• Skip to main content
  • Skip to secondary menu
  • Skip to primary sidebar
  • Skip to footer
  • Contact Us
  • Post A Job

Agency Checklists

Massachusetts Insurance News & Job Opportunities

  • AC Interviews
  • Agency M&A
  • Career News
  • CAR News
  • DOI News
  • Coverage Cases
  • Innovation
  • InsurOp-Eds
  • AC Podcast
You are here: Home / Market Share Reports & Industry Trends / CAR Market Share Reports / Vermont’s DealerPolicy Raises $30 Million In Series B Funding

Vermont’s DealerPolicy Raises $30 Million In Series B Funding

February 9, 2021 by AC Editor

Series B Funding Will Fund Continued Development of Automotive Retail’s Leading Insurance Marketplace


On two occasions earlier this year, Agency Checklists reported about DealerPolicy, a Vermont-based insurance marketplace for automotive retail. The first time was when it announced its partnership with J.D. Power to create personalized auto insurance quotes to car buyers. The second articles was published after it announced its acquisition of Granite State Insurance.

After a year of growth in 2020, it seems that DealerPolicy will be generating more news in 2021. This month, the insurance marketplace for automotive retail announced that it has raised $30 million in Series B funding led by 3L Capital and Hudson Structured Capital Management Ltd. – doing its re/insurance business as HSCM Bermuda Management Company. The funding will allow the company to accelerate its development of its market-leading insurance platform as well as to expand its team.

“As car buying continues to evolve with the world around us, dealers are prioritizing fully digital, streamlined and connected experiences. Modern insurance solutions such as DealerPolicy’s FastPass™, dovetail nicely into the process and give car-buyers the value and convenience they’ve come to expect,” says Travis Fitzgerald, CEO of DealerPolicy. “DealerPolicy has conducted extensive research into car-buyer sentiments, including access to insurance as part of the process. The results are undeniable – nearly 8 out of 10 shoppers believe that comparing insurance at the point of sale during the car-buying process substantially improves the experience. With an ever-expanding value proposition to dealers, insurance carriers and customers, we are prepared to continue investing in growth.”

Also announced two key hires to help drive growth

As part of the company’s funding news, the company also welcomed two new executives to its team: Wayne Pastore was named as President and Chief Operating Officer, while Tara Kasica was appointed Senior Vice President of Sales.

“I admire the early success the DealerPolicy team has had and the meaningful value its platform provides for both shoppers and dealers,” says Pastore, who previously served as Vice President and General Manager of Dealer.com. Pastore also held numerous leadership positions throughout Cox Automotive and DealerTrack. “With the shopper’s continued desire to complete more of the purchasing experience digitally, I look forward to leveraging my experience to help accelerate the company’s growth as dealers continue to demand fully integrated and digital retailing services.”

As for Ms. Kasica, she joins the company bringing her leadership experience from one of the country’s top P&C insurers.

“Spending much of my career in various insurance and automotive leadership roles, I immediately recognized the value of DealerPolicy’s offering to the market, and dealerships in particular,” says Kasica, who joins the company from Allstate, where she was responsible for overseeing countrywide deployment, production, retention, and growth of dealership owned insurance agencies. “I am thrilled to be joining this incredible team and to use my experience at the intersection of P&C insurance and automotive retail to further support the company’s expansion plans.

An independent agency that built an insurance platform

DealerPolicy is an interesting case of an independent insurance agency that has transformed itself into an “integrated insurance solution to the automotive retail industry.” The company, founded in 2016, also owns DealerPolicy Insurance, its wholly-owned insurance agency. Together the platform is able to offer its network of 800 dealers both automotive and insurance options, creating a seamless integration of insurance into the car-buying process.

According to its latest results, the company states that: “[I]t has provided $13 million dollars in annualized insurance savings and over $60 million in increased buying power for its customers. DealerPolicy Insurance customers who save get an average of $64 per month back into their budget, which is often reinvested into other vehicle protection products offered by the dealer. For that reason, dealers in the DealerPolicy network report an average increase of 34 percent in back-end gross profit.”


Primary Sidebar

Job Board

Career News

Salem Five Insurance Services appointed Gregory Grintchenko as senior vice president of insurance sales to support the agency's continued growth strategy.

Salem Five Insurance Services Expands Leadership Team with Addition of Gregory Grintchenko

Gavin McPhail, Vice President and Chief Data Officer at Plymouth Rock Assurance.

Plymouth Rock Assurance Strengthens Leadership Team with Three Strategic Appointments 

G. Quinn Landers appointed Senior Vice President and Chief Claims Officer at The Andover Companies

The Andover Companies Appoints G. Quinn Landers Senior Vice President and Chief Claims Officer

View All

Search Our Archives Here

MA Division of Insurance Advertisements

Framed formal notice from Massachusetts Division of Insurance about amending a foreign license for AXA XL Insurance Company Americas, dated July 23, 2026.
Official Massachusetts Division of Insurance notice from Safeco Insurance of America about an amended Foreign Company License to transact Property & Casualty insurance; dated July 20, 2026.
Official certification: Commonwealth of Massachusetts, Division of Insurance, license amendment for First National Insurance Company of America, 225 Borthwick Ave, Portsmouth, NH, dated July 20, 2026.

Listen Now

Sponsor

Interviews

From Nuptials, Tickets, and Taxes to Trusted Advisor: One Agency’s Unique Path to P&C Success

A Conversation with Evan Silverio, President & CEO of Silverio Insurance Group

Deland, Gibson Celebrates 125 Years: A Conversation with CEO Chip Gibson

The Fourth-Generation Family-Owned Agency is Based in Wellesley

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual | Agency Checklists

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual

Mr. Welch is CEO of Massachusetts-based Hospitality Insurance Group

Born and Bred in the Bay State: The Special Agent Story

Our Latest Agency Interview is with the Founder & President of Special Agent

A Conversation with Daniel C. Bridge – The 2023 Insurance Professional of the Year

Daniel Bridge is Board Chair, President, and CEO of Vermont Mutual Insurance Group

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Our latest Agency Interview is with Nadeen Vella, the founder and owner of a virtual scratch independent agency.

View All

InsurOp-Eds

InSurOp-Ed: Fried Chicken and Customer Loyalty

By Bill Wilson

What is the Best Insurance Sales Channel, Direct or Agent-Assisted?

By Bill Wilson

How Agents Can Ensure Home Improvement Projects Are Reflected Properly Within Their Clients’ Homeowners Policies

By Jim Hyatt

InSurOp-Ed: Am I Legally Liable?

InSurOp-Ed: Am I Legally Liable?

By Bill Wilson

View All

In Memoriam

Gordon Elliott Taylor, longtime owner of the Blackmer Insurance Agency in Shelburne, Massachusetts, who served the local insurance community for decades.

In Memoriam: Gordon Elliott Taylor

William R Berkley founder of W R Berkley Corporation and leader in commercial insurance industry

W. R. Berkley Corporation Announces the Passing of Its Founder and Executive Chairman, William R. Berkley

Michael R Quinn longtime leader of Allan M Walker Insurance Agency in Taunton Massachusetts

Taunton Insurance Leader Michael R. Quinn Dies at 70

Footer

Contact us

We offer a variety of ways to get help promote your company or product.

Announcements
Email Sponsorships
Partnerships
Custom Collaborations

*Affiliate Disclosure

Please note that any of Agency Checklists’ articles might contain one or more affiliate links. This means that any subsequent purchase resulting from these links may result in a commission for us, but at no additional cost to you. For example, as an Amazon Associate, Agency Checklists earns a commission from all qualifying purchases. By working with affiliates we can continue to keep Agency Checklists subscription free. Thank you for your support.

Explore Our Archives

Copyright © 2026 · Agency Checklists · All rights reserved.

Loading Comments...