Breaking Barriers and Opening the Path to Leadership Roles for Women

Automatic Summary

From Wall Street to a Technology Career: A Personal Journey

Welcome everyone. I'm Jeanette Leeds, the Managing Director of Olio for Americas. The trip from Wall Street, two largest banking firms, to leading a technology company for a region making up 40% of the company revenue, was not a smooth sail. Today, let me take you through my journey toward tech, the challenges I faced, and how I overcame them.

Transition from Wall Street to Technology

I spent a significant part of my career at Lehman Brothers and Credit Suisse, before a big career change to a technology company, Olio, made me a technology enthusiast. The major question I often get is, "how did you make the jump?" The answer to this is quite easy. Lessons learned from past experiences and the ability to take risks were key to my successful transition.

Don't Let Fear Stop You From Taking Risks

In reflection, my career's best decisions were risk-based. Being tired of the fear and deciding to take the bold step into technology was the most career-defining moment. The old adage — nothing ventured, nothing gained rings true in this context.

Ask For What You Want

Direct communication about career progression is critical. A significant turnaround came for me when I started asking for what I want, clear about my ambition, and supported by a strong case to back it up. Be passionate about what you want and express it to your superiors.

Importance Of Relationships

Moreover, building relationships has been an essential aspect of my journey. A deep understanding of your team and how they operate can be incredibly powerful and helps in solving complex issues. It also provides a platform to gain insights and suggestions about moving forward.

Conclusion

Progressing in your career entails having the courage to take on new challenges, asking for what you want, and maintaining key relationships. Always remember to promote your accomplishments and be proud of them. No matter what role you play or company you work in, these principles can help you make significant inroads in your career. Feel free to connect with me on LinkedIn and Twitter. Let's explore and overcome our career challenges together.


Video Transcription

Welcome everyone. I am um Jeanette Leeds. I'm not sharing any slides. I'm just gonna talk to um I um just by way of background, um what we're gonna do today is talk a little bit about my story and how I've gotten to where I am today.Um I um head up Olio, uh which is a technology company. I head up um the Americas, I'm the managing director. Um And I was a recruiting enablement platform and we focus a lot on diversity and automation and, and A I. Um but I'm not here really to talk about. I, I'm really here to talk about my um journey um from really Wall Street to, to technology and how I've gotten to where I am today. And so a lot of times, um no people ask me the question. Well, how did you, you know, make the jump? So first, just quickly, I, you know, I spent a large chunk of my career at Lehman Brothers before they, they went under. Um and then I ended up um I credit Swiss and then again, made a very big career change from a recruiting practitioner over to o and technology And so I get the question a lot of, well, Jeanette, how did you make that jump? That's a really big change. You went from, you know, being in hr um to being in a revenue generation role and, you know, ultimately moving from the first employee in your region to running the entire region that makes up 40% revenue for a company. Like, how did that happen?

Um So, you know, I've been thinking about it and one of the big um lessons as I think back through my career, how I've gotten today and some of the best things I've done have all been based in what I would say first lesson, which is um don't let fear get in the way of taking risks.

And that to me has been something that's been, you know, really, really OK, don't be afraid of taking risks. Um And so let, let me, let me tell you a story about, about that and how that's really, you know, resonated in my life. So, um iii I knew I always wanted to do something entrepreneurial. I was in at Wall Street, I was at credit Suisse. Um I was in a global role um in uh campus recruiting. I had a one year old and a three year old. Um when I was, um it's like my daughter was four months old. I was asked right after I got back from maternity leave to fly to India. I'm based in New York. Um, and, you know, I knew at the time, you know, how, how am I, how am I going to try and be a mom and be around for my kids? But also, like, have my career and do what I really like to do. And that was always something that's been really important to me and, and it was one of those things where, um, you know, I'm like, well, how do, how do I sort of make my, my life work. I spent, you know, up until that point really my entire career on Wall Street. This is what I knew. I knew how to be in campus recruiting.

Um, you know, all this and what was interesting was I started having conversations with the CEO of, of where, where I work now. And at this point, I, I know from my days when I was at Lehman and Credit Suisse, we put in the oe system twice. Um, you know, I had gotten to know, not just him but his team, I knew the product. Um, I had always done lots of reference calls and events and whatnot and, and Charles and I started talking and he said to me, he was like, why don't you just come work for me? You know, and at the time we just had people at o in London and I'm in New York. He's like, why don't you come work for me? Um, you know, let's like, you you know, so much like this could be really great. And I sat there and I, you know, really thought about it and it was scary. It was a scary proposition but yet like, really exciting. Um And, and I thought about, well, I've always wanted to do something entrepreneurial. Um you know, this, this is so different. This is like, you know, I, I'd be responsible for revenue. Um you know, this is really where the rubber meets the road. Um, and I said to myself, you know, what not? Why not?

But what I said was, I'm, I'm tired of being afraid and not doing things, um, that, that I might want to do because I'm, I'm, I'm scared, I'm, I'm afraid and, and I thought to myself, what's the worst thing that could happen? And literally, I thought to it, what's the worst thing I leave? I go, I work for all. I try and expand out the region. It's a disaster. What's the worst thing? It's a disaster. I have a life lesson and I figured, well, I can always go back and doing what I was doing on Wall Street. I figured that that's always an option. And once I sort of got past that, what's the worst that can happen and thought through it? I was like, ok, like, let's, let's do this and it was the riskiest but absolutely best career move. Um, II I ever could have made and it was because I just, like, you know, said, I'm tired of being afraid and, and if I look back, um, at other moments, you know, when I, when I had that confidence in myself and saying, hey, you know, what's worse can happen? Like I'm not gonna be afraid, let me just do this. It's, it's been the best, best outcome.

So that would be really, as I think about it, like one of the best, um, lessons I can say, you know, as you're thinking about your career or really just life in general is, you know, what's the worst that can happen? What's, you know, but don't be afraid, just sort of go and embrace things and, and you'll be surprised. Um So my next um I feel like aha moment and, and, and lesson came um sort of earlier in my career and, and the lesson is ask for what you want, which is hard at times. Um So let me tell you a story about that. So I was at um Lehman Brothers. So this is going back many years since Lehman went under an 08, which is a whole other story for another day of how to survive when your company goes bankrupt. And um you might be on your last two weeks of maternity leave, but that's another story. So, um when I was at Lehman, I made the assumption that I was going to be put up for a title promotion. Um and not a functional promotion but like a title and, you know, a lot of times people would be like, if you were in a role for so many years, you would just, you know, I assumed very naively by the way that, oh, ok.

So many years I'm gonna get, you know, put up for a VP title. Um, didn't say anything to anyone and when promotion titles came out, I didn't get it. Which now in hindsight was like, well, obviously, and I was really devastated. It was one of those times at work, which is rare where I was like, you know, crying in the bathroom and, and, you know, just sort of, you know, like, oh my God, I was just beyond devastated, but I was like, OK, what can I do? Let me take a step back and think through and I made it really clear to those that I worked with over the next year was, hey, I want to be put up for a promotion next year. I want the VP title. Here's what I'm doing. Here's the reasons why and, you know, I, I asked for it, I didn't assume and that again has been, you know, huge, huge lesson. So, you know what happened? Yeah, like that following year, I made VP and I was beyond, you know, thrilled, you know, it was, it was just, you know, an unbelievable thing. I was so happy. Um But I realize you have to ask for what you want. So people ask me today, you know, Jeanette, you are, you know, manager managing director, Head of America's at Olio. You sit on the global leadership team. Well, how did that happen?

Like you started out first employee us like company been around like, and, and you know how that happened, how I actually got on the, the global leadership team because I wasn't at first, um I literally asked my CEO it was almost a water cooler conversation and I was like, hey Charles, I want to be on the global leadership team.

I want to be in those Monday meetings. Um You know, we're expanding out in the U si think it's incredibly important. I want to be there. I didn't even, it wasn't even a real thought out full conversation with all reasons why it was like, hey Charles, I think I should be on this and you know what he was like, yeah, you're right. And that was it. I asked for it. It sounds so simple and so easy. But uh as women at times and that they ask for stuff all the time, they always ask for stuff. You have to ask for what you want, have reasons. Don't just ask for something where it doesn't make sense, but ask for what you want. Tell people it really makes a difference. Hey, I'm doing a quick time check. OK, next lesson and I debated what to call this one. gonna say relationships, it's all about relationships and how powerful they can be. Um You know, it, I could call this section almost focusing on um solutions and not problems because that's a real big thing. Um Playing to your strengths, hearing what others are saying all of that.

But in the end, I decided like one of the most important things is to emphasize relationships and the power of relationships. So let me tell you a story and this is much more recent and I'm going to protect the innocent and I, you know, share a whole lot of details. Um But I very recently was, was uh you know, hearing it at work at Olio. So if anyone from was, um there was, there was a big global project that was happening and everything had gotten done, it was very visible. Um Everything had gotten done, except for one thing, the project had sort of stalled. People were frustrated. I was frustrated. When is this happening? When is this launching? And I sort of talking to people and digging in and um it's two different people that were involved. One was on the leadership team, the other one was one level down. Um And I was talking to the person who was one level down and it was like, well, it's stalled because of this and you know, this person da da da da and they're holding things up and like, hang on. I'm like, let me have a conversation and I had known this person who was supposedly holding it all up for many years. Um, and I knew at times, you know, this person could be cranky guy, you know, cranky.

But I also knew like, he didn't just do things to be a jerk. Like there's usually a reason. Um, so I just, I got on his calendar, I just called him up and I said like, hey, you know, what's, what's going on here? Um I know, like, I know you're not trying to be difficult, purposely, you know, you know, like we, we need to get this thing launched for, you know, all of these reasons. There was like, you know, critical revenue pieces um that would be tied to it. And I was like I said to the person, I'm like, you know, I don't want to, you know, have us take this crazy risk and bring, you know, being dramatic like the company down or, you know, set us up or what not. And so we ended up, you know, and I was like, I've known you for so many years like what's going on and he just, you know, again, we're on a video call just like that and just explain to me, Jeanette, here's the situation, here's my concerns, you know, we need to get this information so I can approve this and get this thing out the door, you know, and here's the concerns and I was like, OK, I can work with this.

And so I heard his concerns and I went back to the other person who was again one level down and I was like, oh, OK, I think I can work with it. And so in the end, literally, I was able to get this project like launched and that, which had been stalled for months because I just had a few conversations and listened to what people had to say what the real true concerns were and everyone wanted this thing done. Um And in the end, what was really interesting is I realized it was actually a game of telephone. Someone on the, you know, this person's team was concerned to talk to this person. This was there, what was the real issue, the other person, you know, was talking to this person. And so in the end, I was like, these two people who were like a few steps apart, it was almost like this game of telephone. They needed to be connected to talk turkey. I was the one who actually realized that and I was like, let's get these two guys. I think this is how we can solve it. This should be easy when I tell you, this was literally fixed and done and I don't wanna say 10 minutes, but it was like two half hour conversations.

And within a week or so this project was done and launched and I was like, whoa, and it felt easy to me. And so one of the reasons why it felt easy to me was because I had great relationships with people. All of those there, I knew all these people, I knew what motivated them, how they thought. Um, and so that, that is really, really key. And so I would, you know, absolutely say, you know, think about the relationships you have with people. Um, what motivates them, listen to what their concerns are. People aren't difficult just to be difficult. I mean, maybe there's a few people like that, but for the most part, there's a reason why someone is, you know, maybe I don't know, being cranky or difficult. And so if you can dig into that and figure out why and then figure out the other side's, you know, concerns and try and problem solve through that you can really be um incredibly powerful there. Um And so related to that, it was funny, I was telling my dad this story when my dad, you know, is an entrepreneur, started his company. Um and I was telling the story and he was like, you know, Jeanette, you need to tell, you need to tell your CEO what you did.

Um And I was like, ah whatever, you know, and he was like, no, no, this is like, you know, you have to know your strengths, you have to brag, you have to say things and, and, and he reminded me so here, you know, you know, I'm, I'm into my career, you know, doing lots of things.

My dad reminded me, you have to brag, you have to say what you're doing and let people know. Um, and I've done that throughout my career, but I needed that reminder. And so listen, it's hard sometimes to, um, you know, shout your successes and what, what you're doing really well and some of that stuff might even seem easy to you. But it's hard for other people and, and so you have to play up your strengths and what you're really good at. And so, you know, it's hard, it's hard sometimes to brag about ourselves. It's not, you know, again, guys will do this very easily all the time. And so, you know, I would say one thing that has made me successful is, you know, and I hate to use the word brag but, you know, telling people what I've done. Um And so I, you know, a few days later had a conversation during my, you know, weekly with, with my CEO and I was like, hey, by the way, that thing that, that project that was so, like, I like, that's, you know, yes, there were so many people who were involved in getting it to that point.

And so by the way, I always give credit to other people and what the work they've done, it's not just about you, it's about others and that's sort of a whole other separate lesson I was like, but by the way, you know, and I joked with him, I was like, my dad told me I should tell you this.

Um, and, um, you know, I, I share with him just, you know, that the little part I played, which was little but important. Um, and, you know, I've done that throughout my career. So whether it's, um, I don't know, anytime you can quantify things and, and share, you know, what, what you've accomplished, talk about it, tell people send the emails on, you know, an update on something you've worked on, that's been successful, um Whatever it is, that's really a big thing as well.

So I know I'm at like the very tail end of my time and maybe have, you know, time for one question um or two. But what I would say is, you know, I'm, I'm on linkedin, I'm on Twitter. I love connecting with people. Um You know, talking about things that, that I've done hearing what other people have accomplished and just, you know, working together. I feel like if we're all here for each other, it's been a crazy year. So please don't hesitate to reach out to me. Um And, you know, tweet look in whatever and um you know, so with that out, I if there, if anyone has questions, I guess, type it into the Q and A, um you know, and I'll try and answer in the two minutes I know that we have a hard stop in, in two minutes otherwise, um you know, I, I appreciate everyone who's been here today and um hopefully everything I've shared has been, something has been helpful and will make you think a little bit um about, you know, how you can, you know, continue to move up, move up the ladder in any way that makes sense for you.

Oh, question. Should we switch to leadership roles early in career or wait for more experience? That's a great question. So what I would say, there's a huge benefit to making some lateral moves and getting experience in a variety of areas. Um You know, at the same time, if there's an opportunity to put yourself in a leadership role in a manager role, don't be afraid of that and, and, you know, um taking that stretch assignment, you know, don't be afraid you'll figure that out. So it's, I, I'm sort of saying both. Um I, I think, I think both, you know, for, for me, um my, my first leadership role was actually managing my former team, which was sort of an interesting piece there. Um You know, I didn't have as much um other experience in, in lateral areas. Um So to me, it's like, hey, if you have that opportunity, go for it, like go for it again. What's the worst that can happen? OK. You know, it doesn't work out, then you go and get experience some, you know, and it, something else, um, it can't hurt, can't hurt to try. Um, I mean, that, that sort of has been, let's not be afraid, just sort of embrace it and it's listen stuff is scary. It's ok, it's ok to be scared. Like the guys are scared, they just don't talk about it so just go for it.

So, um, you know, that's, I will leave you, I will leave you with that. It was a really good question. Um And um you know, I hope everyone has enjoyed uh the, the conference. I think it's been incredible. I've, I've learned a lot and, you know, again, connect with me. It's um Jeanette leads, it's spelled with two ES on the leads and you can find me um online. So thanks everyone and enjoy the rest of the day. Take care.