Paralegal Spotlight: Zachary Westmoreland
Zachary Westmoreland is a North Carolina State Bar Certified Paralegal working in the Real Estate Finance Practice Group at Winstead PC, a Dallas-based law firm with national practices serving clients across the country. Zachary works at the Charlotte office, where he supports a team that primarily serves as lenders’ counsel on transactions ranging from eight to nine figures.
The Charlotte office is a small team of roughly twenty people, including attorneys and support staff. Zachary works on-site most days, and most of his day is devoted to due diligence. Zachary provides transactional support in different ways. He reviews contracts, purchase agreements, leases, and corporate governance documents; drafts and abstracts and lengthy loan documents; assists with title and survey review; and helps prepare ancillary loan documents that move a deal from diligence to closing.
The work spans multiple jurisdictions, which keeps the learning curve steep and the days interesting. “It is new and detailed,” Zachary says, “and I like the challenge. The scale is different from the localized transactions I worked on before.”
Zachary works on-site most days and appreciates the accessibility of attorneys and staff.
Built for the Challenge
Zachary’s path into the legal profession was something he was interested in, but he had no idea where to start when he began his undergraduate studies at The University of North Carolina at Chapel Hill. He found himself drawn to the legal field after taking courses with political science professor Isaac Unah, whose research and teaching focused on judicial institutions. Unah’s research pulled Zachary into the inner workings of law and courts. He describes the experience as “the moment things started to click.” When Zachary discovered that UNC-Chapel Hill offered a paralegal certificate program, Zachary enrolled. “I decided that I wanted to have the paralegal certificate and get my bachelor’s degree at the same time,” he recalls.
Setting a demanding pace comes naturally to Zachary. Before he began his undergraduate studies, Zachary had already earned an associate’s degree while still in high school through Central Piedmont’s Early College Program. He carried that same level of discipline into his undergraduate studies and the paralegal certificate program. He completed a double major in Political Science and Peace, War, and Defense with a Minor in Politics, Philosophy, and Economics while simultaneously completing the paralegal program and then sitting for the North Carolina State Bar Certified Paralegal exam in June 2024, just one month after earning his degree.
Early Career Lessons
Zachary’s first paralegal role in a small Chapel Hill firm offered broad exposure to estate planning with some corporate and tax work. He enjoyed the client interaction and found the tax side intellectually stimulating, but inconsistent staffing and an unstructured environment made mentorship hard to access.
A second similar role offered more structure and support. Ultimately, those experiences clarified two things for Zachary: he enjoys complex legal work and prefers to work in collaborative, professional environments with high standards and organizational stability.
When personal priorities drew him home to Charlotte, Zachary joined Winstead PC in September 2025.
What Work Looks Like Now
These days, Zachary supports transactions in several ways. He reviews due diligence documents, flagging issues and extracting key provisions that matter most for underwriting and document preparation. He also provides drafting and revision support across a variety of documents central to the execution of financial transactions. His work spans anywhere from New York to Texas, Florida, California, and beyond, giving him a real-time education in how different state and local laws can shape a transaction. The learning curve is steep, but he leans into it. Zachary drafts with some assistance from drafting tools and reviews manually, page by page, line by line, but he is curious about AI-assisted tools that automate and streamline the search for key terms, generate summaries, and can quickly create a draft for more specific provisions. Zachary supports the technology but believes a sharp human eye will always be necessary.
Looking Ahead
Zachary enjoys the pace and challenge of firm life. His focus now is building depth: strengthening his skills, broadening his knowledge across jurisdictions, and expanding his exposure to additional corporate practice areas, including his growing interest in mergers and acquisitions and corporate tax matters.
Just as Zachary invests in his own growth, he’s equally committed to serving the profession. He is currently serving a three-year term on the NCBA Paralegal Division Council and sits on the board of the Raleigh-Wake Paralegal Association. He is interested in opportunities to apply his skills for corporate-focused pro bono work for small businesses and aspiring entrepreneurs.
Advice to New Paralegals
Like Zachary, many new paralegals face demanding first years, often because they fear disappointing supervisors, worry about making mistakes, feel pressure to prove themselves, and are unsure how to set boundaries without jeopardizing their jobs. Often, without prior experience to draw on, new paralegals do not know what a typical law firm work environment is or isn’t, which adds to the pressure they already feel. Zachary understands that pressure and now has a strong sense of what he wishes he had known sooner.
For him, it starts with mentorship. During interviews, Zachary recommends learning how a firm trains new staff, who will provide guidance, and how attorneys and support staff make themselves available for questions. A supportive environment can shape your growth more than any single assignment.
Once you have the job, keep a list of your assigned tasks and time estimates. Some attorneys may not remember everything they have assigned you. Keeping an updated list not only helps you stay organized but also helps you communicate capacity issues with your supervisor before you become overwhelmed.
Zachary also learned to stay mindful of changes in his work environment, such as staff turnover, reductions in staff, workloads that grow beyond what is sustainable, or other shifts that affect your ability to perform effectively. If an environment no longer supports your well-being and professional growth, reflect on what settings might allow you to thrive.
Finally, Zachary stresses the importance of discretion during a job transition. The legal community is closely connected, and keeping transition details private protects your options and your professionalism.
Beyond the Office
Outside of work, Zachary, a former Eagle Scout, makes good use of North Carolina’s state parks. He enjoys hiking, camping, and kayaking, and is exploring opportunities for whitewater rafting. As he gains experience and prepares for his next challenge, Zachary is returning to the piano after playing for nearly eight years as a child. It is a welcome way to slow down, recharge and bring a little creativity back into his week. He also maintains his longtime involvement with an international nonprofit serving rural communities in India.
Lakisha Chichester, ACP, NCCP, is a certified paralegal and real estate broker in Durham, NC. With over a decade of experience in legal and regulatory compliance, real estate, and corporate governance, she is passionate about staying at the forefront of legal and real estate trends. When not working, Lakisha enjoys reading, spending time outdoors, and making memories with her six grandchildren.
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