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Excelling at Public Speaking & Building Diversity with Stellar Women's Shannon Brayton

Mary Rechtoris

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Mila and I had a much-anticipated guest on this episode of Stellar Women: Shannon Brayton. After hearing Shannon speak with our CEO Mike Gamson at a company event, we knew we had to have her on the podcast for her energy, authenticity, and wealth of experience in both marketing and the world of tech.

Shannon brought that same energy to the podcast. During this episode, we discuss why innovative companies are making diversity a part of their strategy early in their founding, her most controversial piece of advice, and how she became an all-star public speaker who has interviewed Michelle Obama, Richard Branson, Chelsea Clinton, and more.

Heena Bhambhlani

Shannon Brayton

Bessemer Venture Partners


Mary Rechtoris: Hey Stellar Women fans. I'm your host, Mary Rechtoris.

Mila Taylor: And I’m your co-host, Mila Taylor. Stellar Women shines a light on female leaders making their mark in tech.

MR: Mila and I are really pumped. This week, we have Shannon Brayton on the podcast. Some fun context for our listeners: at a company event about a year and a half ago, our CEO Mike Gamson was interviewing Shannon because they worked together at LinkedIn and did a speed round of questions. One of them, I think, was something to the effect of “What are you watching?” Shannon, you said, “Fleabag.” I had heard good things and that was the final motivator, so I binged it in a couple of days because as people know, I'm a very big binge TV watcher. I just want to say thank you. Listeners who haven't watched “Fleabag,” it is just a work of art. I highly recommend that show.

Shannon Brayton: It is. I will say, though, it is a little risqué. I thought badly after I recommended it without giving that caveat for people who wanted to watch it. But I do think it is a work of art in many ways. Super talented.

MT: I love it. We’re so excited to talk to Shannon. I remember hearing her at Relativity Unite, which is an event where she came and spoke. Immediately, Mary and I kind of looked at each other and we were like, “One day we have to get her on the podcast.” I feel like it's so refreshing to see someone who's achieved so much in their career, but then still come and be so real. Thank you for that, and we are so excited to talk to you today.

SB: That's nice of you. Thank you.

MT: To start this off, what we do every podcast is go through a highlight of the week—anything that happened this week, last weekend, whatever you can think of. I'll get us started. I started a new role at Relativity on Monday. Before, I was on the social media team, and now I'm on the PR team. I didn't move far, but it’s a new, exciting chapter for me so that’s my win.

MR: Very excited for Mila. My win is going to be personal in nature. So, for those of you that are in the Chicagoland area, there's this place in Deerfield called Tony’s Subs. It's one of my favorite places. I had a turkey sub with mayo and pickles—the works. It just made my whole week and probably month, so I highly recommend Tony’s Subs. Shannon, not sure if you can live up to a sandwich, but what's been your highlight?

SB: God, what a high bar, Mary. My personal/professional win is intertwined. I started a new job on May 4 and the team pulls off an event every year that I've been hearing about all throughout the interview process in terms of how much work it was. It happened yesterday and I thought it went incredibly well. I was super proud of the team. Watching them pull it all together with limited supervision and input was awesome. I had very little work to do and very little credit to take for that event, but it was fun to be part of and see everybody execute the way they did. That was fun.

MT: So, Shannon, you are a big figure in the tech space. You are the CMO at Bessemer Venture Partners and a board member of Quizlet, Vidyard, and Him for Her. Generally, what excites you about the tech space?

SB: Being in the venture space … I worked inside five companies for 27 years over the course of my career, and I switched over to venture capital just in May. I totally loved it. It's so different and very intriguing compared to what I have done previously, where it all kind of felt similar. I mean, obviously, I encountered lots of challenges and different things along the way, but venture is a very different business than what I was used to. It is fun to be sitting in a partner meeting every Monday and seeing these companies come in and present to us on all the different problems that they're trying to solve in the world. It's interesting. I mean, venture, right now, there is so much money flowing around. There are so many wonderful ideas. The interesting thing about venture capital is trying to pick the right ones. Someone's got an idea for everything, and I wish I was more like that in the way that I think it's really inspiring to see these entrepreneurs of all types come in and pitch the firm on their idea. I feel like the next generation of companies is going to be even better than what we've seen to date. With a lot of these founders that are coming in, they really do have a nice vibe to them. Some of the founders from previous generations of internet companies had this crazy, brash way about them. And I don't see that as much. I think people are realizing early on how important it is to build a great culture. Start it early and think about diversity, not 10 years after your founding, but now, when you're building it. I feel good about what I'm seeing in terms of the types of people and the way that they're thinking about building out their enterprises. It's fun and gives me hope for the future.

MR: It's great that that's not an afterthought, right? It's hard to retroactively go and try make your company or your product more inclusive and diverse.

SB: It’s very hard once you get down that hole to climb out, right? I think it's so impressive now to see that people have really taken the idea that we need to be more diverse from the beginning so seriously early on.

MR: For sure, and we've talked about on the podcast and Relativity has talked about it. Statistics back up that you're going to be more lucrative in the long run if you have a more diverse repertoire of teammates because there's more innovation and creative thinking due to more diverse experiences. The list goes on and on. In the same vein, what we're trying to do with this program is create a more gender equitable field. You're on the board for Him for Her, and its goal is to diversify corporate boards specifically in the tech space, correct?

SB: Really, all boards. But yes, it is. It is to make sure that there's female representation on literally every board out there.

MR: So why don't you kind of set the stage? What do tech boards currently look like generally? For Him for Her and other organizations, why is it imperative to have that gender equity at the board level?

SB: It’s what you just said, actually … You have a way better company, and you build a way better product if you have a lot of different people helping to steer the company. I think if you have the same type of person across the board table, you're not going to crack the diversity problem at the same level with the same urgency or at the same pace whatsoever. I read a story yesterday that said: is this the end of the all-white, all-male corporate board? They basically said yes. Companies now are looking around and they're seeing it as a real detriment to their reputation and who they are as a business to only have white men on their board. I think there's still a lot of companies that do not have a lot of diversity, but I think it's on people's minds. A [non-diverse] board is not necessarily going to be inspiring or going to build the best company. People are really leaning into the diversity angle. And I think it's excellent. It's a little too late for sure in many places, but I'm happy that it’s part of the conversation now. Him for Her is all about getting male allies to sponsor board-ready women to take board seats at private or public companies. And I think it's a worthy mission, especially bringing men into it to help be that supporter for women. It’s a good dynamic and they've done well with their placement so far.

MR: Looking beyond gender, are there certain other diversity measurements [organizations are considering]? Looking more broadly at diversity, what are some forward-thinking organizations looking at in terms of the makeup of their boards, such as different geographies? Are there other considerations that some tech companies should evaluate when staffing their boards?

SB: It is important to sort of say, what are we building and what skills are we lacking? What diversity initiatives are we missing on the board that will eventually help us, right? I think you start with a skill base. [For example, let’s say] we are building a company that is targeting marketing professionals. It's marketing automation, but we have no one who's been a marketer on the board. That’s a problem, right? You start with the skillset. But I was reading something today as well that basically said that, now, what's happening on board search conversations is you're starting out basically saying, “Look, I need a marketing leader. I would like a female who’s LGBTQ and is based in the Midwest because everyone else is a white male based in New York.” I'm using that, obviously, as an example and not a real life one, but I think people are getting specific about the type of person they want to add to their board. It starts with skill, and then you choose from there. What other pieces of the diversity puzzle are you missing on this board and just how important is it?

MT: To that same point, I think obviously a diverse board and diverse leadership team makes for a more successful company. But looking forward, I think that the talent that's coming up now is looking at that when making decisions about which kind of companies they want to join.

SB: Oh, absolutely right.

MT: I don't know how many years ago that it was maybe an afterthought for [people to say], “I like this company. Let's look at the leadership role in the board.” Now, it's like in that initial research phase. It's like, “Do I see myself at this company? Am I going to be set up for success at this company? And what does the makeup of this company look like?”

SB: I think it's becoming part of an employer's brand. When you think about who you are as an employer in the world, you are looking at the diverse makeup of your board, that team, and realizing that there are some people that you really want out there that don't want to apply because you haven't done a great job moving the diversity needle, right? I think it is part of how the company is perceived and how it's showing up to candidates. Absolutely. You can't be what you can't see, right?

MT: I'm kind of switching gears a little bit. What advice do you have for emerging female talent who are trying to grow professionally?

SB: Oh my God, Mila. That could be like a five-hour discussion, but…

MT: The first thing that jumps to mind.

SB: I think the first thing that jumps to mind is my most controversial thing. You might get a bunch of your listeners writing a note saying “That woman is the dumbest person I've ever heard in my life, I can't believe she said that,” because I've gotten lots of mixed feedback on this. You said first thing that comes to my mind and that is: when women end up crying at work, they get painted with a brush for the rest of their tenure as like, “Oh, she's emotional. She seems sort of unstable. She doesn't seem like she can separate work and personal.” There's always the stigma that gets attached to women when you cry at work. I've cried in the bathroom; I've cried to one person. I've gone outside to the parking lot and called my husband crying. What I mean is breaking down in a large meeting or having some type of emotional outburst, which I've also had. It's hard to back off that perception internally. I think if a man does it, it's like, “Oh, that was so sweet. He really got emotional about it.” If a woman does it, I swear to you, I think it's years before sometimes you can shake the perception. I think partly because it's so etched in people's brains when a woman cries in the meeting because it's, like, hard to see. So, it's hard to forget, and it's easy to attach those adjectives to it. So, if you feel like you're on the verge of tears in a meeting, it's perfectly fine to excuse yourself. You don't have to make a big song and dance about it. If you're crying to a boss, that totally happens, and that is not a big deal. But if it's like in a larger group setting, I think it's hard once you do it to shake that perception that you are emotional. I know that is not bringing your full self to work, and I know all those things that people are going to say. But, seeing this happen, I feel like my most controversial feedback is probably the most applicable.

MR: I mean, I agree, and I'm not just agreeing because you're a guest on our podcast. I think it comes to an ideal world versus the world we're operating in. In an ideal world, you would see emotion as how much someone cares. They’ve dedicated the time, sweat, blood, and tears into a project or a deliverable. That person probably cares a hell of a lot more about it than someone who is willing to pivot on something they don't feel strongly about. However, that's not the world we're in, right? You must operate within the confines of where you're working. If you're in an environment where it's toxic, maybe it's time to look elsewhere? I think to your second point, we've talked about this before … If you were to cry to your manager, be cognizant of the relationship with your manager. Do you have that trust with them? If you don't have a relationship built on trust, you might want to save some of those tears for your boyfriend, wife, husband, whomever. I think it's a valid point based on the reality of some workplaces and cultures.

SB: I don't like it either. I'm not saying it's like, “Wow, this is such great advice because I'm so proud of it and it's so amazing.” It’s more around that I've just seen it happen, and I always wish I could save the person from it because it's so jarring for people that it's hard to forget, right? Then, it just becomes this thing of like, “Well, you know Mila, she's kind of unstable.”

MT: The mission of this podcast is to reach a state of being in that equitable place, but we're not there yet.

MR: Listeners, if you need someone to vent to, Mila and I are always open for a good venting session.

SB: Same with me. Find me on LinkedIn and cry to me on LinkedIn. That would be totally fine with me.

MR: Sometimes, you just need to.  

SB: Sometimes you need to. It's true.

MR: Great. Totally switching gears to talk about Michelle Obama … You are pretty much an all-star interviewer. You have interviewed some big names Richard Branson, Chelsea Clinton, Reid Hoffman, and Michelle Obama. Public speaking and interviewing are acquired skills. We'd love to hear about your process. How did you get over some shakiness or fears you might have had and get to where you are right now?

SB: I started my career when I was 19 so I was very much like, “Oh, I could do this, no big deal.” Then I started to spend more time in corporate America, and I realized that people really judge you when you're speaking, and I really needed to get amazing at this. I ended up creating this awful deficit for myself where I was like, “I am terrible at this.” I sent myself into a downward spiral where I was like, “I hate public speaking.” I went from amazing public speaker to, “Oh my God, this is like a death trap.” My heart would pound like you would not believe, and then I got more used to it because I had to do it all that time. We piloted a program at LinkedIn—I went and did it before I started recommending it to people—around how to become a great public speaker. I went to this two-day course in New York. You were basically put into these small groups of like seven or eight people and you were with them the entire time. You would do the small group presentation with them, practice, and then you'd get up on the big stage. They just have you presenting all day long. You sort of roll with it, and you get really used to it. At the end, I gave a speech to this group, and then they called your group the “trust circle” because they were really going to tell you what they thought. So, I give my little speech. I'm not liking that and whatever, so I come back to the little group. It came down to them saying, “In a small group, you're dynamic, you're funny, you're casual, and you seem super confident. But when you get up on stage, you're totally rushing. You talk super quickly. You're playing with your hair. You’re not yourself.” A light bulb went off in my head so big I cannot even tell you. I realized that the reason I had learned to hate public speaking: because I was rushing to get off the stage so that I could go back to being myself. When I got off stage and when they said that to me, I finally went, “Oh my God, this light bulb has gone off so massively for me. I just need to be myself when I'm on stage from now on.” This was about 2013, and it really changed everything for me. I started not even thinking about public speaking because I just knew I could just be myself when I was up on stage. I could wing it and I could make jokes. I could go slowly if I wanted to, and I could interact with the audience. I could just be myself and own that stage. It changed literally everything for me.

MR: Ending on a fun note, in addition to what you mentioned, what do you like to do outside of work and your passion for tech and all that?

SB: I do The New York Times crossword every day. I'm in a constant race with myself. I have done a Monday puzzle in four minutes and three seconds, and I've never been able to crack sub four. That's a big goal of mine. Do I sound so dorky right now or what? I have two kids that I spend a lot of time with. I love to exercise. I like to hike. I like to travel. I like to sit and drink wine. I'm a Netflix binge watcher. Outside of that, I liked to do angel investing. I used to do it, but now that I met Bessemer, I mostly just do Bessemer-backed companies. I did a lot of angel investing and counseling of people and their issues. I have a lot of varied interests and that is a nice thing in life because for years I worked so much and so hard. I had zero hobbies, like when people would ask me this, I'm like, “I don't really know.” But now, over time, I've really learned how to incorporate both.

MR: Mila and I have talked about this before with hobbies. Watching Netflix and sitting and doing nothing is a hobby in and of itself. Sometimes we felt self-conscious about it; people have hobbies like “I'm almost a professional rock climber.” I'm like, “I've been binging this show all weekend and I’m quite proud of myself.”

SB: We’re such a society that's all about productivity. [We’re like] “Oh, I should be doing this. I should be doing this.” And the reality is, we all need time to just sit and do nothing.

MR: Well, Shannon, this was so much fun to chat with you and just learn more about you. As I said, this is something we've been wanting to do for a little bit, so we appreciate you joining.

SB: Thank you so much for having me. I'm glad we were able to make it happen. You had such big dreams for it, so I hope it met your expectations.

MT: You brought that same realness that I was hoping for. Thank you so much.

MR: Thanks, Shannon. And for Stellar Women, I’m Mary Rechtoris.

MT: I’m Mila Taylor.

Both: Signing off.

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Mary Rechtoris is a senior producer on the brand team at Relativity, where she's always collaborating and looking for new ways to develop and socialize stories.