Leadership to me is all about trust: a good leader trusts their team and is trusted by their team in return. There are many ways to build that foundation, but it certainly doesn’t have to be confined to those in a traditional leadership position.
As part of my series about “individuals and organizations making an important social impact”, I had the pleasure of interviewing Bridget Haile.
Bridget Haile is the VP of Operations and Client Experience at Summer, a fintech startup and certified B corporation on a mission to simplify student debt repayment and forgiveness. After years spent at the intersection of finance, tech, and human advice, she is passionate about using technology and empathy to make complex financial systems more accessible and understandable for everyone. Previously, Bridget led the Client Experience team at Ellevest, an investment platform designed to get more money into the hands of more women, and she is a graduate of Harvard University.
Thank you so much for joining us in this interview series! Can you tell us a story about what brought you to this specific career path?
Like so many people, I had a bit of a winding road to where I am now — I didn’t start out knowing I would be working to help people with student loan debt. In fact I started out as a professional musician, singing classical music both here and abroad. During those years of trying to pay down my student debt while pursuing my career in music, I took any odd job under the sun: I was a waitress, a closed captioner, a receptionist, a content writer, an SAT tutor… the list goes on! Anything to make my minimum debt payments while giving me the flexibility to pursue my goals.
After a few years, I realized I needed a new set of professional ambitions — one that could grow into a sustainable lifestyle while I still performed as much as I could. I stumbled into my first job outside of music at a wealth management firm, and surprised myself by actually enjoying it. I liked being able to take a complex and opaque system and harness it to help individual people get meaningful results. It feels impactful on a few different levels to help hard-working individuals maximize their retirement savings, and a real passion for financial planning and management developed in that first role. Everyone should have the opportunity to make the system work to their advantage (even while recognizing that the system itself is unjust) — I wanted to be the expert so that my clients didn’t have to be.
Eventually I wanted to take these skills to groups that needed it more urgently, which led me to Ellevest, a mission-driven startup focused on closing the gender investing gap, and then to Summer. As someone whose student debt pushed me into this field in the first place, I wanted to help provide the answers that I was never able to find on my own. Even in the financial advising field, there are very few resources for borrowers who aren’t in a position to pay off or refinance their debt. I truly value feeling like I am making an impact every day in people’s financial lives — student debt is often square one in figuring out a stable financial future.
Can you share the most interesting story that happened to you since you began leading your company or organization?
I sometimes like to call the student loan world the Wild Wild West — anything can happen! We’ve seen that so clearly over the past three years as payments and interest have been paused on federal student loans for the first time in history, and nearly every week since has brought fresh policy changes to existing student loan programs as leaders try to bring incremental positive change to a challenging system. (Those waiting anxiously on the fate of the new $10,000 forgiveness program will know this very well.) My time at Summer has been a lesson in adaptation — a constant revolving door of new rules, new programs, new next steps for borrowers to take. The challenge has been to provide a voice of sanity, clarity, and empathy in all of the noise.
One salient example was the introduction of the Public Service Loan Forgiveness Limited Waiver in October 2021 — this was a temporary and retroactive expansion of the strict rules for this program that had resulted in a 98% rejection rate. Demand for Summer’s tool’s exploded during this time as borrowers tried to untangle the changes, and my stalwart and wonderful team worked to navigate a brand new set of guidelines and an unprecedented level of interest. We’re proud to say that Summer has achieved nearly eight million dollars in loan forgiveness under this program — and counting! We expect that to continue to rise as more and more applications are processed. Every one of those dollars is a dollar back in someone’s pocket, and we’re lucky to get to celebrate that with the borrowers and also with each other.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
On my first day of work at my first real job, I asked one of my coworkers what a mutual fund was. (Mutual funds were a big part of our business, so this was not a great thing to betray my total ignorance of so soon after being hired!) Rather than stare at me like I was crazy, this coworker instead took the time to gently and clearly explain funds and how they fit into the bigger picture of investment vehicles. More so than my own mistake, in retrospect I’ve learned from my coworker’s response. I try to channel that level of patience and kindness (not always successfully!) with people I interact with professionally — she set a wonderful example and made me feel safe and supported in a brand new environment.
Can you describe how you or your organization is making a significant social impact?
When you’re dealing with student loans, particularly federal loans that make up more than 90% of the total, you’re dealing with an absolute labyrinth of programs and requirements. Approaching your student debt on your own is like filing your taxes without an accountant or tax software. There are plenty of people who do it on their own! But it’s hard to do and easy to mess up: you might not get the best deal that you possibly could, or you might make a mistake that can have severe negative consequences.
Summer is like your accountant or online tax program — we can help you both maximize what you are eligible for while also helping you avoid critical mistakes. We help people save money and simplify their student debt through combining personalized recommendations and streamlining access to federal repayment and forgiveness programs.
Summer is a combination of smart people and smart technology: we use both human support and online tools to make sure that you can afford your monthly payment and get any forgiveness that might be on the table. Our goal is not just to educate you, but actually make sure you’re taking action and getting the successful outcomes from these programs.
Summer has helped over 100,000 borrowers save an average of $350 per month on their student loan payments and $32,400 on average over the course of their student loan repayment. It’s a huge impact, especially when those savings are going toward buying a home, saving for retirement, having children, or reaching other financial goals — something that far too many borrowers need to postpone.
Can you tell us a story about a particular individual who was impacted or helped by your cause?
There are so many I can think of here, and that’s a wonderful position to be in! Our team likes to celebrate “Forgiveness Fridays” where we share our favorite forgiveness stories from the week.
Two of my all-time favorite stories are Nicole and Richard. Nicole is a non-profit worker in Cleveland who wasn’t eligible for forgiveness not because of her employment, but because of the details of her loans. Under new expanded rules, Summer helped Nicole get about $147,000 in student loans forgiven tax-free. I still read this quote from Nicole when I’m having a tough day and need a reminder of why we do what we do: “The Summer program has changed my life which means “CREDIT” score by a whopping 70 points! Five more years of stress have been eliminated with the PSLF waiver! I am forever grateful, I have GREAT CREDIT now! Didn’t really see paying $145K+ off in this lifetime without winning the lottery.”
Richard is a long time community college professor who is going to retire next year. It’s a common misconception that student loans are just a millennial and Gen Z problem. The fastest growing group of student loan borrowers is actually people over 50, many of whom are taking out student debt for their children. Summer also helped Richard get over $90,000 in forgiveness, and he’s now heading into retirement debt-free. I feel so genuinely honored to be able to contribute to this type of impact.
Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?
One of the most important things we can address is the cost of higher education. Student debt is a symptom of our broken college cost funding system, and the crisis will only continue to grow unless we offer affordable access to higher education. Of course, we still need to support the more than 40 million student loan borrowers who are currently dealing with this problem, but nothing will truly get solved until we address the fundamental issue.
The second thing we need to address is persistent money gaps that exist across race, gender, and disability lines, among others. Student debt exacerbates the existing economic inequalities in income, wealth, investing, and funding access. And it’s a compounding problem — on average, a Black borrower needs to take out more loans for college than a white borrower does. Because of the income gap, they may earn only 80% compared to their counterparts and pay back their debt more slowly, owing more over time in interest, and therefore have less time to build equity and assets in other financial areas. These endemic issues are interconnected and need to be addressed together.
Finally, we need to improve financial education. One of the most common questions I get is: “Why didn’t I learn any of this in school?” And I can’t come up with a good answer, because we should have! Part of the reason I’m in this career is so that not everyone needs to become a student debt professional to know how to handle their own. The same goes for credit card debt or retirement savings. An investment in basic financial principles in our education would go a long way to avoiding some of the most common financial traps.
How do you define “Leadership”? Can you explain what you mean or give an example?
Leadership to me is all about trust: a good leader trusts their team and is trusted by their team in return. There are many ways to build that foundation, but it certainly doesn’t have to be confined to those in a traditional leadership position.
I think one of the interesting things about working in the startup world is that the people who have made the biggest impact on my career are often my peers, not my managers. There’s a difference between a mentor and a sponsor, and I have found through my previous work that my peers are my sponsors — they’re the ones who speak my name when I’m not in the room and advocate for me when I can’t myself. And I hope that I do the same for them! We coach each other, make sure everyone gets credit, and support each other as we go through our careers. It’s been wonderful to rise together, and I’m excited that we will continue to do so.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
In college, I was fortunate enough to know and learn from the Reverend Professor Peter J. Gomes. One of the things he said that I’ll always remember is: “Gladness should never be excluded from our daily routine.” I’ve carried it with me every day since. I hear it as a call to celebrate the beautiful, mundane, daily things, which to me are an essential component of being human. Sometimes it can feel like we’re tilting at windmills as we fight for student loan borrowers in an unjust system. Knowing Professor Gomes, I’m sure he chose his words very carefully — maybe happiness can’t be achieved every day, but I think that gladness can be.
Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂
Professionally, it has to be Eileen Fisher — I love not only her clothes, but also her commitment to sustainability and equity as she’s thoughtfully and built a successful business. I want to pick her brain about the beautiful way she’s identified and leaned into her own strengths and weaknesses as both she and her company have grown.
Personally, it will always be my Grandma Iris. She is the most elegant, kind, and loving person I’ve ever known. If she’s cooking our meal, even better!
How can our readers further follow your work online?
You can follow me on LinkedIn and check out Summer’s Blog.
This was very meaningful, thank you so much. We wish you only continued success on your great work!
Social Impact Heroes: Why & How Bridget Haile of ‘Summer’ Is Helping To Change Our World was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.