When Ilana Davidi Reeves walked into the computer science placement test at the start of college and she was the only woman, she walked out and found a new major. But internship and work experiences along the way, just as the web was dawning, pulled her into that world anyway. Against the odds, she exceled in software engineering, but found the odds stacked against her in other ways in her personal life, too. Find out how sticking through the hard things can set you up for success and a sense of gratitude later.
When Ilana Davidi Reeves walked into the computer science placement test at the start of college and she was the only woman, she walked out and found a new major. But tech-related internships at ESPN and an early internet company kept her interest piqued and on the second day of her first consulting job out of college, she found herself in their Java lab and kept programming and technology front and center in her career.
Seemingly against the odds, she exceled in software engineering as one of the only women in the field. She had to deal not only with the volatility of the industry but also the discrimination there during the 2009 recession and later when she needed to juggle it all with motherhood. The struggles and the support she found from her network at that time, however, would prove to be beneficial when she found the odds stacked against her in other ways in her personal life later on.
In this episode, find out from Ilana how sticking through the hard things can set you up for success and a sense of gratitude later…on today's Roads Taken, with me, Leslie Jennings Rowley.
About This Episode’s Guest
Ilana Davidi Reeves is a software engineering and architecture leader with 25 years of experiences across diverse industries, who currently serves as Engineering Lead, Fulfillment at Square. She has managed, mentored, and directed local, off-shore, and near-shore teams including the new wave of women in the space. She lives in Atlanta with her husband and their two boys. (252)
For another story about being an outlier in your industry and leading through it, listen to our episode with Tim Chow.
Find more episodes at https://roadstakenshow.com
Executive Producer/Host: Leslie Jennings Rowley
Music: Brian Burrows
Email the show at RoadsTakenShow@gmail.com
Ilana Davidi Reeves: I do career day every year at my kids' school. Like give my schpiel about being a software engineer. And then I'd say just because they don't look like you in a job that you wanna do doesn't mean you can't do it. You could do anything you wanna do and don't let that feeling, you know, like I had when I walked into that computer test back at Dartmouth where I was the only woman, like, you can't let that scare you. You’re there 'cause you deserve to be there.
Leslie Jennings Rowley: When Alana Davidi Reeves walked into the computer science placement test at the start of college and she was the only woman, she walked out and found a new major. But internship and work experiences along the way, just as the web was dawning, pulled her into that world anyway, against the odds she excelled in software engineering, but found the odds stacked against her in other ways in her personal life, too. Find out how sticking through the hard things can set you up for success and a sense of gratitude later…on today's Roads Taken with me, Leslie Jennings Rowley.
Today I'm here with my friend Alana Davidi Reeves, and we are going to talk about little pivots, big pivots, and all of the things that get thrown up in the air to make a good life. So Alana, thanks so much for being here.
IR: Thank you, Leslie. This is great.
LJR: So I start these conversations with two questions with all of my guests, and I'll ask the same of you and they are these: When we were in college, who were you? And when we were getting ready to leave, who did you think you would become?
IR: You know, like so many others that you've interviewed, I knew those questions were coming and I've been thinking about them and they're still such tough questions because it's so hard to look back now at who we were and not micromanaged from this level. When I think about who I was, especially when I got to Dartmouth, I was so…not necessarily sheltered, but naive into how everything worked. But I was extremely energetic about it, so I wanted to try all the things. Once I got to Dartmouth, I thought that I might be a computer science major, but then I walked in to take that placement test and I didn't know what I was doing and—funny for how my career turned out—but I remember walking into this room and being the only woman out of 50 people and thinking, oh geez, I don't know what I'm doing. I really don't wanna walk out in front of all these people. But I did. 'cause I was like, well, this isn't what I wanna be doing. And then I thought, maybe math, maybe psychology. And I managed the football team and I was trying all these different things, all with a lot of energy.
LJR: That's funny that you had this like…You said it's funny being in a room with all men given your career, but then you actually turned to the football team. Maybe it was just a calling.
IR: Yeah, it was the sports side of things. I played three sports in high school and I'd captained two of them and I loved sports. Like I've, sports have always been a big part of my life. I've never been particularly great at them. Like I was always good enough to get by, but definitely not at the collegiate level. So I knew I wanted to keep sports in my life. So when I got into Dartmouth, I said, yeah, I'd love to manage a sport. And I'd actually managed my high school football team my senior year. And so that was just a natural progression. Yeah. That's all men too.
LJR: Well. Yeah. But it's really, it's not, it's not the men, it's the loving of the sport and having the leadership skills to do that. So yeah.
IR: Yes. Yes. Absolutely.
LJR: Okay. So you did find your way though, with a double major or a kind of combined something?
IR: Yes, I majored in English and then I got a certificate in environmental studies because it wasn't yet an official minor.
LJR: Oh, right. That's right. And so as we were leaving, did you have a goal direction? A dream?
IR: I really was pretty clueless because I was an English major, but I knew that I did not have the patience to teach. And maybe someday I'd write a book or something, but I wasn't ready to do that. So I did corporate recruiting and I remember trying to figure out what consulting was…like, what were you consulting about? And why would somebody ask me anything? I'm only 22 and I don't know what I'm doing. And I just happened to luck into this small boutique consulting firm in Boston who did technical consulting. And so they hired me on and by the second day at work, I'd found my way into their Java lab. Java is the main language I programmed in, and it was at 1.02 at that time, which was the version, and now it's at 21. They're just releasing 21. I'm like, wow, that's a lot. Yeah, so I, it's funny, I didn't really know what I wanted to do, but I found something that was perfect for me.
LJR: Yeah. But then you did have little hankerings of like, maybe another life is out there for me. Didn't you have a Sports Illustrated run?
IR: I did. I did. It's pretty funny. When I was in college, I did two internships. I did one for BB&N, which became GTE Internetworking, which was one of the first companies to really make it big in the internet, and I had a cousin that worked there. So I was, they just needed somebody to do their testing. And I did that freshman year and decided I definitely wasn't going to go into computers because, again, it was just, at that time it didn't feel right, which, you know, it definitely grew on me as I did it more and more. But I also did an internship at ESPN, and that was in marketing and sales. And I just, again, loved being surrounded by sports.
So I was finishing up at my first job outta college and looking for jobs in Boston, and I was slacking off and reading the news, and I saw this job opening for somebody that knew Java and loved sports and, thinking Sports Illustrated was in New York, I applied. And when they called me and said, you know, we wanna interview in person, I was so excited. And I said, do you want me to take the shuttle? And they said, what shuttle? And I said, the one to LaGuardia and the guy paused and said, you can do that, but we're in Atlanta. So I booked a flight to Atlanta, visited for the first time, and then got the job and moved down there.
LJR: Wow. So that's how you got to Atlanta and [IR: Yes.] was it everything you wanted in that it had the computer side and the Java, like language stuff? And then being in that environment, or could it have been anywhere? Did it feel sporty? Did it, did it have that flavor?
IR: Yeah, it was wonderful. That was such a fun job because it was still, you know, 1998 and it was the Wild West for the internet. So there's just so much opportunity and things were just crazy in such a good way. I was working out of the CNN Center in Atlanta, which is always such an exciting place to be. You could walk through the newsrooms and see how they work, which was just so intriguing and the sports side was amazing. I just loved testing with data that I knew, you know, I still remember a lot of the player IDs, which was how we identified different professional players. And I for some reason was always testing with Dan Marino, number four. And yeah, the sports were awesome. I got to have a couple of fun experiences where like sitting in a room in a meeting and the person next to me turned out to be Tiki Barber and like it was just a lot of fun. He was also a computer geek.
LJR: Oh good to know.
IR: We definitely bonded over that. Yeah.
LJR: Funny. Well, but you know, being a computer geek as this whole field was really emerging, you were getting to grow with it and mm-hmm. That probably was a very good thing for your career. So how did that career kind of progress as the world itself progressed and you, you know, grew up in it?
IR: Great question. One thing I remember from Sports Illustrated was I would get so frustrated that they never promoted the website online. I, oh, online. On tv. See, it's like so easy to say ‘online’ now. That's how we see things. But then it was like, why don't they put a link to the article in the magazine? And they had the television network as well, and they wouldn't promote our site. And I said, just tell them to go to the web. You know, this is new thing. You could see all the statistics. And so it was interesting to go from that where I'm just pushing, pushing, pushing, you know, feature us, talk about us to now, you know, people go to the web first and then maybe tv. So. That's been a huge change.
And then, you know, I said the Wild West of, you know, this team of five people doing all of the work for the entire Sports Illustrated website, which you could never do today. Now I'm at Square and we have teams that are just huge because there's so much. There's so many more threats out there and there's so much more to do and you have to, people buy things online and yeah I mean, it's been such a crazy trajectory, watching the web grow.
LJR: Yeah. And that trajectory kind of also paralleled your life. Your life was growing too. So talk about what Atlanta brought for you in other ways.
IR: Oh God. I really do love it here. So I was at Sports Illustrated for five years, and I told my parents who were in Boston that when I moved to Atlanta, I'd go down and work for Sports Illustrated for a couple years and then move home. And so after five years I thought, oh, it's time. And I moved back to Boston and I thought, oh, I think I might've made a mistake because I miss Atlanta. But one thing I was gonna move back for was to be near my family and to go to grad school. So after a year, I thought, I'll apply to grad school and if I don't get in, I'll move back to Atlanta. So I applied to one grad school thinking maybe I won't get in and probably won't get in. And I got in, I ended up going to MIT for two years and getting my master's degree in engineering and management, which was awesome. Like, you know, being at Dartmouth was amazing and the people are amazing and the professors and the ratios. But you know, the age when you're there, like 18 to 22, you know, you're still figuring out like who you are and what you should be doing as I mentioned earlier. And then I was at MIT and I knew exactly what I was doing and who I was and what classes I needed to take to keep going in that direction. So I really built up a great network while I was there. I built up some leadership skills, some tech skills, and a lot of, like, especially being a female in tech it’s really easy to have imposter syndrome and to feel like I don't belong here. I'm only here 'cause they needed to hire a woman. I'm only here because like luck. I'm only here…and I hear this a lot with women I mentor now. And that really made me see, oh no, I'm running with the big boys and I deserve to be here. So that was a great feeling. And then, yeah, the day I submitted my thesis, I also got engaged in. Decided, well, I'm gonna move back to Atlanta now.
LJR: Because he was in Atlanta.
IR: Yes, yes.
LJR: Yeah, yeah. Okay. And so that happened, and how did that parlay into the next step of your career as well?
IR: Yeah, so when I moved back to Atlanta, I became a director of software engineering at a startup. I'd actually been at CarGurus in Boston. So like coming out of one startup into another was kind of an easy transition and had a couple teams, you know, one in the states, one in Canada. You know, you were talking about like the evolution of the internet as my career was growing too, and this was a new thing like offshore, even though it was like the same shore, you know, having this team up in Canada that I was also managing.
And so I worked there quite happily until at six months pregnant I got quote laid off. And really felt like we had lost everything and it turned out to be illegal what he'd done; he basically got rid of me to not cover my maternity and took somebody who was way underqualified, put him in my position. So this was kind of like the first big, oh my gosh. Like how did that even happen? But what was so amazing about what we went through is how much support we got, especially from everyone at Dartmouth. When I posted on Facebook, like I just got laid off and I don't think it's legal and I don't know what to do I had so many people reach out and say, oh, you know what, let me know if you need legal help. Let me know what you need. Do you need clothes? 'cause, you know, being six months pregnant, the baby was coming and my husband had lost his job seven months prior to that because it was, you know, 2008, 2009. And we really got scared. It was one of those things where you've lost pretty much everything. We'd bought a house, sunk all our savings into renovating this house. We were maxed out on all our credit cards and looking for jobs, I would put on a blazer to cover up my big belly and go into these interviews.
And you know, they, when you're in tech, they make you write on the board. They say, can you code this on the board? And so I would get up to code and I would like rip around so they couldn't see me from the side.
LJR: Did that work?
IR: It did. It did. We'd set a deadline. If we didn't find jobs by this date, we were just gonna walk away, sell everything, move in with my sister. Just start over. Move up to New York and just leave everything behind. And that day at about 5:00 PM I got a call from a company and they said, you know, we wanna make you an offer. We talked through the offer and they said, do you have any questions? And I said, no, but I have something I need to tell you. Like, I'm not fat, I'm pregnant. And so the manager, the man who became my manager, paused and he said, okay, that's fine. You just, we'll work through that and we're just happy to have you on board.
LJR: Wow. So you started before you had the baby and then went right back?
IR: Yep. I worked for six weeks, had the baby, and then I felt so indebted to this company because they said, you know, we're gonna treat you like any other employee that has a child. We're gonna say you've, you know, like, like you've been here for a year. And so because of that, I was only out for six weeks with my first son and went back to work, which was really hard.
LJR: Yeah. Yeah. I did that with my second and realized those were days you can never get back, but oh, yeah. So, You, but you charge ahead and there you are still in the field that you love and now you've been even, you know, more acutely trained in and it's progressing and we're all becoming way more tech literate and hopefully, and yeah. And so life chugs along until another catastrophe befalls. Yeah
IR: Oh gosh, yes. So like you said, I was, again, going along, I was a director of software architecture at a financial firm. And I had teams all over the world, which I just loved. Like having teams in India. There's one in Eastern Europe, one in Boston. There were so many, it's been a few years and I can't quite remember. But I was on the phone from like 7:00 AM to 7:00 PM and so when I was pregnant with, well actually it was after I'd had my second son. This time I took off four months, which was just lovely. And he had a couple problems as a baby, he had trouble breathing. And they would call me from daycare and say, oh, Calvin's not really breathing right. Can you come get him? And I thought, I can't do this. I can't do both things right now. I need to take a step back. And then once again, I just had a lucky break where somebody called me that I'd done some consulting work for and said, Hey, would you mind coming on full time? You wanna work for us? And I said, well, I can't, I'm trying to take a step back. And they said, well, you can come on part-time. So I left this position where I was, you know, had these teams and you know, was a director. And I moved into this senior software architect role where I was building systems, but really working by myself, which was great in that it allowed me to be like a class mom for my older son and spend time with my son and get him when he was sick at daycare. And that's the company I was at for the longest. 'cause I really built up such a nice close knit group that we're all in Atlanta and really supportive. There was a team in Boston, everybody was super nice. And so I was able to do things like play tennis and I was playing tennis and doing the things I normally do, and I thought, huh, I've lost a step. Something feels off. And I realized like I was going to the gym five days a week and I was in really good shape and I was losing weight and, but not in a good way. 'cause when I work out, I gain weight. And I thought I've lost 10 pounds and I've lost a step. Something's not right here. So in October of 2017, I went to the doctor and I said, I know this sounds weird, but I think I might have cancer. And, you know, I kind of beat around the bush with that. And she's like, no, you're just perimenopausal. It's nothing. You'll be fine. You know, this is just what happens. And so I was like, oh, okay. That's good news. And I left and everything was normal until my mammogram in December and they found cancer. So I had a little bit of cancer in my left breast and we figured it was gonna be an easy surgery. They said, you know, it's just tiny little bit. We're gonna take it out, have a lumpectomy and you'll be on your way. So I did that in February, February 2nd, 2018, and then a week later I got the call that it had spread. So it was in both breasts and I needed a bilateral mastectomy. And so they took both breasts and you know, just we didn't tell our kids for the first surgery 'cause it seemed so minor. And so for the second one had to gather up all that energy and share that with our sons. And I remember sitting them down and saying, okay guys, this is…
LJR: How, how old were they at this time?
IR: Oh, let's see. So they were really young. Calvin was he was about to turn five, and so Scott was about to turn eight. They were young. [LJR: Yeah.] And so I remember saying, you know, mommy's been a little sick because that's all we'd said to them was, mom's just in bed 'cause she's a little sick. But you know, I told them it's actually I'm gonna be sick a while longer. It's something called breast cancer. And they're like, okay. And then they went running off. I go, wait, did you understand what I said? I said, breast cancer. They're like, did you hear me? And Scott's like, yeah, breast cancer. And so it was so funny 'cause you, you look at like that age, you think, oh my God, I'm gonna break their hearts. And they're just like, Yeah, they knew something was wrong and they were so supportive and snuggled me all the time and they knew they couldn't have hugs. Especially our little one, Calvin, he loves hugs and it was really hard for him to not be able to hug me. But we were very, very lucky. We had friends come over and they would hug Calvin and snuggle Calvin and bring us food. We didn't cook for four months, so we felt very, very supported. So even though breast cancer was, you know, not something I'd really recommend, not the greatest amount of fun, it was really interesting to look back on because it's one of those things like when we went through 2008, 2009. That recession we went through, you just realize that you're not alone and that people are there for you. And so sometimes I look back on that time and I'm like, you know, that was actually not a lot of fun. But on the other hand, there were things that I experienced that I wouldn't have experienced if I'd been healthy, like having my friends and my…there was one time, like we were all just hanging out in my room 'cause I couldn't really get outta bed, especially after the mastectomy. And all of a sudden I realized like there were like eight people in the room with me and we were sitting on my bed and like they were in chairs around and we were just giggling like it was a slumber party, you know? It was like, it was really nice to feel that again. 'cause you know, as a professional, as a mother and all those things, you don't ever put yourself first. And that was one of those moments that I was like, oh my gosh. Like this is just so on one level, just so pure and good. [LJR: Yeah.] So, yeah, it is funny the things that we, you know, find out at those rotten times.
LJR: But I'm glad that you had the people around you, not just out in the ether—that you had, you know, made these connections all over the world and teams and things—that you actually had a solidarity team around you at the time. So that's great. So that is behind you now?
IR: Yep.
LJR: All good? Checking out? Good. And so what has life been like in the last few years and where do you see things going professionally with the family, all of that?
IR: Yeah, so I've stuck around in software, came back, worked at that same company a little while longer, and then decided I wanted to get back into leadership, which I chose an interesting time to do. In January, 2020, I changed jobs to be a director of software engineering and it was contract to perm as many of those types of jobs are these days. So for, I had the three month trial and of course they laid off all contractors. So Covid hit, which again was another blessing in disguise. 'cause I got to be just with my kids during, you know, when they needed us the most. And we were fortunate to have a house on the beach down in Florida, so we went down there and sheltered in place there.
And then I ended up working for Square through kind of a windy road. And I remember coming into Square and you know, looking back on my career, I worked with so few women. It's been such a struggle to get women into technology. I do career day every year at my kids' school. I always volunteer. And something I noticed over the years is like when my kids were in kindergarten, this happened for both of them, and I demonstrate something from my laptop. All the kids would gather around and they'd kind of push, as you know, kids do, and the girls and boys would be pushing. By the time they got to fourth and fifth grade, the girls weren't pushing anymore. They were standing back and I thought, oh my God, like this can't keep happening. And I would always address the girls, I'd give my schpiel about being a software engineer, and then I'd say, I'm just gonna speak to the girls in the room. And you know, underrepresented minorities. Just because they don't look like you in a job that you wanna do, doesn't mean you can't do it. You could do anything you wanna do and don't let that feeling, you know, like I had when I walked into that computer test back at Dartmouth where I was the only woman, like, you can't let that scare you. You're there 'cause you deserve to be there. And so all through my career, I only worked with very few women—under 10—and all of them, except one, have left software engineering, gone into other fields. 'cause it's hard. Like I, they ask me now what I've been through as a female. And it's crazy like having to sue for equal play twice, like just all kinds of up and and downs. And so when Square called me for my final interview and they said, what would you like to see in your last interview with us? And I said, you know, if there's a female that's leading engineering anywhere in the company, may I please speak with her? And they said, oh, we've already got two engineering managers. Would you like more? And I thought, oh my God, I'm finally going to a place where there's women. Like, this is crazy. It's this west coast company and it's just been amazing. Like not only am I like in a women in engineering group, I have a women engineering managers group, which I am actually leading up now. There's a lot, there's a whole group for women that are, you know, second level and above engineering leads and that's just…It is been crazy like in such a good way. And being able to mentor and help women who are struggling with what I struggled with has been just so rewarding.
LJR: And in what ways have you seen that change or affect the culture that you've seen at all these other organizations and this organization? Is it reflected at that level?
IR: As far as the demographics or as far as how the teams run?
LJR: Yeah. Kind of like the operations of it, the feel of day-to-day, anything that like, is there a demonstrable difference when you have women in these roles?
IR: Yes. Yes, there definitely is. And what's really interesting, there's still, as far as the engineers go, I'm excited to be with women at the same time. When I say that I have an organization of 50 people and there's five female engineers, which is still like really small obviously, but those five engineers are amazing. They're top. They're just so good. And we're hiring more and more. So, you know, we're always looking to fill out those groups. And so that was last year that we had those numbers. And now it's up to like, I think we've got 10 female engineers because, you know, they see someone as a lead and then they think, oh, that's an organization I wanna join and be there. And then, I finally had like my first woman ever reporting to me, one of my managers is a woman. And having a female report to me was such a new experience. I thought, oh my God. And I was her first female lead. And it's just great because this team now, the people on her team have her as a manager, me as the skip level, and then the, my boss is a woman. So just such a dream come true. And you asked about like the feeling around like having more women and it is, it's a warmer feeling and you know more and you know, you can't really generalize on gender. But at the same times there are certain differences. Not being the only one and being expected to behave more like, you know, I'm just one of the guys. I could just be who I am and you know, speak very frankly and having that support system where if something happens, I turn to other female managers, other female leads, and, and talk to them about it. And it's, it's so supportive. Yeah. It's been really awesome. Yeah. So we need more of that.
LJR: Great. Definitely great for you to be taking the lead on that. So actually that's a great place to go and ask my other favorite question, which is if you went back to the 20 something in college, Ilana, and said, I know that you just skipped out on that test and yeah, but let me show you where you will have been. What would she say?
IR: I think she'd be really amazed at where she got to. You know, I do this thing where sometimes I just send my past self messages. I know it sounds a little, I am a geek. I am a nerd. We all know I'm in engineering, but I like to sometimes pause in my life and just send it back to that confused person and let her know it's gonna be okay. Like you don't have to know where you're going. Sometimes things just happen and like all these happy accidents that happened along the way. You know, I'll be walking around outside and be like, I'm just gonna send my past self this message about how amazing it is to be surrounded like and have two kids and a husband that loves me and that I love so much, and just at this wonderful point in my life. And so I think she'd be really happy.
LJR: So what message do you need to hear Ilana, from the Ilana of 2064?
IR: Ooh. I think it's the same thing. You know, it's just, it's gonna be okay. Like, life's not like a straight line. It's very, very windy. I have this quote and it's just so corny and I love it. It’s “I got lost on the way to a dream and I found a better one.” And it seems like we always set these goals that we have to get to. Like I set the goal coming outta college like I wanna be in management by five years out. And I got to that goal and then I thought, now what? Like, I didn't really know where I'd go next. And I was like, oh, I'm just gonna see what happens. I think like all these happy accidents just come along and make you who you are, like no matter how painful they may be at the time, I feel like everything I've gone through, like those worst times have made me so much stronger and such a better person. And I'm happy to be in a field where I just love what I do.
LJR: Yeah. And I love having these conversations now because I do think that we're at the point where we've kind of gained all the wisdom we're gonna need for the rest of it, and it's coming back in spades to help us, and I just, well, I do wish you all of that knowing that it's gonna work out just fine and you're gonna end up where you need to be, and I just am very appreciative that you've shared this part of your story thus far with us today. So thanks so much, Ilana.
IR: Thank you so much, Leslie, and thanks for doing this for all of our class. It's been so wonderful to listen to everybody's stories. They're also inspirational.
LJR: That was Ilana Davidi Reeves, a software engineering and architecture leader with 25 years of experiences across diverse industries, who currently serves as Engineering Lead, Fulfillment at Square. She has managed, mentored, and directed local, off-shore, and near-shore teams including the new wave of women in the space. She lives in Atlanta with her husband and their two boys.
Just as Ilana said, it's hard to remember the days when an online-first approach wasn't the go-to strategy for any brand. It's certainly the rule of thumb for us if smart phones still count as online. Be sure to follow and subscribe to our show wherever you get your podcasts or do go online to roadstakenshow.com to find our archives, show notes, transcripts, and great then and now photos. Either way, you'll be able to catch up with all our guests and me, Leslie Jennings Rowley, on Roads Taken.