Let's Talk Tri Delta

Fearless in Finance With 2025 Woman of Achievement Jacqueline Reses, Pennsylvania

Episode Summary

In this episode, we sit down with one of our 2025 Women of Achievement, Jacqueline Reses, Pennsylvania. Jackie is a powerhouse in business, finance and innovation. She’s led major financial institutions, is a pioneer in fintech and is the co-author of a guide to help small business owners. As the chair, CEO and co-founder of Lead Bank, Jackie is redefining banking for today’s digital age. Join us as we dive into her career, her Tri Delta experience and the advice she has for all women looking to take charge of their voices!

Episode Notes

Jackie shares how her time at in the Tri Delta chapter at the University of Pennsylvania shaped her leadership journey, giving her a lifelong network of strong, ambitious and fun women who continue to inspire her. We’ll dive into her impressive career—from lessons learned at Goldman Sachs to leading Square and now running her own company. She gets real about the challenges she’s faced, how she tackles setbacks (spoiler: hope is not a strategy!), and why women should always put themselves in the game, especially in finance. Jackie also reflects on the meaning of the Women of Achievement honor and why giving back isn’t just a side project—it’s a way of life. Plus, you won’t want to miss her surprising hidden talent and her refreshingly honest take on work-life balance!

Episode Transcription

[Jackie Reses Transcript] 

This transcript was created using automated technologies and may contain errors.

Welcome to another episode of the Let's Talk Tri Delta podcast. I'm so glad that you

joined us today. I am Mindy Tucker. I serve as Tri Delta's CEO. And each year,

Tri Delta recognizes a few really extraordinary women who exemplify our values and are

really paving the way for the next generation of women. And today I'm so excited to

talk to one of those 2025 Women of Achievement, Jackie Reses from our penciling

chapter. Hi, how are you? I love it. I'm so glad you're here. And I'm so excited

to tell everybody about you. And I kind of don't know where to start because it's

such a long list of accomplishments in your career. Jackie is a powerhouse in the

world of business, finance, innovation, from leading major financial institutions to

shaping the future of Fintech, her career has really been remarkable. She's currently

the chair, CEO and co -founder of LEED, which is a chartered banking as a service

platform for Fintech consumer e -commerce and digital asset companies. She co -authored

a book called Self Made Boss, which is a guide for small businesses on running and

growing their ventures. She holds multiple patents and payments, credits,

and cryptocurrency. She serves on boards, including for her alma mater, Wharton,

at Penn, where she earned her Bachelor of Science in Economics with honors. There

are so many accomplishments to list, Jackie. We're never going to get through all of

them, but I'm so happy to welcome you to the podcast today. Thanks, Mindy. Well, I'm

so happy to be here. Thank you very much. I'm honored. Good. Let's start a little

bit with your story, how you started in college. You went to the University of

Pennsylvania. What drew you there? I only ever wanted to go to Penn. So I'm not

sure I ever perceived there to be another option. I had a cousin who went to Penn.

My older brother went to Penn. And the reality is if you're a kid who loves

business and likes to start a bunch of businesses. Penn and Wharton in particular as

a sub school of the university is like the holy grail of education. And so I got

lucky that it was close enough to my house that I was familiar with it. It was

about an hour away from Atlantic City where I'm from. And I had enough visibility

from family members that it just became so obvious and I skip my senior or high

school, which is weird, I know, but I really want to go to school, I really want

to work and Penn was the institution that I absolutely fell in love with.

I love it. So they let you in early. Well, you can go to college early. It's

really weird. most people don't know that, but you can apply to college without

having graduated from high school. And I actually went back and graduated high school

after my first year of college. Very weird. Interesting. Very weird.

Yeah, really. That's so interesting. Yeah. Okay, so you get to Penn. You learned

about Tri Delta. What made you want to join Tri Delta? So Tri Delta was pretty

foundational in my life from a friendship point of view and just as a cohesive

group of women that kind of bonded together for kind of commonality of interests.

And what I found at Tri Delta at Penn was this unusual group of women who combined,

you know, a lot of fun. These were women who were social and loved going out at

school and making the most of their time at Penn while also being incredibly smart

and switched on. And so I'd like that combination. They were somewhat salt of the

earth and more of people who wanted to make the most in the world with their

lives. And so they were very comfortable on their own skin. And that was a group

of women that I found perfectly suited what I wanted to do in my life.

I think Penn Tri Delts, my peers, and I know it's even today,

are wickedly smart and incredibly focused on their careers and being good citizens in

the world.

And, you know, I got lucky that it was such a good house and I met so many

wonderful women that I'm still friends with today. - Yeah, you do a great job of

describing that. What I've seen, the last, I think three or four years in a row,

we've had a woman from Penn who's been a woman of achievement. So really remarkable,

capable, accomplished women. But they all go back to these really close net

friendships they have too. And so the way you described that is perfect. It's just

these really smart dynamic women who wanna do a lot in the world, but also wanted

that social and friendship aspect and have kept that up over the years. So-- - Yeah,

and there's a lot of research that talks about when women go to single -sex schools

when their kids and how they benefit out of being able to use their voice and the

power of the way that they can connect with one another that they're not made to

feel stupid or they don't dumb things down. And I think the cadre of friends that

we had at Penn was this amazing cohort of women who were focused on their career

and also wanted to build more purposeful lives in lots of different ways,

whether it was my roommate who went to the military or other roommates who went

back to countries that they were from. And I've got other roommates who were

professors, who are professors. And so, you know, each one of them kind of found

their way in the world That's so different, but they all were just driven and,

you know, poised and comfortable as who they were at the time in college.

And so I feel like the peer group really benefited from that cohesion. And even

today, there are some women that I cross paths with who have extraordinary

achievements. And someone will last week, like in the world of finance, like, Oh,

how do you know? So and so on. I'll say like, Oh, she was my sorority sister. And

I say it with pride. And maybe, maybe it's, you know, my generation,

I'm not sure this is factual accurate, but I feel like my generation is one of the

first generations that can really say, I've got a baller friend who also works in

finance. And she was my sorority sister. And I feel like, you know, for scores of

years, men have been able to say that. And I feel like women are coming into their

own in order to be able to say that as well. And I love it. I find so much

pride in that. That, you know, I really, I enjoy it a lot.

I do too. I think we have this amazing network of women and we don't talk about

that and utilize that enough. It's just this, But men have done that forever.

They've known how to do that forever and they've done that forever. So it makes me

so happy to hear you say it in those words and be able to go out into the world

and share that. So let's talk a little bit about your career. Nothing short of

exciting. Can you walk us through some of like, some of your most major milestones

in your career, some of the standout points for you?

- So pan was a pretty significant standout moment. For me, it really changed my

world view. You know, I commented about my peers and what they went back to do,

but my cohort of Tri Delts was a very international group of women.

And so it's an example of how I opened my perspective to seeing a cohort of women

that I had never quite appreciated. And Penn more broadly showed me this

multinational operating view of how businesses could evolve in the world.

And so it was a pretty formative experience for me in building relationships and

building an educational foundation that was unforgettable. And to this day, the people

from my Wharton and Penn Network absolutely have an impact in my life.

And then they helped me make the decision to go work at Goldman Sachs, which was

my first full -time job after graduating from Penn. I would have never done that had

I not gone to Penn. And so Goldman Sachs was also a pretty formative place for me

to learn, you know, I learned professionalism. I learned teamwork.

I learned about mentorship. And sure, my job at a skill level was actually finance.

And I worked in the merger department and the principal investment area of Goldman

Sachs, investing partners money. But I more learned about what it's like to be an

important citizen in a community of colleagues. And so as I mentioned,

the idea of teamwork and mentorship and excellence, those I use today in my day and

day out life, and I often refer to the operating principles at Goldman Sachs and

invoke them in my own company. Goldman was a pretty key milestone. Then I spent a

decade plus working in private equity, and then I transitioned to tech at Yahoo and

at Square, and Square was a pretty transformational experience in my life. At Square,

I ran financial services products, and I built a bank, and I ran the human

resources team. It wasn't something I had done for a long period of my career, but

I think of HR more akin to doing private equity, putting levers of growth into a

company, albeit with people, which is usually how tech companies drive their

intellectual talent. And so in running these financial services products like lending

and debit cards and credit cards, I really built products that started to change the

way finance was happening for businesses. And that was pretty eye -opening experience

and doing it with someone like Jack Dorsey, who I believe is one of the most

creative tech founders in the world and just an extraordinary human being. So Square

was pretty important in my life. And then after Square, I left and went and bought

a bank with colleagues who worked with me at Square and were building a fintech

infrastructure company to lay the foundational rails for how fintech is done globally.

And so, you know, each one of those steps,

working in private equity, working at Goldman Sachs, working at Square, helped lay

the foundation for what I'm ultimately doing now, because I feel like I learned so

much in each of those steps. And now I'm doing something that I absolutely love

with people that I of, and it feels like my entire career finally built up to this

moment of owning my own company. - Yeah. - It's been pretty magical. - So in a lot

of these places, especially when you're getting into technology, not everything goes

as planned and there's a lot of moving forward and stepping back and moving forward

again. How did you learn to handle the setbacks and keep moving forward when those

things happened.

So just like anyone, when you're faced with setbacks, I find that I perseverate on

the topic for weeks. And I can't get out of my own head.

And it takes me a little while to think through it. But thankfully, I am a pretty

steady -eddy thinker. and I often think aloud with colleagues, I think that's why I

have such wonderful co -founders who are very open and honest intellectually.

And I find that I can think through an issue by voicing it,

talking through it, talking through the ups and the downs and then trying to work

my way through it with others. And So that's my methodology of trying to tackle it.

I never thought hope was a strategy. You can only work through all these issues if

you go from top to bottom through the thinking and try to think through every

scenario. And in my mind, that just makes your thinking crisper in trying to solve

an issue and pushing forward. And So thankfully, I don't get paralyzed by it. It

just causes me to have, you know, I definitely have some moments where I go into

my head, but then I really do use people that I trust to kind of work through

these issues. Yeah. Well, that leads into a good question, which is, you know, you

are bringing people together to solve problems. You're leading. What have you learned

about leadership? what's really important to you in terms of your leadership qualities

that you've brought to bear in some of these roles? I think most importantly is you

have to be authentic to who you are. You know, I often get asked questions about,

you know, what would you do in your career? How would you think through this? And

the reality is the people who know you best are often the people who can give you

the closest advice to helping you do what you're best at.

And as a leader, I think you have to be true to who you are and follow the

advice of those closest to you as well. And so I do try to listen to my

colleagues, take very honest feedback, try to be open -minded to any advice that

people have. It doesn't matter where it comes from. There's always room to improve

what you're doing. And so I'm pretty receptive to hearing it. I think the only rule

that I have with regard to feedback and hearing comments is that it has to be with

good intent. And so I'm very focused on making sure that if someone wants to

comment on something, they really do have to say it with a positive intent towards

it, no matter how biting it could be as feedback.

That's how I think about leadership is kind of leading with authenticity, leading

with an open mind, leading with a mindset of growth and trying to make things

better. And so, you know, I've modulated that approach over the years,

you know, like there were times when I feel like I was too reactive.

There are times now when sometimes I feel like I'm almost too approachable in a

way. And I have to find ways of pulling back because I have to moderate my time.

But throughout All of that, I just try to be open about who I am and how I

operate and how I want to engage with people, and my ultimate goal is to make my

company better, make my colleagues better, have everyone learn, because I feel like

when everybody's doing that, they themselves can make all of us better as people and

as corporate citizens, and so I do feel like that is a holistic fit. Yeah,

I love that. And that whole the right people around you and bringing their advice

in, I think is critical just to anyone who's who's trying to lead a team or an

organization. I'm gonna let you give a little bit of advice here. What would you

say to women, young women who are looking to break into finance? What would your

advice be to them?

One, I think it's important to take classes that or do something if you're mid

-career that shows that you have a capacity for math. And just because you're in a

field of finance does not mean you're a math expert, but you have to be facile

with the concepts and willingness to talk about it and engage in math as part of

an overall concept of like what you do. And so I would either take classes online

or take classes at school, just that you could get more acquainted with concepts of

financial statements, financial management.

That's point one. Point two is put yourself in the game and don't stop yourself in

advance of a job because you fear that you're not going to be good at it. I find

women can get in their head and stop themselves from even trying when in reality

put your head down, do good work, get more acquainted with it and put yourself out

there and go try to get the job. You don't have to be an accounting expert to

work in finance. And so even I run a bank,

I would say I'm terrible at a few things-- accounting and hardcore math. But I am

fast -forward with the idea of financial statements. But I know there are places that

I'm not good at, so how do I manage that? I cover my blind spots. I have an

amazing CFO who is excellent in the weeds at all the things I am not. And she's

excellent at a lot of things beyond what I'm good at. But I cover my blind spots.

And so you can comment the finance sector from lots of different ways,

given your own strengths. And so my advice is to try to pursue it.

And if you think it'll be interesting and something you enjoy, learn a little bit

more and put yourself out there. Love it. So you are juggling a lot. How do you

find balance with all of it? I don't try to find balance. I love what I do.

I love my kids. I have great friends.

And somehow I try to prioritize in any given week what matters the most in that

week. And so, you know, I'm an empty nester, and so my kids are all on the East

Coast, so I prioritize calling them and trying to do things for them or with them,

but they're not at home. And that affords me the time now when I can invest in

work and lead. And I love what I do. I love what I do. And if you love what you

do, I don't consider it work. I consider the people I spend time with at work,

often friends, my co -founders, I'm friends with, and I enjoy my clients.

I enjoy, not every day, by the way, I enjoy what I do. And so I could spend all

day long doing it. I could wake up in the middle of the night and think about

what I'm doing. I love it that much. And it enables me to engage in a more

holistic way that at any given time, I might prioritize one or the other more or

less.

I always try to do things with my kids. I describe myself as a puppy. Like when

they're around, I literally just wait for them in my house and try to go do things

with them. And like a puppy, you're just waiting for You know, they know that they

have my unconditional love and they know that I would jump at the moment to do

anything with them, but I do try to engage them in my job as well in that I want

them to learn what it's like to run a business in ways that they might find

interesting to who they are and what they like. You know, my Middle daughter

Charlotte, for example, loves writing. And so I'd want her to work with one member

of my team who does more of our marketing. She's not going to be an engineer, like

my eldest is going to be. And so I don't want to have my middle spend time with

my engineers when she's going to hate it.

But I do try to engage my kids and even their friends. I run an internship

program. program, I call the ineptism program. And if my friends or people who work

with us have kids that need summer jobs, I want to employ them. And I do,

you know, I don't, I don't stop people I know from getting jobs. I do the

opposite. People I know who have kids that want to be employed, I want to hire

them because I want to meet them and I want them to love what I do. And if I

can help engage them and make them more excited about working in finance, I'm happy

about that. And so I call up my nepotism program and I try to run this summer

internship program for people.

It's not the most organized program, but I do try to make sure these kids have

summer jobs and get started somehow. - I love that. I can tell that's just another

way you step into your relationships too. That's like you leaning into those

relationships that are important to you, which I love seeing. - It is, although

sometimes I get a little bit too mom, like last summer we had interns and I knew

half the parents and I would literally take pictures of these kids and like send it

back to the parents as if I was their camp counselor. It was very hard to remove

myself. - I loved that, their parents probably loved it. Their parents - You loved

every bit of that. - I couldn't help myself though. I remember one time I called

one of the dads and I was like, okay, your daughter is killing it. No one would

ever tell me this, but I just want you to know this. Like your daughter is a

killer intern and here's what she did. And honestly, like it brings tears to my

eyes. Like the dad was so appreciative because like it's not like someone's boss

it's so it's half inappropriate but I don't really care. That's what kids are

signing up for when they come to the lead bank nepotism program is that they're

going to get me reporting into their parents on what it's like to work with them

as a colleague. Yeah I had an instance recently where a good friend of mine from

way back in my days in DC her daughter was doing something in Tri Delt on I got a

huge compliment on her and I sent it to her mom I said, "You don't get this. You

don't get to hear about your grown children doing amazing things very often, so I'm

going to share this with you." I think it means even more as they grow older

because you just, you don't get report cards and teachers telling you things and so.

No, I love it. And I also, we've had a lot of great young women in turn and I

use it as an opportunity to make sure they understand what it's like to work in

finance. I have a great group of women who work with me and they're each impressive

in their own right and I think they're great role models for a lot of the interns

and so if I can take someone's child and have them work with me even for a few

weeks in the summer to me I maybe it'll help you know create a spark in their

head I'm happy to do it. Yeah I love that. So tell Um, you get this call that

you've been named a 2025 woman of achievement. How does that feel? What does that

recognition mean to you? And I was really touched, um, tried out meant a lot to

me. And I love meeting tried outs in life. Um,

and someone sent me a note, someone in Silicon Valley sent me a note and she saw

the tried out announcement And I honestly, it made me tear that someone saw it,

who I didn't even know was a try -doubt. And I just got touched by it because he

was a try -doubt from another school. I think the power of women's networks is

incredibly important in women's lives where it's such a pivotal point in the world

right now when we need to assert our own voices and have the power to control the

narrative about what we want for our own lives. And I think women's networks are

really important in doing that, in building relationships, in building camaraderie,

building business networks. And so Tridel is one of the more formative ones in my

life. And so I'm certainly thankful for it. And I'm appreciative of being recognized.

I'm not, I don't consider somewhat of an achievement, but I get it. You know,

I find it weird actually, but I do understand, and I'm just appreciative that I had

the network and I have great peers from school and that I've met along the way who

are Tri Deltaz that I can have a shared experience with. - Yeah. So I know one of

the other things we get from Tri Deltaz is this sort of this thinking of service and

philanthropy, this foundation of service and philanthropy. For you, I know you serve

on several boards and you're deeply involved in philanthropic work. How do you decide

where to put your efforts these days? - I've tried not to make it performative. You

know, where I've been involved in philanthropy, I've tried to be on an investment

committee, for example, associated with my high school, which was the Petty School,

or at Penn, where I'm involved with Wharton. Like I try to actually make it quite

action and business driven. And I also have tried to do things that are core to

helping people. So for example, we took in a foster child and helped him.

He was a UN refugee from Somalia and I thought I had no agenda other than helping

a child want to have a better life. You know, I wasn't trying to get anything from

the system. I just saw a need to help support someone who was a teenager who was

living in the United States and if I could do that and have someone live in my

home because I had tons of space, I would love to contribute in a way that

actually helped people. And so I've tried to do both ends of the spectrum,

but really stay away from performative charity where I sit on a board that I do it

for a visual meaning as opposed to something that truly is meaningful to me. I only

have a limited amount of time and so I've really tried to stick to very sincere

things. You know and then I've also tried to take care of the people who are in

my life and if there was someone who I felt made an impact in my life and I

could help educate their child and support their child in whatever school they go

to. That's the kind of thing I want to go to. It's invisible, but it's not

invisible to the person who has made an impact in my life over the years.

And so those are the things that matter more to me. I describe it as if I go to

one less chicken dinner and I actually can help a kid whose mom has been in my

life in some support or service know,

that's kind of what's important to me.

And, you know, try out an example,

like try to have an impact in my life, if I can be important to try to let me

try to do things that that give back to the community in ways that that gave back

to me. Yeah, I love that. You definitely know your impact. Alright,

I'm going to lighten it up a little bit here. A few lighthearted questions. What's

one app that you can't live without?

I can't live without Instagram. Okay. I can't live without news apps.

I'm a pretty diehard news reader. And so I have, you know, the journal, the post,

the FT, the New York Times, ground, Axios, the information,

so holistically news. And then I like the new Peloton Strength app.

I think Peloton's killing it. And then there's a Pilates app that I really, I know

that's more than one, but there's a-- - Oh, that's exactly. - I really like-- - That

sort of leads into the next question maybe, which is what's your favorite way to

unwind after a long day? - I have a workout routine that has changed my life.

- Okay. - And it's a combination of strength -based Pilates, so legre and Pilates I'm

obsessed with, obsessed. And I do it almost every day.

I have my own Pilates machine. I go to legre in classes. I really enjoy it. And

I've never had abs in my entire life until doing Pilates. I didn't even know abs

were under there. And then the second thing I do is I walk on a treadmill for

miles during a day. And if I have a one on one with a colleague, I try to do it

on the phone and I walk on a treadmill, even if I'm in flip flops like Hoka flip

flops. Yeah, I'm in jeans. I just try to go very slow speed, get an extra mile in

while I'm on a conference call. So that is my methodology. If I want to watch a

TV show for an hour, rather than lie in bed and watch it, I get on a treadmill

and walk it like very low speed. Totally changed my life.

Okay, those are good tips. Last one, what's the most unexpected skill you've picked

up over the years? First,

My most unexpected skill is that I know how to twirl the baton.

It's so jersey. We have this in common. Oh, really? I twirled in high school.

This is so funny. Yeah. All right. So I know how to twirl. I was, uh, that was

like my skill as a kid. And for my fiftieth birthday, I surprised my dearest

friends by doing a routine in a full sequined outfit in Mexico.

And I had my friends crying. And it was pretty epic because nobody expected me to

twirl fire for them at age age 50 love this.

I love this so much. Okay, you're definitely coming to convention next summer. And

I'm definitely bringing my batons and we're gonna twirl. I'll do it. We'll terrify

people. I love it. I love it. I love everything about that. Um, well,

I'm just so excited to talk to you. What what's next for Jackie? What comes next

in life and career?

- You know, now that my kids are out of the house, I'm trying to help them evolve

as independent citizens of the world. And, you know,

it's a hard thing to deal with when you're used to living under the umbrella of

your parents. And I'm trying to teach them about work, you know,

getting first jobs, learning how to write the resume, learning how to be good

professionals. And that's the thing I'm most focused on other than my own work life,

that and my own personal life. And so, you know, I do think it's fun to watch

your kids become young adults and apply for jobs. and I obviously want to help them

where I can but just like I do to kids who apply to me and I know the parents

you know like they need to learn how to be independent and I really enjoy helping

them learn okay write an email and send that email to XYZ person like I'm not

doing it for you you go do it it's your job and I'm enjoying watching them

flourish as independent young adults. It really, it makes me so happy every day.

I love that. Well, that's a good place to end. Happy family time.

Jackie, thank you so much for joining us today. We're just so honored to have you

in the sisterhood. So excited to recognize you as a woman of achievement and really

appreciate you taking some time to share your story today. I know everybody will

love hearing it. Oh, very appreciative. Very appreciative. Thank you for the honor.

Thanks. And to our audience out there, we hope you'll like, subscribe, and rate our

podcast. We have three stars in our crescent, but we love those five star ratings

for the podcast. Thanks for joining us, and until next time, Delta Love.

(upbeat music)