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Jennifer Ives, Watering Hole AI

Episode Transcription:

Trac Bannon: 

I was introduced to Jennifer Ives through a mutual colleague, Sejal Amin. Sejal is one of the growing alumni of the Real Technologist podcast. Sagel and I were discussing how to move the needle from mentoring to refocusing on sponsoring others. What’s the difference? Mentoring is often talking, teaching and strategizing. Sponsoring means taking steps to make opportunities. Sponsoring means investing in someone and truly advocating for them. In this context, Sejal talked about the value she personally gets from being part of an industry organization called Chief. Chief was founded to drive women forward into positions of power and to keep them there. Another Real Technologist alumni, Shannon Leitz also shared with me how important Chief was to her. 

Jennifer Ives is a founding member of Chief which now boasts over 20,000 experienced, diverse and influential executive women. I’m not a shy person, nor am I someone who is easily intimidated. That said, when Jennifer rapidly responded that she would love to be a guest, I started to wonder what sort of powerful or possibly intimidating presence I would encounter.

I always do a light amount of research putting a time box around the effort bob or I put into our detective work. We scheduled the recording and sent the invite. 

I dialed in one minute before the meeting was set to start only to find that Bob and Jennifer were already online and deep in conversation. As it turns out, Jennifer had done her own detective work to find out more about me, and in the process, had learned about “the Ops to my Dev”, that is Bob. I listened for a moment to a delightful conversation that I can only describe as Jennifer interviewing Bob. 

What I encountered embodied in this life force known as Jennifer Ives is something unique and insightful. She is simply lovely in every dimension. Visually, she was wearing gentle lace on a modest blouse and an absolutely glowing smile. She positions her camera so she’s looking directly at you, and as we all know from our lockdown days, that can be pretty tough to do… you know, positioning a camera so it’s pointed at you straight on as opposed to looking downward at it.

I noticed Jennifer make constant eye contact, nothing distracted her. She didn’t reach for a phone to turn off the ringer and no messages popped up on her screen taking her eyes away from me. Jennifer is instantly warming. When she speaks, you immediately sense how smart she is. There is a natural sense of trustworthiness.

I can see why C-Suite executive women and those like me, who drive change want to engage with her. She’s authentic. When I found out that she’s a geospatial engineer who worked with super secret government agencies, I was hooked. Our 60 minute conversations stretched into nearly an hour and a half. 

We are both passionate about humans and about technologies. We both believe that the best solutions are those that have a wide range of diverse thinkers involved. We both seem to position ourselves between diverse positions, ever negotiating. 

It turns out we are both middle children. Middle children are considered the “stealth leaders” of the birth order pack, according to Katrin Schumann, author of The Secret Power of Middle Children. Jennifer has all the telltale signs: she’s a negotiator, a consensus builder, a risk taker, and an innovator. 

Jennifer Ives: 

I’m a really good negotiator and negotiator in the best sense of the word. I know from a very early age I learned how to compromise. I learned how to see lots of at least two perspectives… I had an older sister and younger sister and they had different perspectives.

And many times people that I work with will say, you’re so nice or you’re so understanding. And I almost immediately say I’m a middle child. 

Trac Bannon: 

Jennifer is Washington DC born and bred. Not many residents can say that they were born at GW Hospital. Her parents were originally from New England and relocated to the DC region after her father completed his PhD work. Like the child of a movie star, constantly exposed to Hollywood’s Elite, stopping by for dinner. Jennifer and her sisters grew up in a household where guests were scientists, engineers, and researchers. 

Jennifer Ives: 

From a really young age, I was in literally like 3, 4, 5, 7 years old… I was introduced to all of these brilliant scientists, many of whom were behind the Iron Curtain at that time, right? So this was when these are still communist countries and only one of them would be able to come at a time.

My dad specialized in water resources and clean water for people around the world. And early in his career, kind of my first 10 or 14 years of life, he worked in Hungary, in Poland and at the time, Czechoslovakia… now Czech Republic. And we just had this amazing opportunity to meet some really smart scientists who also really loved children. 

Trac Bannon: 

Jennifer is naturally curious and had a well-rounded love of science, mathematics, and liberal arts. By 7th grade, she was winning awards at the school science fair and was in love with science. Each quarter, her science teacher used their lab facilities and focused on a different area of science in engineering, even touching on the 7th grade version of electrical engineering. She was all in. Her teacher, Dr. Rowe, had attended medical school and realized she wanted to shape the next generation of science learners.

These are the positive events we want our children to have. The next year would, however, cause Jennifer to shy away from science. The cause was a biased 8th grade teacher. 

Jennifer Ives: 

I had a terrible, terrible science teacher in 8th grade who was… like across the board… your typical boys know science girls don’t.

 I was so involved in grade school and first year in middle school and science, and then 8th grade, I will tell you, it kind of took me out of it. It reinforced unconscious bias… maybe even in myself.

I don’t know that, I do know that… I went to 9th grade. I took an earth science class and again, was kind of brought back into science and loved it.

This is why I credit my mom and dad because they didn’t let that be so… it wasn’t okay in our house.

But it really was my mom and dad who made sure that in high school, even as I was kind of pulling away, to be quite honest, pulling away from kind of the sciences, they kept me very interested. 

Trac Bannon: 

How influential teachers and parents are in the lives of our youngsters. Children need to be constantly challenged and constantly shown unconditional love. What they don’t need are damaging labels and preconceived notions. 

As Jennifer prepped for high school graduation and considered her major, science and engineering were not slam dunk choices. She really had no idea what she wanted to study or what she wanted to be. She only knew that she loved to learn.

Jennifer Ives: 

I didn’t know what I wanted to do. And my mom and dad said to each one of us as we went to school… you can be anything you want in the world, you know that… I’ve raised you that way… that’s who you are and that’s what you can do. You need to get a STEM degree. And that was the end of that conversation. 

Trac Bannon: 

Her father’s recommendations and persistence resulted in three scientific daughters. One is a data scientist and statistician, another is practicing medicine, and Jennifer graduated with a degree in Geospatial Engineering from George Mason University. Having started as a chemistry major, she found herself disappointed and lacking excitement with chemistry. It simply wasn’t amazing to her. 

Jennifer Ives: 

So I went to George Mason University for undergrad. And here in the DC area, the university had at the time and still does, had a very close connection to a lot of the super secret agencies in the DC area. And those super secret agencies needed something called a geospatial engineer.

I didn’t know what that was. I was walking across campus one day. I’m super curious by nature, and there was a guest lecturer who was talking about satellite imagery analysis. I was listening to him speak and I was like, this is amazing… what is this? I kind of looked around. I found the geography department.

Trac Bannon: 

Inquisitive, adventurous, and one to follow her gut, jennifer changed her major. Her parents were supportive while at the same time, not quite understanding geospatial engineering. They understood other engineering focus areas like chemical engineering, computer engineering, and electrical engineering. Jennifer was convinced that this was her path and her passion. Her family supported her decision. 

Her first job out of college was on the engineering team at a small, fast-growing technology company in the DC area. Photo Science PSI, worked for the super secret agencies. The work was really interesting and important, so much so that it even impressed and interested her family of engineers. She was not starstruck though, having the government as a client. While it was new to her, she had grown up in the DC area where parents worked for the government, and a lot of professors at George Mason were government scientists and engineers.

Imagine being new in your career, exposed to mid-career and senior scientists and engineers who were truly interested in your insights and opinions. Keep in mind, when they were in school, geospatial engineering was not a field of study. 

Jennifer’s story reads like a dream scenario: brought up in a home with engineers, groomed by scientists, diving into a new world of geospatial engineering and working for the three letter agencies. I have to admit, there is fun in imagining Jennifer as a super secret spy, doing cool super spy things. When I joked with her, she gave a heartfelt laugh… the kind that is honestly amused.

Two years into her career with PSI, she had a catalyst moment that kickstarted her next round of studies: her master’s degree at the University of Virginia.

Jennifer Ives: 

Our CEO took me to a meeting with our clients and said, you’re on the engineering team, we’re working on a project and we’d like your perspective. And that was really, It was about two years in. Now they’re called sales architects or it’s very, very common to have someone technical in the room having business discussions. But a couple decades ago that wasn’t typical. And so it was the first time that I got to sit and ask all the questions. And understand how they were using the technology and how they were using the product that we were creating for them. And it made me become very, very interested in, that was kinda my first foray into, oh, there’s a business side to this and there’s a business use case, a very specific business use case and outcomes that we’re trying to design for them. 

Trac Bannon: 

Remember that Jennifer is comfortable being in the middle seat, being that middle child. She realized at the moment that she loved being between business and technology. Picking the University of Virginia, she worked with the faculty to build a course of studies for her master’s including environmental law and business law. Her goal was to take her technical background and apply her knowledge to real world problems. 

It was at UVA that she met her future husband, Dave. 

Jennifer Ives: 

So my husband and I met in grad school. I did not go to graduate school to get married. I did happen to meet him and think he was one of the smartest, kindest, funniest people I had met. And we kind of couldn’t be separated from each other… Like all of our friends were like, oh, aren’t you dating? And it was just, it was, he, he’s amazing.

Trac Bannon: 

Their relationship was dynamic and supportive even as Jennifer began international travel. Dave respected her independence and they quickly became very important in each other’s lives. They kept in touch while she traveled the globe including being in China. When she returned, it was a simple lunch date that fanned the flames. Jennifer is naturally assertive and I jokingly asked her if she popped the question and proposed to her now-husband and life partner, Dave. She swears otherwise, and I believe her. They have been married for over 20 years and have two children and a Burmese mountain dog. 

Her life may read like Skittles and Rainbows. But like all Real Technologists, Jennifer’s genuine story and journey is filled with twists, and turns and fate molding her into the leader she is now. 

During her travels in China, Jennifer was with her father when he suddenly died. And I have to be honest to those listening, it has taken me three attempts to try and narrate the next event in Jennifer’s life, and I simply cannot. 

Jennifer Ives: 

So my dad died literally right next to me. I was driving into the emergency room. I was in my early twenties. He was having chest pain. He was very young. He was only 60. He was very active and athletic. We grew up skiing and being very active, hiking and all these things.

He did all of those things. He didn’t smoke, he didn’t drink excessively, he didn’t have high cholesterol. And he died next to me as I was driving him to the emergency room… by the way, in a town that I wasn’t familiar with. We were out of town traveling, and he died right next to me. That really, really recentered my life and crystallized.

I would never wish that on anyone. I would never wish on anyone that one, they lose someone they love. It happens and that is life. And I would never wish on anyone that they see the person die next to you as you’re trying to help them.

It was an incredibly pivotal moment in my life, and I really think that there’s kind of a before and an after in my life from that moment forward. 

Trac Bannon: 

Life is short and every moment is a gift. We all feel the highs and lows of life. Up to this very day, Jennifer shared with me that this single event was the worst thing that has ever happened. It has given her a perspective and a balanced that has shaped her into a balanced mother wife, mentor, friend and innovator. For Jennifer and her family, discussing the pros and cons of a situation or a decision are practical and pragmatic. That isn’t to say that Jennifer has not had her share of career related stress events and situations.

In one instance, she was brought into a company by the CEO. She was ” their person”. Within a few months of her arriving, though, they left the company. It was her first exposure to corporate alliances. With new leadership in town, she had to dig deep quickly to figure out her next step. 

In part, it was her mother who helped her through this time.

Jennifer Ives: 

I remember turning to my mom who was very, very strong and very strong human being. I was clearly, we were all devastated when he died.

We were very close family. He was someone that we all loved very much. And she said, you have to put one foot in front of the other.

Trac Bannon: 

One foot in front of the other. With Jennifer, I can imagine her not walking, but always jogging and moving fast. She is always connecting, innovating, and negotiating her way into new situations. And she is ever the middle child… taking a seat in the middle. 

She always positions herself between technology and business. She moved to the commercial side of technology companies to ensure that they were going to market things correctly, so that the amazing product or technology service would be known about by everyone. 

Jennifer Ives: 

I never thought about it like this before, but to sit in between these two worlds and have known what it’s like to be on the engineering team and things that are really important as an engineer… and then also to be on the commercial side and know the things that are really important on the commercial side, and to bring those two worlds together.

Trac Bannon: 

Jennifer made a commitment to staying close to her family. She has never left the DC area and is embedded in Arlington’s economic development. Her choice resonates with me because Bob and I have had to make a similar choice. We both grew up transplanted away from cousins, uncles, aunts, and grandparents. We contemplated moving though we decided to stay put. Why, my parents were getting a little older and our siblings were relatively close…. that was the tail end of 2018. In January of 2019, my mom was diagnosed with terminal cancer and I was able to be there and care for her. 

Jennifer has stayed put and is a driving force for Arlington County. She has worked with multiple organizations doing economic development work with high tech companies. With her education and vision, she began to treat Arlington County as an ecosystem and began to focus on growing and enabling technology-based businesses. Today, this is called innovative economic development. She has worked with CEOs and founders throughout the DC region to shepherd connections, relationships, and economic growth. 

Jennifer is a master networker and connector – it shows. She is blazingly fast to respond to emails and is unusually earnest and sincere in all her communications. She has co launched and co-founded several organizations and has a special place in her heart for deep data technology startups. She co-launched an organization called Tandem NSI that helps to take technology once it is declassified and apply it to the commercial world. Often folks think that the commercial industry feeds the government technology; that’s not always true. 

Her resume would almost seem to have a gap though diving deeper, she has always been passionate about that innovative economic development. 

Jennifer Ives: 

Actually, I was working with both the private sector and federal technologists… really building out the economy of Arlington and making sure that the economy was based on the innovation of the next wave, and making sure that the technologists knew, and those founders who knew each other, knew how to grow their companies together. 

Trac Bannon: 

For nearly 15 years, Jennifer has been making the needed trade-offs between family and career and continually making connections. It’s just part of who she is. No matter what hat she’s wearing at the time, she connects people, she connects businesses, she connects technologies. It is a sincere passion and part of the fabric that makes Jennifer, Jennifer. 

Jennifer Ives: 

I really believe in connecting people and technologies… not only for business growth, more so in particular in the last 10 to 15 years. It’s just been a personal desire of mine and something that I believe that there’s enough room in the world for everyone to shine. 

Trac Bannon: 

There is room at the table for everyone. There is enough room for everyone to shine. Other Real Tech alumni share this passion for diverse thinking and empowering others. Empowering can take the place of connecting, of mentoring, or of sponsoring. Perhaps Jennifer is paying forward because of those who have helped her and believed in her. 

Jennifer Ives: 

So I’ve had people mentor and sponsor me throughout my career, especially early and mid-career in particular, and actually recently as well. I’m very, very specific about reaching out to people and asking them for their mentorship and their sponsorship.

Earlier in my career I didn’t know to do that, and I was blessed a couple of times with a couple of folks that I rolled to who always saw in me, something that maybe I hadn’t seen in myself just yet and really encouraged me to the next level of my career.

Trac Bannon: 

Like me, Jennifer’s early and mid-career mentors were all male. These were all leaders who went out of their way to notice, to take interest in professional growth and to mentor through some big decisions. Perhaps it was that there were not many senior women at the time. Neither of us thought too much about it in the moment. Today, however, Jennifer both mentors women and seeks out women mentors who are 10 or so years ahead of her in her career. She is strategic and deliberate with who she engages with as her mentors maintaining roughly a 70/30 split of women to men. They are all above her in their careers and in their lives. She is always thoughtful with their time and the energy that they spend on her. 

Beyond her mentors. She is quick to be inclusive of her husband when she is talking about her career and her success, giving full credit to others. When we were wrapping up her episode and had stopped the recording, she started to talk about her husband, and her words were so poignant that we clicked record with her approval.

Jennifer Ives: 

I could not do any of this without my partner. My husband balances me… he noodles ideas with me. For a few years there, the kids knew at school, the school knew, and the kids knew they needed to call dad first. Like I was not available. I was overseas or I was in a meeting… and that wasn’t because I wasn’t available to them. They knew call dad first. The dentist knows my husband. There are no stereotypical gender roles in my marriage, and I love it. And I love him, and I could not do this without him.

Trac Bannon: 

Energy is something that Jennifer exudes. She is often like a kid in a candy store with such varied interests. She often says that she loves to talk to intelligent people. We can imagine that was sparked by growing up as she did with a constant stream of the world’s leading scientific thinkers .That love drove her to dabble in podcasting.

Jennifer Ives: 

And I had the opportunity to be meeting really smart global CEOs and chief human resources officers and chief strategy officers in my work. We decided to start a podcast and start asking them interesting questions about their career and how they build teams and what leadership meant to them.

And so it was this wonderful platform to not only talk about the research and data around teams, team building, leadership, all these things. I was also able to interview some of the best of the best around the world when it comes to leadership and leading Fortune 100, Fortune 500 companies around the world.

Trac Bannon: 

A second podcast was called The Innovation Engine, where she was the stand-in host, and then later a co-host. 

I see Jennifer as the amazing child of her environment. She is a lovely person who is not only interested in others, but who is an advocate. She’s an advocate for diversity and in particular for women in technology.

She’s a woman in technology and she knows that we are still small in number. For that reason, when Jennifer finds another woman in tech, she keeps ’em close. She adds them to her network. Jennifer’s story is far from over. She is returning from a sabbatical for the first time in her career. She praises it as being the best thing that she ever did. 

Jennifer Ives: 

I have gone through lots of times since having kids that I had no balance and I actually just came off a sabbatical first time in my career and it was the best thing I ever did. My last role, I was fortunate enough to, when I stepped out of it, to be able to take some time and I took more than six months to travel, to hang out with my kids, to walk the dog, to get my creativity back, to be quite honest. Just to get my creativity back. My family will always trump my career. I know that life is short and you don’t get the promise of living to a hundred, right? Life is short. The people in your life are important.

And here’s the thing, from the professional perspective, life is short. So if there are things you want to do, go do them.

Trac Bannon: 

Accessible. That’s the word I would use to describe Jennifer Ives. In a world of powerful corporations, rapidly emerging technology, and still as of yet, disparate numbers of diverse voices at the table, she is making room for others and is always open for a chat. What is next for Jennifer Ives, connector of people? Beyond mentoring and empowering diversity and women in tech, she is founding a new company. 

Jennifer Ives: 

I just co-founded an artificial intelligence company. We’re still technically in stealth mode on LinkedIn, but we have a landing page and we’re working with some clients, and I’ll be speaking in London this October to CEOs and chief strategy officers and private equity investors on the topic of our artificial intelligence. My co-founder Julie Holden is a computer scientist, cryptographer, and the two of us have co-founded this company and it’s called Watering Hole AI.

Trac Bannon: Throughout our entire conversation, I could never imagine Jennifer as ever having lacked confidence. She’s truly inspiring, resilient, and strong. It may surprise you though, to learn what she would say to her younger self.

Jennifer Ives:

I would’ve said, bet on me. I would’ve bet on me long time ago. I bet on everybody else. I would’ve bet on me. And I mean I’ve got confidence… But I would bet on me.

Trac Bannon: 

And that’s a wrap for today’s episode of Real Technologists. I want to thank my guest, Jennifer Ives for sharing her story. Your insights and experiences are truly inspiring. I’m grateful for the opportunity to share them with the audience. This podcast is a Sourced Network production and updates are available weekly on your favorite audio streaming platform. Just search for real technologists and consider subscribing. Special thanks to our executive producer, Mark Miller, for making this show possible. Our editor and sound engineer, Pokie Huang has done an amazing job bringing this story to life. Thank you both. The music for today’s episode was provided by Blue Dot Sessions, and we use Descript for spoken text editing and audacity for the soundscaping. The show distribution platform is provided by CaptivateFM making it easy for our listeners to find and enjoy the show. 

That’s all for today, folks. This is Trac Bannon. Don’t forget to tune in next week for another intriguing episode of Real Technologists and something new to noodle on.

Episode Guest:

Jennifer Ives is an award-winning business executive with more than 20 years of experience leading high performing teams, crafting successful GTM strategies, and driving double-digit financial results at VC- and PE-backed digital product and data intensive companies around the world. She is the current CEO/Cofounder of Watering Hole AI, a fast growing AI intent data company with the belief that bespoke, small data sets are the new currency.

Jennifer’s exceptional contributions throughout her career have garnered widespread recognition, earning her the title of ‘Connector Extraordinaire’ by Forbes, and consecutive placements on the Software Report’s prestigious ‘Top 50 Women Leaders in SaaS’ list. Additionally, she has been honored with inclusion in Constellation Research’s esteemed ‘Business Transformation 150’ list. Jennifer’s expertise is in high demand, making her a sought-after board member and advisor across various industries. Recently, she contributed to the top-selling book, ‘Heels to Deals: How Women are Dominating in Business-to-Business Sales.’

Who Jennifer is otherwise…
Mom, wife, sister, lover of Bernese Mountain Dogs, an extroverted introvert, hiker, down hill skier, former science fair winner (and current science fair judge), off the beaten path traveler, mentor, and someone who believes that there’s enough room in the world for everyone to shine.

Episode Guest:

Jennifer Ives is an award-winning business executive with more than 20 years of experience leading high performing teams, crafting successful GTM strategies, and driving double-digit financial results at VC- and PE-backed digital product and data intensive companies around the world. She is the current CEO/Cofounder of Watering Hole AI, a fast growing AI intent data company with the belief that bespoke, small data sets are the new currency.

Jennifer’s exceptional contributions throughout her career have garnered widespread recognition, earning her the title of ‘Connector Extraordinaire’ by Forbes, and consecutive placements on the Software Report’s prestigious ‘Top 50 Women Leaders in SaaS’ list. Additionally, she has been honored with inclusion in Constellation Research’s esteemed ‘Business Transformation 150’ list. Jennifer’s expertise is in high demand, making her a sought-after board member and advisor across various industries. Recently, she contributed to the top-selling book, ‘Heels to Deals: How Women are Dominating in Business-to-Business Sales.’

Who Jennifer is otherwise…
Mom, wife, sister, lover of Bernese Mountain Dogs, an extroverted introvert, hiker, down hill skier, former science fair winner (and current science fair judge), off the beaten path traveler, mentor, and someone who believes that there’s enough room in the world for everyone to shine.

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