Kushal: Hi there. Welcome to “On the Flip Side”, a podcast for anyone who wants to live their best sales life. We're going to be talking to buyers, sales managers, SDRs and AEs about things like, what does it take to be a great sales manager? Or how can you go home happy month after month? So let's dive right in. 

Hi, everyone. Welcome to another episode of “On the Flip Side” with Wingman. I'm Kushal. I'm really excited to introduce our guest today, she's been the driving force behind many successful launch when it comes to sales and marketing. She has also been a key member of the Virginia's community, and has been involved with scaling the member onboarding program. She's also super involved with diversity and inclusion efforts across the board. Katherine, welcome to the show.

Katherine McConnell: Thank you so much for having me. I remember during the beta test of Wingman, and it's completely flourishing, and I'm so thrilled to see how it's performing on not just LinkedIn, but obviously as a business and helping many salespeople.

Kushal: Great. Thanks so much, Katherine. So I guess let's jump right into it. You're obviously a member of the women in revenue group of leaders. And you're also passionate about education and awareness of diversity and inclusion in the workplace. So my first question is really, despite all of this awareness around and the all efforts, where do you think companies fall short, and why?

Katherine McConnell: I hope that in the last 18 months, more research, more data, the work from home, obviously, COVID, we're, you know, terrible, terrible things happen. But the sliver of a silver lining to me is that we were able to embrace whole people, and not just their like their small part of what they do at work. And to me, that means that we are appreciating the relationship building and the collaboration, and all the other skills. I don't want to gender stereotype I always like have a fine, it's a fine line between perpetuating stereotypes, and embracing inequalities that maybe women bring to the workforce, and particularly to sales. And I feel that there's a lot more data, there's been a lot more focus, and there's been a lot more research. And I don't feel like discouraged about it. I feel that yes, maybe we all agree, everyone agrees diversity means more money, it's great for the world. And I feel like now we're having the frameworks and the mechanisms by which to actually make that happen. So I feel like focusing on the actual tools and the data and how to use that data to like really dig deep into an organization's structure, and provide more training for leaders. I'm optimistic that we can make actual inroads on this massive and unnecessary gap in the near future and an ongoing process.

Kushal: Katherine, I think it's really interesting about how you talked about perpetuating stereotypes when it comes to gender, right. I think that's actually an interesting line, like, how do you kind of do that balance between, you know, (a) kind of shining the light on how things are, and (b) the thing. 

Katherine McConnell: I was thinking about this a lot recently, because I've been very involved in and I'm very passionate about female founders. And as we know, I could rattle off the stats, but you can Google them what percent of money go to female founders, what percent of companies are actually female led versus the revenue and the funding they get. And there's a big debate in the female founder community that I just want to be a founder, I don't want this other label on me, I don't want to be a female founder. And for me, I grappled with the idea that until we are at equity, until we are at parity, until we don't need these labels, I think it helps to initially shine a light on something to notice the gap, to understand the gap to research the gap to really dig into the tools we can use to overcome the gap. And then have a future where it's just salespeople. And it's just founders. And it's just CEOs and doesn't have to be 50. You know, I love the 50 over, 50 on Forbes that they just did, which is great. And then they don't, we don't have to be like, Oh, only two women made the top five, you know, fortune 500 CEOs. Like we don't need to label it like that. But I don't think obviously we're there yet. So I think I tried to look at the immediate impact that putting as few labels on and not trying to perpetuate stereotypes, it can really showcase and highlight this gap, and make more people aware of it, and then find the ways to overcome it. But it's definitely a balance and I struggle with like each time it comes up, where do I stand on it?

Kushal: I think it's interesting how you talked about, you know, a lot of founders don't want to be labeled as women founders. And it's interesting, because I have, you know, I've had the exact same discussions with Shruti, our CEO at Wingman, as well about how she doesn't particularly enjoy kind of the label of you know, what it means to be a female founder, because her early taught is always what does it need to be or what is right, exactly. Like, you're you no one. Yeah. So I think that's super important to kind of, but I think a balance that, again, comes from knowing that not everyone has the same experience. And like you said, for some people, their gender or any, you know, any part of that identity doesn't hold them back but that's not true for everyone. So until we reach that point of maybe things being more equitable across the board, maybe some of these stories still need to be told?

Katherine McConnell: Yeah, I totally agree. And that this, you know, gender is just a small piece of it. Obviously, the racial, the sexual orientation, the able bodied, I mean, there's a whole spectrum of other isms that we need to overcome and I also recognize that, I know feminism has been entrenched in, you know, racial divides as well. So how do we collectively look at each piece of this, but recognize that their unique experience as a white woman, as a woman of color, as a gay woman of color? And how do we all work together for the greater good and appreciate the nuances that each person has to bring and overcome into their channel.

Kushal: So that's when you're talking about talking to companies about kind of, you know, upping their diversity and you know, creating a workplace that is inclusive, what I believe the maybe the top five things or the top pointers that you give them on how to get started on it? 

Katherine McConnell: There are people are a way that are experts on this than me, I'm just very passionate about it. And I certainly included in all the work I've been doing. I mean, it's across the spectrum. It's not just like, okay, now we're going to target the historically black colleges and get a few more people in the pipeline. It's the whole spectrum it kind of like the customer journey. It's the employee journey, right. It's the employee engagement journey. So it's the true diversity, equity, inclusion and belonging. So it's looking at all the facets of your organization, and not just the mission statement that you put in the annual report. It's looking at the organizational level, the business unit level, and then the manager level. I went to an excellent masterclass a couple of weeks ago with a woman from the Golden State Warriors, which obviously is very topical, given the NBA playoffs and things. And she had a great way like the Warriors do it that is for basketball, but I think it could work for a lot of companies. They talk about feet, tongue, heart, and I can't remember the other one. But it was that how they talk about things in the community and how they talk about their diversity inclusion and how they act in the community and how they target unknown and undiscovered places that they can recruit crew talent, and it is their values, the heart of it, like what are their policies, or their training their managers? How are their managers navigating conversations or situations they haven't had before? And are they having employee resource groups. And then they're also looking at their vendors and suppliers and their sponsors like their sponsors a big part of their cater cashflow, and their revenue, that they really, really care that their sponsors are aligned and their vendors are aligned, and their suppliers are aligned with their values and what they're trying to do. So they have a very multifaceted framework. And I think that's the key, like having a framework and not just being like, okay, we're gonna do this one thing. It's like looking at each piece of your employee experience across you know, all levels and across the whole journey as someone comes as someone gets recruited, or even before that, where they find out about you how the experiences when you're getting recruited, and you're going through the interview process, how you're onboarding, and then just looking at their continued learning and development. So it's, it doesn't have to be as complex, I think some people make it, it just takes a lot of work and have to be committed to it. I think that's the key to me, if I had to summarize it, from the top down and the bottom up, like people need to be committed to it and make it happen. 

Kushal: I think that's a great point, Katherine. It’s kind of a lot of work to do on the back end, okay. Here's another question for you when it comes specifically to women in sales or really in business overall, do you think that we've actually achieved parity and say, wages, equality, respect, do you think something's still missing and what do…?

Katherine McConnell: I mean, I feel like I don't want it to be a slow boat, you know, that we're, you know, eking out a 1% change here. But I do try to appreciate my very first job as was shooties on Wall Street, where you're totally a young woman on Wall Street, I was on the trading floor with 700 plus men, maybe 50 of us were women. And I tried to appreciate the people that have come before me that have got us to the place I was when I started. And now I hope to pay it back. And it's a continuous spectrum. But when I started, I've told the story before, but it really has stuck with me, obviously, in my training class, I was the only female in the sales and trading group. And then we were combined with the investment banking, and we finished our training class, and it's supposed to be like, get pumped, you're starting a new career, we want you to be here at Merrill Lynch for a long time, and like you're the best of the best. And we had wars, kind of like high school wars that they have in American high schools. And it was the, who's going to be my most likely to be a managing director, and only the men were candidates. I was like, okay, yes, if you look at the data, there's like only 5% of us that are women that are starting, so out of the gate, if you're a bookie, you're gonna put your odds on the men and you look at over the time, they didn't have great maternity leave programs, they had great mentoring programs, etc. So statistically, yes, the men you're, the bookie would put the money on the men. But it wasn't a bet. It was like an organization trying to make you feel welcome your first few weeks on the job. And so I was so outraged. So I went up to the headhunters. I'm like, you're pretty presupposing that no women are ever going to be a managing director. This is kind of a spoof award. So what would it have mattered if you included who if you females even though there's only very few of us. Anyway, I clearly still get worked up thinking about that. 

Kushal: What happened at the end of that, I’m curious?

Katherine McConnell: Yeah, and so for the ongoing piece, I like to look at it, what can I do individually to bring situations forward? What can I do to help women you know, at all stages, you know, it doesn't… I don't feel like a mentor relationship has to be an age based thing. There are people that are much younger than me and I learned a ton from them. And likewise, I hope to, you know, help and support women of different ages and men to be allies. And so I look at what I can, what can I do individually. And even if it's like you were chipping, like the smallest piece away, it's bringing attention to when something doesn't work like. So for instance, you mentioned some of the communities if there are examples where men are saying, oh, well, only men will understand these sports analogies, or only men learn lessons from sports, and what are you doing? What are your business lessons from sports and things like that? I don't try to be strident about it. But I say, hey, we're supposed to be an inclusive community. And women are 50%, in the US of like high school sports athletes, we learned a lot of lessons from sports to, and by the way, I worked in professional sports. And we also can be sports fans, it doesn't have to be gender based. 

So I think in small instances like that, is that going to change the world? Obviously not. But I think in those situations, you speak up, like you, other people might not have the capacity to speak up, but I'm at the stage where I'm definitely going to speak up and hopefully do it in a again, like a meaningful, you know, kind of way that creates opens people's eyes, as opposed to make them defensive, in a collaborative inclusive way. And there's the collective piece. So we're all like we're doing the studies, we're thinking about how we can hold companies accountable. So there's the individual piece, and then the collective piece, where we're, you know, it's like, we're coming out in two ways. So I feel really strongly that each person has a role to play if you're an intern that just started your job last week. Okay, maybe you're not going to call out the SVP at the meeting, when he said something super sexist. But it's like you're connecting with other women in your organization, and you've joined women in revenue, and you've joined a ton of other different organizations where you can get support and, and start to understand how you can get your power and like, where are you going to? What are your values? And where are you going to define where are you going to take a stand, you can't take stand for everything, you might be completely exhausted if you do that. And so I think it's about finding where your values are individually, where you have your power, and where you have comfort and where you think you can make the most difference, and then collectively make, you know, getting these women in revenue and types of groups like that. So we're all sharing resources, we're supporting each other. And we're hopefully then also chipping away at the bigger, bigger situation.

Kushal: I really love that point about speaking up, right. And especially if that's especially important, because for a lot of people who are still younger, sometimes you don't have that confidence to go into a room, like you said, and kind of say, you know, call out, you know, any form of really bias or stereotypes. So I think it really is up to a lot of people who may have that stronger voice to maybe kind of be bearers of that voice?

Katherine McConnell: Yeah, in the US, there's a lot of talk about bullying. I mean, I hope in the schools, the bullying is less, I'm sometimes not sure where it is. But they have a term here called “Be an upstander”, which I know is a universal term as well. But it's that a key piece that I didn't mention before is the male allies. So that they're you're not operating in a vacuum, you're bringing them into the fold. And you're like showing just connecting with them on a personal one on one level. So they can appreciate whatever challenges you individually or collectively we might as women be going through, and they can be an advocate, they can be an ally, they don't have to be like waving the flag if the annual company parade, but they can at least again be seeking, it would be kind of fun. And so it's a situation where if in a in a setting in a meeting, they're like, oh, Sally, why don't you take the minutes? If a male ally is there, they can be like, actually, John, why don't you take the minutes this time. So just little things like that. So you don't perpetuate the women is going to take the minutes, like there was something I was a very inclusive community that was supposed to be happening. And there was a situation was a meeting, and it very much was like, oh, you take the minutes. 

And I was like we're supposed to be this inclusive community. I don't think we should just jump to like this person taking the minutes, we should figure out a better way to do this, not just make assumptions. And so the male ally ship is that, you know, even as adults, we still want to belong, we still want to feel like we're part of the cool crowd. And so if your back and say, you know, everyone's back at work, or whatever, say annual meeting, whatever it is where people are actually physically together again. And you know, when John is by the water cooler and he hears some guys like the cool guys, whatever, talking, talking smack, or talking to saying terrible things. Like if he's empowered and feels connected to the plight and the advocacy of women, he can speak up be like, Hey, I don't think this is appropriate conversation. So it's not just the you could have the advocates being upstanders when you're not even there, but they also putting themselves on the line, right? Because they maybe they want to go play ball golf with Bob. And now they're going to not get the spot to go about. So they have to be, you know, feel a stake in it as well. So yeah, being an upstander is something that I've learned through my nieces who are 9 and 13. And it's a wonderful idea that you're not just sitting on the sidelines hoping you don't get bullied, like you're actually putting yourself forward to redirect a conversation to redirect a dialogue to redirect points of view that people have and hope that you can make small little.

Kushal: I think the idea of, you know, men, for instance, if it's a gender divide that you're kind of dealing with kind of being equalized right from the beginning is so important. For instance, you know, if you go back some 20 or more audios in some schools you're right when you have sex education class because they would put them you know, so during all of the sessions around reproductive health, girls would be separate and that boys would be separate and in life for me, I never understood that, right. So you can't have a discussion around gender equality without everyone being in the same room, I doesn’t work. 

Katherine McConnell: That's nice. I think that they have some classes combined now with boys and girls. And sure they're in fifth grade and sixth grade, and they're like, what's going on with my, you know, my body myself, and they're feeling awkward, and our hormones are starting to kick in. However, it's like the men, the boys are learning about the women and the women are learning about the boys, right? It's like, right from the start, where you start to recognize the, you know, physical differences, and whatever the differences happen between boys and girls as they grow into men and women. But yeah, separating it right from the start is creating a divide of knowledge, and appreciation. 

Kushal: So I guess that sounds like community is really sort of the way to go when it comes to losing a lot of these things, right, which I feel really perfectly puts us into the next segment of what I'd love to talk about with you, which is really about community led growth. And you've obviously been one of the key people at RevGenius. And you've helped scale up their member onboarding program as well. I'm really community led closer to coming. What would you really want to tell people who probably come up to you and ask, oh, you know what, maybe I should kind of, maybe we should do this?

Katherine McConnell: I know, some products, communities have been around for a long time. And I'm, like less familiar with those. I don't want to represent that sector. And I was new to LinkedIn. So I basically to take a step back, I was working, you know, partially not full bring capacity, not full productivity, to bring my nieces to the swim meet, and the soccer practice and whatever. And so I was content with what I was doing. And then I slowly started poking my head out. And for a project I was doing for a startup accelerator here in Vermont, we started going on LinkedIn, and I'm like, oh my gosh, LinkedIn is the greatest thing ever. Like there's so many people, there's so much information in my brain is exploding. It's amazing. And I was usually very analytical. And so I would have been like, who to follow and what to do. But somehow the universe connected me with some people. And two of those people were Jared and Galen. And then I also met Jen Ferguson, and she invited me I was member 97 for RevGenius, which is I think, now like 15,000 people. And so I'll speak to the community piece, it's to me, I didn't know any different, right? So to me, it was come bundled in with LinkedIn, it was like, oh, this communities like people are getting together and they're doing stuff. And sure, you know, there was revenue collective I knew about and modern sales pros and all the other groups. But they were like a distant, I don't know, for some reason, they weren't as much on my radar maybe being on the ground floor. And they'd RevGenius, like who. And so to me, it was heightened by the pandemic, certainly we're all working from home, we're all looking for connection, we're all looking for ways to feel part of something bigger than ourselves beyond our family or beyond our workplace. And especially with the labor market. Right was that's when it was still really tricky aspect of it was just be as inclusive as possible, come up with guidelines, and it didn't have to be perfect. So it was, you know, really moving so quickly that trying to onboard 500 people a week, like obviously, you're not going to win any wars, like you're making the best onboarding possible. But just quickly coming up with what are some basic things people need to do. And I realized with time that I actually just naturally do this, like so when my niece is trying to swim team. I'm like, I don't know what's going on. Where's the information? Where's the meet? How do we get to the meet? What are the families need to know? What do we need to bring this swimbag? What how did the event work? What is the order? And so I offered to volunteer and I'm like, here's I mean, the whole manual, like, here's 15 things, you know, 15 different, you know, one cheaters about swimming. And similarly, that's how it started with RevGenius. I literally was a member for like two days. And like, I think we need a frequently asked question. And they're like, Sure, why don't you do it? Like, okay, and you're at and then and Alish and Christina were the community leaders at the time working with Jared and Galum. And then Christine Whitehead joined the fray. And we kind of traded the baton back and forth. And it was, it's funny to me, because I've just recently looked at the root genius onboarding information. And sure, it's been slightly revised. But the core of it is pretty much what we did you know, when we were flying by the seat of our pants, just quickly throwing it together. So we can have at least some information for people back in June. And so what I feel about that is that it's again, part of it was ironic, it's like we're on sales and marketing, it should be like the customer journey. And we didn't quite have all the pieces. And I tried not to get caught up that Oh, we didn't have the pretty diagram where we didn't have like each you know, the status segmented right away. And just embrace the idea that initially, people just want to feel connected. They want to jump in a couple channels, maybe they want to have funny memes. Maybe they want to express gratitude. Maybe they actually have a sales question. They want to answer it and someone can help them. And then there's the separate women in revenue channel. 

And, yeah, so it was a great, great experience. And it just got me right in the mix. And to me, I feel like it's, I never thought about community as a job because I don't know again, I did most of it living in a cave or something. But it really is like now, it's flourishing thing like I can't look on LinkedIn without seeing five different or starting a community there's a job open for community. And so I think the key piece, it's like any other any other customer journey, it's like, who, what is our purpose? What are we doing and who we trying to reach? And then how are we reaching them? How are we getting them interested? How are we getting them approved or become members? Some of them are free, some of them are paid, these communities, and then how are we onboarding them? And then how are we continuing to re-engage them? And how are we turning them into evangelists. So it's like the same principle. But just looking at the supportive communities, whether your sector is customer success, or ironically communities for communities, or revenue, or products, marketing or whatever, there's 10,000 communities now. And I think it's all predicated on the same premise that we all use in our sales and marketing lives to create the connection and create value for others while add value to others while we're also, you know, learning ourselves embracing and enriching.

Kushal: Katherine, do you think it's fair to think of communities is really the magic bullet when it comes to growth for companies, right. Do you think that's how we should be approaching it, because for a lot of companies, that's literally the one lens we'll put on almost?

Katherine McConnell: I think it's the clubhouse. The Clubhouse work for some people, there was like the tipping point, at least on LinkedIn in January, it was like, oh, my gosh, Clubhouse. And some people went all in, and they're flourishing. And it's working for them. Because they were really clear about what they wanted out of it. Other people felt like they missed the TikTok B2B, they're like, oh, my gosh, I gotta get in front of the curve here. And then other people just tried it like me, and I'm like, oh, I did some cool rooms, I did some things. And so and it's not I'm not as active in Clubhouse anymore. And I feel like people tend to gravitate towards the hot new thing. But like any hot new thing, it's like, you have to have a strategy, it has to fit with what you're trying to achieve, and just thinking, I'm going to be in clubhouse, or I'm going to build a community. And they will come I mean, it's, I feel to dreams, right. Like you still need to do the work. And you still need to be really has to align with your strategy and your values. And the most important thing is your resource allocation. You can build a community and invite a lot of people but if you're not nurturing it, and you haven't devoted human and other resources to getting sponsors, so there's, you know, extra events, so there's people overseeing and, you know, cultivating the community, then you're, you're just have an empty Slack channel or a couple of SEC channels. So I think like anything else is like, what's the ROI on your time and investment? What's the opportunity cost? Like, if you hire someone to do community, what else could they be doing for you, if they were doing straight marketing or some other they're doing fillip marketing, or if they were doing you know, like the liaison between sales and marketing, whatever, whatever the title may be, is that going to get you more bang for your buck. But I do feel fundamentally that communities are an essential piece of it, because everyone wants to feel connected and ever wants to feel together. And there's a lot of value in how people with similar interest and desires and knowledge can help each other and feel part of something bigger than themselves through a community. 

Kushal: A lot of people think of RevGenius, as you know, a case study for communities and sort of community led growth as well, right. And rightly so. What do you think is really the main thing that has kept RevGenius, the way it is? 

Katherine McConnell: It's interesting, I've definitely thought about this a lot. So in the beginning RevGenius was almost a case study in hyper growth. And was it going to be sustainable? I mean, Jared, and Galum are amazing. And the other people they've brought on board, you know, I stopped volunteering, maybe end of October. So they now have full time people. And GJ just joined as a full time person, and they just hired Asia, who she's amazing. So there was the tipping point where it was, is this going to be sustainable wasn't just a COVID thing. But they were pretty smart about making it very inclusive, making it again, a threshold of numbers. So it wasn't just like 400 people sitting in a Slack channel that wasn't maybe going to, you know, stay sustainable, because whatever percent of people participated, like, you have to look at all the stats on that. And then getting sponsors like, I think a key piece was like really making partnerships and Ally ships and alliances with SalesLoft and with Dooly, and with all these other companies that are very active on LinkedIn, so they're, they're doubling their bang, you know, they're making the good, the sum of the parts greater than there.

Kushal: I think it's interesting how you talk about, you know, the sum of all of these things being greater than each of them individually. And I think that's really true for so many of these initiatives, right, like whether it comes to community, whether it comes to diversity and inclusion efforts women in sales, I think the fact is that people together can do so much more than they probably could do in isolation. And now's a great time to learn that. I think the other cool part is also that with the entire world, kind of not the entire but with such a large part of the world going online, and digital, it's so much easier for people to connect with each other, right. And that's probably part of the reason why we're able to rally community so much great. I love that Katherine. Yeah, I think it's powerful, how technology and people can really come together into a lot of really amazing things, no matter where they may be based. So Katherine, we're kind of towards the end of this. I guess one of the things I'd love to know from you is, you know, what can people really reach out to you for and what's the best for you? So I think that sounds pretty incredible. The idea of yeah, just the courage to do things differently, even if they don't scale, right. But yeah, I think that's powerful. I feel like you know, so my personal thought on that my hypothesis rather, is that a lot of these crashes happen when you're talking, when you're kind of scaling up things, right. If to a smaller team, if they're just you know, one person sort of leading on something or a couple of people just with one head, then it's sort of easy to keep everyone valued and part of the same team. But when you kind of scale up and you have one person in charge of one separate thing, then I think there are many more chances of people stepping on each other. So that's possibly what happens here as well to sales and marketing. It's sad, though, the funniest thing is Katherine, you know, I've read that article a couple of times as well. And whenever I'm speaking to Shruti, maybe about a new idea, I'm like, is this thing like, oh, I want to hold on to all this. Well, like I want to share, and let go off make. Katherine, thanks so much. I think this was a super amazing chat to have. Thank you for being here.