Episode 8: Meet Jennifer - Educator, tech leader, and southern powerhouse

What happens when a high school English teacher accidentally becomes the Director of Technology at a school with over 1,200 students? You get a woman who knows how to lead a team, command a server room, and keep her cool in a sea of tech bros—and oh yeah, she just happens to be my sister-in-law...Dr. Jennifer Santi

In this episode, we dive into her unexpected journey from the classroom to the IT office, how she navigates being a woman in a male-dominated field, and the deep personal work it took to heal from a chaotic childhood. From calling out inappropriate behavior without losing her cool, to unlearning the pressure to play small, she drops wisdom that every woman needs to hear—especially if you've ever felt like an outsider.

Quotes from Jennifer we love:

• "I think anytime that you are then leading people, guiding people or evaluating people or their performance, that becomes challenging because you have to learn a new way of speaking to someone. You have to have very courageous and fierce conversations that are, and that is not a skill most of us are innate with." 
• "If there's a situation that is uncomfortable, intimidating, or frightening, even let's get to fear, then you need to know that you can say whatever it is that you need to say in any of those situations and do it and not feel that you have to diminish yourself the way that we always do."

Transcript

Stacee: Jennifer, tell us a little bit about yourself. 

Jennifer: Okay. I am 48. I work in education. I have been for a little over 25 years. I started out as a high school English teacher. I am married, may will be 17 years married. 

Stacee: Oh wow. To my brother. 

Jennifer: To your brother. That's right. 

Stacee: God bless you. 

Jennifer: I should get an award. And then I have one son who is about to turn 14 and I am currently the caretaker for my 91-year-old grandfather. So we're very busy all the time at our house. 

Stacee: And you guys live in Atlanta? 

Jennifer: Yes, we do. 

Stacee: Are you ever going to leave there and come west where the rest of us are? 

Jennifer: I don't know if we'll come west. I don't know. I do know we want to leave Atlanta, so when my son graduates from high school and is settled wherever his college is going to be, I think then we'll start to look for somewhere else. I know the house that we live in is not our forever home and I would like to experience something other than the south. 

Stacee: So you're saying there's a chance 

Jennifer: There's a chance 

Stacee: And what's your current job? 

Jennifer:  So currently I am the director of technology for a private pre-K through 12th grade school. And we have about 1,250 kids, which is very opposite of how I spent the vast majority of my career. I was in public school. And so right now I oversee any aspect of technology that happens within the school. The IT department is underneath me, the instructional education and the instructional technology department is under me. Data records, all of that kind of falls under this umbrella. So one part of the day I could be in a teacher's classroom helping them with some software that they want to try out with their students. And then later in the afternoon I can be working on something for the network and then having a budget meeting for trying to make sure that the elementary school has all the tech that it needs for the upcoming year. So it's incredibly varied every single day. I'm never bored. There's always something and I get to be creative and innovative in ways that I didn't think I would be. So that's been really exciting. 

Stacee: That's not a very traditional teacher job. 

Jennifer: No, it's not at all. 

Stacee: Did you have to carve out your own past on that? 

Jennifer: I did. I fell into this job accidentally. I had been an assistant principal over curriculum and instruction and then they found that there was a real need for instructional technology in the school, and I have a degree in that. One of my degrees is instructional technology. So they asked if I would step in and kind of fill that need. And while I was there, there wasn't a physical place for me, so they had an extra desk in the IT office. So that became my home. And so I came in there to do my work and I could see pockets of dysfunction. And then of course the physical disarray of the room drove me crazy with my ocd. So I just started fixing things 

So that I could survive in that space. But then I would hear them talking about what projects they were working on and I would recognize that, well, that's completely out of order for a teacher. And so I would make suggestions about, well, if you should do this one first and then do this so that it's more effective and more streamlined for teachers. And I continued to do that until it got recognized that I was sort of leading the way. Even though I wasn't a leader for that team, they actually had me sitting in on interviews for a director of it. And at the end of the interview sessions, the hiring director would say things like, why would we keep hiring when we have you? And I was like, because I know nothing about it might be a really good reason, I know nothing. But it turned out that with the team, they didn't need another person to do the work of it. What they needed was somebody to lead the team. And that I fit very well. 

Stacee: I imagine it was quite interesting and eye opening for them by happenstance when they got a teacher's viewpoint on their technology products because I found that the people that put the best products on the market are actually people that happen to be an end user themselves. You might be building this product for yourself and if you don't know the ins and outs of a nuance of a job, you're kind of in the dark a little bit. 

Jennifer: You are. And so you are making decisions based on a very limited amount of understanding or limited amount of knowledge. And so for them it was a growing experience. IT folks are very linear and they're sequential and it gives them peace. The first ticket in is the first ticket you address, but that is not how schools function. We do have a needs based and some needs are greater than the others and need to be met first. And so it was a very big adjustment for the IT team and less of an adjustment for the other teams. I think it was also very difficult at first for them to one, work for a woman because it is predominantly male and two, work for someone who absolutely had no idea about even some of the words that they were saying. I'm looking, trying to figure out what they're talking about. So I think for them it was a much harder transition than for the rest of us. 

Stacee: Did you suffer from any kind of imposter syndrome? 

Jennifer: I think on some days I still do, especially if it's highly complex and highly, if it's something about the network, I know just enough to be dangerous. But what I have learned from that is it's not about me having all of that knowledge because I can't know all things about all things, but I can know enough to be able to hire and put the right people in the right job at the right time. And that's what I have learned through my time and I've gained enough knowledge to be able to do that piece of it well. And then once I have that right person in the right job at the right time, then it's my job to clear the path so that they can do the work that they have been hired to do. And so I've learned how to remove obstacles. I've learned how to create space and time and autonomy for my people so that they can do the work, but even more so they can be creative in their work, they can find new ways to do the work. Which if you think about it, you really think of that as more of a very stringent kind of straight path. So to say, let's be creative with them and find new ways to do things. They've actually blossomed with that. They're actually incredibly creative when they're given the time and space to be creative. 

Stacee: That's amazing. And I imagine that it's pretty hard to be a micromanager, at least I was in a somewhat similar boat in that I knew nothing about the job I was supposed to speak to. But the beauty of it is you can't micromanage and you put all the autonomy and trust in the person you hired. And I think they actually really like that. 

Jennifer: I think most people do. They want to be valued. They want to be seen as someone of worth and someone who has something to offer. And when you don't micromanage, it doesn't mean that you're not there. It doesn't mean that you're not paying attention or guiding even. A lot of times my job is to be a buffer between them and anything that might cause stress or might cause them to not have what they need to do their job. So if it's there's too many tickets coming in and they're getting overwhelmed, well then it's my job to step in and say, Hey guys, to who's sending those tickets in? It is overloaded right now. So can we only send in high priority items and things of that nature. It doesn't happen very often, but a lot of times it's not so much that I'm leading them, but I'm just supporting the work that they do. 

Stacee: Yeah, you're just removing roadblocks. 

Jennifer: That's right. 

Stacee: That's great. And what's been some of the more challenging parts of your career path? 

Jennifer: Teaching never was a challenge. I don't want to say that it was easy. That's not what I mean. But I loved it so much. It was my passion. And so anytime there was a challenge, it was seen as a positive thing and it charged me and it I think made me a better teacher to try to overcome whatever that was. And so it didn't get very challenging until I left the classroom and I became an administrator. And I think anytime that you are then leading people, guiding people or evaluating people or their performance, that becomes challenging because you have to learn a new way of speaking to someone. You have to have very courageous and fierce conversations that are, and that is not a skill most of us are innate with. It's something we have to learn how to do. That was a challenge that took me a long time to feel comfortable doing. 

You're in that sense of conflict all the time, and that's very difficult. And then once I felt a little bit more comfortable with that, I don't think you ever fully get comfortable with that. But once I did, the next big challenge for me was being a female in a predominantly male environment. So when I go to tech conferences, if it's not instructional education, then I find that the room is filled with men and then there's a different kind of relationship to be built there. And it's difficult when you walk in and you don't feel like you have people like you in the room or people that will understand you or walked in your shoes. So that can be challenging. 

Stacee: What's your go-to strategy, claiming your space? 

Jennifer: I do a couple of things. One of the first things I do is I start with questions. So they get to say what they know. They get to preen a little bit and share, but it is also very disarming because eventually my questions change and it's less about giving them the floor and more about them, challenging them to think differently about whatever it is that we're doing because obviously we cannot continue to do things the same way that we've always done them and expect new results. And so I think that questioning gently, but then getting into deeper and more probing questions is great. I think also a lot of times I assume the best, I try to assume the best when they make comments or when we're interacting with one another, but I think that the most important piece of it is to just not be intimidated. 

And that's difficult at times, but there's so much that I don't know. And there's so much that you don't know and there's so much that everyone doesn't know. And so when I get into those situations, I'm there to learn. So I just put on that face of what can you teach me? Teach me something. I'm here to learn. I'm here to grow and be better. Otherwise I wouldn't be at a conference. And so what can you teach me? And I just kind of go into this mindset of every person that I come into contact with is going to give me something. I just have to make sure I get it. 

Stacee: I love that. Have you ever been in a situation where a male coworker or colleague of some sort has been inappropriate? 

Jennifer: Oh, many times. And I think as a woman and a stepmother to two girls, I've tried very hard to show them and teach them that it's okay to say, I'm so sorry you're standing a little too close to me. Or to say to someone, especially a man who's maybe using their size to intimidate, to say, would you mind stepping back? I find this context a little intimidating and I don't appreciate that. Or to say whatever it is that this person is making them feel. And I think that when we give women the permission to say what is happening, to call it out, I think a lot of times most men back down, sometimes they don't even realize they're doing it. They just are so used to using their physicality as a means of manipulating conversations or getting their point across that they don't realize how that feels to a five foot five woman who is standing next to them. But I think even more than that, if someone says, anyone male or female says something that is inappropriate or feels inappropriate or makes you feel uncomfortable, I think that we do have the right, or we should say, I'm so sorry. That makes me feel uncomfortable because there's a nice way to say it. 

Stacee: I think that's the kicker there is you don't have to come out and be afraid like, oh, I've got to be this mega bitch to get my message across. You can do it in a very, maybe this is your southern superpower, Jen, but I find southern women are very good at telling you to step away or F off with a smile on their face. That's right. And they say things like, bless your heart, we all know what that means 

Jennifer: That's right. It does not mean that! 

Stacee: But I think what you're saying, and that strategy has worked for me too, is to just either joke about it, say, whoa, you're getting a little close here. That's right. You can try joking. If that doesn't work, then you have to be super direct. But I say, Hey, this isn't working for me. That's right. Or one of my favorite sayings is, I'm not loving this X, whatever X is, I'm not loving it. And I'm not saying you are a bad person and you are a jerk. I'm saying, this isn't working for me. This situation. 

Jennifer: That's right. 

Stacee: And it needs to change. And I don't feel bad about that when I do that. 

Jennifer: One thing that I have noticed about myself probably in the last few years is I've gotten a little bit more reflective, is that I apologize far too much at times. I'm actually apologizing for my existence. And I am working really hard now to quit saying I'm sorry. It's 

Stacee: So common for women. It's like almost, you know how everyone says when they're talking, it's just a filler word now. That's right. I find that, I'm so sorry, is a filler word for most women, 

Jennifer: But I think it has a negative effect on us. It totally is. It makes us smaller 

Stacee: And less. It gives the perception that your meek. 

Jennifer: That's right. 

Stacee: That you're sorry. 

Jennifer: Yeah. And I have nothing to be sorry for. 

Stacee: No, you don't. We'll do things like, I'm sorry, can I squeeze by you? Nope. If you're trying to get around someone at the grocery, why just say, excuse me, I need to squeeze 

Jennifer: By you. That's right. 

Stacee: If you smile, it's so very nice. It is. So if you have an ugly face on you, then they might get annoyed. But you can say all of these things with a smile. 

Jennifer: That's right. If there's a situation that is uncomfortable, intimidating, or frightening, even let's get to fear, then you need to know that you can say whatever it is that you need to say in any of those situations and do it and not feel that you have to diminish yourself the way that we always do. 

Stacee: Or be upset that this person might not like you. That's right. Who cares. That's right. A funny thing happened to me once I was at some team event, and this guy I worked with was sitting next to me at the dinner and he'd laugh and throw his arms up, and then his hand would come down right on my leg, right on the top of my quad, my upper leg. I'm thinking, alright, I don't know. This feels weird. There's something icky about it. I was hesitant to make a scene. I wasn't sure if he meant it. I started rationalizing it away like, oh, I'm just making a deal about it. And I called my husband later and I told him what happened? And he's like, oh no. He said, it's very clear that made you uncomfortable and he needs to be set straight. What are you being wishy-washy? 

Who cares if you're going to hurt his feelings? And I thought, boy, he's still black and white and here I'm trying to rationalize away the situation. He's like, no, you need to tell him it's inappropriate. So I went to this guy and I said, listen, I don't know if you did it by accident. You seem like a nice person. But when you did that, it made me feel very uncomfortable and I don't want you to do that anymore to me or any woman. That's right. Women don't like that. And maybe you don't know that. And he actually responded like, oh my gosh, I'm so sorry. I didn't realize that at all. And whether he did or not, I'm not sure. But it worked talking to him, and I was able to still be at events with him and I set a boundary. 

Jennifer: I recently had to have a conversation with a male colleague. I know that he was completely unaware that he was doing it. And if we were in a group setting, he had a way of just physically moving in front of me so that I would literally have to come around to the left or right of him to rejoin the conversation. And at first I was like, what is going on? Is this a joke? I was really just so startled by it, and it happened again, and I reached out and I touched his shoulder and I said, I'm going to need you to stay over here. I said, you keep blocking me. I said, but this is a conversation that I absolutely need to be a part of. I'm not here just to listen in. And he kind of looked at me, he goes, oh my, I'm so sorry. 

And again, it's one of those situations. I don't know if he was aware or not. I'm assuming that he was unaware, but I think whether they are aware or not, there is this disconnect because women don't stand up for themselves. And so it's incumbent upon us to change this. And I don't know. How do you raise strong girls that are able to do this if you're not modeling the behavior for them? Right. Well, I mean, we teach our girls if they're coming across, if they're coming out of a grocery store at 11 o'clock at night, we teach them how to be aware of their surroundings. Their fathers don't, because their fathers don't feel that same need when they're walking across the parking lot at night because they're big, strong men. But we are always looking around. We're looking under the car, we're seeing where the lights are. We're looking for other people. And so we teach that to our girls. Why not teach them? Also that when you're in an uncomfortable situation, you have every right to put an end to it in some way, whatever way. That makes sense. 

Stacee: I love that. What has been some of your more challenging times personally? Because a very successful woman, you have your doctor, you have this amazing career, and you've had a lot of success professionally. But personally, have you had things that have been hard for you to overcome to get to where you are? 

Jennifer: Yeah. I had a really rough childhood and lots and lots of trauma. And I think when you're a child that experiences those kinds of trauma, you create these coping mechanisms to get you through the trauma and beyond the trauma. And sometimes they're healthy by accident, I think mostly, but most of the time, time they're not, are not sustainable into adulthood. And I think that I brought a lot of, or at least a couple of very unhealthy coping mechanisms from my childhood into adulthood. I think in my most important relationships, I had a tendency to shut down when something got really hard or when communication was needed the most. And that causes trouble, of course. 

Stacee: Is that what you did when you were a little kid is kind of withdraw? 

Jennifer: Yeah. 

Stacee: Is that your strategy? 

Jennifer: I would withdraw from the situation and look for the nearest exit. Right. And I mean that in a very literal meaning. As a child, I was always looking for how do I physically get away? 

Stacee: When you say childlike, how old were you? 

Jennifer: I would say from very early on, toddler time to probably 12 or 13 years old. Those were the traumatic years. And so for instance, that one is something I brought into my marriage. It took a very long time, and thankfully I have a very patient husband that will wait me out and I still have the to want to go hide in my room and not talk about it until I'm ready to talk about it. But I've worked very hard to make sure that I am having the conversation when it needs to happen, not after I've hidden away for a while. That's been very difficult. It doesn't translate to my professional life, which is very interesting to me that it only happens in those very important personal relationships because I think those are the ones that have the most power to hurt me. 

Stacee: It kind of makes sense though, because I think all of us professionally, you almost get to play a little bit of a different version of yourself outside of the house. At least I always felt that way. And then when I come home, it's like real me. 

Jennifer: It's like the persona that you have at work versus the reality of who you are. 

Stacee: A little bit. I mean, I know I'm the same person, but when I'm at work, I feel like I can assume my character a lot easier. 

Jennifer: And as much as I love the people I work with and I do because I am very relational as a person, I don't love them. I love my husband. And so him being disappointed in me or him there being conflict in that relationship is so much more important. It has so much greater value to me. And so I think that with those high risk situations, I'm more likely to shut down and not make any sudden movements, if you will. And so that's something that I've worked on and I continue to work on. I don't think I've mastered that yet or overcome it completely. 

Stacee: How did you get out of your difficult situation growing up? 

Jennifer: I got very, very good at observing people and sort of anticipating what was about to happen. 

Stacee: You can predict when people are about to blow a gasket? 

Jennifer: Yes, I'm very good at that. Or when they're about to be completely unpredictable, right? Because there's a moment when people become that way, and then I would find a way to exit somehow from that situation. So I got really good at that as a kid. And now sometimes I still have a tendency to, if I walk into a room or if we're in a restaurant, I like to have my back where I can see the exit. I still have some leftovers of that, but not quite so much anymore. 

Stacee: Did you find education of yourself the way out of your home life? Was that one of the strategies that worked for you? 

Jennifer: It wasn't in the beginning. It became the strategy. In the beginning, I read to disappear, right? I read to be able to bring this kind of dome down over myself, and I could escape into all these other lives that looked nothing like the one that I was living. And so I turned to books and stories, which is probably why I became an English teacher, a literature teacher, because they gave me a relief from what I was living, even if it was just while I was in the story. So I think that was a huge part of it. And then later I realized that if I didn't want to live the same kind of life that my mother and father were presenting me with, then I had to make different choices than they did. And then education became that choice. I saw it as a way to open a door and be able to go. 

And in fact, later I realized it wasn't just one door, it was thousands of doors, right? Everything in my life that was a positive choice somehow stemmed from me learning and growing. And it's probably why I continue to get all the degrees. I think on some level, maybe even it was proving something to myself that I could do these hard things, but I love education. I don't mean college. I am not going to put it out there that every child has to go to college. But I think learning in general and growing in whatever capacity that is for you is so important.