Leslie Shaunty – Skyward Specialty Insurance 

Learning on the fly is essential when an insurance company delves into new areas. Fortunately for Skyward Specialty Insurance Group, Inc., General Counsel Leslie Shaunty relishes self-education and learning by doing, which is critical for a company that innovates and creates solutions for niche markets. 

Leslie Shaunty | General Counsel  | Skyward Specialty Insurance

So, when the Houston-headquartered specialty carrier wanted to enter the cannabis market, a business many insurers hesitated to enter because of concerns about its criminalization under federal law, Shaunty worked to determine how to make it happen.  

“It is important to me to partner with the businesses to help them find solutions and avenues to accomplish their goals,” Shaunty said. “While I know I am supported and can I say “no” if something is unsuitable or too risky for the business, it is far more rewarding to say ‘yes.'”   

After some research and meeting with several experts, Shaunty found limits to the regulations where the federal budget bill doesn’t permit the Department of Justice to use the money to prosecute cannabis businesses operating legally under state law.  

“This fact helped me realize the risk of insuring cannabis operations was manageable,” she notes. 

After realizing the low risk of legal actions and developing contractual protections to terminate relationships should laws change, Shaunty gave the company the green light to enter the business.   

For the past three years, Skyward Specialty focused on expanding into other niche markets and exploring opportunities to raise capital to support its rapid growth and expansion. Skyward Specialty launched its initial public offering in January last year, and Shaunty and her team played a central role in ensuring the company followed the complexities of securities law. Ultimately, the company issued nearly nine million shares of common stock and completed two follow-on offerings in 2023.   

“The journey to the IPO was long and arduous and required a lot of learning on our feet as we went through the process. Before our IPO, I did not have much securities experience, and now, well, I can say I am well-versed,” Shaunty shared.  

With 30 years of legal experience, primarily in-house, Shaunty continues to find opportunities to challenge herself, an easy feat with a constantly changing job.  

“My job is different daily, keeping me interested and engaged,” she says. 

Never a Dull Moment  

According to Shaunty, it’s never insurance as usual at Skyward Specialty, so after supporting the company as her law firm’s biggest client, she returned as an employee. Much has happened on her watch and with her guidance, especially over the last three years, and Shaunty and her teams play a key role in the company’s growth.

For starters, in 2020, upon returning to the company, she worked with the CEO to rebrand and rename the company. As a result, the marketing and communications function report to her, an uncommon structure in most businesses.    

With the company’s rapidly growing surety business, the company acquired a key Managing General Underwriter and Shaunty’s teams handled licensing issues and drafted and filed the bond documents required in all 50 states.   

In 2021, when the company entered the healthcare solutions business, the legal, compliance, product development and communications groups—all under Shaunty’s umbrella—developed new policies, appointed new agent business partners and launched the new product.      

Whether it is new or existing types of insurance, Shaunty stresses to her department how important it is to understand the company’s business and operations to be more effective.  

Lasting Impressions  

While not imminent, Shaunty says that when her career ends, she wants to look back and know that the legal department helped create a positive corporate culture while embracing different challenges.  

Despite all its changes and challenges, she says being an in-house lawyer is gratifying and fulfilling. It enables a lawyer to immerse themselves in a project from conception to completion and see the results of their efforts. Although Shaunty did not foresee being in this position today, she always envisioned she’d wind up in law.  

As a fifth grader, her social studies class put the witch from “Hansel & Gretel” on trial. Shaunty found it fun to argue for the witch—she was misunderstood, Shaunty says with a laugh. Years later, she’d graduate from the University of Texas at Austin and proceed to the University of Virginia School of Law. 

She began her career in 1993 as a litigator, handling corporate litigation and employment law matters, which positioned her well for an in-house generalist job. She notes that finding true generalists prepared for in-house counsel positions is now more challenging, as many attorneys are specialized. As a result, she spends time helping her attorneys to broaden their legal expertise. Shaunty also credits her success to her diverse industries, including retail, death care and petrochemicals.  

Shaunty notes that another thing that has changed in the last three decades is the advancement of women in the legal field.     

“When I started practicing, judges believed women should wear pantyhose and dresses, never pants,” Shaunty says. “Male associates would work out or play basketball with partners; activities and opportunities weren’t available to me.” 

While she notes things have advanced, she also knows there is more to do to ensure women rise to the highest positions in the legal field and business. As the only woman on Skyward Specialty’s executive leadership team, she mentors women in her departments and across the company. 

“Many women still struggle with the things I struggled with during my career, things that often men do not. Many women struggle with self-promotion, which is not emphasized when women enter the workforce. So, I help women recognize that celebrating their achievements is okay and won’t diminish their respect.  

Teaching and mentoring are what Shaunty finds the most rewarding. With her and her husband being empty nesters with their two sons on their own, Shaunty isn’t sure what comes next.  

“Right now, my job is fun, challenging, and allows me to share my knowledge and experience with others,” she says. “Maybe one day I’ll want to work on my golf game more, but in the meantime, I’m happy to work on the growth and advancement of Skyward Specialty.” 

View this feature in the Vanguard Winter III 2024 Edition here.