Leaving Chicago — or even Illinois — never crossed Phyllis Cavallone-Jurek’s mind.
“We’re South Side Chicagoans, and we pride ourselves as always having that ZIP code,” she said.
Over the years, Cavallone-Jurek’s commitment to Chicago and her community expanded from starting as a math teacher to, most recently, serving as executive director of the nonprofit Ladder Up.
The Chicago-based organization has 13 locations and offers a number of financial resources to Illinois residents, from free federal and state tax preparation to helping students get financial aid for college. Last year, Ladder Up helped more than 27,000 people, returning $45.5 million back to the community.
Cavallone-Jurek joined the nonprofit in 2021, after serving as chief of academics for the Office of Catholic Schools for the Archdiocese of Chicago. She also served as principal at St. Therese Chinese Catholic School in Chinatown, where she helped transform the once-struggling school, receiving a Stanley C. Golder Leadership Award from the Golden Apple Foundation in the process, and was named a national distinguished principal of the year in 2017.
Cavallone-Jurek recently spoke with the Sun-Times about how Ladder Up is preparing for the upcoming tax season, the widening digital gap and her goals for the organization. This interview has been edited for length and clarity.
Q. You have an extensive career as an educator and administrator. Was it a big transition moving into the nonprofit world?
A. I connected with the founder of this organization [Robert Burke], and as they say, I was hooked. What a great mission. The three services that we do and how they intertwine is always about education. Think back on your own educational experience. You rarely had a full course on financial literacy. A lot of norms in families is they don’t talk about financial literacy. We don’t talk about money, period. So where do we learn this? We see a few habits around us and then — boom — we are forward in some adult decisions around 18, sometimes sooner and sometimes later. If they’re not the best decisions, or we don’t have good habits, individuals can find themselves in places that they would not have guessed they’d be in. So to me, it is indeed full circle. I’m still an educator. I’m just doing it in a different capacity.
Q. How has this role challenged you?
A. We’re serving the Chicagoland area right now, but trying to reach out to more corners of Illinois and rural communities. Obviously, in the role of an educator at the principal level and then my diocesan level when I was with the Catholic schools, we either covered a community or a larger community. So geographically, I am trying to understand better the communities we serve. It is incredibly important that we understand our clients — those we work with we call clients — and the communities. We shouldn’t go in and make any assumptions. We need to do our homework.
Q. Expanding to other parts of Illinois — is that part of the nonprofit’s growth plans?
A. Yes, that’s it. We’re one of the biggest VITA [Volunteer Income Tax Assistance] programs in the country. I’d like to solidify it, not just to wear that, but to serve more points in Illinois. We always talk about in large cities, and Chicago’s one of them, there are times that there are deserts for financial services — reliable, trusted services. Sometimes the services could be predatory in nature, so what we do is really, really important in the communities that we serve. There are large geographic regions where there isn’t a VITA program. We are working with our different agencies and government partners to figure out what areas can we expand to.
We went a bit farther north this year. We’re adding a site in Waukegan. We’re adding another site out west. Next year, I hope to go a little farther south and a little farther west. I hope when we connect in five years you’ll see us perhaps literally all over Illinois. I would be thrilled.
Q. But I’m guessing this means the demand for volunteers will also need to increase?
A. Correct. This year, our target is about 900 volunteers. We had about 750 volunteers last year. Pre-COVID, the volunteer numbers were about 900 to 1,000, so it’ll feel good to go back to that. When we think of a location, it’s more than, ‘Oh, you have a physical site.’ We have to think around that area. Would there be corporate partners? Would there be universities and colleges? So that we can both staff it with a combination of not only our internal team at Ladder Up but maybe college interns, college volunteers and corporate partners. It’s a bit of a formula to make sure we serve appropriately. We don’t want to have our doors open and not be able to serve.
Q. Have you ever needed to turn people away because you couldn’t meet demand?
A. We’ll see a spike in the beginning of the year for taxpayers that might have just a couple things, a pretty straightforward filing, and then it’ll dip just a bit in March, and then the last two weeks of March until April 15 is heavy. You will see some significant lines.
We do our best. But I’m always impressed when I go to a site and there’s a huge line. You just feel the volunteers — it’s almost like the fourth quarter in a football game, they really just rally and do their best. And we’re always looking at how to increase efficiency, whether someone will come out to help with the intake line so we can process faster.
Q. The IRS is making a bigger push to offer free e-file services and make the tax process more paperless. Is that a concern for Ladder Up?
A. We must not forget that particularly during COVID, I think the digital divide got amplified. What I mean by that is … [video calls] became norm. Well, I think of people like my mom. She is never going to know how to download a document, scan a document, go on the Internet. She may learn how to do some basic stuff, but that is very advanced for a lot of people. When you work one-on-one with a number of people, you realize some are really not able to access things via the internet even if it is accessible. And then there’s a whole pocket of people where it’s not accessible; they don’t have it. And if they’re low-income, they might not even have the technology even if they have the skill. So it’s just layers and layers.
We try to help clients as much as we can, but that is definitely a reality. And yes, over and over again, that we have to think in terms of if we build out one thing, we have to keep building out the other service, like also in-person and digital. The IRS, they’re great partners with us. We very much enjoy working with them, and they’re committed to improving the taxpayer experience on every level. They come out many times, and they talk to us, and they want to see how things are in action, and they take that back into their thinking, and I applaud them for it.
Q. You recently completed your doctorate in interdisciplinary leadership. How do you see your research on volunteerism helping Ladder Up become more successful?
A. As you can imagine, to recruit volunteers is a lot of work. It’s a pretty competitive space. There’s a lot of lovely organizations out there that someone could say, ‘Let me volunteer.’ I want a volunteer that wants to do taxes and wants to go through training and is willing to take a certification test — that’s a lot. I have to really understand how and why they come to us in the first place and for them to return, which I want them to do.
Success is really increasing our impact every year — significant growth so that we know we bring no cost, reliable, trusted service to those that need it and to more areas of need and communities that are without the resources. So just looking back and going, ‘Wow, I started and here are our numbers, and I just had a really nice growth over that time.’ Yeah, I want us to connect and go, ‘Remember when we talked about going to all corners of Illinois?’ I want to be there.
