Update: Dueling Legal Tech Lawsuits: Turns Out Exec Who Sued Former Company in NY Had Herself Been Sued By them A Week Earlier in Dallas.

In a lawsuit filed this week in federal court in Manhattan, the former chief operating office of a legal technology company claims she was fired after attempting to exercise stock options valued at over $1 million.

The former executive also claims she was regularly sexually harassed during her employment and was urged by superiors to flirt and become romantically involved with customers.

The plaintiff, Silvia Diaz-Roa, filed the lawsuit against Hermes Law, a Texas law firm, and ClaimDeck, a litigation management system for insurers and insurance-defense firms that spun out of Hermes Law. The lawsuit also names Dwayne Hermes, the founder and CEO of both the law firm and the company, and Andrea Hermes, the cofounder of the company and legal compliance specialist at the law firm.

I emailed Dwayne Hermes asking if he wished to respond but I have not heard back from him. The defendants have not yet filed an answer in the lawsuit.

In her complaint, which you can read here, Diaz-Roa says that she started at the firm as an intern and quickly earned promotions as senior project manager and then director of innovation.

She says that she and Dwayne Hermes came up for the idea for ClaimDeck in 2019 and that it was incorporated in 2020. Starting in 2021, she alleges, she became “the driving force” behind ClaimDeck, while employed by both the law firm and the company. For ClaimDeck, she became head of product and chief operating officer.

In December 2020, Diaz-Roa alleges, the defendants awarded her compensation in the form of options to purchase 58,825 shares of ClaimDeck stock, or about 10% of its total shares.

Three years later, after her options had fully vested and were worth more than $1 million, she alleges that she informed Dwayne Hermes, along with ClaimDeck’s accountants and attorney, that she intended to exercise her right to purchase her options. Within weeks of expressing that intent, the defendants fired her without cause, she claims, alleging that their actual motive was to deprive her of the compensation she had earned.

Diaz-Roa also alleges that she was subjected to sexual harassment during her employment. Both Dwayne and Andrea Hermes regularly encouraged her to flirt and use her appearance to attract customers, she says. On other occasions, they encouraged her to become romantically involved with “certain individuals in the industry to benefit her employers.”

“Dwayne Hermes especially fixated on Diaz-Roa’s appearance, humiliatingly directing her to ‘fix’ her makeup and accusing her of looking ‘tired’ in front of other ClaimDeck and Hermes Law employees,” the complaint alleges.

Based on these allegations, Diaz-Roa’s complaint states causes of action for sexual harassment, breach of contract, deprivation of earned compensation, and others, and requests appropriate damages.

Photo of Bob Ambrogi Bob Ambrogi

Bob is a lawyer, veteran legal journalist, and award-winning blogger and podcaster. In 2011, he was named to the inaugural Fastcase 50, honoring “the law’s smartest, most courageous innovators, techies, visionaries and leaders.” Earlier in his career, he was editor-in-chief of several legal publications, including The National Law Journal, and editorial director of ALM’s Litigation Services Division.