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Providing you with the right coverage for your business.

We get it. Business insurance can be tricky and daunting. That’s why we’re here to help educate and guide you through the day-to-day risks while providing you ways to save money, find gaps in coverage, and keep your assets and your employees protected from the unexpected.

small business owner insurance

When it comes to commercial insurance, we understand each company is unique in its own way.

At Prosper, we believe your insurance policy should be personalized to fit your individual needs as a business owner so you aren’t paying for coverage that you don’t need.

That’s why our commercial agents work with over 30 insurance partners to find you the best coverage at a great rate so you can feel confident that your business is protected in all the right ways.

The Coverages

  • Cyber Liability & Data Compromise

    The threats modern businesses face are not the same as they’ve been in the past, particularly in the world of cyber liability and crime. Prosper Commercial can implement protection against:

    • Loss or damage to your businesse’s electronic data
    • Breach of customer, client & employees confidential data
    • Infecting others (often unknowingly) with damaging computer viruses
    • Cyber extortion & ransomware
    • Wire transfer fraud (often called social engineering)
  • Employment Practices

    Employment Practices Coverage (often called EPL or EPLI) protects businesses from lawsuits by either employees (first party) or outside parties (third party) claiming their rights have been violated. This includes but is not limited to:

    • Sexual harassment
    • Discrimination
    • Wrongful termination
  • Professional Liability / Errors & Omissions

    Professional liability coverage, sometimes called Errors & Omissions, fills coverage gaps for professionals not covered by General Liability. This coverage is often required either by contract or legislation.

    Prosper can help serve the needs of professionals such as:

    • Real estate agents
    • Property managers
    • Technology companies & computer programmers
    • Attorneys, accountants & consultants
    • Engineers, architects & more
  • Workers Compensation

    Workers compensation insurance is designed to cover medical expenses and part of lost wages for employees who are hurt or become ill on the job. This coverage is often mandated by state law once a business surpasses a certain threshold of employees and, depending on which state you’re in, owners and officers may elect to be covered or not.

    Workers comp premiums coincide with employee’s payroll, and today’s policies offer more flexible payment options than ever before, including:

    • Standard payment options (10 pay, quarterly, monthly, annual)
    • Pay-as-you-go monthly reporting
    • Automatic payroll integration
  • Property & Flood

    Property often represents a business’s greatest asset. Prosper can help protect your building and contents from:

    • Fire, theft, collapse & more
    • Equipment breakdown, including spoilage
    • Loss of business income or rental property income

    There are many forms of property we can insure, such as:

    • Buildings & warehouses used by your business
    • Buildings, offices, & warehouses rented to others (lessors risk / LRO)
    • Hotels, apartments, condo master policies & other habitational rentals

    Being close to the coast represents an even greater risk to business assets. Coastal exposure face increased risk of damage due to:

    • Wind damage from hurricanes, tornados and storms
    • Rising water, including storm surge & flood
  • Commercial Auto & Fleet

    Commercial auto insurance provides both liability and physical damage coverage for the vehicles and trailers your businesses uses every day at the higher protection limits demanded by today’s market. This coverage includes:

    • Liability (protection for both property damage and bodily injury)
    • Comprehensive & Collision
    • Hired & Non-Owned
    • Uninsured & Underinsured Motorist
    • Auto Medpay

    We can help you correctly insure your:

    • Commercial Fleet – including trucks, vans, box trucks, flatbeds & rollbacks
    • Private Passenger Fleet – including everyday cars & SUVs used by salespeople & owners
    • Trailers – including utility trailers, covered trailers & mobile workstations
    • Classic & Antique Vehicles – with sentimental value to the business
  • General Liability & Umbrella

    General Liability coverage isn’t just a box to check to fulfil certificate requirements, it’s the first line of defense in protecting your business from many types of lawsuits.

    General Liability coverage can help provide coverage for:

    • Bodily injury
    • Property damage
    • Damage to rented premises (similar to renters insurance for businesses)
    • Products & completed operations
    • Personal & advertising injury

    Does your business carry enough coverage to protect against lawsuits?

    A Commercial Umbrella is a cost-effective way to increase coverage for General Liability, Auto Liability, and Workers Compensation.

  • Inland Marine / Installations Floaters / Mobile Equipment / Builders Risk

    Not all your assets stay on site. Mobile equipment, property in transit, property contracted for installation, and many other assets can be covered through a well-written inland marine policy.

    Ready to construct a new building, either for your business or a client? Builders risk policies are designed to cover property under construction, including both the existing structures and construction materials until the job’s complete.

Prosper Perks

When you choose Prosper as your agency, we throw in some pretty cool benefits. Just to name a few:

  • The right coverages at the best price
  • Industry leading service, including same-day certificate processing
  • Fully independent, in-house claims advocates
  • Simple and straightforward sales and renewal process
  • Competitive pricing

Meet Our Team

It matters who you buy from.


Adam Appleton

Senior Commercial Agent – Virginia Beach, VA

Adam joined the commercial team after spending many years in food services management, where he helped small businesses reach their full potential. He finds passion in providing small and large businesses with the tools necessary to protect their greatest assets from the unforeseen. Adam is a Virginia Beach local and lives at the oceanfront with his wife Carissa, their young son Wolfgang, and their rescue pup Winston. 426-4021


Kevin O’Brien

Senior Commercial Agent – Chesapeake, VA

Kevin enlisted in Prosper’s commercial team after 8 years of decorated service in the US Army. After graduating Airborne & Ranger school, he went on multiple deployments in the Middle East as a sniper platoon squad leader. Kevin also dabbles in cooking and even spent time as a chef in New Orleans before relocating to Virginia Beach. A true family man, Kevin enjoys spending his time with his wife, Freshta, and their three kids, Anosha, Mike and Ali. 971-3396

Mandy Scoville

Commercial Sales Agent – Virginia Beach, VA

Mandy comes with over 15 years of service background, serving as Prosper’s small business agent. She has a natural desire to help others, which is reflected in her relationships with her clients. As a Virginia Beach native, Mandy is a true beach girl at heart. She enjoys spending time paddle boarding and being at the beach with her boyfriend Ryan, his two children, and their Chesapeake Bay Retriever, Luna. 614-1130


Chris Henderson

Commercial Sales Agent – Virginia Beach, VA

Chris grew up in Suffolk, Virginia. Being the youngest of 6 boys who were all athletes, it only made sense that he spent most of his life playing sports. Chris’s competitive nature developed into a love for sales when he was in college. He’s extremely passionate about helping people and building lasting and meaningful relationships. In his spare time, he loves hanging with friends and family, and watching sports (obviously). 892-4648

Anne Cole Howell

Commercial Service Agent – Virginia Beach, VA

Anne Cole comes to the Prosper family with over five years of insurance experience under her belt. She’s a natural problem solver and enjoys finding creative solutions for her clients. Anne Cole loves spending time with her husband Nate and their two children, Maclin and Shafer. This supermom does it all while keeping up an impressive Instagram aesthetic. 324-5578

Ryan Tinney

Commercial Lines Manager – Virginia Beach, VA

Ryan is a longtime sales and leadership junkie and heads the commercial division of Prosper Insurance. As a former coach and collegiate athlete, Ryan is thoroughly addicted to helping his clients and coworkers win. So much so that he has spent the past decade working hard to fulfill the insurance needs of business owners. Ryan resides in Virginia Beach with his wife Jenna, their daughter Brooklyn, and their rescue lab Penny. 401-6758


Dylan Bratton

Commercial Sales Agent – Virginia Beach, VA

Dylan comes to Prosper with 9 years of Sales and Account Management experience. He is passionate about making sure that his clients always receive the highest level of customer service imaginable. When he’s not working, he can be found on the ball field coaching his son Sandler and daughter Piper, with his wife Kayla. Dylan’s goal is to increase Prosper’s Commercial footprint throughout Suffolk, Isle of Wight County, and Southampton County. 705-6009


Trey Highton

Commercial Sales Agent – Virginia Beach, VA

Trey was born and raised in Virginia Beach where he grew up playing on Hobie Cats and chasing waves. After spending the last twenty years working in the higher education and environmental non-profit sectors, Trey joins the Prosper team where he empowers local business owners to overcome operational problems with pragmatic and meaningfully tailored solutions. He lives near Sandbridge Beach, with his wife Erin and two kids Charlotte and Hank, and continues to spend as much time as possible with his toes in the sand. 337-1675


Kellie Bournes

Commercial Service Agent – Virginia Beach, VA

Kellie joins the commercial team after spending several years in our personal lines and life insurance departments. Kellie enlisted in the Navy for 9 ½ years and served two deployments to the Middle East, performed ASW and taught Aviation Water Survival Training. Through teaching, Kellie uncovered a passion for helping people and that’s when she decided to make the switch and enlist in the insurance industry. Now she’s guiding her clients and ensuring they’re properly protected. She enjoys gaming, golfing, and spending time with her Bostin Terrier, Moxie. 802-4506

How We Do It

We pride ourselves on our simple and straightforward sales process. Let us guide you on your insurance needs so you can feel good knowing what you worked so hard to build is protected.

Request Quote
  1. Get to know each other.

    Tell us about your business so we can learn your needs.

  2. Find your perfect policy.

    Our team will thoroughly access your business to develop creative, comprehensive, and cost-effective solutions that suit your company’s needs.

  3. Sit back and relax.

    Choose the coverage that best matches your company needs so you can feel good about your insurance.

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