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Community Spotlight:  Stephen Kyriacou, Head of Litigation and Contingent Risk Solutions, Willis Towers Watson

By John Freund |
March 12, 2025

Community Spotlight:  Stephen Kyriacou, Head of Litigation and Contingent Risk Solutions, Willis Towers Watson

Stephen is a seasoned litigation and contingent risk insurance broker and former practicing complex commercial litigator who joined WTW in February 2025 as Head of Litigation and Contingent Risk Insurance.  In his role, Stephen evaluates litigation-related risks and structures bespoke litigation and contingent risk insurance policies for litigation finance, hedge fund, private equity, law firm, and corporate clients. 

Prior to joining WTW, Stephen was a Managing Director and Senior Lawyer in Aon’s Litigation Risk Group.  Stephen joined Aon in 2019, and was the first insurance industry professional dedicated solely to the litigation and contingent risk insurance market, leading the Litigation Risk Group’s origination and business development work, in-house legal diligence, efforts to advocate for coverage with underwriters, and negotiation and structuring of insurance policies.  During his time at Aon, Stephen was a three-time Risk and Insurance Magazine “Power Broker” (2022, 2023, 2024); spearheaded the development of judgment preservation insurance and insurance-backed judgment monetization as well as the synergy of litigation and contingent risk insurance with litigation finance; and was responsible for placing billions of dollars in total coverage limits – including the largest ever litigation and contingent risk insurance policy, and several policies that each provided over $500 million in coverage limits – and delivering hundreds of millions of dollars in premium to insurers.  Stephen additionally provided consulting and broking services on litigation-driven, insurance capital-based investment opportunities and sales of litigation claims, insurance claims, and subrogation rights as part of the Aon Special Opportunities Group.

Prior to joining the insurance industry, Stephen was a complex commercial litigator in the New York City office of Boies, Schiller & Flexner from 2011 to 2019.  While at BSF, Stephen amassed significant trial, appellate, and arbitration experience representing both plaintiffs and defendants in the U.S. and abroad across a wide array of practice areas, including securities, antitrust, constitutional, insurance, first amendment, employment, government contracting, and criminal law, as well as in multidistrict and class action litigation.  Stephen’s clients included banks and other major financial institutions, private equity firms, technology companies, foreign sovereigns, professional sports teams, television networks, insurance companies, corporate executives, and other high-net-worth individuals.  

Stephen earned his J.D. from the New York University School of Law in 2010, and is a member of the New York State Bar.  He also clerked for the Honorable Tanya S. Chutkan in the United States District Court for the District of Columbia.

Company Name and Description:  Willis Towers Watson

Company Website: https://www.wtwco.com/en-us

Headquarters:  Stephen is based in New York

Area of Focus:  Litigation and contingent risk insurance for litigation finance, hedge fund, private equity, law firm, and corporate clients

Member Quote:  “I have been working with litigation finance firms to insure their litigation-related investments since I first entered the insurance industry in 2019, and I view litigation finance and funder-backed plaintiff-side litigation as the most important growth areas for the litigation and contingent risk insurance market, as well as the areas where coverage can be most value additive for clients. 

I have also been bringing litigation finance firms into insurance transactions as financing counterparties since I first devised the concept of insurance-backed monetization for judgment preservation insurance clients back in 2020, which concept has since expanded to the point where litigation finance capital has become inexorably intertwined with all forms of plaintiff-side insurance coverage.  

As the market for this insurance pivots away from single-case risks and towards portfolio-based policies for litigation finance firms and the law firms that they fund, litigation finance clients can trust that WTW will be at the forefront of innovating new coverage structures and concepts to address their unique risk management needs and ambitious financial goals, will deliver best-in-class client service utilizing our incomparably strong and longstanding relationships with underwriters, and will be a vocal champion of litigation finance both within and outside of the insurance industry.”

About the author

John Freund

John Freund

Commercial

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Commercial Legal Innovation

LSC Showcases Access-to-Justice Tech at San Antonio ITC

By John Freund |

The Legal Services Corporation (LSC) brought the access-to-justice conversation squarely into the technology arena with its 26th annual Innovations in Technology Conference (ITC), held this week in San Antonio. Drawing nearly 750 registered attendees from across the legal, business, and technology communities, the conference highlighted how thoughtfully deployed technology can expand civil legal assistance for low-income Americans while maintaining ethical and practical guardrails.

Legal Services Corporation reports that this year’s ITC convened attorneys, legal technologists, court staff, pro bono leaders, academics, and students at the Grand Hyatt San Antonio River Walk for three days of programming focused on the future of legal services delivery. The conference featured 56 panels—16 streamed online and freely accessible—covering topics ranging from artificial intelligence and cybersecurity to court technology, data-driven decision-making, and pro bono innovation.

LSC President Ron Flagg framed the event as a collaborative effort to ensure technology serves people rather than replaces human judgment. Emphasizing that technology is “not the answer by itself,” Flagg underscored its role as a critical tool when grounded in the real needs of communities seeking civil legal help. The conference opened with a keynote from journalist and author David Pogue, setting the tone for candid discussions about both the promise and limitations of emerging technologies.

A notable evolution this year was the introduction of five structured programming tracks—AI beginner, AI advanced, IT operations, client intake, and self-help tools—allowing attendees to tailor their experience based on technical familiarity and organizational needs. The event concluded with hands-on workshops addressing cybersecurity incident response, improving AI accuracy and reliability, change management for staff resilience, and user experience evaluation in legal tech.

Beyond the conference itself, ITC reinforced LSC’s broader leadership in access-to-justice technology, including its Technology Initiative Grants, AI Peer Learning Lab, and its recent report, The Next Frontier: Harnessing Technology to Close the Justice Gap. Senior program officer Jane Ribadeneyra emphasized the dual focus on informed leadership decisions and practical tools that directly support frontline legal services staff handling matters like eviction, domestic violence, and disaster recovery.

For the litigation funding and legal finance community, ITC’s themes highlight a growing intersection between technology, access to justice, and capital deployment—raising questions about how funders may increasingly support tech-enabled legal service models alongside traditional case funding.

Commercial

Litigation Financiers Organize on Capitol Hill

By John Freund |

The litigation finance industry is mobilizing its defenses after nearly facing extinction through federal legislation last year. In response to Senator Thom Tillis's surprise attempt to impose a 41% tax on litigation finance profits, two attorneys have launched the American Civil Accountability Alliance—a lobbying group dedicated to fighting back against efforts to restrict third-party funding of lawsuits.

As reported in Bloomberg Law, co-founder Erick Robinson, a Houston patent lawyer, described the industry's collective shock when the Tillis measure came within striking distance of passing as part of a major tax and spending package. The proposal ultimately failed, but the close call exposed the $16 billion industry's vulnerability to legislative ambush tactics. Robinson noted that the measure appeared with only five weeks before the final vote, giving stakeholders little time to respond before the Senate parliamentarian ultimately removed it on procedural grounds.

The new alliance represents a shift toward grassroots advocacy, focusing on bringing forward voices of individuals and small parties whose cases would have been impossible without funding. Robinson emphasized that state-level legislation now poses the greater threat, as these bills receive less media scrutiny than federal proposals while establishing precedents that can spread rapidly across jurisdictions.

The group is still forming its board and hiring lobbyists, but its founders are clear about their mission: ensuring that litigation finance isn't quietly regulated out of existence through misleading rhetoric about foreign influence or frivolous litigation—claims Robinson dismisses as disconnected from how funders actually evaluate cases for investment.

Commercial

ISO’s ‘Litigation Funding Mutual Disclosure’ May Be Unenforceable

By John Freund |

The insurance industry has introduced a new policy condition entitled "Litigation Funding Mutual Disclosure" (ISO Form CG 99 11 01 26) that may be included in liability policies starting this month. The condition allows either party to demand mutual disclosure of third-party litigation funding agreements when disputes arise over whether a claim or suit is covered by the policy. However, the condition faces significant enforceability challenges that make it largely unworkable in practice.

As reported in Omni Bridgeway, the condition is unenforceable for several key reasons. First, when an insurer denies coverage and the policyholder commences coverage litigation, the denial likely relieves the policyholder of compliance with policy conditions. Courts typically hold that insurers must demonstrate actual and substantial prejudice from a policyholder's failure to perform a condition, which would be difficult to establish when coverage has already been denied.

Additionally, the condition's requirement for policyholders to disclose funding agreements would force them to breach confidentiality provisions in those agreements, amounting to intentional interference with contractual relations. The condition is also overly broad, extending to funding agreements between attorneys and funders where the insurer has no privity. Most problematically, the "mutual" disclosure requirement lacks true mutuality since insurers rarely use litigation funding except for subrogation claims, creating a one-sided obligation that borders on bad faith.

The condition appears designed to give insurers a litigation advantage by accessing policyholders' private financial information, despite overwhelming judicial precedent that litigation finance is rarely relevant to case claims and defenses. Policyholders should reject this provision during policy renewals whenever possible.