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 AE's 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 there. Welcome to another episode of “On the Flip Side” with Wingman. I’m your host Kushal. And I'm so excited to introduce our guest for today. She describes herself as a global digital product and tech executive, growth catalyst, board member, author, guest lecturer and mother. Jennifer, welcome to the show. So excited to have you here. 

Jennifer Ives: Oh, thank you so much for having me, Kushal. This is really, it's such an honor. 

Kushal: So Jennifer, first things first really, I know we've chatted about, you know, your background, your history, you know, a lot of interesting highlights and there's so many interesting highlights there. But it would really be great if you could maybe tell us what you think are maybe the top five sort of defining moments or really the milestones across that journey that really make you who you are today?

Jennifer Ives: Oh my gosh, okay. So I never thought of myself as a STEM person, although I was raised by engineers. And I did in fact, win my eighth grade science fair…In eighth grade, talking about the environmental impacts on paramecium caudatum, and then I went to college. And you know, a few years later, I went to college, and I had no idea what I wanted to do or what I wanted to be. And I found a major called geospatial engineering, which I'm going to date myself. That was back in the early 90s. And geospatial engineering was not known. Even in my family of engineers, we have many types of engineers in my family. And everyone was wondering if I was going to be able to get a job. This was before the days of Google Earth and Google Maps and Waze and all other sorts of ways to take in satellite imagery, and also to map the world in a digital format. And so that was one pivotal moment, making that decision, and really finding a major because I tried out a few different majors, and nothing was really clicking. And then I found geospatial engineering after listening to an amazing, world renowned professor come in and give a guest lecture. And I'm a naturally curious person by nature, so stopped in and took a listen and was like, what is he all about? And what is his study all about? This is really interesting to me. 

So geospatial engineering became a love in college, and I got my first job and sat on the engineering team at a very fast growing, emerging technology company, really working with some super-secret agencies as well as private sector. And it was one day that our CEO came and asked me if I could come and have a conversation with one of our clients. He was going to a client meeting. And today, it's known as a sales engineer or sales architect, back then it wasn't really known as anything except someone on the engineering team coming and having a conversation and talking about some of the goals of the project. And I did that and loved it. And that was another pivotal moment in my life. I'm all about not putting blinders on. And also kind of leaning into saying yes, even when your stomach is like, I don't know, can I do this? Being really strategic about saying yes, but saying yes to things that sometimes make your stomach flip a little bit. And that's what happened when my CEO… so I respect him greatly. I didn't really have a close relationship with but when he tapped me on the shoulder and asked me to come to that meeting, my stomach flipped a little bit and I said, “Yes”. 

And then when I was able to talk with clients, that client and then clients in general, and really straddle the engineering team, as well as the commercial side of the company, and that's where I fell in. That's another pivotal moment for me. I fell in love with the commercial side of product, digital product and engineering, technology companies. It's a real love of mine. And if the market doesn't know about your amazing technology, or about your amazing product, it's not going to matter. It's like the tree falling in the woods, if no one is there to hear it – does it make a sound? And it's the same thing with digital products and technology products that… you could have the most amazing product, the most amazing technology, and if your market, if those who should be buying your digital product or services, if they don't know about you, it really won't matter. As I said, you won't win the race, someone else is going to win that business and win the race. Even if yours is technically more savvy or more further along in the technological lifespan, it won't matter. So I moved over to the commercial side. That was a pivotal moment for me. 

And I don't know two or three pivotal moments, I think, really finding my voice and understanding what leadership is in a world of technology where I didn't see too many female leaders. I'm seeing more women leaders today, which is amazing. And I do a lot of mentoring of women who are coming up in their career to make sure that they're looking at those leadership positions as well. But I had a number of amazing mentors, both men and women who tapped me on the shoulder at various points mid-career and even as of kind of a year ago, and this is you know, I'm in my career 20 plus years and those mentors are still they still play a really big role in my life. I call them my board advisors. I recommend everyone start and start choosing your own personal professional board of advisors to help you in your career. So hopefully I answered your question. There were few pivotal moments in my career. And again, in the last 15 years, there have been some pretty amazing individuals who have played a big role in my life and in my career.

Kushal: I think it's amazing how you've also bundled in so much life advice, I think really along the way, while sort of describing your journey as well. Jennifer, you also talked about how, you know, maybe initially, you didn't see too many women in very senior positions. And that's maybe a reality in a lot of ways, today as well, where maybe those ratios are becoming better, but they're not exactly where we'd like to see them. Given all the experience that you've had, why do you think you know, what do you think are maybe the biggest barriers to women getting into more leadership positions especially in technology? Are these external barriers? Are these barriers we create? How do you really think about that?

Jennifer Ives: There might be a little bit of both, I believe there's a little bit of both. One is an internal barrier that that we create, studies show all the time. And a lot of people know this research this particular study from a few years ago, but they looked at men and women reviewing job ads. So opportunities in the market, and men overwhelmingly will self-select into jobs that they may not have all… they may not check every single box, they may check something, even 5 or 6 out of 10 and say, I can do that, I'm gonna step into that role, I'm gonna give that a try. 

Women are the opposite. And research shows this and that's why mentorship is so important. And that's why also it's really important in companies for external leaders, internal to the company but maybe external to a department or a division, really keep an eye on and look for amazing women on their team diversity, on their team that may be you know, leaders of the future. Because women tend to, women specifically tend to look at a job opportunity and see maybe 10 boxes that need to be checked. And women will say, I don't have the 10 and actually, I need 12 or 13 to think about applying for that job or think about moving into that role, and that's just not the case. And so that's again, that's where leaders in a company, that's where mentors can step in. I know that in my professional lifetime, those early leadership opportunities came to me because someone tapped me on the shoulder, someone who cared about me, cared about the organization that I worked for, and saw something in me that maybe I didn't see in me, because I was looking to fill in 12 of the 10 boxes. And they tapped me on the shoulder so to speak, and said, you know, “You should really think about this opportunity”. And the first time someone did that with me for my first leadership position, I remember thinking, “Oh, no, no, no, that still I remember going back to kind of like, I only have 10. And I really should have 12, I should really be overly qualified for that position”. And it was a gentleman that I used to work with, and a wonderful mentor of mine who's since passed away. He was really thoughtful about it. And he said, “Well, I believe you can do this role and do this job. But if not you, who? like if not you then who”. And if you can look around the room, and if you see someone that might assume that leadership position, and you think you can do a better job, or you're not sure of their own leadership capabilities, you should really be sure to try, you should really throw your hat into the ring. And I remember looking around and seeing the person who might have that role and I thought, “Oh my gosh, I can do an amazing job in that role”. And I did, I stepped into that first leadership role. And it was thanks to someone who tapped me on the shoulder and quietly said, kind of you know what, why don't you think about this? What's holding you back? Why do you think that you're not qualified for this particular role, and encouraging me a little bit to ask some questions of myself? So it is a little bit internal, where we as women and research has shown this that we like to be overqualified. 

So the short answer is, we like to be overqualified for things. And we need to stop that and we need to say, “Yeah, I have six or seven of the 10 items that they're looking for. And I can do an amazing job and I can learn the other three on the fly, I can learn it on the job”. 

The other is that the market still tends to write job applications and job opportunities in a certain way that women and those with different backgrounds, they don't see themselves in those roles, those job opportunities don't speak to them in a certain way. And so a lot of HR and people in talent organizations, the smart ones and the creative ones, are really starting to rewrite, and that this has kind of been in the last five years, in particular the last two years, they're starting to rewrite those job applications and those job notifications so that people with diverse backgrounds can see themselves a little bit more in those roles. And it's not so much about the qualifications, it really is about the wording. It also requires leaders to proactively look for diverse leadership teams. You need to go and sometimes tap someone on the shoulder and say, I think you do really a great job in this role. Why aren't you considering it? Why don't I see your application and that's internal to an organization. The external piece is you need to proactively go out and find diverse candidates. It's up to your talent teams. It's up to you as leaders to proactively go out, sift through your network and really work to find the diverse talent pool. So it's a little bit of both. So I'll pause there for a moment and see what your reaction is and your thoughts.

Kushal: So I think it's really important to talk about how sometimes the ways we describe roles, or just the words we use, I think in job descriptions is really telling. For instance, you know, I recall a lot of people talking about how job descriptions will say, you know, Marketing Rockstar, or, you know, Sales Rockstar or Ninja, Ninja is still you know a lesser offense maybe, but a lot of those terms are really not how a lot of diverse people describe themselves. It talks to maybe only a certain personality type in some sense. And a lot of those are really just again, enforcing stereotypes. So I think there's a lot of merit in what you're saying about really kind of closely looking at the kind of words that you're using, because that's really the message in some sense that you're putting out about the kind of talent that you hope to, and maybe you appreciate in the long term, definitely there.

Jennifer Ives: Words and phrases matter. 

Kushal: Yeah, I think also, you know, around your second point around, I think it's amazing that, you know, you've had mentors along the way who've unwittingly, sort of, like you said, you know, tapped you on the shoulder, told you the kind of stand up, you know, make use of an opportunity, that's great. I think as companies, we definitely need to think about how we can institutionalize some of this thinking really, which is where, you know, kind of encouraging your talent teams to really go out and look for that sort of talent is going to be really key. So to kind of maybe drive that from the top level in some sense is what I think is really useful. Are there other, you know, initiatives, Jennifer, that you think, you know, company leadership or board should really be taking to ensure diversity and especially women? 

Jennifer Ives: Well, it starts at, you just mentioned, it starts at the board. It's really taking a look at your board and making sure that you don't have an entirely male board with a similar backgrounds. Again, research McKinsey, Gartner, you can go on and on, research shows that diverse boards, diverse leadership, you'll get a stronger return on your investment or return on that particular company's efforts in the market. And so when you're looking to diversify, and make sure that you have a diverse pool of candidates and team members, it really needs to start at the top with the board and then with a C-Suite. And then throughout the different levels of management at a company, if you don't see that that is extremely telling. And if you're a leader in that company, you can be doing lots of things like making sure that you have programs specifically for people with different backgrounds, different gender, different race, and different sexual orientation. There are different groups that you can create within your company to make sure that that everyone feels included, everyone is aware of the different steps that they can take to reach those leadership positions. And once in those leadership positions that they're… you continue to evolve and create additional diversity, it's good for humanity, and it is good for business. 

So when someone… When I have these conversations, I advise a number of companies and people tapped me on the shoulder sometimes to come in and talk about this, and so I will use statistics and a lot of data with them to show that diversity is good for business. So if for no other reason, they should be thinking about the business. It starts with humanity, it is good for people, it is good for your teams, it is important that all people feel included and welcomed. And then if someone is just thinking about the numbers, you can put numbers in front of them too. And it is good for business. 

But some things that some companies can do right, organizations of any size that can make sure that they have specific groups within their company for women, for different sections, sexual orientation, for different race background, religious backgrounds, like it depends on the size of the company, and how many groups you feel that you need to have to help support your team members. But I highly recommend the subgroups within the company. Actually, I'll be speaking with a company next week with their subgroup of women in sales and women in leadership, talking with them about what it is like to be a woman in sales in growing companies and some of the things that we as women need to keep an eye on in our careers and careers are our… you know, they are really our path to pave. you own your career. So I have had a couple of folks in my life that were wonderful to tap me on the shoulder. I've had to make some other decisions on my own. I do reach out to mentors to run some ideas by them, but I do need to and everyone needs to own their career. 

So if I had any information kind of on the table and out there in the world today on your career, as a woman on your career, make decisions, don't be afraid to say yes, strategically, really think through where it is you want to be in 2 to 3 to 5 to 10 years and make decisions that are good for those, for that trajectory. But don't be afraid to say “Yes”, I find that many women will turn away from a particular opportunity because again, they don't feel like they have all the qualifications. And don't feel comfortable saying “Yes” that say “Yes”, make sure that you're paving your pathway to the career and to the life.

Kushal: Yeah, that’s a great way to put it, Jennifer. I think there's so much power in just saying “Yes”, and you know, just kind of showing up and saying, “You know what, I am going to try this and let's see how it goes”. I think we also talked a little earlier about, you know, how it's also important to really encourage young generations really, you know, younger folks, you know, kids who are in school, really to kind of get into the same mindset of, you know, really being able to choose what they want to do, or not being held back by, you know, their gender, or anything else. You mentioned a little bit about the initiatives, you know, that you're running around that as well. We'd love to hear more about that, and really, about how we can encourage really, you know, younger minds, you know, whether those are, you know, folks in our own families or, you know, even much younger colleagues in the office. How can we really kind of go about encouraging, you know, the next, you know, set of people to really own their own power? 

Jennifer Ives: Yeah. Gosh, I love this question. So you hit on one of my passions, which is making sure, and ensuring that girls have girls and non-binary students have access to special wonderful memories at a young age when it comes to engineering and coding. So again, I go back to research and data research and data shows over and over again, they show over and over again, how important it is to encourage again, girls and non-binary students as early as third grade, and to do it in a warm and welcoming environment. And so I get to talk a little bit about the nonprofit that I'm a board member of Boolean Girl, they do just that that is their mission is to introduce technology, engineering, and coding to girls, non-binary students, ages third grade to eighth grade. So we're talking kind of 8 years to 14-ish. And there's some wonderful organizations around the world who also do similar work for those girls and non-binary students who are ages, you know, 14, 15, 16, throughout high school, and then also into college. I'm very interested in making sure that we give confidence and creativity and a love of coding and engineering to girls at a very young age. So that third to eighth grade is something that I feel really special and passionate about. 

So that's something that everyone can do is make sure that even if girls and non-binary students are kind of self-selecting out of some of those opportunities to find organizations such as Boolean Girl to get them into opportunities and learning opportunities that put them in front of various types of technologies, and STEM opportunities. Because you never know what's going to click, you never know, you know what, 8, 9, 10 years old, what's going to click, and then when they go to high school or college, them have the confidence of saying, “Oh yeah, I coded that” I was coding in Python when I was 10, or 11, I guess I didn't give myself that much credit for it. And now we're going into a class where we're going to be learning you know, Python, and I'm pulling, it's a language, it's just like being exposed to foreign languages, when you speak a foreign language at a young age, it's very similar, so it builds confidence. 

So that's something that that everyone can do keep an eye out for, for girls in particular at a young age and make sure that we're exposing them to engineering, whether it be mechanical or computer or you know, digital products, and that they have the ability to have access to those learning opportunities in a fun and welcoming environment. And then also in high school and college, making sure that they are, at the very least, if they're drawn to a different, maybe they're drawn to English, or literature or a liberal arts degree, making sure that they have a minor in something technical. So data analytics, or computer science, mathematics, something… have a minor, I also strongly recommend that, it's not just me, a lot of universities around the world are starting to do this, that for those technical degrees, right, if someone who's getting a degree in some form of engineering, that they have a minor in a softer skill, because those soft skills make amazing leaders, and you have to have a little bit of both, you have to have a little bit of that knowledge of technology, as well as the softer skills, the writing, the communication, the ability to interact with and to share your wisdom and your knowledge, again, both written and verbal, it's really important that you can also see things in a different way. And again, the softer skills and the liberal arts will help you do that, really see things in a very creative way, that someone who is very technical may not see. Not saying that they don't always see it, but it's a really nice balance for someone, for people in general.

Kushal: Got it, Jennifer. And I think that was incredibly useful. I think kind of, you know, going towards wrapping up this episode, it's been incredible. I think there's so many other questions that I have for you, but I'm just going to maybe choose the very last few to kind of go ahead with. So for really women, and you know really other diverse groups as well, and companies, what do you think are some of the best ways to also explain and sort of bridge those gaps with others in the company and create a sense of allyship. Because a lot of that education is also you know, sort of, in some sense, and you can't really grow in a silo. It's also about kind of educating and taking people along with that journey. How do you think people can kind of really go about that and you know, instead of… a proactive sort of approach that you can take as well? 

Jennifer Ives: Yeah, proactively make friends with and understand the perspectives of those around you in different positions and departments. This is going to help you throughout your career. This isn't just an answer to kind of one question, you should always be building bridges and allyships with people not only on your own team but in other teams. In finance, if you're, again, if you're in engineering, you should really understand marketing, you should understand finance, you should understand sales, you should understand different pieces, operations, you should understand different pieces of the company, because it gives you a different perspective and appreciation not only for the people who love to do those roles, and how they interact with you, right? How they interact back with maybe you as a person but also you as a division or department in that company. So proactively across the board, I highly recommend proactively reaching out to and creating allyship creating friendships, creating relationships with people in other departments. It will help you do your job better, it will also help you grow as a human being to understand what it is they love about finance, what it is they love about engineering, what it is they love about marketing where you can go on and on with the different pieces of what makes a healthy robots company, what it is they love about people and talent? And you'll also gain some knowledge as you grow in your leadership as you carry forward and grow in your leadership journey.

Kushal: Which kind of takes me very neatly towards my last question on this segment, which is really fun. We played a segment called wrong meanings only, which means that I will throw three terms at you. And you have to give me what is maybe a wrong, sarcastic funny sort of meaning of that word. So anything but what the word actually means. Are we ready for this? 

Jennifer Ives: I don't know. I don't know. So you're gonna give me a word. And I'm going to give you a synonym or I'm going to tell you if that sounds sarcastic or funny.

Kushal: So I’m going to give you a normal term, and you're going to give me what you think is a wrong meaning for that word. 

Jennifer Ives: Oh, the wrong meaning of the word. 

Kushal: And then give me a wrong one. 

Jennifer Ives: Okay, we might have to do this a couple of times.

Kushal: We will treat the first one as practice on that. So my first word for you is “Leadership”. What's a wrong meaning for leadership?

Jennifer Ives: Dictatorship. Is that what you mean like, what could you know, leaders? 

Kushal: Yeah.

Jennifer Ives: Leadership is not the dictatorship. Leadership is creating bridges. It is shepherding your teams and your company through incredibly exciting and challenging times. Is that what you mean, so the wrong definition? So okay, I'm hearing leadership, but a lot of people might think that leadership is dictatorship. Okay. Got it? 

Kushal: Yeah. Okay, so the second word we have is “Technology”.

Jennifer Ives: Difficult, hard to understand. Technology is none of those. If you have the right teacher and you have the right mindset, and you have the curiosity for it, a technology you can break that down pretty easily and pretty quickly doesn't mean you might love it, or want to do it that particular job for the rest of your life but don't shy away from technology, don't be afraid of it.

Kushal: Okay, and here's my last one, “Mentorship”.

Jennifer Ives: Well, that's a passion of mine. And I think everyone should be looking for mentors and mentors should actually be proactively looking for when they when they see someone that that they think could use some guidance or just a shoulder to lean on and talk through mentorship. I think a lot of people think that mentorship is again in that area of I have to tell them what to do. And I don't want to be in that position. So mentoring may be perceived as something that that feels very big and scary and strong. And for the mentee, I often see that the mentee believes that mentorship is like something that's unattainable. Like I can't ask him or her to be my mentor because they're, you know, I have them on this pedestal. So I don't know that I gave you word for word mentorship.

Kushal: We got the gist of it. Great. This has really been incredible. Jennifer, thank you so much. I think there's so much really inspiration, motivation and just so much for everyone to sort of take away and really apply in their own lives. Really appreciate you being “On the Flip Side” with us today. 

Jennifer Ives: Thank you so much, Kushal. I really appreciate it. I'm really honored. Thank you.