What is the highest paying job at Chesapeake Benefits?

Based on our latest data, the highest paying role at Chesapeake Benefits is President, earning approximately $728,325 annually.

Where is Chesapeake Benefits located?

Chesapeake Benefits is headquartered in Chestertown, Maryland, but may have operations in other locations within the Insurance sector.

What industry is Chesapeake Benefits in?

Chesapeake Benefits operates in the Insurance industry.

Chesapeake Benefits Average Salary, Pay Ranges & Benefits

Q: What does Chesapeake Benefits do?

According to the company's overview, Located in historic Chestertown, Maryland, Chesapeake Benefits provides counsel, administrative support, and benefits solutions to employers and employees across the United States.

Chesapeake Benefits Salary

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Salary at Chesapeake Benefits

How Much Does Chesapeake Benefits Pay for Different Roles?

Explore detailed salary information for specific jobs at Chesapeake Benefits. Based on our data, the highest paying job is the President, with an annual salary of $728,325. The table below outlines the annual salary ranges for most popular roles within the company.

President

$728,325 / year

Salary Range: $557,546 - $917,809

Executive

Account Manager

$91,100 / year

Salary Range: $78,667 - $104,210

Account Management III

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Current Job Openings at Chesapeake Benefits

Ready for your next career move? Explore current job openings at Chesapeake Benefits. Use the search tool below to find available positions by title and location and apply directly to start your career.

Is Chesapeake Benefits’s Pay Competitive? Salary Benchmarking Analysis

How does Chesapeake Benefits's compensation stack up against the industry and its key competitors? Our salary benchmarking analysis provides a clear comparison. The chart below visualizes this comparison alongside select peer companies.

Competitor / Benchmark	Avg. Salary	Variance	Primary Market Influence Factor & Explanation
Strateben Inc	$100,174	+6.5%	Data suggests Strateben Inc's workforce skews heavily towards veteran, high-tenure roles.
Modern Senior Health	$85,850	-8.8%	Normalized for lower cost-of-living zones where Modern Senior Health primarily operates.
Redbridge Group of Florida Inc	$87,717	-6.8%	Reflects market rates for standard general contracting, differing from specialized roles.
Casey Insurance Group	$95,712	+1.7%	Confirms Casey Insurance Group is a direct competitor vying for the exact same talent pool.
Insurance Industry	$123,858	+31.6%	Pay variances are driven by organizational scale, specialized skill requirements, or geographic cost-of-living factors.

Need More Granular Data? The analysis above provides a high-level market overview. To benchmark specific job codes, adjust for real-time cost-of-living changes, or access verified HR-reported datasets, upgrade to Salary.com for Business. Precision matters when building your compensation strategy.

How Chesapeake Benefits's Salaries Compare to Similar Companies?

Explore companies in the same industry to compare average salaries, benefits, and career opportunities with those at Chesapeake Benefits. Click a company name to learn more.

Strateben Inc

$100,174 / year

Salary Range: $88,135 - $113,257

Bethesda, MD

Modern Senior Health

$85,850 / year

Salary Range: $75,535 - $97,063

Jacksonville Beach, FL

Redbridge Group of Florida Inc

$87,717 / year

Salary Range: $77,175 - $99,185

Coral Gables, FL

Casey Insurance Group

$95,712 / year

Salary Range: $84,213 - $108,221

Annapolis, MD

Benefit Watch LLC

$93,392 / year

Salary Range: $82,169 - $105,587

Nottingham, MD

Insurance LLC

$102,643 / year

Salary Range: $90,307 - $116,049

Bethesda, MD

Sweat Pants Agency LLC

$92,791 / year

Salary Range: $81,647 - $104,916

Owings Mills, MD

Voluntary Benefits Shop

$92,084 / year

Salary Range: $81,024 - $104,112

Havre De Grace, MD

Perry Hall Insurance Brokers Inc

$94,120 / year

Salary Range: $82,811 - $106,416

Nottingham, MD

Employee Reviews: Working at Chesapeake Benefits

Considering a career at Chesapeake Benefits? Explore authentic employee reviews to learn about the work environment, career growth opportunities, pay transparency and benefits. These first-hand insights can help you set realistic compensation expectations and make informed career decisions.

Highly recommend for insurance experts looking for growth. Benefits like health coverage and bonuses are excellent. The work is challenging but rewarding, with clear career progression paths. While the job may not be exciting every day, it offers stability and a decent work environment. Performance reviews are fair, and high achievers are rewarded.

Commented in May 31, 2025

Career growth is encouraged, with mentorship programs available. Colleagues are collaborative, and the office vibe is energetic. My experience here has been stable and reliable. The team is motivated, and leadership is visionary. I appreciate the opportunities for growth and the inclusive culture. The workload is fair, and the team is always willing to help. I’m satisfied with my role and the oppo...

Commented in March 07, 2025

I’ve had a fulfilling experience working here. The leadership is transparent about company goals, and employees are recognized for their contributions. The insurance field can be complex, but training is thorough. The office environment is professional, though some departments have more interaction than others. The company provides excellent training and resources for insurance professionals.

Commented in January 06, 2024

Chesapeake Benefits Overview

Website

www.chesapeakebenefits.com

Founded In

2005

Employees

<25 employees

Industry

Insurance

Headquarter Address

860 Washington Ave Chestertown Maryland MD 21620

Revenue

$5 Million - $10 Million

Phone Number

+1 4107789008

About Chesapeake Benefits

Located in historic Chestertown, Maryland, Chesapeake Benefits provides counsel, administrative support, and benefits solutions to employers and employees across the United States. We market quality and affordable group plans to employers, business associations, multi state employers, as well as serving the needs of our local clients.

What Benefits Does Chesapeake Benefits Offer Beyond Salary?

A competitive compensation package is more than just a salary. Chesapeake Benefits offers a comprehensive benefits package designed to support your health, financial future, and overall well-being. Below are the most common key benefits:

Social Security

401(K)

Disability

Healthcare

Pension

Time Off (days)

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How Much Should You Be Earning?

Get an estimated calculation of how much you should be earning and insight into your career options.

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What Is the Cost of Living Near Baltimore?

Understanding the cost of living near Baltimore is key to truly evaluating a salary offer or your current compensation at Chesapeake Benefits.

Baltimore's Cost of Living Index is approximately 91.8 (8.2% less expensive than US average; 18.8% less than MD average). Major city, historic, affordable housing in many areas, but varies greatly by neighborhood. MTA bus/Light Rail/Metro Subway. When planning your budget based on a salary from Chesapeake Benefits, consider these typical monthly expenses:

Expense Category	Estimated Monthly Cost	Key Considerations / Notes
Housing (1-BR Apt Rent)	$1,200 - $1,900+	A significant portion of Chesapeake Benefits salary. Location choices impact this heavily.
Utilities (Basic)	$150 - $250	Electricity, Heating, Cooling, Water etc.
Public Transportation	$77 (MTA CharmCard 31-day pass)	Essential for most commuters; car ownership is costly.
Groceries (Single Person)	$420 - $620	Can be higher with more dining out or specialty stores.
Personal & Leisure	$400 - $750+	Dining out, entertainment, shopping. Highly variable.
Healthcare (Individual)	$380 - $700+	Varies significantly by plan & employer contribution.
Subtotal (Excluding Taxes)	$2,627 - $4,227+	This subtotal does not include income taxes (federal, state, local), which can significantly impact your take-home pay.

FAQs of Chesapeake Benefits

1. What is the typical salary range (low to high) for most roles at Chesapeake Benefits?

The typical annual salary range for most roles at Chesapeake Benefits is approximately from $82,783 to $106,380. It's important to remember that these are overall averages, actual salaries vary significantly based on specific job titles, years of experience, skills, and location.

2. How much does Chesapeake Benefits pay compared to Strateben Inc?

The average annual salary at Chesapeake Benefits is $94,088, or an hourly wage of $45, in comparison to Strateben Inc which pays $100,174 per year or $48 per hour.

3. How does experience level affect salary at Chesapeake Benefits?

Experience level is a significant factor in determining salary at Chesapeake Benefits, as it is with most employers. Generally, employees with more years of relevant experience and a proven track record can command higher salaries. For example, a senior-level role will typically have a higher pay band than an entry-level or mid-career position within the same job family.

4. How can I determine if a salary offer from Chesapeake Benefits in Baltimore is fair given the local cost of living?

To determine if a salary offer from Chesapeake Benefits in Baltimore is fair, first compare the gross salary to our data for similar roles at Chesapeake Benefits and its competitors (see our similar company salaries section) . Then, critically, use our "Cost of Living Insights for Baltimore" to understand its purchasing power.

5. Are the salaries listed for Chesapeake Benefits on Salary.com pre-tax or after-tax?

All salary figures displayed for Chesapeake Benefits, including average base salary and estimated total compensation, are pre-tax amounts. They do not account for federal, state, or local income taxes, nor deductions for benefits like health insurance or 401(k) contributions.