Jenna Castleman knows firsthand how the work of a lawyer can be life-changing. It dramatically changed how she practices law as a corporate general counsel.
Just weeks before Castleman was scheduled to take the Texas bar examination in 2017, her father died while working on a construction project in Abilene. A dispute arose over the ownership of the construction business her father and mother had founded and built over 25 years.
Facing the loss of the family business, they hired a lawyer, Kyle Watson, who took over the litigation. The case went to trial, where a jury ruled in her family’s favor, and it later settled favorably on appeal.
“That period changed both my life and my understanding of what it means to be a lawyer,” Castleman told The Texas Lawbook. “I experienced firsthand what clients are going through when they come to us during a crisis. To a lawyer, something may be a case or a legal issue. To the client, it may be their business, livelihood, family or legacy. I will always be grateful to Kyle for helping my family during one of the most difficult periods of our lives and for taking a chance on a young lawyer at the beginning of her career. His example also taught me how much it matters when someone opens a door for you. I try to carry that forward in how I lead and mentor others today.”
A decade later, Castleman has employed those personal and professional experiences to build from the ground up a thriving and ambitious legal department at Alterman, one of San Antonio’s oldest and largest electrical contractors.
As Alterman witnessed tremendous revenue growth during the past few years, the company turned to Castleman to be its first-ever general counsel and to create a sophisticated and integrated legal department that includes a team of nine professionals. Leaders at the business said Alterman had “little existing legal structure to inherit.”
“Rather than simply recreating a traditional corporate legal function, Alterman used the opportunity to build a legal department around a different philosophy: move upstream,” Castleman said. “Legal creates the greatest value when it becomes involved early enough to change an outcome, not merely after a contract has been negotiated, or a receivable has become delinquent, or an accident has occurred, or a dispute has arisen.”
“That philosophy,” she said, “has transformed legal’s relationship with the business.”
The evidence is overwhelming that Castleman has achieved extraordinary success during her first two years as a GC, including:
- Transforming Alterman’s contract lifecycle management process;
- Improving payment protections and preservation of lien rights;
- Helping to reduce vehicle incidents and claims through proactive risk prevention;
- Embedding the legal function as a cross-functional business partner; and
- Creating a legal function capable of scaling with transformational growth.
And Castleman accomplished all of this during the past two years as a first-time corporate in-house counsel.
“Alterman is a 103-year-old, employee-owned company experiencing tremendous growth. That growth brings increasingly complex legal, operational and financial challenges,” Alterman CFO Rod Streets said. “Jenna has been instrumental in helping our legal function evolve alongside the business, becoming a trusted advisor who helps us manage risk while supporting our continued growth.”
“Jenna thinks like a business executive who happens to be an attorney,” Streets said. “She understands that successful businesses must take calculated risks, and her focus is on finding practical solutions that protect the company while enabling progress. Her commercial judgment and genuine interest in understanding the broader business make her an invaluable member of our leadership team.”
The Association of Corporate Counsel’s San Antonio Chapter and The Texas Lawbook are honoring Castleman with the 2026 San Antonio Corporate Counsel Award for Rookie of the Year, which goes to lawyers who have been in-house counsel for three years or less and who have already achieved great success. The San Antonio Corporate Counsel Awards ceremony will be on October 29.
In nominating Castleman for the award, Alterman leaders said they built the legal department with Castleman as general counsel to be a proactive contributor.
“Alterman built [legal] to collaborate rather than operate in a silo,” Castleman said. “Alterman built it to prevent risk rather than merely manage its consequences. And, Alterman built it to measure its success by the value it creates for the entire enterprise.”
“We built the legal department while the business was in flight — and, from the beginning, we built it to help Alterman fly higher,” she said.
Lawyers who work with Castleman agree that she is a rising star in the corporate legal community.
“Jenna has earned a great deal of respect because she’s thoughtful, practical and has a strong ethical compass. She’s risen to the rank of general counsel with exceptional speed,”said Dykema member Nicholas J. Monaghan. “Jenna is very practical and business-minded. She has a natural ability to evaluate risk, but she also understands that businesses have to take risks in order to be successful. She doesn’t approach her role as simply identifying reasons why something can’t be done. She sees the bigger picture, helps the business understand the risks involved and then helps find a practical path forward. She’s also highly ethical and very well respected.”
A Front-Row Seat to Growing a Business
Castleman was born and raised in San Antonio.
Her mother worked as a waitress at San Antonio-based Jim’s Restaurant, which is known for its great breakfasts and charbroiled burgers. Her father worked hanging vinyl. Both only had high school diplomas.
The year before Castleman was born, her parents started a construction company called Castleman & Young Construction in 1984. Because of their “incredibly hard work,” her parents and the business earned professional success and tremendous respect within the construction industry.
“In many ways, the company grew up alongside us,” she said. “My mother handled most of the administrative side of the business from an office in our home, while my father spent much of his time on the road managing projects. I had a front-row seat to what it takes to build something from nothing.”
“More than anything, my parents taught us what is possible with a strong work ethic, a strong moral compass and an unwavering commitment to doing things well,” Castleman said. “They never allowed the absence of formal education or opportunity to define what they were capable of accomplishing. That example has influenced virtually every aspect of my life and career.”
After earning her bachelor’s degree in communications from the University of Texas at San Antonio in 2011, Castleman received her law degree from St. Mary’s University School of Law.
She credits her mother for her interest in law.
“She was very active and successful on the debate teams at both MacArthur and Lee high schools,” Castleman said. “From the time my brother and I could talk, she encouraged us to analyze issues from every angle and advocate for our positions — even if the issue being vigorously debated was whether we deserved an extra Fruit Roll-Up.”
“I also watched my mother grow into her role in my parents’ construction company,” she said. “She regularly handled contracts, claims, liens and difficult business conversations, and as I got older, she would sometimes let me help her. I did not realize it at the time, but I was getting my first exposure to many of the same issues I deal with today. My mother laid the foundation for my desire to become a lawyer long before I understood what practicing law actually meant.”
“I cannot put into words how proud my mom was when I became a lawyer,” she said. “She would have been proud of me for earning any degree, but earning a juris doctorate was extra special to her.”
After completing a legal internship with the Texas Court of Criminal Appeals, Castleman joined the Lesser Law Firm, where she started as a law clerk and then worked as a lawyer for three years. She then joined Goode Casseb Jones, where she primarily focused on civil litigation for three years.
In 2021, Castleman’s mentor at Goode Casseb Jones was transitioning toward retirement. With his advice and encouragement, she opened her own practice, Castleman & Associates
“Running my own firm was an invaluable experience because I was responsible not only for practicing law but also for running a business,” she said. “I had the privilege of representing clients who, much like my own family had been, were often navigating some of the most difficult periods of their lives. It reinforced two lessons that have stayed with me in-house: clients need practical advice, not simply technically correct legal answers, and every legal decision has a business and human consequence behind it.”
Building a Legal Foundation at Alterman
In January 2024, Castleman was contacted by a family friend who told her about the position opening up at Alterman.
“I had not previously done legal work for Alterman,” she said. “When I began researching the company, I was immediately struck by Alterman’s history. Here was a company founded in San Antonio more than a century ago that had grown through generations while maintaining a strong reputation and culture. I also recognized many of the values I had grown up around in my parents’ construction business: hard work, relationships, accountability and taking pride in what you build.”
Castleman initially joined Alterman as director of contracts.
“Once I was inside the organization and understood the breadth of the business, it became apparent that Alterman’s growth and complexity had created a need for a broader internal legal function,” she said. “With the support of our executive leadership, that ultimately led to the creation of Alterman’s first legal department and my role as its first general counsel.”
“For me, there is something very full-circle about it,” she said.
Castleman said her biggest challenge has been building the department during a time of substantial growth.
“Alterman was growing rapidly, so we could not stop the incoming contracts, disputes, claims and day-to-day legal issues while we designed a department to handle them,” she said. “We had to address today’s needs while simultaneously building the people, processes and infrastructure we would need tomorrow.”
Another challenge was establishing the legal department’s relationship with other parts of the business.
“We did not want to become a department people called only when something went wrong or when a contract was ready to be signed,” she said. “We have worked hard to earn the trust of our departments and colleagues so legal can move upstream in all internal processes. The philosophy was to become a proactive partner rather than reactionary.”
Streets, Alterman’s CFO, said Castleman is distinguished by her “ability to see beyond the legal question and understand the business decision behind it.”
“Jenna combines sound legal judgment with practical business thinking, helping our leadership team navigate complex issues and make informed decisions,” he said. “I think an important question is what makes a truly exceptional general counsel in today’s business environment. The best general counsel do more than manage legal risk; they help shape strategy, strengthen operations, and create long-term enterprise value.”
“Jenna embodies that evolution, and I believe her greatest contributions to Alterman are still ahead of her,” Streets said.
Click here for a Premium Subscriber Q&A with Castleman, where she shares her best day working at Alterman.
Fun Facts
Favorite book: Bossypants by Tina Fey
Favorite music groups: The Strokes, Elvis Presley
Favorite movie: A League of Their Own
Favorite restaurant: MAARS Pizza in San Antonio.
Favorite beverage: Mexican Coke
Favorite vacation: Every year since 1992 the only vacation we could manage as a family was to Port Aransas, and that continues to be my favorite place to unwind.
Hero in life: Aside from family members who were monumental in my life, my hero in life is Nick Saban. I tried to instill his “process” in the foundation of our legal department and throughout our team.