Protecting What Matters Most

COVERAGE YOU CAN COUNT ON

Personal protection for your family and commercial solutions for your business — Overwatch Insurance delivers comprehensive coverage from Annapolis, MD.

Call us today: (443) 994-4549
A+ Rated Agency
Licensed & Insured
Annapolis, MD Based
24/7 Claims Support
Multiple Carrier Access
Employee Benefits Specialist
What We Cover
PERSONAL & BUSINESS SOLUTIONS
Whether you're protecting your family or your business, we have the right coverage from top-rated carriers.
Personal Lines
Coverage for you & your family
Auto Insurance
Liability, collision & comprehensive
Home Insurance
Dwelling, liability & belongings
Life Insurance
Term, whole & universal life
Health Insurance
Individual & family medical plans
Umbrella Insurance
Extra liability beyond your limits
Surplus & Specialty
High-value & non-standard risks
Business Lines
Commercial insurance for every risk
General Liability & BOP
Core protection for your business
Property & Asset Protection
Buildings, equipment & inventory
Workers' Comp & Commercial Auto
Protect your team and fleet
Cyber & Professional Liability
Errors, omissions & data breaches
Management & Specialty Lines
D&O, crime, builder's risk & more
Professional Liability (E&O)
Mistakes, negligence & oversight
Employee Benefits
Group plans for your workforce
Group Health Insurance
HMO, PPO & HDHP options
Dental & Vision
Preventive care & eye coverage
Group Life & AD&D
Employer-sponsored life coverage
Short & Long-Term Disability
Income protection for your team
Voluntary & Supplemental
Critical illness, hospital & more
Compliance & Enrollment
ACA, ERISA & open enrollment
Why Overwatch
BY THE NUMBERS
We measure success by our clients' peace of mind.
20+
Years of Experience
Local expertise serving Anne Arundel County families and businesses.
15+
Carrier Partners
We shop multiple carriers to find you the best rate and coverage.
98%
Client Retention
Our clients stay because of the personal service and results we deliver.
24/7
Claims Availability
When you need us most, we're always just a phone call away.
Client Stories
WHAT OUR CLIENTS SAY
Real feedback from families and businesses we protect across Maryland.
★★★★★

“Overwatch Insurance made switching my home and auto incredibly easy. They found us better coverage at a lower rate than we had been paying for years. Highly recommend to any Annapolis family.”

SM
Sarah M.
Annapolis Homeowner
★★★★★

“As a small business owner I had no idea how much I was underinsured. The team at Overwatch walked me through every gap in my coverage and built a commercial package that actually fits my business.”

RK
Robert K.
Small Business Owner, Severna Park
★★★★★

“Setting up employee benefits for our team of 12 felt overwhelming until we called Overwatch. They handled everything — carrier comparisons, enrollment, even the compliance paperwork. Our employees love the plan.”

JL
Jennifer L.
HR Director, Annapolis
★★★★★

“When we had a water damage claim they were on the phone with the carrier within the hour. The claim was handled in under two weeks. That kind of service is why we've been clients for over five years.”

TD
Tom D.
Glen Burnie Resident
★★★★★

“I have a classic car collection and standard insurers wouldn't touch half of them. Overwatch found agreed-value coverage for every vehicle at rates I couldn't believe. They know the specialty market.”

MC
Mike C.
Collector, Edgewater
Reach Us
GET IN TOUCH
Questions or ready to get started? We're here for you.
Phone
Mon–Fri, 9am–5pm EST
Email
Reply within 1 business day
Address
Annapolis, MD 21401
Website
Request a quote anytime
Home › Personal Lines
Personal Lines

PERSONAL INSURANCE

Comprehensive personal coverage for your home, vehicles, health, life, and more — tailored to fit your life and your budget.

Personal Coverage
PROTECTION FOR YOUR FAMILY
We shop top-rated carriers to find the right personal coverage at the right price.
Auto Insurance
Vehicles & Drivers

Protect your vehicle and your finances. We compare rates from multiple carriers to find you the best deal.

Liability & bodily injury
Collision & comprehensive
Uninsured motorist coverage
Roadside assistance & rental
Home Insurance
Property & Belongings

Your home is your most valuable asset. Protect it from unexpected damage, loss, and liability.

Dwelling & structure coverage
Personal property & valuables
Personal liability protection
Loss of use / additional living
Life Insurance
Family & Legacy

Give your family financial security no matter what the future holds.

Term life insurance
Whole life insurance
Universal life policies
Final expense coverage
Health Insurance
Medical Coverage

Navigate the complex world of health insurance with an expert by your side.

Individual & family plans
ACA marketplace plans
Medicare supplement options
Dental & vision add-ons
Umbrella Insurance
Extra Liability Layer

When a major claim exceeds your standard policy limits, umbrella coverage protects your assets and future income.

$1M–$5M+ in added coverage
Covers auto & home liability gaps
Legal defense costs included
Affordable for most households
Surplus & Specialty Lines
Non-Standard & High-Value Coverage
WHEN STANDARD POLICIES DON'T FIT
Some risks are too unique, too high-value, or too complex for standard admitted carriers. Surplus and specialty lines markets provide coverage where others won't — and we have access to those markets.
High-Value Home Insurance
Luxury & Estate Properties

Standard homeowners policies cap out well below the replacement cost of high-value properties. Specialty carriers provide the limits and coverage quality your home deserves.

Guaranteed replacement cost coverage
Fine arts, jewelry & valuables included
Cash settlement options
No itemization required for contents
Classic & Exotic Auto
Collector & Specialty Vehicles

Standard auto policies use ACV (actual cash value) — not what your classic or exotic is actually worth. Agreed value coverage ensures you're made whole in a total loss.

Agreed value — no depreciation
Classic, vintage & collector vehicles
Exotic & high-performance cars
Flexible usage & mileage options
Watercraft & Marine
Boats, Yachts & Personal Watercraft

From bay boats to offshore vessels, standard homeowners policies offer minimal watercraft coverage. A dedicated marine policy covers you on the water the way you need.

Hull coverage & physical damage
On-water liability protection
Towing & assistance coverage
Fishing equipment & personal effects
Jewelry, Art & Collectibles
Scheduled Personal Property

Homeowners policies typically limit coverage on jewelry, fine art, and collectibles to a few thousand dollars. A scheduled floater covers individual items at their appraised value.

Jewelry & watches at appraised value
Fine art & sculpture
Wine, spirits & rare collectibles
Worldwide coverage included
Excess & Non-Standard Risk
Hard-to-Place Policies

Prior claims, unique property characteristics, or high-risk locations can make standard coverage hard to obtain. Surplus lines markets specialize in exactly these situations.

Prior claims & loss history
Coastal & flood-prone properties
Vacant & seasonal properties
Non-standard driver placement
Are you a business owner?
We offer commercial insurance and employee benefits packages for businesses of all sizes.
Business Lines →Employee Benefits →

READY TO GET STARTED?

Talk to a licensed agent — no pressure, just answers.

Home › Business Lines
Business Lines

COMMERCIAL & BENEFITS

Comprehensive commercial insurance for every risk your business faces, plus employee benefits to attract and retain top talent — all under one roof.

Core Liability Protection
Shield your business from third-party claims and catastrophic losses
General Liability
Core Business Protection

Covers third-party claims of bodily injury, property damage, or reputational harm resulting from regular business operations. Every business needs it.

Bodily injury & property damage
Completed operations coverage
Personal & advertising injury
Products liability
Professional Liability (E&O)
Errors & Omissions

Covers financial losses caused by mistakes, oversight, or negligence in professional services or advice. Essential for consultants, advisors, and service firms.

Negligence & errors in service
Claims of inadequate work
Legal defense costs
Settlement & judgment coverage
Product Liability
Manufacturers & Distributors

Protects businesses that manufacture, wholesale, distribute, or retail physical goods from claims that a product caused bodily injury or property damage.

Design defect claims
Manufacturing defect claims
Failure to warn coverage
Recall-related liability
Commercial Umbrella
Excess Liability Coverage

Extends liability limits beyond primary policies when a catastrophic claim exceeds baseline policy caps. A cost-effective way to add major protection.

Excess coverage over GL, auto & WC
Catastrophic claim protection
Legal defense cost coverage
Flexible limit options
Property & Asset Protection
Protect your physical assets, premises, and income stream
Commercial Property
Buildings & Contents

Shields physical assets like buildings, manufacturing equipment, inventory, and office furniture against hazards like fire, theft, or vandalism.

Building & structure coverage
Equipment & inventory protection
Fire, theft & vandalism
Tenant improvements included
Business Interruption
Income & Expense Protection

Replaces lost operating income and pays ongoing bills if your business must temporarily shut down due to a covered physical disaster.

Lost revenue replacement
Fixed expense coverage
Payroll continuation
Extra expense coverage
Inland Marine
Tools, Equipment & Cargo

Covers specialized tools, high-value equipment, and cargo while they are in transit over land or stored at off-site locations.

Tools & equipment in transit
Off-site property coverage
High-value equipment floaters
Cargo & goods in transit
Operational & Workforce Insurance
Keep your people, vehicles, and data protected day-to-day
Workers' Compensation
Required in Maryland

Mandated by law in most states, this covers medical expenses and lost wages for employees injured or falling ill on the job.

Medical treatment costs
Lost wage replacement
Rehabilitation & retraining
Employer liability protection
Commercial Auto
Business Vehicles & Fleets

Personal auto policies don't cover business use. Protect company vehicles and drivers with dedicated commercial auto coverage.

Owned, hired & non-owned vehicles
Fleet & single-vehicle options
Collision & comprehensive
Cargo & tools coverage
Cyber Liability
Data & Network Security

Covers financial recovery costs, notification fees, and legal liabilities following data breaches, ransomware attacks, or network security incidents.

Data breach response & notification
Ransomware & extortion coverage
Cyber business interruption
Regulatory fines & legal defense
Employment Practices (EPLI)
Workforce Liability

Protects against employee lawsuits claiming wrongful termination, sexual harassment, discrimination, or wage and hour violations.

Wrongful termination claims
Harassment & discrimination suits
Wage & hour violations
Third-party EPLI coverage
Management & Specialized Lines
Tailored protection for leadership exposure and niche business risks
Directors & Officers (D&O)
Leadership Liability

Protects upper management and corporate board members against personal financial losses from lawsuits alleging mismanagement or breach of duty.

Personal asset protection for leaders
Shareholder & investor claims
Regulatory investigation coverage
Derivative suit defense
Commercial Crime
Fraud & Theft Protection

Safeguards cash, securities, and property from fraudulent acts committed by dishonest employees or external bad actors.

Employee theft & embezzlement
Forgery & check fraud
Computer fraud coverage
Funds transfer fraud
Builder's Risk
Construction & Renovation

Provides specialized coverage for structures, materials, and equipment while a building is actively under construction or renovation.

Structure under construction
Materials on-site & in transit
Temporary structures & scaffolding
Soft costs & delay coverage
Not sure which lines apply to your business?
We assess your specific industry, operations, and risk profile to build the right package — nothing more, nothing less.

READY TO GET STARTED?

Talk to a licensed agent — no pressure, just answers.

Home › Employee Benefits
Employee Benefits

EMPLOYEE BENEFITS

Help your team thrive with a competitive benefits package. We design, implement, and manage group benefit programs for businesses with 2 to 50+ employees.

Why It Matters
ATTRACT, RETAIN & PROTECT YOUR TEAM

In today's competitive labor market, a strong benefits package is one of the most powerful tools an employer has. It signals that you value your people — and it shows up directly in your ability to recruit and keep top talent.

As an independent benefits broker, Overwatch Insurance shops multiple carriers on your behalf to design a package that fits your workforce and your budget. We handle the complexity so you don't have to.

From enrollment support to ongoing account management and compliance guidance, we're your long-term benefits partner.


Contact Us
56%
of employees say benefits are a major reason they stay
SHRM Benefits Survey
$4,700
average cost to replace a single employee
Society for Human Resource Mgmt.
88%
of workers prefer benefits over a pay raise
Harvard Business Review
2–50
employees — we serve groups of all sizes
Overwatch Insurance
Coverage Options
BENEFITS WE OFFER
A comprehensive suite of group benefits to build a package your employees will genuinely value.
Group Health Insurance
Medical Coverage

Medical coverage through Maryland's top carriers, structured for your workforce and budget with the right plan design.

HMO, PPO, and HDHP options
ACA-compliant plans
Employee contribution strategies
Spousal & dependent coverage
Dental Insurance
Oral Health Coverage

Group dental plans covering preventive, basic, and major services from large in-network carrier options across Maryland.

Preventive care at 100%
Basic & major restorative
Orthodontia options
Large in-network provider access
Vision Insurance
Eye Care Coverage

Affordable vision plans covering annual eye exams, frames, lenses, contacts, and LASIK discounts for your team.

Annual eye exams
Frames & lenses allowance
Contact lens coverage
LASIK discounts available
Group Life & AD&D
Life Insurance

Employer-sponsored life insurance — one of the most valued and cost-effective benefits you can offer your workforce.

Term life for employees
Accidental death & dismemberment
Voluntary supplemental life
Dependent life options
Short & Long-Term Disability
Income Protection

Protect your employees' income when illness or injury keeps them from working — offered as employer-paid or voluntary.

Short-term disability (STD)
Long-term disability (LTD)
Own-occupation definitions
Employer & voluntary options
Voluntary & Supplemental
Employee-Paid Add-Ons

Employee-paid voluntary options that cost the employer nothing but meaningfully expand your benefits offering.

Critical illness insurance
Hospital indemnity
Accident insurance
FSA / HSA-compatible plans

COMPLIANCE & ENROLLMENT SUPPORT

We don't just sell plans. We help you manage open enrollment, communicate benefits to employees, stay compliant with ACA and ERISA requirements, and benchmark your package annually to keep it competitive.

Contact Us

READY TO GET STARTED?

Talk to a licensed agent — no pressure, just answers.

Home › About Us

ABOUT OVERWATCH INSURANCE

A trusted local agency protecting Annapolis families and businesses with expert, personalized coverage.

OUR STORY

Overwatch Insurance was founded on a simple belief: every person and every business deserves an insurance partner who truly understands their needs — not just a policy number.

Based in Annapolis, MD, we serve clients throughout Maryland and the surrounding region. As an independent agency, we access dozens of top-rated carriers to shop the market on your behalf.

Whether protecting your first home, growing a business, building an employee benefits package, or planning for your family's future, we're with you every step of the way.

Integrity

Honest advice and transparent recommendations — always in your best interest.

Expertise

Deep knowledge across personal, commercial, and employee benefits lines.

Accessibility

Real people, real answers. We're available when you need us most.

Community

Proudly rooted in Annapolis, committed to Anne Arundel County.

By The Numbers
WHY CLIENTS CHOOSE US
Numbers that reflect the trust our clients place in us every day.
20+
Years in Business
Two decades of local expertise in the Maryland market.
15+
Carrier Partners
We shop multiple carriers to find the best rate and coverage.
98%
Client Retention Rate
The best measure of our service: clients who stay year after year.
7
Lines of Coverage
Personal, commercial, and employee benefits — all under one roof.
Our Team
THE PEOPLE BEHIND YOUR PROTECTION
Experienced professionals who put your needs first.
JK
J. Keenan
Principal Agent
Licensed professional with deep expertise across personal lines, commercial, and employee benefits.
SA
Service Team
Client Services
Handles policy changes, billing questions, and day-to-day account needs with care and speed.
BE
Benefits Team
Employee Benefits
Specialists in group health, dental, vision, life, and voluntary benefits for employers of all sizes.
CL
Claims Support
Claims Advocate
We advocate on your behalf through every step of the claims process for a fair, prompt resolution.
Home › File a Claim

CLAIMS CENTER

We guide you through the claims process and advocate on your behalf for a fair, timely resolution.

How It Works
THE CLAIMS PROCESS
Four straightforward steps from incident to resolution.
01
1. Contact Us First
Call or email us immediately. We'll advise on next steps and help you avoid mistakes that can affect your claim.
02
2. Document Everything
Take photos, gather police reports if applicable, and list damaged or lost items. Strong documentation means stronger claims.
03
3. We File on Your Behalf
We submit to your carrier and act as your advocate — following up, pushing for timely responses, and explaining every step.
04
4. Resolution & Follow-Up
We review the outcome with you and ensure you're fully restored — and update coverage if needed.
Contact Now
REACH OUR CLAIMS TEAM
Overwatch Claims Line
Call us first. We guide you and contact your carrier on your behalf.
Email Our Claims Team
We respond within one business day to begin the process.
After-Hours Emergencies
Your carrier's 24/7 line is always available. We provide that number when your policy is issued.
Visit Our Office
Available by appointment.
317 Halsey Rd, Annapolis, MD 21401
Home › FAQ

FREQUENTLY ASKED QUESTIONS

Answers to the questions we hear most often. Don't see yours? Call (443) 994-4549.

What is an independent insurance agency? +
Unlike captive agents who represent a single company, independent agents like Overwatch Insurance work with multiple carriers. We shop the market on your behalf to find the best combination of coverage and price — without being tied to one insurer.
What's the difference between Personal Lines and Business Lines? +
Personal Lines covers individuals and families — auto, home, life, health, and umbrella insurance. Business Lines covers your company and employees, including commercial liability, workers' comp, commercial auto, and employee benefits like group health, dental, and vision.
How much does insurance cost? +
Premiums vary based on location, property value, driving record, age, and coverage limits. The average Maryland homeowner pays around $1,800–$2,200/year. The best way to find out is a free, no-obligation quote from us.
What employee benefits do you offer for small businesses? +
We offer a full suite of group benefits for businesses with as few as 2 employees, including group health, dental, vision, life insurance, short and long-term disability, and voluntary supplemental plans. We design the package, handle enrollment, and provide ongoing support and compliance guidance.
How do I file a claim? +
Call us at (443) 994-4549 as soon as possible after an incident. We'll walk you through the process, help you document your loss, and file on your behalf with your carrier. We act as your advocate throughout the entire process.
Can I bundle personal and business policies together? +
Yes — many of our business owner clients bundle their personal lines with their commercial coverage. We'll always look for bundling opportunities and multi-policy discounts when preparing your quote.
How often should I review my coverage? +
We recommend an annual review of all your policies, and also whenever a major life or business event occurs — buying a home, hiring employees, purchasing vehicles, getting married, or retiring.
Do you serve clients outside of Annapolis? +
Yes. While we're based in Annapolis, we serve clients throughout Maryland and surrounding states. Many interactions can be handled by phone, email, or virtually — contact us to discuss your situation.
Home › Resources

INSURANCE RESOURCES

Tips, guides, and industry insights to help you make informed decisions about your coverage.

Learning Center
GUIDES & ARTICLES
Helpful content for policyholders and those shopping for coverage.
Personal — Home
What Does Homeowners Insurance Actually Cover?
Many homeowners are surprised by what is — and isn't — covered. We break down key coverages, exclusions, and how to fill the gaps.
May 2026
Personal — Auto
5 Ways to Lower Your Auto Insurance Premium
From bundling policies to improving your credit score, several proven strategies can reduce what you pay without sacrificing coverage.
April 2026
Business — Benefits
Building a Benefits Package That Actually Retains Employees
Health insurance is just the start. Discover how dental, vision, disability, and voluntary benefits combine to win the talent war for Maryland small businesses.
April 2026
Personal — Life
How Much Life Insurance Do You Really Need?
The old rule of thumb — 10x your income — is a starting point. The right number depends on your debts, dependents, and long-term goals.
March 2026
Business — Commercial
Does Your Small Business Need a BOP?
A Business Owner Policy combines general liability and commercial property into one affordable package. Here's who needs one and what it covers.
February 2026
Industry Trends
Why Home Insurance Rates Are Rising in 2026
Climate-related losses, rising construction costs, and reinsurance pressures are all pushing premiums higher. Understanding why helps you make smarter coverage decisions.
January 2026
(443) 994-4549