Jenny Bradley
Attorney / Firm Owner
Overview

Experience
- Practicing Family Law for 28 years
- Board Certified Specialist in Family Law
- NCDRC Certified Mediator – Family Financial
- Practices Collaborative Law
Assigned Paralegal
Jenny has always loved a good competition — whether it was on the softball field, at a trivia night, or during an intense board game. She likes to win as much as anyone, but she’s also learned that the real victory comes from knowing when not to compete. That belief has shaped everything about how she practices law and how she built Triangle Smart Divorce.
After years of watching good people get stuck in unnecessarily painful, expensive, and dramatic divorces, Jenny decided to create something different. Her philosophy is simple: divorce doesn’t have to be the battle you see on TV. The best outcomes come from staying out of court whenever possible, focusing on realistic resolutions, and helping people move forward.
This became the foundation of Triangle Smart Divorce. Jenny built the firm to help smart people make smarter choices about marriage and divorce. She hand-selects attorneys who share her mindset and trains them in “the TSD way” — a collaborative, strategic, empathetic approach that helps Clients get to the other side of their case with clarity, confidence, and dignity.
These days, Jenny spends more time leading and mentoring than litigating. She believes the best results come from collaboration. Every attorney and paralegal brings a unique background, perspective, and area of expertise to the table. Through regular mentoring and case review meetings, the TSD Team works together to tackle questions, share insights, and find creative solutions. The goal is simple: every Client benefits from the collective experience of the entire Team, not just one attorney’s point of view. It’s a philosophy that keeps the firm smart, innovative, and always focused on what’s best for our Clients.
And although she might have hung up her courtroom cleats, Jenny still enjoys working directly with Clients on one of her favorite parts of family law: helping couples protect their future and avoid divorce altogether through smart, thoughtful premarital agreements.
Jenny also gets it on a personal level. As a stepmom, she knows the effort it takes to make a blended family work. And as a small business owner, she understands the long hours, the risk, and the heart it takes to build something from scratch, and why it’s worth protecting when life shifts. That personal perspective guides the way TSD supports families and business owners — helping them protect what matters most while keeping the process as clear and calm as possible.
Triangle Smart Divorce has come a long way since Jenny started it — now one of the fastest-growing law firms in the country and featured on the Inc. 5000 list for 3 years in a row. She built the firm in Cary because she loves the Triangle and the people who make it what it is. The folks around Raleigh, Durham, and Chapel Hill are smart, driven, and down-to-earth. They care about doing things the right way, not the dramatic way, and that’s exactly who TSD was built to serve.
When she’s not leading the TSD Team or championing a smarter approach to family law, you’ll find Jenny reading or listening to books and podcasts, exploring local restaurants, or driving her Jeep through Aruba. She’s still a competitor at heart and still loves 80s trivia, but these days she finds she’s more likely to be slipping 80s facts into conversation than racking up trivia wins.
Education
- 1998 University of North Carolina JD – Juris Doctor
- 1995 Emory and Henry College Bachelor's Degree
Recognitions
- 2025 Super Lawyer, North Carolina Super Lawyers
- 2024 Super Lawyer, North Carolina Super Lawyers
- 2023 Legal Elite, Business North Carolina
- 2023 Super Lawyer, North Carolina Super Lawyers
- 2022 Super Lawyer, Super Lawyers Magazine
- 2021 Distinguished Rating, Martindale-Hubbell®
- 2021 Super Lawyer, Super Lawyers Magazine
- 2021 Legal Elite, Business North Carolina
- 2020 Super Lawyer, Super Lawyers Magazine
- 2019 Super Lawyer, Super Lawyers Magazine
- 2018 Super Lawyer, Super Lawyers Magazine
- 2017 Super Lawyer, Super Lawyers Magazine
- 2016 Super Lawyer, Super Lawyers Magazine
- 2015 Super Lawyer, Super Lawyers Magazine
- 2015 Legal Elite, Business North Carolina
- 2014 Legal Elite, Business North Carolina
- 2013 Rising Star, Super Lawyers Magazine
- 2012 Legal Elite, Business North Carolina
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What Our Clients Say
There aren’t enough words to express what Ashley Fillippeli and her team have done for me… With calm focus, sharp legal skill, and an extraordinary amount of heart, Ashley helped me find my child… That moment would not have happened without Ashley, and my child would not have a father without her help.
Baseer Maroof
Triangle Smart Divorce is the best family law firm in the area, and I am so grateful to have had them on my side. Lisa, Diane, Lauren, Jessica and the whole TSD team were very knowledgeable, thorough and professional. They did an excellent job getting great results for me and my kids during very challenging circumstances.
Book Fanatic
Lauren did an excellent job representing me throughout this entire process. From start to finish, I felt confident trusting her guidance and decisions, and I always knew I was in capable hands. She was professional, knowledgeable, and supportive every step of the way. I would highly recommend Lauren and this law firm to anyone going through a custody battle.
Brian Sechrest
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