Episode 142: Empowering Women to Excel in Sales Enablement

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Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I am Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help practitioners stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

March is Women’s History Month, a time dedicated to celebrating the contributions that women have made to society throughout history. In this special episode, we dive into how women have and continue to drive impact in sales enablement by highlighting expert advice from female leaders in sales enablement.

First, research shows that women are highly effective leaders. Yet, they are still significantly underrepresented in leadership positions in the business world today. So, how can women in sales enablement gain a seat at the table? Mary Shea and Alyssa Clark share their thoughts on the importance of representation in leadership and advice to support personal leadership development.

Mary Shea: Women are dramatically underrepresented in leadership. In terms of Fortune 500 CEOs, only 7.4% of those CEOs are female. For those of you who are entrepreneurs or who make investments in companies – 85% of venture capital funding goes to all male-led companies. And what I find fascinating and disturbing at the same time is that female founders are more likely to bring their companies to cash flow positive than males are.

First of all, interestingly enough, we learned that sales teams led by women deliver better commercial results. One of the reasons we wanted to talk about moving beyond “lean in” is because there are institutional responsibilities, corporate responsibilities, policy responsibilities that others have, in addition to female sellers themselves, to breaking some of this glass. Women are subject to both explicit and implicit biases – explicit on the gender pay side, implicit, in not “being in the room” when key decisions are being made. We find both of those types of biases as being very, very harmful for female progress in the workplace.

It’s called the “she’s not strategic enough” roadblock. And one of the things we found in addition to the confidence issue throughout the survey was this concept of feeling that you were being treated or thought you were being treated differently because of your gender. If you’re told you’re not strategic enough, how do you actually work on that? What we recommend is that you start to think about developing your own personal leadership, recognize your own strengths, and cultivate a range of leadership styles.

We all appreciate that Sheryl Sandberg brought forward an important conversation with “lean in”, but we’re at a place now where we can’t say it’s on women wholly to solve these problems. There are policies that need to be made. Policies that need to be changed at the governmental level, at the organizational level, and business leaders need to take responsibility: Are there visible women on the executive committee or board? Is there a commitment to diversity across the company? Do you see those folks that represent a range of backgrounds and views? Is there a chief diversity officer or does that role not exist within the organization?

Alyssa Clark: I think for me as I started to mature in the corporate learning space, I don’t see a lot of women as I look left, right. I want that, I want that for us to make sure that we are equally represented, and there’s so much room around race, sexuality, etc., to continue on to. But I think for women it’s really important for us to see our leadership positions as an opportunity to groom someone else to take our spot. We need to be committed as peers and allies in this battle of representation to look at each other and say, “Hey, we know what it took to get here. And it’s our responsibility to bring others forward.” One of my recent hires, she actually was someone who, as I was talking through the process, I just kept thinking like, “wow, like I should be working for her.” Right? Like she is the one who should be making these decisions because I feel like I’m better off every time we interact. And as I reflected on my experience, a lot of those mentors for me were men and men that I still to this day admire and respect.

Quite honestly, I modeled myself after, but I think about the future and I think about how much more empathy, how much more awareness can we share on certain topics in the workplace if we simply had a better representation of females, in these senior leadership positions. And that is something that I’ve made a cornerstone of my personal career is trying to make sure that I’m committed to, empowering and supporting, and hopefully motivating other women to continue their hunger and their lust for their curiosity and for responsibility and for wanting to make an impact.

SS: Peer support can be a powerful way to overcome obstacles and help colleagues ascend to leadership positions. Shannon Hempel, Lisa Hammack, and Sally Kim share how women can support each other in professional development and career growth.

Shannon Hempel: I think one of the most empowering ways a woman can support other women is to be a champion for them in meetings. No matter who is in the meeting, it could just be a small group of people that is your team. Maybe you’re on a team of people and you want to speak up for somebody and just highlight that was a great idea. Something as small as that, just being a champion in a room. If you are a leader and you have people that are your direct reports, start championing them and leading in meetings that you have with people that are two levels above them in a way that is meaningful. Not just because they’re a woman, but because the work is really good.

The other thing that I would suggest is just sitting and listening to others and digging in and asking them questions. I say that because the more you listen to somebody, women specifically in this case, the more you’re going to hear what is it that they really want to do with their career, how they want to drive enablement in their company and grow the position. It’s more visible depending on the kind of company that you’re in. And if something that they say is something that you have a strength in, talk to them and volunteer to say “I will do this particular thing for you. I know of a great book that I just read that is super empowering. Let me send you the link to it.” Start small because people are going to start coming to you because they see that you are empowering if you build trust. Whatever you do, follow through with it. If you say you’re going to help somebody with any particular task, do it. If you are asking them questions to explain things so that you can learn more about them, really listen and show that you heard them. It really is all just a bunch of small acts that I think are the big drivers.

Lisa Hammack: I think the best thing we can do is really encourage each other, always be authentic and vulnerable. And take the time to know those strengths and not be afraid to speak up even when it’s awkward sometimes because let’s face it, sometimes when you’re in a room with a group full of men, it feels awkward. So, I think we have to challenge ourselves and our fellow women coworkers to not be afraid to speak. Another thing I think is too, I think sometimes we are afraid that if we are outspoken, that if we’re assertive, that we might come away as sounding arrogant, but I think we have to get comfortable with being uncomfortable sometimes. It’s really up to us and our teammates to encourage each other and consistently find ways to give each other feedback and to really, to pull each other up.

Sally Kim: There are so many more opportunities for career advancement for women that are just an arms reach away, that when you see those opportunities for other women, all you want to do is be able to extend the hand and help. I think more tactically, how that happens is everyday actions. If you see, for instance, that a colleague of yours isn’t getting the time and attention in a meeting, even though they have great ideas, and if you’re in a more senior position, or even if you’re just a colleague being able to step in on their behalf to say, “Hey, let’s hear from this person.” It starts with small actions like that, and giving opportunities to your peers that might not always be as easy to find all the way to being allies and sponsors when it comes time for things like reviews and performance reviews, right? How can you be a sponsor to another person who you know, has done great work?

SS: Whether you are seeking career advice or looking to pay it forward, mentorship can be an extremely beneficial way to support leadership development for both mentors and mentees. Shannon Hempel and Jen Scandariato share how mentorship can help professionals develop leadership skills.

Shannon Hempel: Be a mentor, find a mentor, and remember a mentor doesn’t have to be someone you know well. It can be somebody you’ve had a certain acquaintance with. It can be somebody who you just see that in your industry on LinkedIn or whatever forums that you’re following, that you have a lot of respect for and schedule a meeting with them to just say, I want to talk to you about how I can move forward in whatever area. But be assertive. When I know for myself that if I get a note from a young person in their enablement career and they are truly asking for help, I am all over it. I’m going to make the time because finding people who reach out and ask for that help honestly is not often found. In my opinion, in my experience, definitely the obvious is find networks, reach out to them, but to really engage yourself because that’s where the learning is going to take place. That’s going to be where you see it grow your career and your enablement career much faster.

Jen Scandariato: I think what I did was I wanted to surround myself with people that were brilliant and then I could learn from. You never want to be the smartest person in the room because then you aren’t learning anymore and growing. They always say, if you’re in your comfort zone, and you’re not taking risks then you’re not learning. I think my aptitude to learn and grow was just an important part of my career development. I just had that affinity to take on the world. I do recommend now to have individuals be that sponsor or be that mentor. And it doesn’t have to be a formal conversation. I think it’s about finding people that you admire, and you want to emulate. It’s difficult in the virtual world to have a cup of coffee with somebody these days but if you could saddle up with them and learn by their example and then emulate that in your real world, I think those are the best mentors when it’s unofficial.

But I do believe you need a sponsor, you need somebody advocating on your behalf when you’re not in that room and in order to do that I think it’s important to tell your supervisors and people that you work with that you’re looking for an adventure, you’re looking for a new opportunity. You want to raise your hand and take on something that maybe is out of your comfort zone, out of your wheelhouse. When you put it out there that you’re looking for more opportunity and you’re raising your hand, people are much more willing to give you that opportunity and give you that room to grow. You have to have trust though. So, I think it’s important that you set yourself up for success, show your capability on what you can do, and then people will trust you.

SS: In addition to supporting one another, there are also several things that women can do to take ownership of their career development and seek out opportunities for professional growth. Alyssa, Sally, Lisa, and Jen share advice on how women can proactively build the skills that will help them continue to advance in their careers.

Alyssa Clark: I would encourage people early in their careers, especially women to think about how are you using your voice? And what I mean by that specifically is your lack of speaking up is sometimes even louder than being silent. And I would really encourage women who are sitting in a meeting thinking, should I ask this question? Should I raise this complaint? Should I voice this concern? I would say if you’re thinking it and you have a reason for it, ask the question, but ask it from a place of curiosity. That is something, a secret weapon of mine that I’ve really tried to home in on over the years is coming from a place of curiosity and not allowing that to kill the cat. Thinking about the why behind the what, and asking for it, sometimes relentlessly. That is what earns respect. That is what earns credibility and honestly, stamina.

Career progression is driven by you. Your curiosity is driven by you and your success ultimately is driven by you. And I know first hand that it is an absolute responsibility of mine. I know you’re committed to it as well, Shawnna, to invite women into these conversations. Your voice is wanted, it is heard, and your unique perspective is what makes you not only a viable asset to an organization, but to the world, to our communities as well.

Sally Kim: I would say to not be afraid. Everybody is willing to help and just dive in and ask for the plethora of wisdom that lives within the industry. Don’t shy away from the stigmas that exist within helping a sales organization or a customer-facing organization that might be dominated by biases or preexisting stigmas. There are more and more women that I see entering sales enablement, and some of the best mentors that I’ve had within the space have been women as well. There is a lot to take away from the rockstar women that are within sales enablement. So reach out and ask for all the help that you can get and not be afraid to dive in because I’ve been learning a lot and it’s still a continuous learning journey. There are always offering hands to help.

Lisa Hammack: I would recommend that they find ways to first volunteer to assist them in enablement efforts. For us, we’re always looking for subject matter experts. We’re always looking for sales reps, sales managers that want to be involved in our initiatives. So, I would definitely recommend that they look for ways to get involved, to find out like, is this something that I would want to do as a career? For myself, I started out, I had a couple of jobs in business development where sales enablement was just a little piece of what I did, but I fell in love with it. And so that’s where I kind of determined that that’s where I wanted my career to go. So, I would just recommend looking for opportunities to get involved, to kind of check it out before you actually jump in with both feet.

Jen Scandariato: Get out of your comfort zone and learn, grow, take a new class. There are so many offerings right now, especially in the Zoom world. Join a network, whether it’s a woman in tech or an agile meetup or tech meetup. Find your passion and surround yourself with people that share that passion. I would say the second part that I would recommend is really around your brand. You have to figure out, what is your brand? What are you telling people when they meet you? What is your passion? Who am I when I’m meeting with people, do I say, “I’m a mother of two teenagers?” Do I say, “I’m a woman in tech?” Do I say, “I love big data?” You have to have that tagline. I think you surround yourself with those allies and those mentors. And this is great advice, somebody told me this, and I never thought about this before: You want to be that person that people want on their team.

SS: Thanks for listening to this special episode to honor Women’s History Month and International Women’s Day. For more insights, tips, and expertise from sales enablement leaders, visit salesenablement.pro. If there’s something you’d like to share or a topic you’d like to learn more about, please let us know. We’d love to hear from you.

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