Meet the Sasso Guerrero & Henderlite Team
CRAIG SHOUP
Craig Shoup is the Chief Operations Officer at Sasso, Guerrero & Henderlite, widely regarded as North Florida’s premier family law firm. In this role, he oversees the firm’s business operations, administrative functions, and strategic projects, ensuring efficiency, growth, and exceptional client service.
Craig brings extensive experience from both the legal and public sectors. He previously served as Executive Director of the Jacksonville Bar Association, managing organizational operations, membership engagement, and major initiatives supporting the region’s legal community. Earlier in his career, he served as a Staff Assistant in the Office of the Public Defender and as Special Assistant to the Clerk of the Court for Duval County, roles that provided valuable perspective on court administration and public service.
A graduate of Flagler College, Craig remains active in the community through his work as a high school and college football official and his involvement with Jacksonville University Athletics. He lives in Jacksonville with his wife, Carrie, and their two rescue dogs.
ALEX BLINN
Alex Blinn joined Sasso Guerrero & Henderlite in 2026. Born in raised in Jacksonville, she is a graduate of Bishop Kenny High School (Class of ’16) and attended the University of Florida with a Bachelor’s in Sociology. After moving back from Gainesville, she began her Master of Business Administration with a specialization in Marketing online with the University of West Alabama. Alex brings her experience and knowledge of Marketing to the firm to expand brand awareness as the premiere North Florida Family Law Firm.
In her free time, Alex enjoys attending sporting events and concerts. She also enjoys spending time her family, friends, boyfriend (when he is home from Navy deployments), and their rescue German Shepard, Pinot.
PAULINO ESTEVEZ
Paulino Estevez joined the Sasso & Guerrero family in April 2021. As a Tampa native, he moved to Jacksonville in 2015 to begin a new chapter in his life. Upon living here, he attended the University of North Florida and obtained his Bachelor’s Degree in International Studies and Spanish. As a native Spanish speaker, his goal in life has always been to follow the footsteps of his parents in helping the community.
Thanks to a little help from others, a little bit of kismet, and a little bit of “right place, right time,” he is happily embarking down his path in the field of family law. His initial position at Sasso & Guerrero was the firm’s receptionist/intake coordinator, but he was quickly promoted to operations manager, a position in which he thrived. With the growth of the firm to Sasso Guerrero & Henderlite, he has undertaken the new role of Finance Administrator, helping to support the financial side of operations at the firm. In his spare time, Paulino enjoys going out for hikes with his family, enjoying the local gastronomy Jacksonville has to offer, and cracking the “best” dad jokes.
JOSH WALLER
As our Firm Administrator, Josh Waller brings over 20 years of experience in Family Law. Born and raised in Jacksonville, he is a graduate of Riverside High School (Class of ’98) and attended Jacksonville University, studying Music Theatre and French.
Josh is passionate about the performing arts and is a multiple award-winning actor and singer, having performed on almost every stage in Jacksonville. He is also a co-founder of The 5 & Dime, one of Jacksonville’s many theatre companies. Josh lives in Murray Hill with his partner, Christian, and their dogs, Mabel & Olive.
CARI BARKSDALE
Cari graduated from Santa Fe College in Gainesville, Florida in 2011 with her Associate of Applied Science Degree in Legal Assisting. She began working in the legal field during her studies in college at a personal injury firm in Gainesville, Florida.
Prior to her employment with Sasso & Guerrero, she worked in the field of family law for over eight years, starting as a receptionist and moving up to the position of paralegal. Born and raised in Florida, Cari is a lover of all things outdoors including hiking, gardening and kayaking. Cari also is the proud mother of an 11-year-old son named Kahlil.
COURTNEY GILBREATH
Courtney Gilbreath is a Jacksonville native. She graduated from Bishop Kenny High School and attended the University of Florida and the University of North Florida, earning a bachelor’s degree in psychology. She joined the firm in 2008, after working in early childhood education and the financial sector for a number of years. She then returned to school at Florida State College at Jacksonville to complete the legal studies program.
As our paralegal, Courtney uses her background in banking and her knowledge and understanding of human behavior to help clients through the often daunting and overwhelming discovery process.
Courtney enjoys cooking, restoring her home located in the historic Avondale neighborhood, and spending time with her “fur babies,” Porter and Billie Rose.
JANELLE BRANTON
Janelle Branton became a part of the Sasso and Guerrero family in 2017. She was born and raised in Jacksonville, Florida. She attended the University of Florida, earning a Bachelor’s degree in Linguistics with a minor in teaching English as a Second Language.
After returning to Jacksonville, Janelle attended Florida State College at Jacksonville and obtained her Associates degree in Paralegal Studies. At the time of graduation, she was uncertain which field of law she wanted to pursue. After accepting the position at Sasso and Guerrero, she soon realized her passion for helping others. Working for Molly and Christie played a major role in her determining that working in family law was the perfect fit for her life.
A cornerstone member of the Sasso & Guerrero team, Janelle is responsible for some of the first stitches running through the fabric of the amazing camaraderie of the firm as it has grown. In her spare time, Janelle enjoys spending time with her family and traveling around the country to enjoy beaches. She is a proud mother of a little girl. She has made it a point to strive for her goals, which are nothing less than her grandest dreams.
STACY JIMENEZ
Stacy Jimenez joined the Sasso & Guerrero family in August 2021. She was born in New York and moved to Orange Park when she was 14 years old. Stacy attended Florida State College of Jacksonville where she earned an Associates in Arts degree and a Bachelor’s degree in Supervision and Management.
After college, Stacy started working at a family law firm and found her passion for helping families. She fits right in working with the strong (passionate) women at Sasso and Guerrero! Stacy has been married for three years to her Husband and she is the proud bonus mom to his daughter. Stacy enjoys spending time with her family and friends, attending Jacksonville Iceman hockey games, anything Disney related, and taking cruises to tropical destinations.
stepHAnIe KIMBLE
Stephanie was born in Amsterdam, New York but raised in Jacksonville, Florida. She started with Sasso & Guerrero in June 2023. She has worked in the legal field for almost 20 years and been a paralegal for 15+ years in various areas of the law. However, she believes that family law, where she has been working since 2014, is her true calling.
As dedicated as she is skilled, she enjoys helping others navigate through the emotional process of family law. During her free time, she enjoys spending time traveling with her family and loves music and comedy. She is a proud mom to a fabulous daughter, Kylie, who is pursuing a degree in radiography. She is also a crazy cat lady as a mama to a Mainecoon named Misha Stormborn.
ALANA MARTIN
Alana is a proud U.S. Navy veteran who served for 7.5 years. She moved to Florida and separated from the Navy in 2022. Alana is Mom and bonus mom to four kids and a poodle. A current Navy spouse, she knows all about balancing family and military life.
When she’s not at work, Alana loves to spend time with family and friends, reading, playing video games, hitting the beach, and indulging in all things nerdy, like Renfaire, anime conventions or anything else that sparks the geek within.
HAILEY RAILEY
Hailey is a native of Byron, Georgia, and a graduate of Georgia Southern University, where she earned her Bachelor’s degree in Criminal Justice and Criminology. Hailey’s career began in the legal field at a Criminal Defense firm in Macon, Georgia, where she discovered her true passion for helping others. Now, when she’s not working with her clients in the office, Hailey is running her small business, Sojourney Travel by Hailey Teston, a travel agency dedicated to curating memorable travel experiences.
Outside of work, Hailey enjoys spending quality time with her husband, Cameron, and their two fur babies, Remi and Rosie. Whether it’s planning or taking trips, spending time with family, or diving into a good book, Hailey loves balancing her adventurous side with moments of relaxation.
MAYA RANDALL
Maya is a proud full-time mom of 3 teens (two boys and a girl), originally from the island of Aruba. Prior to joining SGH, she spent the last 8 years shaping young minds as a VPK teacher, fostering creativity and growth in her students. She also attended Broward College where she majored in Accounting and Business.
When she’s not balancing family and work, she enjoys spending time outdoors, soaking in the beauty of nature. Whether it’s exploring new destinations on spontaneous day trips, or enjoying the vibrant energy of live music, she is always seeking new adventures and experiences.
STEPHANIE HEBERT
Stephanie started her legal career in Memphis, Tennessee, in 2019 where she attained experience in multiple areas of law and became a Certified Paralegal through the National Association of Legal Assistants in 2022.
After moving back to Florida, Stephanie joined the Sasso, Guerrero, & Henderlite family in May 2025. “Shebert” uses her empathy and competitive determination to help clients, and she loves seeing her work positively affect others. She is also our SGH Events Coordinator and enjoys creating events for our team.
In her free time, Stephanie enjoys activism, promoting positive mental health, and most importantly being her cat Wilson’s “fur mom”
and Aunt Steph to three littles.
KYLIE CHIARELLI
As one of our Intake Specialists, Kylie Chiarelli serves as the first point of contact for our clients, creating a welcoming and positive experience from the very beginning. She brings an organized and intentional approach to everything she does. She is known as a reliable, and collaborative team member. Kylie believes in finding balance, contributing positively to the spaces she’s part of, and continually striving to be better than yesterday.
Born and raised in Jacksonville, Florida, Kylie graduated from Oakleaf High School in 2024 and is continuing her education at Florida State College at Jacksonville, where she is pursuing a degree in Radiography. She successfully balances full-time work while attending school, demonstrating strong time-management skills.
Outside of work and school, Kylie enjoys planting and caring for her many houseplants. She also loves spending time at the pool or beach and adores her orange cat, Ging.
NICOLE HOLOVICH
Nicole is a Clearwater, Florida native with a passion for helping others. She earned her degree in Elementary Education and Special Education from Flagler College in 2015 and went on to spend five years as a teacher, where she developed a deep commitment to supporting individuals and families.
Building on that experience, Nicole transitioned into the legal field and has served as a legal assistant for the past four years. She brings a thoughtful, detail-oriented approach to her work and takes pride in guiding clients through the legal process with care and professionalism. Her background in education gives her a unique ability to communicate clearly and provide reassurance during complex situations.
Outside of the office, Nicole enjoys spending quality time with family and friends, attending live music events, and taking in Florida’s beautiful sunsets.
MAYLEE SEARS
Maylee brings a diverse professional background, with experience spanning multiple fields before transitioning into the legal profession, along with a genuine, people-first approach to her work. Growing up in a military family, she developed a strong sense of discipline, adaptability, and resilience—qualities that continue to guide her both personally and professionally.
Having also navigated life as a single mother, Maylee brings a personal understanding of the challenges many families face. Combined with her extensive experience supporting attorneys and working closely with clients, she understands that family law matters are often deeply personal. She is known for her calm, compassionate demeanor and her ability to help clients feel heard and supported while navigating complex situations.
Maylee also has a particular passion for organizing and analyzing discovery, where her attention to detail and curiosity shine. She enjoys digging into the details, uncovering key information, and helping build a clear, strategic picture from complex records.
Outside of the office, Maylee enjoys spending time with her husband, her grown daughter, and their dogs. Whether at work or at home, she values connection, loyalty, and creating a sense of stability for those around her.
JULIA FALLON
Julia Fallon is a proud Jacksonville Beach native. She graduated from Florida State College at Jacksonville in 2021 with her AA degree in Legal Assisting. Prior to working in the legal field, Julia worked in retail management.
Julia is a lover of the performing arts and has performed across numerous stages in Jacksonville and Florida. She now lives in the Jacksonville Beach area where she is raising her son, Jude, with her husband Brice and their cats.