Jacksonville attorney displays knack for being on a fast track
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Jacksonville attorney displays knack for being on a fast track
By Brian Cox
Defense attorney Hayley Crosby practices law under a straightforward philosophy that she can easily explain to her young son: Everybody play fair.
It’s a mindset that guides how she evaluates cases, how she interacts with opposing counsel, and how she has built a solid reputation in North Florida’s legal community.
Now a partner at Saalfield Shad, P.A. in Jacksonville, Fla., Crosby got an early jump on her legal career, enrolling at the University of South Carolina School of Law at the age of 20. Looking back, she acknowledges that being so young put her at a bit of a disadvantage. Many of her classmates brought years of work experience, marriages, or even second careers with them. Concepts like property ownership or family law carried a practical familiarity for her peers that she had yet to experience.
“I was really learning how to be an adult, too,” she says. “So that was definitely a bit challenging.”
Born in Honolulu to a military family, Crosby spent her earliest years growing up in San Diego before eventually settling in Jacksonville, when her father was reassigned there as she entered fifth grade. Her father’s deployments included a long stretch in Iraq during her high school years, and Crosby learned to adapt and “go with the flow.” Her father expected discipline and rigor from his daughter.
“My parents were always very strict with me about grades,” she says, adding that her dad would email from Iraq asking about her homework. “They instilled that in me, and I always knew they were in my corner.”
At Fletcher High School, Crosby accelerated through her coursework, skipping 11th grade entirely, which positioned her to head off to college at 16.
Initially, she envisioned a future in medicine. She enrolled at the University of South Carolina as a pre-med student, but the reality of clinical exposure quickly shifted her thinking. A summer program that included time in a cadaver lab made it clear that the medical field was not the right fit for her.
“I was the only person in the room absolutely disgusted by what was going on,” she recalls with a laugh. “I looked like I was about to pass out. Even the smells, the sounds, everything was just not for me.”
Hayley and her son, Royce, enjoy a wide range of outdoor activities, including rock climbing on occasion.
At the same time, an elective in criminal justice sparked a different kind of interest – one rooted less in science and more in analysis, writing, and human behavior.
Crosby switched her major to criminal justice and added a minor in English. She had always been drawn to writing, often choosing creative writing courses over other electives, and she found that legal reasoning offered a structured way to channel that inclination. Even so, law was not yet a foregone conclusion.
She graduated from college early, finishing a semester ahead of schedule. That acceleration left her at an in-between period – technically finished with undergraduate education but not yet committed to a career path. She worked on an auditing project for the South Carolina Department of Revenue and explored an interest in politics, including involvement in a statewide education campaign.
Law school entered the picture almost by accident. When a friend began studying for the LSAT, Crosby decided to take the exam as well. When her score came back competitive, she submitted a last-minute application to the University of South Carolina School of Law – on the final day applications were accepted. Within days, she had an acceptance letter.
Just like that, her next chapter was set in motion.
Crosby immersed herself in the academic and extracurricular life of the law school – serving on the Journal of Law and Education, participating in the Student Bar Association, and holding a leadership role with the Animal Legal Defense Fund. She also explored a growing interest in education law, influenced in part by her earlier political work and by research into inequities in school systems, particularly for underserved students.
Still, her eventual focus would shift again.
After graduating in 2017, Crosby returned to Jacksonville and began navigating the realities of early legal practice. She worked in personal injury and family law settings before finding her footing in insurance defense – a field she had not initially set out to enter but one that ultimately aligned with her strengths and instincts.
Her introduction to litigation coincided with another life-changing development. While preparing for the Florida Bar exam, Crosby learned she was pregnant. She took the exam at seven months along and learned she had passed just after giving birth. The transition into motherhood, combined with the demands of a new legal career, reshaped her priorities almost overnight.
As a single mother, Crosby had to build a career that was not only professionally meaningful but also sustainable. Early roles in a high-volume personal injury practice proved difficult to reconcile with that balance. Insurance defense offered a different structure – one that allowed for more predictability while still providing the intellectual challenge she valued.
Over time, Crosby developed a particular appreciation for the investigative side of litigation. Reviewing medical records, analyzing claims, and testing the consistency of a plaintiff’s narrative became central to her work.
“I love to find out if people are telling the truth,” Crosby says. “I like my job because I believe I help keep people honest, and I help keep businesses honest.”
That approach reflects the theme she returns to again and again – fairness. In her view, the legal system functions best when all parties operate honestly, from the accuracy of claimed injuries to the conduct of the businesses she represents. Her role is to evaluate those elements rigorously and advocate accordingly.
Mirroring her academic path, Crosby’s career progression has been both steady and accelerated. She gained significant trial experience at a smaller firm, often traveling with her young son and relying on family support to manage logistics. Those years helped build both her courtroom confidence and her professional reputation.
Hayley and Royce recently took a trip to Universal Epic Universe theme park in Orlando where they posed in front of the Phoenix Arch, a fictional Parisian wizarding monument featured in the “Fantastic Beasts” films.
She later joined Saalfield Shad, P.A., where she now serves as a partner. She reached that milestone just before her 31st birthday, achieving a goal she had set for herself long before becoming a parent. Along the way, she established herself as a prepared and pragmatic litigator, known for professionalism and a straightforward approach to opposing counsel.
That demeanor is, in part, intentional. Early in her career, Crosby often encountered skepticism tied to her age. She recalls being mistaken for a paralegal or being told she looked too young to be the attorney handling a case. In response, she leaned into preparation – ensuring she knew the law, the facts, and the strategy more thoroughly than anyone in the room. Over time, consistent performance replaced other people’s initial doubt with respect.
Hayley has two adorable dogs, Frankie and Lizzie.
“I've found one way to establish credibility is by being honest and being kind and making sure that people know you are in control of the situation,” she says. “I think there's a way to be respectful and to make practicing law enjoyable, and I think I have a good reputation for being easy to work with.”
Her practice today reflects experience and perspective. She handles a range of civil litigation matters, including premises liability, insurance defense, and retail and hospitality industry defense. At the same time, she maintains an interest in education-related issues and sees potential for that focus to reemerge later in her career.
Saalfield Shad has proved to be a good fit for Crosby. She values the mentorship Blake Cole has offered and the camaraderie the firm fosters.
“I think that the firm makes a conscious effort to make sure that we do things together,” she says. “People stay here for a long time. The firm just keeps its promises about where your career is headed and there's room for growth and opportunity.”
Outside the office, Crosby’s world is centered on her son, Royce, and their two wiener dogs, Frankie and Lizzie. The mother and son’s lives are closely intertwined, from daily routines to travel adventures to dinner at fancy restaurants with friends.
“All my friends joke that he's like our 30-year-old friend trapped in a 7-year-old's body,” says Crosby, laughing.
Motherhood can sometimes be a humbling experience, she adds, “but it's definitely made me realize I can do hard things.”