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When glancing at the surface, it may seem like the legal world always remains the same. But if you take a minute to look deeper, you’ll discover that it’s constantly evolving. New tools like cloud computing, AI, and data analytics offer automation and other improvements that have the potential to change the day-to-day life of a practicing lawyer. As these changes happen, the operational side must keep pace and those with good business acumen will thrive.
Alex Cestero is one of those lawyers. He studied political science before heading to Stanford Law School. Seven years into his career, Cestero made a pivotal decision and enrolled in the Rice Business MBA program while working full time. The experience changed the way he leads teams today.
“I think about the legal department and our mission much in the same way my colleagues manage their business units,” he says.
Last year, Cestero joined Virtuoso to serve as the luxury travel network’s first general counsel. He’s on board to build a robust legal team that will ensure Virtuoso meets its goals and services its global partners, members, and those who travel through Virtuoso.
“The legal function and the general counsel are critical to helping any organization, and they are looking to whoever is in that seat to impact strategy.”
Alejandro Cestero
To do so, Cestero will rely on the wisdom, skills, and experiences he’s had over the course of his career. The respected senior executive specializes in transformative corporate environments and high-growth environments in multinational companies. Because of the nature of his work, Cestero has had the fortune to experience various public and private companies and industries.
Along the way, he’s helped each organization and various management teams, as well as boards of directors, address critical challenges, take advantage of marketplace opportunities, improve performance, and grow.
“The legal function and the general counsel are critical to helping any organization, and they are looking to whoever is in that seat [to] not only to be an excellent lawyer and leader, but also to impact strategy,” Cestero says. And that’s exactly what he’s been able to do time and time again.
Born in Puerto Rico, Cestero lived there for several years before his family moved to the mainland and eventually settled in Miami. With creative parents—an actor father and a marketing executive mother, who spent most of her career representing companies targeting the Hispanic marketplace—law was not the obvious career choice.
Cestero, however, had a few lawyers in his extended family, and when he needed pocket money in high school, one of his uncles offered him a job at his boutique law firm. Soon, he was making copies and sending faxes, but also got to conduct research while learning basic legal writing and how to service clients. As he sat in downtown Miami criminal courtrooms as a legal extern during his senior year of high school, Cestero caught the bug and knew he would eventually head to law school.
Years later, Cestero’s passion for business and law remain intact. When he came to Virtuoso, the company had recovered from the profound downturn COVID-19 brought and was poised to meet pent-up demand for global luxury travel.
“I still find time to give back and be with my family because those are the important parts of life.”
Alejandro Cestero
Historically, Virtuoso had one hundred percent outsourced its legal function, but turned to Cestero to add value by tailoring a new department to fit its needs. He spent his first few weeks and months learning the complex nature of the operation. Virtuoso has relationships with industry-leading travel agencies and well-known luxury travel brands across the world, as well as strategic alliances with tourism boards, retail outlets, and others.
Since the company operates across multiple countries and complex business environments, it must keep up with a wide variety of rapidly evolving laws, rules, and regulations. That structure means Cestero and others must carefully manage issues related to corporate governance, compliance, data privacy, technology, artificial intelligence, and other emerging topics.
How can a busy lawyer keep up with the volume of information? Cestero says he reads three newspapers cover to cover (in print form) every morning. He also peruses daily legal and industry bulletins, attends industry seminars, and makes time to talk shop with his peers.
Cestero is midway through the journey of building the department and updating critical law firm relationships. He leads by example, and while he believes in hard work, he also knows that keeping both work and personal life healthy is important.
“My time at international law firms and in the energy industry allowed me to travel and work on deals in over sixty countries, so this gave me a great passion for experiencing and learning other cultures,” Cestero says. “We’re in the travel and tourism industry. Our clients travel to get new experiences and find balance, and this is something our ownership and executive leaders believe in.” The company has an unofficial rule discouraging weekend work email.
Much of Cestero’s approach comes from his heritage. He values faith, family, culture, and volunteering. “I still find time to give back in the community and be with my family because those are the important parts of life,” he says. “We work hard, but we know that it’s not the only thing that matters. There’s no reason to totally sacrifice health, relationships, and hobbies for work.”
Cestero has been married to his college sweetheart for twenty-five years. The family enjoys outdoor and sporting activities together, and Cestero has coached at least one of his three sons’ basketball teams thirteen out of the last fourteen years.
Now, Cestero is working to build his legal function to support Virtuoso’s international footprint and ambitious growth strategy. He plans to make compliance, contracting, and other matters globally consistent but locally relevant. He’s co-chairing an AI task force to study the impact of this rapidly emerging technology on Virtuoso, the travel industry, and the legal profession.
Tourism has rebounded, and travel is back. With travel agency members in fifty-four countries, Virtuoso is ready to help clients discover the best in luxury and experiential travel. The company recently released its nine “must have experiences” for 2024. It includes a trip to view the northern lights, a slow safari in Africa, a cruise to Antarctica, and the chance to charter a private island.
Harper & Bates LLP (“HB”) is proud to provide intellectual property legal services to Virtuoso, Ltd. (“Virtuoso Travel”). Working with Alejandro Cestero and others on the Virtuoso Travel team has been a great experience, allowing HB to showcase its strategic trademark portfolio management, protection and enforcement services. Our attorneys are dedicated to providing “go to” patent, trademark, copyright, and other intellectual property guidance and advice to corporate and individual clients throughout the US, offering tailored legal services and creative solutions depending on the needs of each client.
