Olivia Fines – Constellis

Olivia Fines never planned on being the kind of lawyer portrayed in courtroom dramas. While her earliest inspirations came from TV icons like Perry Mason, she discovered early in her legal career that her true strengths lay not in theatrics, but in strategy, collaboration, and leadership. Since joining Constellis as chief legal, risk, and compliance officer in February 2024, Fines has embraced her role as a key architect of the company’s strategic and cultural evolution.

Olivia Fines | Constellis | Chief Legal, Risk & Compliance Officer

With more than 20 years of legal experience—including general counsel positions and leadership roles at Parsons Corporation—Fines brings a depth of legal expertise and operational insight that is integral to Constellis’ success.

“My interest in law came from a love of research, writing, and understanding people’s motivations,” she says. “Ultimately, I found the in-house role to be the sweet spot for me.”

Now overseeing a team of 45 professionals across legal, ethics, compliance, contracts, procurement, risk, quality, international trade, and health and safety, Fines operates at the intersection of law and leadership. She leads not only by managing legal risk but also by supporting key initiatives that shape the company’s future—efforts that are especially vital in a rapidly changing global security environment.

One company, one culture

Constellis, a global leader in risk management and security services, combines a range of specialized capabilities—from protective services to training and technology solutions—for clients across the government and commercial sectors. The company’s strength lies in the integration of its diverse resources, people, and platforms, enabling it to operate effectively in some of the most challenging environments on the planet.

But such diversity can also pose internal challenges. As Fines puts it, “Constellis is comprised of numerous business entities, some with overlapping services and others with distinct offerings. Integration across governance, compliance, and culture is no small task.”

Enter ONE Constellis, a company-wide initiative led in part by Fines to unify the organization under a consistent set of values, communication standards, and operational protocols.

“Sometimes the way an acquired company used to do things is not the new way—and of course, people can be resistant to change,” she says. “But our mission is incredibly unifying, and that’s made consistent outcomes more achievable.”

ONE Constellis emphasizes alignment in how people communicate, how policies are executed, and how the company defines its identity. As the organization expands its commercial footprint, this kind of cultural consistency has become a competitive differentiator.

Harnessing AI & managing risk

A cornerstone of Constellis’ technological innovation is the development of LEXSO (Layered Extended Security Operations), an AI-powered platform designed to detect patterns, eliminate human error, and adapt to threats in real time. It’s a revolutionary leap in security operations—and it comes with complex legal implications.

“LEXSO is unlike anything else in the industry,” Fines says. “Our job is to ensure it functions within legal and regulatory frameworks while still allowing the technology to evolve.”

Her legal team has been deeply involved in LEXSO’s development, advising on everything from compliance standards to pilot testing protocols with U.S. government agencies.

“We’re helping the company prepare for a national rollout that complies with NDAA standards and ensures client trust,” she explains.

Fines is also leveraging the company’s Elite Training Facility in North Carolina, which serves as a proving ground for new technology like LEXSO. Events like the Drone Rodeo Tactical Expo, hosted at the facility in 2024 and 2025, bring together Constellis employees, clients, and experts to collaborate on the future of security technology.

Beyond LEXSO, Fines has played a pivotal role in broader corporate stability. In 2024, she helped lead a successful recapitalization of over $266 million in debt, securing new capital for the company. And in 2025, her team celebrated a $15 million arbitration award against the Afghan government—an outcome she attributes to strategic litigation planning and thoughtful selection of internal and external counsel.

Compliance, culture & the human element

Fines’ leadership is not confined to tech and litigation. She’s also strengthening Constellis’ compliance culture through updated policies, enhanced auditing, and increased alignment with external ethics organizations like Ethisphere and Ethena. A key initiative for 2025 is Target Zero, a campaign emphasizing zero incidents across operations, with a particular focus on safety.

“Compliance isn’t just about checking boxes,” Fines says. “It’s about fostering an environment where safety, accountability, and ethical behavior are embedded into everything we do.”

She also recognizes the challenge of maintaining engagement through training—a necessity in a high-risk, high-accountability industry.

“Training fatigue is real, but manageable with the right tools,” she says. Her approach prioritizes relevance, brevity, and cadence, ensuring employees receive the training they need without unnecessary disruption.

Fines’ own leadership philosophy helps sustain morale and loyalty. Despite overseeing a complex portfolio of responsibilities, she leads with trust and empowerment.

“I don’t micromanage. I trust my people and they trust me in return,” she says. “Some of my best hires were folks who didn’t check every box but had the fire to learn and succeed.”

That philosophy is paying off: Fines’ department has a remarkably low attrition rate, and the company has been able to recruit top-tier talent thanks to an influx of experienced professionals leaving government service.

A strategic vision

Despite the demanding nature of her work—keeping pace with shifting laws, international politics, and emerging technology—Fines thrives on the daily challenges.

“The hardest part of my job is keeping up with everything happening at home, abroad, and in tech,” she admits. “But I have an incredible team and strong support at the executive and board level.”

AI, she believes, will continue to transform the legal profession.

“AI isn’t the future—it’s now,” she says. “It’s not ready to write a legal brief just yet, but the efficiencies it creates in research, discovery, and analysis are already changing how lawyers work.”

Fines’ personal story is as dynamic as her professional journey. A Virginia Tech graduate with degrees in English and political science, as well as a law degree from George Mason University, she’s a former collegiate rugby player, an avid reader, and a passionate traveler who speaks several languages. She’s also a budding dystopian fiction author who wrote a novel during the pandemic, which she’s currently revising.

Despite the intensity of her role, she remains grounded in gratitude.

“I’ve battled imposter syndrome throughout my career,” she says. “But I’ve been incredibly fortunate to work with mentors and colleagues who remind me of what I’m capable of.”

At Constellis, Fines is more than the chief legal, risk, and compliance officer—she’s a driving force behind its unified culture, a steward of its mission, and a leader helping shape the future of the security industry through innovation, strategy, and a deep commitment to doing things the right way.