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. 

Hey, everyone you're listening to “On the Flip Side” with Wingman. I'm Kushal. And today's show is dedicated to all things women power. And that's why I'm so excited to learn more from our guests for today's show, Jennifer Fisher. Jennifer is the senior sales leader and currently VP of sales at WorldStrides, which provides educational travel and experiences to students. Jennifer has spent almost 30 years recruiting, hiring, training and managing high performing sales teams. Jennifer, so great to have you on the show.

Jennifer: Thank you so much for having me. I'm super excited today. 

Kushal: Jennifer, just to get started. I think we'd love to understand how you got into sales? How did the journey start? 

Jennifer: Absolutely. Well, you know, it's a funny story is… I think like a lot of people never planned on getting into sales. I just kind of fell on my lap. And I was you know, this young person right out of college. And yeah, I thought I can just go in and do anything. Oh, you want me to do sale? Absolutely. And I was horrible at it. What am I doing?

Kushal: I love your kind of insight.

Jennifer: Oh my gosh. And it was such an ego blow because I'm like, I can do this. And I couldn't, it was hard. And it was one of those situations where really, there was no training, there wasn't even any training just on product. It's kind of like, here's brochures, here's this and yeah, go get him, go out and sell. And it was really, really hard. So one of the things that I had to focus on was teaching myself and training myself. So I was very much focused on learning. I was reading every book I could think of and of course, 30 years ago, they did a podcast or other things that they have now. But I was really just asking a lot of questions to senior sales members of the team that I was on and just doing as much as I could to role play and practice and get myself comfortable. And that was really you know how I did it. But at the end of the day, one of the things I did learn, you know, is that sales was really about the relationships. And that is where I was very comfortable meeting people and really building those relationships. So that was very fulfilling for me. And I ended up obviously staying in sales. And yeah, there, as the start of my 30 year career.

Kushal: Great stuff, Jennifer. I think you've already kind of told us how things were maybe not so great when you started out. But you know, you kind of learned and got better at it. What are maybe some of the things that you wish you knew when you started out?

Jennifer: You know, I think the biggest thing for me was the effective questioning part. You know, I didn't know how to really go in and prospect, have a conversation with a prospect, and move that conversation down the path of, you know, getting their interest, finding out what their challenges are, you know, seeing if we're a good fit. And so it was very clunky and awkward. As I was learning that on my own. You know, I kept thinking this, there's got to be a better way to kind of get in here and start these conversations, and then understanding when to pivot and move in towards the business and not just building rapport and building relationship, but not driving any business. 

So that was challenging for me at the beginning. And then as I started getting comfortable with some of my effective questioning skills at the earlier process at the discovery process, then it was all about having the confidence to ask for the business. You know, and that was also very hard, you know, as a, you know, 22 year old trying to do this for the first time. And, you know, I'm up against somebody who's like in their 40s or 50s, who clearly know their business. It was intimidating to even get to that point and then ask for the business. And so those were definitely two big things I had to take time to learn and really work on and perfect over my career. 

Kushal: Do you think that being a woman has kind of, you know, was it more difficult for you when you were starting out? And really, how's it today? Do you think that being a woman still means kind of facing more challenges?

Jennifer: No, I do think that. I definitely feel that as a society, we're heading in the right direction. But obviously, 30 years ago, I was the only female on my sales team. And, of course, you know, at the time, you don't think anything of it like this is life and this is what we do. But when I look at some statistics now, you know, looking at, there was a Gartner study in 2020, where they stated that only 23% of sales reps are female, and only 16% of female are frontline managers. And so when I think about that, in a sense, maybe we haven't come as far as I think we have, you know, so it's definitely difficult and there are definitely challenges But I do think, I do think even the numbers, even though the numbers aren't great, I do see that there's a lot more mentoring programs and female podcast and women in sales podcasts and lot more support there. But we need to do more to kind of get that number a little bit higher. 

Kushal: You talked about mentorship, and of course, but also a mentor at GirlsClub. Can you tell us more about that experience?

Jennifer: Absolutely. And you know, this was just my finishing up my first six months of working with GirlsClub. And that is an amazing organization where their whole focus is on training women not only to excel in sales, but sales leadership, and that's where we definitely see a big gap. And being my first six months, it was more about learning the ropes and learning the processes, and just meeting some of the amazing young women at some of like our all hands on meetings, but it was really, it's a powerful tool where they really have a dedicated curriculum, really, for like a good year of what the women are doing. And they're being paired up with various mentors to ask questions, see what's happening. And interestingly enough, a lot of the mentors are men, they're like the allies, you know, for females. So it's very nice to see that support as well.

Kushal: I was going to ask you, you know, how do you think men and women really can become better allies for women?

Jennifer: Absolutely. You know, I think part of it, and when I definitely look at it, you know, with women, you know, part of it is just some of the challenges that they face in the profession, they may be very good out in sales and getting the business and driving revenue. But within the company, they may not feel that they have a voice, or they're not comfortable leaning in, you know, and, and so there's a lot of different things around like how we can present ourselves better how we can learn to really have confidence, and not arrogant confidence, but that grounded confidence that we do know what we're doing. And we're comfortable to speak up, and not just speak up to say anything, but really have intention, and really help drive the business forward with innovative ideas, and having that seat at the table. And that's really what it's all about for me right now is trying to help other young women, you know, have that grounded confidence and feel that they can, you know, speak up that they can have… make an impact and have that seat at the table to make that impact.

Kushal: I love how you talk about sort of developing this quiet confidence, this humble confidence almost. And I think maybe it's one of the most defining differences, I think maybe between the way that men, women sometimes present themselves at the workplace, when it comes to getting a seat at the table. What do you think is the number one challenge that maybe women face and really get into that sales leadership position? Why do you see so many women maybe opting out at some point?

Jennifer: My first thought is that a lot of women, you know, have what they call the imposter syndrome, women tend to not want to put their hat in the ring for an opportunity unless they feel they can check off all the boxes associated with that opportunity. And if there's one box that they can't check off, women tend to think like, oh, you know what, I'm not able to do this. And just the opposite for the men, maybe they only have one box checked and everything that they have, but they're like, I could definitely do this, let me go in and do this. And not that that's wrong. But it's where women need to have that confidence to say, you know, it's okay, I don't have everything here. But I know I can help make a difference. I know I can lead our company forward. And so really just getting that confidence to say, You know what, like, we got this, we can do this, and we're gonna go ahead and move forward on that. I think that's one of the biggest pieces that I've seen. And then in some cases, you know, as women are trying to, you know, check the boxes are trying to get that confidence. In some cases, they may come off as a little arrogant, you know, and so it's always about don't go try to be somebody that you're not like, use your own authenticity, and let that shine, because everyone has such strong skills that they can bring to the table. So let it shine, but just know that you got this and you know, you can do it. So go ahead and put your hat in the ring, and let's move forward.

Kushal: I love that vote of confidence that you're giving for women everywhere else. When it comes to sort of organizations and leadership, right, how can companies really get it right? What are maybe the top few things that they should be doing differently when it comes to hiring and really sort of training that talent? 

Jennifer: Absolutely. And a lot of it comes down, in my opinion, to the fact that the companies really need to be intentional about what they're trying to do. What are they really trying to achieve? Who are they trying to hire? You know, DEI is so important. You know, we need diversity of thought and ideas. And so companies really need to have intentional plans to say, hey, this is the path that we want to take. One of the things I'm very excited about at my company WorldStrides is, we had formed about, Gosh, I guess about a year ago, various employee resource groups, and I was fortunate enough that I am now the executive sponsor of our women's employee resource group. And so it's really inspiring that my company has taken this opportunity to focus on, you know, many DEI resource groups, the Women's Resource Group, to really help build community around all of our employees. And, you know, WorldStrides is a global company. So seeing all these employees from around the world, you know, come together on zoom right now, or, you know, having these meetings and building that community is so important, because that's where they're going to meet other people. They're going to have conversations, you know, mentorship is something that we are starting to look into a little bit, but just have introductions and knowing that there's somebody else in this group, whether they're, you know, in the next town over or across the world. But really having that intentional space to build that community,

Kushal: I think that a lot of companies might maybe be afraid, in some sense of kind of creating the space and then not having any control over it, though, is that maybe what's keeping some from doing?

Jennifer: It could be, you know, and it's hard to say, I think part of it, too, is that they don't know how to create the space, either. You know, and I think, I think everyone has all good intentions. And even these companies may have very good intentions, but they don't know how to carry it out, right, how to motivate the employees to join the resource groups, how do you motivate inspire them to be part of this or take on a position within the group. And so I think some of that really just comes down to, you know, not knowing, you know, they're not an expert at all, like, well, you know, and especially many companies who have spent the last year and a half through the pandemic just trying to survive. So they know that this is very important. But maybe they don't feel they have the resources right now to do it. They're short staffed, you know, everyone's exhausted. And so just trying to find that piece of where they can say, okay, like, maybe it's okay just to try and start and let's learn as we go. So I think a lot of it is more just knowing that they need to do it and knowing how to do it, or even just starting.

Kushal: To go back a little bit to what you said earlier about WorldStrides really being a sort of global company, right, with employees in different countries. I guess that's a great thing, because it puts you in the position of really speaking to people from diverse backgrounds and cultures. I'm just curious, do you see a difference in women's confidence level? 

Jennifer: I do. And you know, and a lot of that is just culture based, right. That's just like, how they've grown up, what the culture is like, and that they are also amazing, right. When I see this wonderful group of women, oh, my gosh, I mean, you talk about an amazing diverse group of thoughts, ideas, and leadership and we all can learn from everybody. And that's what I love about when we all can come together, because that's just a huge opportunity to build friendships, build relationships, and really just learn from each other.

Kushal: For companies that want to maybe encourage more women at leadership levels and sales, right. What would kind of your advice be, how should they get started with that sort of mandate?

Jennifer: I think the first thing they need to do is, you know, really communicate to the employees of a company that this is a very positive thing. We're trying to create a sense of community where people can get together and feel, I guess, the safe like the safe community really of getting together, which is a very positive message. Getting somebody you know, asking someone to volunteer to lead it or be on this group to help organize it. And then sometimes it's just, you know, get the word out. Let's just try this. I'm more of a doer. So sometimes, it's like, let's just put it out there. Let's try it and we'll continue working to get it right as we go. But then you'll realize you start seeing so many employees, they're like, Hey, this is kind of cool. Let me, let me check this out then. And that's where you start building that safe, that safe community but sometimes you just have to move forward and take that first step and try putting it together.

Kushal: So really talking of first steps for you know, as women often looking for mentorship or for people to kind of guide them through and obviously your mentor at GirlsClub as well, right. What do you think is the right way for people to kind of go about finding a mentor, setting up the right expectations and really kind of getting the most out of that relationship?

Jennifer: Absolutely. I think for the most part it can go two ways. For the young women who are looking for a mentor. They just need to ask somebody, right, I think they can just they just need to take that often which can be a little scary sometimes especially you know if maybe you don't know them as well or maybe you don't know them at all, but sometimes it's just setting up a 15 minute ally meeting and just wanted to talk to you I want to get to know you a little bit you know, tell me about this or that and you know, the reason that hey, you know what, Kushal, like this is amazing I've been watching you I think this is great, you know and how do you do this and how did you get your start and really just have that conversation with curiosity and really just learning, and then at the end, it's like, you know what, I'd love to continue this you know. Would you be available to meet, you know, whether it's once a month or every six weeks, and you know, the person who's being asked that mentor person, then that's up to them. And there may… they may very well say like, you know, I don't have that time commitment, but you know, what chances are, they probably do. And they might say, you know, let's do it every six weeks, and that's what's really good. But you, you do need to put yourself out there and ask and I was in, I was in a position recently, for maybe about six months ago, that I did the opposite, I actually approached some young women, and I said, like, I would love to be your mentor you know. And kind of the same things in reverse that I just saw such potential with them. They were just amazing young women who are getting into some, some leadership, and I just was like, I'd be honored, you know, to mentor you, if you feel that, you know, that could benefit you. And, everyone I asked they all were very excited and said, “Yes”. And but it's also important to you for the mentor, to you know to set those boundaries. Like is it for weeks, is it six weeks, and really try to set the boundaries and the agenda so that you're really adding value, you know, to your mentee, and working closely with. 

Kushal: Jennifer, there's so many questions that I have for you. I know we're kind of running, we will be close to our time soon. Just a few more questions to go though, what's maybe the advice that you give to yourself or to women who are just getting started in sales today?

Jennifer: I would say that, you know, curiosity, approach everything from a point of curiosity and approach it as you know, a beginner's mindset. You know, even 30 years, 30 years I've been in the field, I keep saying that, like, whoa. You know, I'm still approaching things with a beginner's mindset, right? Because again, I don't know everything. And things are different. Now things change, especially post COVID. It's all different. So always, I think just have that open mind, be curious, and really focus on a beginner's mindset that you're always open to learning, I think that's going to be the most important thing, because you're going to learn something from anybody, like, there's always something to learn that you're like, Oh, I love the way that, you know, Kushal does this and the way she approaches, that's amazing. I'm going to try that next time I have a conversation with a prospect and you know, so just be open to things. And again, it may be different than what you do. It's okay, right, be open to it and just be curious and attack it that way.

Kushal: I love your point about curiosity, and really kind of sustaining that. I think, personally as well, I think it's really one of the most important ingredients of even being good at your own job, no matter which stage you're really at, right. If you're curious, if you stay curious, then you will always keep on evolving and learning, which kind of brings me to our last question which is, what's the number one impact that you would like to drive on the world?

Jennifer: So let's see the number one impact that, that I would like to make or that I would deal with, so the number one impact I would like to make is really helping other sales professionals, helping you know, young, young women, sales professionals. I love what I do. I have my own podcast “A life you'd love in sales”. And I really feel that way of like you'd love and really help, you know, not only young female salespeople, but even you know, man, you know, like, there's a whole world out there. And you gotta love what you do. You have to be passionate, you've got to love what you do. And if I can help make that impact in my position, you know, here at WorldStrides and working with young sales professionals. That's what I would like to do help them succeed, help them find their passion. And if it's not sales, if it's sales, but in a different product line or category, that's okay. But let's find your passion there and really help you succeed and grow. And that way you can then go and make a big impact in the world as well. So that's what I get excited about. And that's what I absolutely love.

Kushal: That sounds great, Jennifer. Thank you so much. I really enjoyed you… having you on the podcast.

Jennifer: Thank you. I really appreciate this. So thank you for today for taking the time to meet with me.