Women Lead TV Show - Women, Wellness and the Workplace

In this Women Lead TV episode, host Reena Vokoun (founder & CEO of PassionFit) interviews Jennifer Ives, co‑founder and CEO of Watering Hole AI. Jennifer shares her journey from a geospatial engineering background to becoming a go‑to‑market executive and AI entrepreneur, describing how Watering Hole AI applies generative and predictive AI to improve marketing and sales for Fortune 500/1000 clients. The conversation shifts to women in STEM, where Jennifer cites recent data (e.g., women now 26% of the STEM workforce, projected >30% by 2026) and stresses the value of diverse perspectives and role‑model visibility. She outlines persistent barriers such as unconscious bias, limited mentorship, and under‑representation on corporate boards, referencing studies from Deloitte, LeanIn.org, Anita Borg Institute, and Women on Boards. The dialogue then explores AI’s impact on work and learning, distinguishing automation versus augmentation, highlighting ethical concerns like data bias, privacy, and job‑role evolution. Finally, Jennifer discusses personal wellness strategies—setting boundaries, delegating, a 50/50 partnership at home, and cultivating supportive networks of executive women—to balance a demanding career, motherhood, and health. The episode concludes with contact information for Watering Hole AI (website and LinkedIn).
Chapters
Hello everyone and welcome to Women Lead TV, brought to you by the Connected Women of Influence. I am Reena Vokoun, your host of Women, Wellness and the Workplace, and I'm also the founder and CEO of PassionFit. And I'm so thrilled to have an amazing guest with me today. She is my friend Jennifer Ives, and she is the co-founder and CEO of Watering Hole AI. She's also an author, a speaker, a board member, a mom and wife, and so much more. Welcome, Jennifer, and thank you for being here today.
Oh, Reena, it's so nice to be with you today. Thank you for having me.
Of course. And just a little backstory on Jennifer and myself. We actually spoke on a Global Women's Leadership Summit panel in the Washington, BC area in 2016. I can't believe it's been 7 years, but we were on the panel together and we're talking about being, you know, professional women, moms, and immediately bonded. Do you remember that fun time in that event, Jennifer?
I do. Oh my gosh, Reena, the first time I met you, I was like, she is one of my people. I love this. You're a mom, you're very successful in your career, you're very dedicated to staying healthy and kind of all of the things. And I do remember that very well. I can't believe it's 2016. Where does the time go?
I don't know. I don't know where the time has gone, but it's been wonderful to stay in touch. And I love women supporting women. And I feel like we both have been cheering each other on, and you immediately came to my mind as somebody that I wanted to be on the show. So tell us, let's start by, you know, I'd love for you to tell our viewers a little bit about yourself, your background. And I know you have an exciting new, very important startup. So tell our viewers a little bit about yourself, Jennifer.
Oh, thank you. Sure. So I, yes, as you mentioned, I'm the co-founder and CEO of a company called Watering Hole AI. I co-founded it with someone that I admire and respect and have known for many years, Julie Holdren, who's the co-founder and Chief Product Technology Officer. And we're really applying artificial intelligence models to marketing and sales efficiencies and to create and generate marketing and sales efficiencies. That's something that I know a lot about as a commercial go-to-market executive of more than 20, 25 5 years now. We— I knew the technology was out there. I have advised AI companies for over a decade. And once the technology hit a place where kind of the cost came down, the compute cost, kind of a number of things aligned at the same time. And Julie had been working on the technology in R&D for almost 3 years now. And so we took that technology, we rebranded the company or branded company, Watering Hole AI, and it's all about who's around your watering hole. Um, do you have gazelles, lions, tigers? Do you only want gazelles? And if so, let's work on that with you. Let's put some AI, uh, both generative and predictive models in place to help you with that. Where are the like watering holes? How do you attract and retain, uh, new buyers, new customers? Uh, this is B2B, B2C, as well as direct-to-consumer, mainly Fortune 1000 and Fortune 500 companies, uh, that we've worked with and generating just incredible results for them through the use of AI. My background is geospatial engineering. I come from a technology background and over the years have just worked with some really amazing hypergrowth technology companies on the go-to-market side. And so it's time to, time to put some of that technology know-how to, to work. And, and Julie and I co-found the company.
I love that. What an incredible background you have. And so it sounds like, yeah, after all of those years of also advising other companies, is that what kind of led you to make the leap to start your own?
Yeah, absolutely. It was the, both the executive work that I've been involved with directly, it was the advising of very specific companies. And then also, quite honestly, the private sector board work that I became involved with a couple of years ago and being on a board of a hypergrowth technology company and just knowing that, and again, it was really the right place, the right time, the right technology in terms of cost, need, access to AI in a way that solved a pain point. I mean, a lot of founders will do that. They will solve, they will create a company that solves a pain point that they know very, very intimately, very dearly. And again, when Julie shared the technology with me, I said, well, let's co-found this company today. Let's rebrand and start, you know, Watering Hole today. So we did so about 6 months ago.
That is so exciting. I mean, you are in the early stages, very exciting, fun, but probably also hard stages of putting those bricks in place to set the foundation. So I think that's amazing and what an example you are setting for other women in tech. Speaking of, I'd love to, you know, hear and have our viewers hear a little bit about why you chose a career in STEM and in technology.
Yeah, absolutely. So I don't know that I necessarily chose it. It's an interesting story. So I come from— my mom is a teacher, my dad was a scientist, and my siblings and I were just always surrounded by asking big questions around about the world, asking, you know, taking math, being engaged in science. I won my 7th grade science fair for the entire school, environmental impacts on Paramecium caudatum. And so I was just always surrounded by it. And to be honest, it's not that I loved it. It's not that I, you know, in 7th grade thought I'm going to be a scientist or I'm going to be involved in technology. It wasn't that at all. It's just my parents really raised us to have a balanced education, to, you know, think of math just as important as maybe history, right? And history, to be honest, was something that I really loved. And it was when I went to college, actually, each of our siblings— and my siblings, I've got two siblings— and my parents said to each of us, you can be whatever you want in the world, you'll get a STEM degree. So from that, go forth and prosper. And so I have a sister who is actually in data science, I have a sister who is in medicine, and I chose geospatial engineering after really looking at a number of different undergraduate degrees and just really falling in love with a particular lecture. I guess a lecturer was on campus talking about satellite imagery and geospatial engineering, and I had never heard of it before, even though I was semester after semester taking lots of STEM classes and trying to find kind of my, my niche and what I liked. And, um, and then I worked on the engineering team for a few years after graduation. I, I interviewed, I started for working for a hypergrowth tech company here in the DC area, and kind of moved forward from there. And it was actually during that opportunity, my first years on the engineering team, that I had a CEO who said, "Hey, could you come to a meeting with one of our clients?" I was working on the project, and this is the day and age before they had sales architects or sales engineers, or even before they had engineers come and talk with clients. And he had me do that. And it was an hour's worth of conversation about the project and the technology and why they needed it and what they were using it for. And it just made the project so much better. And then it was during that meeting that I got to know the vice president of what her title was, Vice President of Business Development. I got to spend much more time with the CEO of the company and really start to understand that the go-to-market side of any company, in my world, it was technology, right? The product, product or service that you really need to have a strong go-to-market understanding. You've got to understand the pain points that you're solving in the market. And I also was able to start better connecting the technology that I was involved with, whether at that company and other companies moving forward, with the consumers in the market that needed a solution to their pain point, right? We had whatever the technology was, there is a, you know, you have a pain point, we have a solution for that pain point. And I became very, very interested in spending a lot of time in sales, marketing, messaging, and understanding how to speak the world of the technology language and put that into the market efficiently and effectively.
I love that. And I think you at a very young age learned the importance of looking for a problem out in the marketplace and then being able to solve for it. And with your case, it's with technology. And so to have had that, that knowledge and that insight in that experience at such a young age, it makes sense that it's led you to now doing the very same thing with your own company after all those years of continuing to learn that skill working for others. So I think that's incredible. Yeah. And how do you see women in tech growing and evolving over the years? It's becoming more and more, um, you know, prominent. You hear about, you know, girls that are starting to study, um, you know, STEM careers and get those types of degrees in college and graduate school. But what's your take on it? And you even mentioned your, you know, your daughter is kind of pursuing a tech career just like you.
She is, absolutely. So the good news is that the numbers are improving over the last couple years. But when I was— so when I was in college, 30%, around 30% women were pursuing STEM degrees. So STEM, one of the STEM degrees they were pursuing. Now it's around 11%. It doesn't mean that only 11% of women are getting involved in, in technology and in STEM careers after they graduate. However, in terms of STEM undergraduate degrees, it's about 11% these days. I think it's really important to know that the, the, the— as I mentioned, the good news in the last couple years is that the number of women pursuing STEM careers has been increasing. So I'm just, I'm gonna, I, I'm kind of a data geek and I always refer to when I, when I make a statement, I try to punctuate it with some data. So there's a 2022 report by Deloitte that shares that women now make up 26% of the STEM workforce, up from, as I mentioned, the numbers are increasing, up from 19% in 2011. The, this growth is expected to continue, right, to, I think in 2026 it's supposed to be over 30% of STEM jobs will be held by women. As I mentioned, that number is still not enough. We are 50% of the workforce, depending upon some numbers even more than 50%, but let's just say it's 50% of the workforce. So having only a third of women in the STEM jobs is not the ideal number. However, we are— the world, we, the large, the capital W— is making progress in the right direction. So that's a good thing. Um, women in STEM, in case anyone needs to know why it's important that women or diversity in STEM is important, is because We bring, you know, diverse people in STEM will bring diverse perspectives, diverse experiences, and it leads to more innovative and inclusive products and services and better products and services. And, um, so, you know, there's that as well. And then also it's really important to shatter the stereotypes and to inspire the next generation of STEM leaders, of of a diverse set of STEM leaders. You cannot be what you don't see. So I, and I firmly believe that if I don't see, for me as a woman, if I don't see other women in STEM, even in my early career, right, I was, even though I was one of 30%-ish that earned a STEM degree in my undergrad, I was still one of only a handful of women in a 50-person high-growth company. A handful. I can, I can, it's been over 25 years and I can count on one hand, the number of women. However, 2 of those women were vice presidents. And at the time in our company, VP was the, the, the, the highest title in the company. So 2 of the 4 vice presidents were women. So I almost took that for granted, right? I got— I was in a company that was predominantly not female, not women, not made up of women. However, 2 of the vice presidents, very, very strong, very powerful. Executives in the company were women. And so I saw that from an early age, you know, early age in my career, early in my career.
Absolutely. Yeah, I think it is important to see it, right? I mean, I come from a marketing advertising business background, but I think in this day and age everything ultimately leads to tech. I worked for Google and Yahoo and CNET, and I worked in tech myself for many, many years because even, you know, marketing is a field that ultimately does turn digital. I think everything now will kind of require some technical skills no matter what you are studying in college or graduate school, which is good. And yeah, I mean, I certainly saw women leaders. I had many, you know, bosses and managers over the course of my career that were women. But when you looked at the very top, at the C-suite, obviously that is something that continues to need work, but it's growing. And like you, you know, I'm very optimistic, and I think it's promising. And, you know, the hope is if we especially focus on the next generation and encourage them to get curious and to, you know, represent for their next generation, we'll continue to develop more women in tech and in leadership roles in tech, which is, you know, especially important. And I'm curious, what in your mind, um, you know, what are the barriers that still exist for women getting into tech? Is it a mindset thing? Is there just not enough seats at the table yet? You know, where do you think we're seeing those barriers being caused from?
Yeah, unfortunately, there are unconscious as well as conscious biases and stereotypes. And as early as— I mean, there are studies that show as early as kindergarten. So I'm on the board of a nonprofit called Bullying Girls, and where the mission of Bullying Girls is to engage girls 3rd to 8th grade in STEM. And to actively engage. And the reason that I was called personally to want to be on the board is because of this unconscious and sometimes, oftentimes conscious bias. And it's really important that we engage girls at a very young age to, as I mentioned, you kind of can't see what you, you can't become what you don't see, right? You just don't know. And so to engage girls at a young age. When you reach, you know, when you start into your career, the conscious and unconscious bias continues. It just, it is, it is real. It is a fact. And, you know, it's, it's challenging. So unconscious bias and stereotyping can lead to women being overlooked for promotions, not being paid equal to men, so receiving lower salaries, facing much more scrutiny than their male counterparts during the different phases of their career, in particular, during you know, different times when they're being advised on what steps that they can take in their career. It's, it's challenging. I mean, there are lots of, there's lots of studies and research to show that, for example, LeanIn.org found that women are 1.5 times more likely to leave their jobs than men due to lack of advancement opportunities in STEM. And so it's things like that that are really disturbing and that we all, all need to keep an eye out for and proactively be aware of. There's lack of mentorship and sponsorship. You know, for, for women in technology. And that's something that's changing. And that's wonderful, right? That is something that I am, you know, as an individual, I try very, very specifically to, to, to help bring the next generation of STEM leaders forward. There are organizations that do this and it's, it's really important. There's a study by Anita Borg Institute that found only 24% of women in tech have a mentor. Compared to 38% of men. And I mentioned that this can change. There's a wonderful organization actually that just launched recently called Launch2Lead, and they're dedicated to empowering young women early in their career. You see a lot of empowerment and organizations dedicated to kind of mid and advanced career. What I love about Launch2Lead is that they are really focusing on women in STEM as soon as they graduate from college. So their first 5 years of of their career. So I'm really, I'm very excited to see where that organization goes and the impact that they're going to make. And then, as I mentioned, you have to see it in order to become it and know that it can be real. So the lack of female role models in leadership, and, and there's a, it was either 20 or 22, but a recent study by 2020 Women on Boards, only 28.6%. So less than 30% of board seats in S&P 500 companies are held by women. This is changing. More companies are acknowledging that it is important to have diversity on their boards because of all the research that shows how much better for business. I mean, the bottom line shows over and over again that diversity in leadership, diversity on boards helps the bottom line. And so companies are, you know, across various industries, are looking to diversify their boards. So that's very exciting. I sit on a couple of boards. I mentioned the nonprofit. I'm an advisory board member to a couple companies. And I'm an independent board member for a company, a tech company called Terrazzo. And so it's really important to ensure that there are female role models in leadership positions.
Absolutely. I mean, you've just nailed it. There's so many positive changes that are happening. Boards are a huge key focus, especially for not only women in tech, but just women in the C-suite in general, right across any industry. And I do think, and this kind of leads into my next question for you with AI, I mean, I think of you as somebody who really is knowledgeable. You're an expert in that area. And that is going to change how we learn, how we work, and how we live. And I think that that's going to also be an important factor in women and girls thinking to study STEM as well, because you kind of need to be on the forefront of what's happening with technology, especially when you are thinking about what you want to study in school and even your future jobs and career prospects. So what are your thoughts on— you know, it's funny for me coming again from Google, I just remember with search how that was the, you you know, the big thing 20 years ago, and people were excited about it, but people were scared and nervous about it. They didn't know how it was going to affect our lives, and is this data trustworthy, you know, where are the sources coming from. I think now with AI, you know, even with, again, going back to the younger generations with ChatGPT and other things, I mean, obviously there's a lot where students are being, you know, asked to get information from various sources, and AI is part of that. So just curious about how you think it's going to affect us, how will affect how we work again, live, and, and learn.
Yeah, oh gosh, it's, it's so, it's so interesting that you used, um, when you were at Google, you know, 20 years ago, that even, even the search engine Google, the search engine was seen as scary, right? We have to go back 20 years to remember those, you know, because it was so new. AI is something that's been around for years. It's just now kind of in the last year because of ChatGPT, it's now getting all these news, uh, news cycles of focus. And so everyone is talking about it, right? At home, at work. How do you use it at work for efficiencies or to generate revenue? How do you use it at home to create efficiencies or supercharge your life, you know, personally as well? It is— a lot of people find it very scary. And so it's one of those things that the sooner that's of any age, right, that you can become curious about it. How could AI help me in my day to day at home? How could AI help me in my day to day at work? And again, I think the first step is to become curious about it. I've seen a lot of— not just I'm seeing, studies are showing and lots of amazing institutes around the world are showing that it's, you know, AI in the workplace is going to result and has already resulted in automation and augmentation. So kind of you have these two sides to AI or two benefits, I should say, two buckets. There are the efficiencies that it creates and then there's also if you're going to generate revenue in your company. Those are kind of the two ways that you're looking at AI. And there's generative AI, there's predictive AI. Generative in the sense simplest form is generative is you're literally generating new information. Predictive is you're looking— the system is looking at past data to make assumptions about what will happen in the future. So when you hear these words, you know, generative and predictive or, you know, efficiencies, there's also the revenue generation side of AI. And AI is an umbrella term for machine learning and deep learning. So if everyone can become better acquainted with some of the words that are being pushed out into the world at the moment, and then also personally and professionally become curious about it. So it's the automation and the augmentation you're going to see in the workplace. You know, AI, by the way, for years, as I mentioned, has been automating routine tasks, freeing up humans from— so that they can focus on more creative and more strategic and more collaborative endeavors. And that's going to just continue to increase. This is where you really are going to see a lot of the efficiencies, the supercharging of your workforce. I always talk about AI in terms of human-centered AI and human-assisted AI. You still need the human beings to be thinking creatively while you can tap into the artificial intelligence piece to really help with kind of the crunching of numbers, the crunching of data. You have to be really careful with that, right? You have to keep an eye on the data that's being created because there's inherent— unfortunately, there's inherent biases in data. And so you have to keep an eye on that. It's really important. That's something that everyone needs to have focus on. And there are a lot of important organizations doing work in terms of around ethical AI and the bias, the inherent bias that's kind of baked into, unfortunately baked into AI already. In society, you know, these personalized experiences and enhanced conveniences, you know, imagine where, you know, AI is kind of seamlessly integrated into our lives and anticipating needs and providing us with information and providing us with assistance kind of at the right time, at the right place. Again, pieces of AI have already been in our lives for years. At Google, right, when you type in a search bar, it will, you know, it'll continue, it'll make some assumptions about what you want to, what you're actually searching for. When you are creating a Word document or when you're sending an email, for years you've probably, people have probably noticed that that you might type in a sentence and it might autofill or assume what the rest of the sentence is going to be. That's all artificial intelligence. You're now seeing it supercharged. And in those examples, however, across the board in many other examples as well. So some of the concerns that I often hear is, I'm scared of it, or we as a human population are scared of it, mainly because of job displacement. Well, one in particular, the bias. That, that the inherent bias it holds. Job displacement, and the job displacement, I think that you're going to continue to see not so much job displacement, you're going to start to see job changes and title changes. And by the way, we've seen this with every advent of a new technology come into the world, where jobs have changed, and employees and the workforce has really needed to change with it. And we've not really had challenges changing with it. So you're going to start to see job titles, you already have in the last year, job titles and job needs and responsibilities change. And then clearly there are the privacy and the data security issues. And when I mentioned the— I just can't kind of talk enough about the algorithmic biases that we have to be aware of.
Absolutely. I mean, I like that you addressed that it's not necessarily something to be fearful of. Obviously, yes, people are fearful of the unknown, but as you mentioned, it is something that's been with us us for a long time, and if it can free people up to be creative, to be strategic, you know, jobs are going to inevitably change and evolve and grow, and there are going to be probably expectations to understand how AI works. You know, I've even included it in my Google search results. There are opportunities to now have generative AI search results, and it's great to see. I'm actually really educating myself and comparing, okay, what are some of the results I'm getting from generative AI, and then what am I getting in my traditional search results? And I do think it's important for us to, as you mentioned, still check the data. I think it's also very important to check the sources. Hopefully it's not being used as a replacement for thought and for analytical thinking and creativity, but if anything, it just will enhance our abilities. But I think we have to be thinking about how we use it in the most efficient and productive way. And hopefully, you know, the industry will continue to have some guidelines and regulations as it continues to grow and evolve. So there's just a lot of exciting things happening. And I agree, I think the more we can educate ourselves and as you said, be curious, the better off we're going to be because it's not going anywhere, right? It's going to be a part of our lives. It already is. And I think that that is exciting and not something to fear, but something to be educated about.
I couldn't have said it better. I just need to walk around with you all this. I could not have said that any better.
Oh no, no. You already had a really great, great answer with so much detail. So I appreciate that. And I think our viewers do as well. I know we just have a few minutes left, but I would also love to— a lot of my work is obviously talking to women from different industries, learning about their career paths and journeys. And also, since my focus is on wellness and workplace wellness, I would love to hear from you. I know you have a family, you have this amazing career, you're doing so much, you work so hard. How do you balance it all, Jennifer? And how do you take care of your own health and well-being to allow you to really be present and thriving in your personal and professional life?
Oh my gosh, this is so hard. For one, not only are you a friend, I follow you. I follow your tips. I follow your guidance. It is. So that's— I'm going to say that first and foremost. It is really hard. You know, it's hard. I've gotten much better over the years at setting clear boundaries and priorities and being really truthful with myself about what those boundaries need to be and also what my own personal priorities are, priorities are different for everyone. So even with mentors and colleagues and peers, when I sometimes go down a path of like, oh my gosh, how are they doing it all? Their priorities are different and that's OK, right? It doesn't make it bad or good. It's just really get clear on your own priorities. Delegate and ask for help. So delegate both at work and at home. Like, again, that's something that I've gotten better at over the years. My husband and I are 50/50 partners. I don't know how anyone does it if that balance isn't 50/50. And I have found a support system over the last 10 years in particular. You and I met at a, at a conference for women leaders. I have a group in Boston, in New York, and in DC of— I'm based on the East Coast— of executive women that I have met over the last 5 to 8 years in particular. And when I'm in those cities, we all gather for dinner, and we bring our whole selves. And They have turned into some very, very dear friends, and they are 100% part of my support system today. And then also making time for yourself. I used to feel when my kids were young that making time for myself was, you know, that I was thinking too much about me, that it was me, me, me. And you have— and I— a mentor years ago said, well, you've got to put on your own mask, oxygen mask first, Jennifer, before you can really be helpful to anyone else. And I think her painting that visual to me and sharing it in that way with me was really helpful in me kind of turning my own thought about like, oh, that's right, me time is really important to the— to nourish myself and help those around me and be a better mom, be a better colleague, kind of be more efficient and just healthier overall. So yeah, those are a few things.
I love that. Yeah. And you hit on some really important points. I think before you can even find the time time to take care of yourself and to focus on your health and well-being, you have to make that mindset shift of, like you said, delegating, asking for help, and knowing that it's not selfish to care for yourself so that then you can go out and care for all the others in your personal and professional life. And I know as women, I have struggled with it as well over the years. It's hard for us to ask for help, right? And sometimes it's even hard to ask for our spouses or significant others for help. But you need it. I'm the same way. My husband and I have to split the duties because if we both want to have careers and raise healthy children and, you know, to have all of that, you have to both be willing to give and take. So I think that those are really important points that you make, and you're a shining example of someone who— again, for all of us, it's not easy. It's— it is hard. But you are showing other women out there that you can do it. You can be on boards. You can start your own companies. You change the world and set that example for your children and have a relationship or marriage and be able to balance. And again, it's something that we go through years of trying to figure out the right mix. And I think to your point, it changes at different stages from when your kids were younger to where they are now. But I love that you just were so honest about your journey with that. And again, I think we all have a journey with it. And it's not a linear path, it goes up and down and all around. But I think that that's great that you focus on it as much as you do. So thank you for sharing that with our viewers.
Yeah, thank you.
And so where can people find you if you want people to learn more about Watering Hole AI, Jennifer? Where's the best place that people can get more information?
Yeah, oh, thank you for asking. The best places are on our website, wateringholeai, www.wateringhole.ai. And then you please feel free to link in with me at, you know, I'm Jennifer Ives 1. So Jennifer Ives, you can do a LinkedIn search, Jennifer Ives space Watering Hole AI, and you'll find me. I'd love to, to, you know, have you link in and have your community link in with me. And, uh, yeah, those are the two best ways. Thank you.
That's great. Yeah, and I'm connected to Jennifer obviously, and her posts are very inspiring and uplifting, and she's doing so much and has so much great knowledge. So definitely follow her or link in with her if you can. And check out her company. I think it's, it's really exciting, and it's exciting to see what's going to happen in the world of AI. And it's great to know we have experts like you leading the way for us. So thank you so much for joining. Again, Women Lead TV, brought to you by the Connected Women of Influence. This is Women, Wellness, and the Workplace, and I'm Reena Vokoun. And wishing everyone a wonderful Thanksgiving and holiday season, and tune in for another episode coming in the next few months. Thank you so much again,










