Gerard Gregoire – Allstate

Tech-evolution ramps up insurance claim timelines

Benajmin Franklin may have started the insurance industry in the U.S. in 1752, but Gerard Gregoire has been helping Allstate replace outdated traditions for over two decades.

His method? Partnering with his teams for input, using more technology, cutting back on office space and incorporating artificial intelligence and automation.

“I’ve invested 23 years of my career at Allstate,” he says. “In that time, I’ve seen technology become a time and cost saver for the legal department as well as consumers as we shift deeper into virtual workplaces.”

Gerard Gregoire | Vice President and Assistant General Counsel | Allstate

Gerard Gregoire | Vice President and Assistant General Counsel | Allstate

Recently, Gerard reduced the physical footprint of his staff counsel locations from 81 offices to 32 during the company’s move to virtual.    The key, he says, has been identifying spaces that aren’t often used. For example, he found trial attorneys in one area spent most of their time at court, so he helped create a smaller office. More recently, trial attorneys have become entirely remote in some locations.

On the flip side, he says it’s important to invest in growth — employees need what they need, and the business has extensive operations. Servicing 32 states and Washington, D.C., Allstate was founded in 1931 as part of Sears, Roebuck and Company and then became a stand-alone American insurance company in 1993, with locations in Canada as well. Gregoire joined in 1999 as a trial attorney and rose through the ranks prior to receiving his most recent promotion to vice president and assistant general counsel in April 2018.

Insurance at clients’ beck and (virtual) call

Gregoire is responsible for a team of over 750 employees, 350 of whom are attorneys. Prior to the COVID-19 pandemic, he and his legal team had started work to transform into a completely virtual legal department; by December 2020, they’d sped up the pace.

The idea had been at the back of his mind since advocating for and supporting Allstate staff counsel’s move to paperless around seven years prior. By 2021, they’d accomplished the goal of fully virtual offices. Not only does working remotely save on real estate, Gregoire says, but it allows for the recruitment of staff and attorneys who want to work remotely. This means he can also hire support staff in different states as he increases his pool of candidates.

Gerard Gregoire | Vice President and Assistant General Counsel | Allstate

“We can more easily tap into the knowledge and expertise of support staff across the U.S.,” he says. “It also sets us up to smoothly handle situations like the pandemic or the current sky rocketing gas prices in California — situations where people prefer to or must work from home.”

Such implementations and uses of technology benefit clients, as well. Gregoire says artificial intelligence and automation have not just shortened the duration of litigation but have added convenience. Clients can confirm their depositions via text or utilize automation or bots to complete more manual tasks.

Gregoire is currently piloting an internal AI tool that creates a template answer. As such, he and his team get faster, more reliable insight and can respond quicker to a complaint on behalf of their clients.

“Leaning into data and AI is a better way to approach litigation and will hopefully help us resolve litigation faster,” he says.

Moving a first chair in-house

Gregoire manages the staff counsel and in-house counsel for around 45 offices and law firms across the country, with seven regional managers reporting directly to him. He’s responsible for everything from business strategy and budgeting to real estate and operations.

“I never want to act without knowing how my decisions will impact people, especially as I give input on matters involving operational strategy, state regulations, employee development, human resources, budgeting and staffing, as well as legal,” he says.

Gregoire holds in-person and virtual town halls while visiting regions in different states. He likes getting to know people and their interests because of an opportunity he received after graduating from Texas Southern University with a juris doctorate in law in 1998. The Texas district attorney recruited him right after graduation, making him one of six attorneys hired in the state. While waiting for his bar exam results, he got to sit second chair and was picked for jury first chair.

Gerard Gregoire | Vice President and Assistant General Counsel | Allstate

“I got thrown into the fire, but it was an amazing opportunity to take over 100 cases to trial across nine different county courts,” Gregoire says. “I was promoted to felony prosecutor within a year and the judges liked my style, so they referred me to Allstate.”

He’s loved working at the insurance provider so much, he never left and has no intentions of doing so — especially as he also gets a chance to be a mentor and builder at Allstate. Mentors have played a huge role in his life. Being in the West Indies and growing up in the U.S. Virgin Islands before his family moved to Dallas, he had street smarts but didn’t understand how to run a business.

“I was always the student in advanced classes, but I was a little rough around the edges — until I met some wonderful mentors in high school through a Street Law program,” Gregoire says. “Integrating more technology at Allstate means I can be a mentor to others and give back, and we can all provide the best service, not just to our clients but each other as we constantly improve and strengthen the legal team and our company.”

View this feature in the Vanguard Fall II 2022 Edition here.

Showcase your feature on your website with a custom “As Featured in Vanguard” badge that links directly to your article!

Copy and paste this script into your page coding (ideally right before the closing tag) where you want to display our review banner.


As promised in advance, my feature in Vanguard has increased my visibility within the profession and prompted more than a few people I have not communicated with recently to reconnect. One of the Italian law firms I have used in the past is now in the process of interviewing me for an article on their website and tweeting out the feature story. Activity and the number of people connecting with me on LinkedIn has soared, which is great. The Vanguard writers and editorial staff were great to work with—highly professional and made the effort to make the experience both fun and rewarding (they were also respectful of the time pressures and demands all lawyers face). I was very pleased with the experience and the final outcome. Needless to say, I have been very pleased. All in all working with Vanguard has been a very positive experience which generated good publicity for both Shawcor and myself. My sincere thanks.
– Tim Hutzul, General Counsel, ShawCor Ltd.
The piece highlighting my company, Bob Baker Enterprises, Inc., came out fabulous. Our company is in the new and used car sales and service industry. Everyone was great to work with and extremely professional. They produced a high-quality product and have provided expert assistance and guidance post-production of the article.
– Wade Poulson, General Counsel, Bob Baker Enterprises Inc.
It was a great honor to be featured in Vanguard Law. Working with every member of the team, from the initial interview with Erin Clark, through production with Victor Martins, writing the article with Taryn Plumb and creating the final content with Dave Gushee, was a true pleasure. Everyone was very professional, enthusiastic and supportive, and their creative approach and positive attitude clearly came through in the final product.
– Kevin C. Rakowski, Senior Vice President, Deputy General Counsel, Compliance with Radian Group Inc.
I was honored to be the subject of an article. I enjoy reading Vanguard articles and seeing how other attorneys got to their positions and see their jobs. It's also interesting to see how different law firms partner with the subjects of the articles.
– Henry Marquard, in-house counsel, Stanley Consultants Inc.


Spring I 2024



  • * We’ll never share your email or info with anyone.
  • This field is for validation purposes and should be left unchanged.