? Like fully in, fully out, checking in, not checking in? What's the right answer there?

• 38:40Speaker 03

  For me, I really tried to honor the fact that it was a once in a lifetime or multiple times depending on your family structure. But 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. Really easy for me to say this, let can wait or empower someone else on the team to make a decision. Ideally, what I've done is create a team that can fashion in my absence. Yes, of course, always tempted to engage and folks reach out sometimes and that's really hard to create that boundary. But for me, it was setting up times where I was like, okay, I'm going to devote this hour to thinking about what's going on in the business. And

• 39:23Speaker 03

  then after that, I'm going to sign off, no guilt. I assigned myself a schedule. I'm following the schedule and I'm going to refocus on this again, a really magical, once in a lifetime exhausting experience.

• 39:35Harry Stebbings?

  You clearly never saw cheaper by the dozen, but I'm thrilled that I managed to get in a plug for Slack there. Maggie, you should be so proud of me. Mention Maggie, America's worst parental leave policy. Sometimes I think funny things and then realize I probably shouldn't say them. But 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?

• 39:55Speaker 06

  Yeah, absolutely. Great question. I think about it in a kind of four step structure 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 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 companies within

• 40:39Speaker 06

  your industries. If we are Webflow, who are the maybe top success fund companies that we want to 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 like allies to families. So really get together a group, form a group of people to advocate for change in parental leave policy. Policy together and work on gathering that data across your network. 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

• 41:23Speaker 06

  this discussion at the executive level. So really, you've got this whole group of people, some are more junior in their career, 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 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 and 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.

• 42:02Speaker 06

  Sales in particular has a ton of nuances 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 going to 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 the 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 honestly, one of the most important things that you can do is ensure that you have an adequate leave

• 42:47Speaker 06

  coverage plan, very similar to what Lauren was saying. When I went out on my last 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. Key hirings, final round interviews, firings, terminations. I made it like very black and white of 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 Very clear with what your asks are and what your needs are for when you go out on.

• 43:23Harry Stebbings?

  You mentioned there's like gotcha elements there and there's intricacies. Lauren, I'd love to hear your thoughts on this.

• 43:29Speaker 03

  Yeah, I'll just share my story. I was pregnant when I started at Bypram. And I'd done the high level due diligence of confirming that there wasn't fat differential 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. It's gentle subject to brief and yet employed. 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 C for 12 months. Although that tenure cliff seemed outrageous to me. It was actually a step up from what's been provided to us by the government.

• 44:12Speaker 03

  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 to rewrite the policy. In particular, what I think was most effective in my approach was that we focused on their DEI implications of the policy. So 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 minutia. And Maggie also mentioned on the sales side that 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.

• 44:57Speaker 03

  But it's totally reasonable to advocate that just like any other role, a salesperson should be paid our on-harvest earnings, which includes variable, while we're on leave. It's the only way to prevent penalizing birthing parents or taking leaves that they physically require.

• 45:12Harry Stebbings?

  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.

• 45:27Speaker 03

  Absolutely. And there are nuances to it. Every deal is structured a little bit differently and also depends on the side 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 profitable growth, 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 we're not making our problem their problem.

• 45:57Harry Stebbings?

  You mentioned kind of some tough elements there and they're actually finding the community of people we can talk to. Reni, I'd love to speak to you about this. So she's 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?

• 46:14Speaker 05

  Yeah, absolutely. I know Julie and Lauren, the team, covered this earlier as well. So my oldest is nine, he was born in 2014. His name is Roman. And nine years ago, as you can imagine, being in office was the trend. And when you leave the floor of the office you're sitting in, everyone can see you. It's very visible. And for the last nine years, 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 in my bag and leave the sales floor by sometimes as early as four, even 4:30, depending on where he was in daycare or preschool or with our nanny. But honestly, I'd never felt guilty. And trust me, leaving the sales floor at four, 4:30 is, this is when some of the folks that don't have kids, there's really good energy.

• 46:56Speaker 05

  There's deals being closed, end of quarter, you can imagine with like at this time. And I sat right next to our VP of Sales at Slack for three years. And he would see me, the days I was in charge picking up my kids, he would see me get up at four, 4:30, always with, have a good day, Reni, awesome day today, or whatever it was. And that helped me not feel guilty. That gave me the permission 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 the 9:00 AM first swim lessons that Roman had in a pool that was across the city. And my team, people that I poured into, the people that poured into me, always knew that this was something that was very important to me. How can you speak up as a leader?

• 47:39Speaker 05

  Know what your team's non-negotiables are. Ask them. Be curious, Jess said. Give them the permission they need to go to their kids for swim lessons or their spring musical that's always like at 1:00 PM or the parent-teacher coffees that are always at 10:00 AM, right? Make sure that you as a leader know what's important to your team.

• 47:58Speaker 03

  And 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. And don't be afraid to tell them that you want to be at your child's swim lesson or at pickup every day.

• 48:10Harry 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's lovely to have that support. And when I think about that, I think about kind of mentorship. Lauren, if we think about how mentorship or support from others has really impacted, well, Journey is a working mother. There are some points which really are central for you.

• 48:27Speaker 03

  Yeah, I think it's critical to get creative in building your personal board of directors. I'm part of an incredible women's circle made up of other alumni from Stanford Business School that span from their fifties to their seventies. And so there's something really magical about sharing the ups and downs that you're carrying with that 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 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 spans outside of your company, outside of your industry and other cases.

• 49:11Speaker 03

  And for me, when I started at my current company, I mentioned it, I was pregnant and my boss, current boss, and the guy who hired me just that yeah, was 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. When Jim gave me my verbal offer, I said, listen, you need to think critically about hiring me for VP of Sales 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. Not only is it tolerable, but it's celebrated.

• 49:53Harry Stebbings?

  Can I introduce one, which is, I said to someone the other day on the team, 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 because I was giving them the room and the space to be what they needed to be?

• 50:15Speaker 03

  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 outside of 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 and create a space for people to be, as Dee said, vulnerable in their thoughts.

• 50:36Harry Stebbings?

  Yeah. Phew, I was worried. Maggie, Rainu and Judy, you have the mental commonality of Kevin Egan, who I actually spoke to for this wonderful man, we had a great chat. But I'd love to hear, how was that impactful in terms of how you think about really your journey as a working mother?

• 50:51Speaker 07

  I'm happy to start. I still work for Kevin. I think it's just having a great mentor empowers you to be who you are. It opens the door for you to work freely, live freely. And what Rainu said, like, we have to demystify that 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 how you get the work done, but it's that do the work. And I find that when we give people the avenues to get their work done and work in the way that best suits them, we see people

• 51:35Speaker 07

  at their best. And I think Kevin was a great leader and is a great leader in showing that way. 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. 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 at the end of the day, we all want to be successful. So the sooner we can get to that mindset, the more successful and happy you will be and your teams will be.

• 52:15Harry Stebbings?

  Jess, who's been really impactful for you in your career and enabling that feeling from you?

• 52:19Speaker 02

  Before we went on leave, The first time we had on to this big reorg and I was reporting intramally to our global VP of Revenue, Thomas Hansen, and I didn't really know him that well. 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. I was a random afternoon, I was walking down the hall and he stopped me and he was so excited for me. And he was just like, you're gonna go out and leave. He encouraged you 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 spend that time with your family. He didn't have to stop and tell me that. He made me feel so confident in

• 53:03Speaker 02

  being able to do what I needed to do for my family and for me. And I'll never forget that feeling. And maybe for him, he doesn't even necessarily remember it, although I work with him now in Amplitude and I, we, I'm miserated over this story. 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's also about making people feel the way you make them feel. And if you're not doing that, then I don't think you're doing the right thing.

• 53:31Harry Stebbings?

  So funny. I said that Maya Angelou quote to one of our interns the other day in my fund and I tried to pass it off as my own quote and then they told me that they were an English student and that it was Maya Angelou's. And I told them that's venture capital. We package other people's knowledge instead of Zoro. And so that's lesson one. Next, didn't go down so well. Anyway, Stevie, who was your shining light in terms of this mentor?

• 53:52Speaker 04

  I have been so lucky on this front. 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 all parents. So Alison reported to the CRO, Mark Boroditsky, 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.

• 54:36Speaker 04

  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. 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 just celebrating life moments. And Harry, 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?

• 55:19Speaker 04

  Can I talk about this? Is it okay? And by talking about your mom, you make it more safe. 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.

• 55:37Harry Stebbings?

  It's so kind of you. I just hosted my AGM for my LPs in my fund and we have the biggest institutions in the world. My mother organized everything. She was there for everything. CIOs of the biggest endowments in the world. She smashed it. Maggie, tell me, in terms of actually getting granular and improving situations, how can we create a more inclusive and supportive environment for working mothers in sales leadership roles?

• 56:01Speaker 04

  So I think similar to what everyone said is to normalize having children. Back in the day, it wasn't normal for children to be around, to be talked about. My mother-in-law was Lieutenant Governor of Colorado and she went back to work, I think it was something like two weeks after having both of her sons. 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 going to love it because it's so fun and it breaks things up. Be honest when you're

• 56:41Speaker 06

  Kids are sick or when they have their preschool or their daycare or their school is closed. Don't try to hide it. Say, hey, there might be a visitor who's going to jump in to our call or have them over in the background. Your companies and teams again are going to look up and mirror what you do. And then the other thing you can do is create resources and support and affinity groups. So something that 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 been on their pregnancy journey and wants to help support 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.

• 57:23Speaker 06

  Something that we also had at Slack that I absolutely loved is every month, 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, things like kids and being a parent are going to come up. So really being open to sharing these things. Other things too that I've seen for in-office type cultures, family days at work, bring your kids in. We used to have a Halloween party every year. All the families and all the kids would come and it just continues to normalize. Oh, my CEO has kids, my COO has kids, my CRO has kids. And here's that person's family, which just brings it to a different level. Or if you're a virtual type company, and many of us are,

• 58:08Speaker 06

  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. 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.

• 58:29Harry Stebbings?

  A magician comes in. I think that's called a head of sales in 2023, Mackie. But sure, you 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. I just think we're so much more productive in office. We're all in London anyway. But is that bad of me? And is remote just so much better in terms of being the best in this balance?

• 58:50Speaker 06

  It's going to be different to every single company. I just went from Webflow, which is fully remote, and now to OpenAI, which is more of a hybrid model. So it's going to be, every company is going to have its different choices. The one thing I wouldn't say, though, is still always remember to be flexible. While in-office may be a requirement, again, doctors, preschool, or different school events, or outings, soccer games, parent-teacher conferences. In a remote world, it is so much easier to just 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, family event, sick event, whatever it might be, it is totally okay.

• 59:34Harry Stebbings?

  All right, we're going to do a quick fire. So we're going to do a quick fire on advice, which is like a short snippet of wisdom from each. And I'm going to 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?

• 59:50Speaker 06

  Absolutely. It's believe in yourself. So have the confidence in the swagger and your ability to have a career and 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 going to feel it. But you also need to accept this guilt as normal and normalize it and move on.

• 1:00:16Harry Stebbings?

  Lauren, what do you think? What's the advice?

• 1:00:18Speaker 03

  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 stork 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.

• 1:00:37Harry Stebbings?

  Jess, what's your advice?

• 1:00:39Speaker 02

  Choose the right partner. I think being able to have the conversation before family around.

• 1:00:44Speaker 05

  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 partner wants to do and just envisioning life after kids and how you're going to deal with it together.

• 1:00:57Harry Stebbings?

  Yeah, sadly, Bumble premiums not paying off for me. Julie, your turn. What advice do we have? I was completely distracted there. That was great advice, though, by the way. Pick your barn is absolutely a brilliant beat. I think it's Warren Buffett's biggest piece of advice, too. Julie, what advice do you have?

• 1:01:12Speaker 07

  Yeah, 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 so time in your life or work where you have to make decisions and make compromises, you want to 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 much time with these people. Make sure you love who you work with. Make sure you love the culture. Make sure the journey is one that you can embrace. And then the sacrifices or the guilt, it feels a lot more manageable.

• 1:01:45Harry Stebbings?

  Stevie, your turn. Hit me with some wisdom. Tom, what advice?

• 1:01:49Speaker 04

  Oh, my gosh. Mine is don't apologize for yourself because you're always going to have other commitments, things you need to leave for. Your child is going to show up on camera during Zoom calls. It's going to 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.

• 1:02:22Harry Stebbings?

  Rainu, final one. Wisdom. What advice do you have?

• 1:02:26Speaker 05

  Go for it. I tell my team this a lot. Put your head down and just do good work. Sales are the numbers dashboard game. Let the numbers speak for themselves and to find your tribe, right? Find your tribe. 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 life advice. Your tribe is out there. Go find them. Go find your community and you'll be surprised by how many people want to support you on your journey.

• 1:02:50Harry Stebbings?

  I absolutely love that. This has been so much fun. I feel like I've been ingratiated into this like tribe, which I probably barely haven't as not a sale leader, not a parent and as a young single guy, but I'm going to take that moment. Anyway, I can't thank you enough for welcoming me into your tribe for an hour. This has been so much fun and I've actually learned a huge amount bluntly. So I so appreciate it and this has been wonderful.

• 1:03:14Harry Stebbings?

  What a fantastic and fun show that was too. I'm so proud to have done that show to commemorate the amazing mothers all around the world. We could not do it without you and we so appreciate you. But before we leave you today, you might remember in our amazing episode with Maggie Hott, she mentioned a tool she could not live without called Pocus. What is Pocus? Well, Pocus is a revenue data platform that makes it easy for go-to-market teams to analyze, visualize and action data about their prospects and customers without needing engineers. Pocus helps companies like Miro, Webflow, Loom and Superhuman focus their sales and success teams on the highest priority opportunities by surfacing insights at the right moment so reps can take action quickly. Pocus gives you a 360-degree view into product usage,

• 1:03:59Harry Stebbings?

  empowering you to act on insights and fill your funnel efficiently. Sales teams save 10-plus hours per week digging through data to surface millions of new revenue opportunities. Learn more about why top PLG businesses trust Pocus as their revenue data platform by visiting pocus.com/demo. And Sales Loft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify and Stripe all love a new

• 1:04:40Harry Stebbings?

  Sales Loft and so can you. It's the new way to sell. Find out more at salesloft.com. And finally, finding your next customer is hard, but it really doesn't have to be. Zoom Info is the answer. So Zoom Info handles the full revenue pipeline from marketing to sales, even ops, all based on the number one ranked business data. It's the single best way for B2B professionals to find their next customer, close their next deal and streamline their operations. And best of all, it's all in one place so your revenue teams can collaborate easily and close deals faster. Customers include enterprises like Snowflake, Workday, PayPal, Dropbox, Unilever and thousands of startup and growth companies. 30,000 customers and growing. Zoom Info is making that

• 1:05:23Harry Stebbings?

  Go to Market Playbook available for free for anyone's try. So if you want to find out how you can use intent data to target key prospects, or how to revive a stalled deal by expanding your buying committee outreach, head on over to zoominfo.com/20vc to see for yourself and sign up for a free trial of the ZoomInfo platform. Now, we have an amazing episode coming for you on Friday with Clem at Hugging Face, so stay tuned for a cracker there.