Join Our Team
At Staples & Associates Insurance, we believe insurance is about more than policies—it’s about protecting families, businesses, and futures. For years, we’ve built our reputation on trust, exceptional service, and strong relationships within the communities we serve
What truly sets us apart is our people. We are a team of dedicated professionals who support one another, celebrate success together, and are committed to continuous growth. Whether you’re an experienced insurance professional or looking to start a rewarding career, you’ll find opportunities to learn, develop your skills, and make a meaningful impact every day.
We foster a collaborative environment where ideas are valued, achievements are recognized, and career advancement is encouraged. Our team members enjoy the satisfaction of helping clients navigate life’s uncertainties while building lasting relationships that make a difference. When you join Staples & Associates Insurance, you’re not just accepting a job—you’re becoming part of a familyoriented organization that values integrity, professionalism, and personal growth. We invest in our employees because we know that our success begins with their success.
If you’re looking for a career with purpose, a supportive team, and the opportunity to grow both personally and professionally, we’d love to meet you.
Build your future with Staples & Associates Insurance.
Why Join Staples
- 5Family-Like Culture
- 5Company Outings & Team Events
- 5Supportive Leadership
- 5Meaningful Relationships
- 5Opportunities to Learn & Grow
- 5A Positive Work Environment
New Hire Stories
When I was a senior in college, my friend Molly told me about an internship opportunity with Staples & Associates. At the time, I was looking for a place where I could learn, grow, and begin building my career. Staples & Associates took a chance on me and brought me on as an intern, and that opportunity ended up changing my future.
From day one, I was surrounded by an incredible group of people who were always willing to help. Insurance can be a complex industry, especially for someone starting with no experience, but my coworkers and mentors were patient, supportive, and eager to share their knowledge. They welcomed me into the family they had built and made me feel like part of the team right away
As my internship progressed, I realized this was where I was meant to be. I enjoyed the challenge of learning something new every day and appreciated being part of a team that genuinely cared about helping both clients and one another. When I was offered a full-time position, accepting it was an easy decision.
One of the things I value most about Staples & Associates is how the leadership invests in its employees. Rather than trying to fit everyone into the same mold, they worked with me to create a role that matched my strengths and allowed me to continue growing professionally. They taught me everything I know about insurance, supported me through the licensing process, and helped me successfully earn my insurance license. Looking back, I am incredibly grateful that Molly shared that internship opportunity with me. What started as a chance to gain experience became the beginning of a rewarding career. The support, encouragement, and opportunities I have received at Staples & Associates have shaped both my professional development and my confidence, and I am proud to be part of such an outstanding team.
Britney Lines
Customer Service Advocate
When I was in college, I began looking for an internship that would challenge me to learn something new.
Something that would help me become more of a well-rounded individual. After discovering Staples & Associates
Insurance, I never imagined that it would lead me to a growing passion for the insurance industry.
Over the course of my career, I have grown tremendously—not only in my insurance knowledge, but also in my confidence. I was thrown into the commercial insurance world early on, which was intimidating at first, but I was constantly encouraged and reminded that I was capable of succeeding. Having leaders and coworkers who believed in me made all the difference.
Like any career, there have been challenges along the way, but I have never had to face them alone. One of the things that makes Staples & Associates so special is the people. There is always someone willing to answer a question, offer guidance, or step in when life throws a curveball. Through both professional and personal ups and downs, this team has been incredibly supportive. They truly care about one another, and that kind of culture is hard to find.
I have also been given countless opportunities to continue my education and grow within my career. Staples & Associates has invested in me from the very beginning, providing the tools, training, and encouragement needed to develop professionally and reach new goals.
If you had told me a few years ago that I would end up working in insurance, I probably would have laughed. But joining Staples & Associates has completely changed the game for me. What started as an internship became a career, and what started as coworkers became family.
I am incredibly grateful for the opportunities, support, and friendships I have found here, and I am proud to be part of a team that truly feels like home.
Molly Daly
Commercial Service Specialist
Employee Testimonials
Emma Scott
Insurance Services & Marketing Director
Originally from Frederick, Maryland, I moved to Salisbury to pursue my passion for Graphic Design at Salisbury University. At the time, my plan was simple: earn my degree, gain some professional experience, and eventually move back home after graduation. What I didn’t know then was that Salisbury—and Staples & Associates Insurance—would become home in ways I never expected.
I joined Staples & Associates as a college intern while completing my Bachelor’s degree in Graphic Design and minor in Business Administration. During my time here, I not only gained valuable professional experience but also discovered a workplace culture unlike any other. After graduating and earning my Property & Casualty Insurance License in Maryland, I had every intention of returning to Frederick. Instead, I chose to stay—and it remains one of the best decisions I’ve made
What started as an internship quickly turned into a career filled with growth, opportunity, and meaningful relationships. While I enjoy the work I do every day, the people I work alongside are what truly make Staples & Associates special. The support, encouragement, and genuine care that everyone shows one another creates an environment where you feel valued both professionally and personally.
Many companies describe themselves as a family, but at Staples & Associates, that isn’t just a phrase—it’s a reality. We celebrate each other’s successes, support one another through challenges, and build relationships that extend far beyond the office. The culture here has made it easy to grow, learn, and build a career while feeling surrounded by people who genuinely want the best for you.
Today, I’m proud to call Salisbury home. Looking back, what began as a temporary internship became a place where I found both a career and a community—and I’m grateful every day that I chose to stay.
Jacob Smith
Commercial Account Manager
Growing up in Easton, Maryland, I was raised with a strong appreciation for hard work, responsibility, and serving others. After graduating from Easton High School in 2021, I began building my career in the insurance industry, earning my Property & Casualty License in Maryland, along with my Commercial Lines Coverage Specialist and Personal Lines Coverage Specialist designations. I am also farm certified, allowing me to better serve the diverse needs of our clients and community.
At the same time, I have had the honor of serving as a member of the United States Marine Corps. The values I have learned through military service—integrity, discipline, commitment, and teamwork—have shaped who I am both personally and professionally
One of the things I appreciate most about Staples & Associates is the opportunity it has given me to serve in two different but equally meaningful ways. Every day, I have the privilege of helping protect individuals, families, farms, and businesses in our community through insurance. And when duty calls, I am able to serve my country as a Marine. Having the support of a company that values both community service and military service has meant a great deal to me.
The culture at Staples & Associates is something truly special. It’s a place where people genuinely care about one another, where teamwork comes naturally, and where everyone is encouraged to grow both professionally and personally. Knowing I have the support of my coworkers and leadership allows me to confidently pursue both my career goals and my commitment to military service. I am excited about the future, grateful for the opportunities I’ve been given, and proud to be part of a team that allows me to make a difference both at home and across the country
Frequently Asked Questions
What are the typical work hours for our agency?
- To help our team stay organized, focused, and prepared to provide the highest level of service, we set aside a dedicated 30-minute preparation period each morning from 8:30 a.m. to 9:00 a.m.
- During this time, team members focus on reviewing priorities, responding to urgent items, completing follow-up tasks, and preparing for the day ahead without interruptions. This focused work period helps ensure that when we begin serving clients, we can do so efficiently and with our full attention.
- While our office remains committed to excellent customer service, this brief preparation time is an important benefit for our employees and ultimately enhances the experience we provide to our clients throughout the day.
What is the office culture like?
- At Staples & Associates Insurance, our culture is truly one of a kind. We often describe ourselves as one big family because we genuinely care about one another, support each other through busy seasons, and celebrate wins together—both big and small. Our team is built on trust, respect, collaboration, and a shared commitment to helping each other succeed. Whether someone needs guidance, encouragement, or just a friendly laugh during the workday, they can count on the people around them. We believe that when employees feel valued and connected, they’re able to do their best work for our clients and our community.
What is the dress code?
To maintain a professional image for our clients and community, employees are expected to wear business casual attire during regular business hours.
Can I listen to music while I work?
- Absolutely! Whether you’re a fan of country, classic rock, pop, or podcast marathons, feel free to enjoy your favorite tunes while you work. As long as you’re delivering excellent service to our clients, the soundtrack is up to you. Just don’t be surprised if a coworker starts singing along
Are Insurance licenses required?
- Yes. All full-time agency employees are required to obtain and maintain a Property & Casualty (P&C) insurance license. Depending on the position, licensing must either be completed prior to employment or obtained within the employee’s first 90 days of employment during the probationary period.
Do you celebrate birthdays?
- Absolutely! We never pass up an opportunity to celebrate our team. On your birthday, enjoy a delicious custom cake from Classic Cakes in Salisbury—made in your favorite flavor, of course. Calories don’t count when it’s your birthday!
Are office pets ever allowed?
- While we don’t have an official office mascot, we’re always happy to meet your furry family members through photos and stories. Pet pictures are highly encouraged and have been known to brighten even the busiest days
What’s the fastest way to become everyone’s favorite coworker?
- Easy: bring snacks. Our team loves good food, and sharing a favorite treat is a surefire way to make friends. Around here, food has a way of bringing everyone together.
Current Openings
Commercial Account Manager – Salisbury, MD
Job Description
We are seeking a highly motivated and experienced Commercial Account Manager to join our dynamic team. The successful candidate will be responsible for managing and growing a portfolio of commercial accounts, ensuring client satisfaction, and driving revenue growth.
Key Responsibilities
- Manage a portfolio of commercial accounts, serving as the primary point of contact for clients.
- Develop and maintain strong, long-term relationships with clients to ensure their satisfaction and loyalty
- Identify opportunities for account growth and work to expand our services within existing accounts
- Prepare and present proposals, quotes, and contracts to clients
- Collaborate with internal teams to develop customized solutions that meet client needs
- Resolve any client issues or concerns in a timely and effective manner
- Stay up to date with industry trends, market conditions, appetites and carrier processes and procedures
Benefits
- A supportive team and fun energetic work environment
- 401K with Corporate Matching
- Employer Paid Life Insurance
- Employer Supported Disability
OUTSIDE SALES AGENT
Job Description
We are seeking a motivated and self-driven Commercial Insurance Outside Sales Producer to join our growing independent insurance agency. This role will focus primarily on generating new Commercial Insurance business while also identifying opportunities to quote Personal Lines insurance when appropriate.
Key Roles & Responsibilities
- Prospect and develop new commercial insurance opportunities through networking, cold calling, referrals, email outreach, and in-person business visits.
- Build and maintain strong relationships with business owners, referral partners, and clients.
- Identify client insurance needs and recommend appropriate coverage solutions.
- Gather underwriting information and documentation necessary for the agency to quote accounts effectively.
- Work closely with the internal agency team during the quoting and proposal process.
- Follow up consistently on leads, quotes, renewals, and pending opportunities.
- Maintain an organized sales pipeline and document activity within the agency CRM system.
- Cross-sell additional insurance products, including Personal Lines and other coverage opportunities when appropriate.
- Meet or exceed monthly sales activity and production goals.
- Stay motivated and persistent through longer commercial sales cycles and carrier underwriting challenges.
- Represent the agency professionally within the community through networking events, business relationships, and local outreach.
- Continue developing knowledge of commercial insurance products, coverages, and carrier appetites.
- Provide excellent customer service throughout the sales process to build long-term client relationships and retention.
Benefits & Perks
- Employer-paid life insurance
- Employer-supported disability insurance
- Employer-supported health insurance
- Paid time off (PTO)
- Closed on weekends
- Positive and collaborative work environment
- 401(k) plan with company matching up to 6%
About Us
The Staples Agency is a full service insurance agency with fully trained specialists in both personal and commercial lines of insurance. In addition, we are a Premier Farm Certified agency. This provides our agents with specific knowledge of the risks faced by our farming friends. Our goal is to get to know each and every insurance client’s needs and exposures, so we can customize an insurance program that is right for them. We develop long term relationships with constant contact and annual insurance reviews to keep up with our clients’ changing lives and businesses. Licensed in Maryland, Delaware, District of Columbia, Florida, Kentucky, Missouri, North Carolina, New Jersey, Ohio, Pennsylvania, South Carolina, Tennessee, Texas, Virginia, and West Virginia. As part of our vibrant team, you will play a crucial role in empowering individuals and families through tailored insurance solutions. We believe in creating a workplace that celebrates diversity, encourages growth, and values each member’s contributions as we work together towards a common goal: securing peace of mind for our clients!
COMMERCIAL ACCOUNT MANAGER
Job Summary
We are seeking a highly motivated and experienced Commercial Account Manager to join our dynamic team. The successful candidate will be responsible for managing and growing a portfolio of commercial accounts, ensuring client satisfaction, and contributing to the agency’s continued growth and success.
Key Responsibilities
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Manage a portfolio of commercial accounts and serve as the primary point of contact for clients.
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Develop and maintain strong, long-term client relationships to ensure satisfaction and retention.
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Identify opportunities for account growth and expand services within existing accounts.
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Collaborate with internal teams to develop customized insurance solutions that meet client needs.
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Prepare and present proposals, quotes, and contracts to clients.
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Resolve client issues and concerns promptly and effectively.
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Stay current on industry trends, market conditions, carrier appetites, and underwriting guidelines.
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Ensure accurate and timely servicing of client accounts.
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Maintain detailed client records and documentation within agency management systems.
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Provide exceptional customer service and support throughout the client lifecycle.
Qualifications
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Strong customer service skills.
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Excellent written, verbal, and interpersonal communication skills, including active listening.
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Strong organizational skills with the ability to effectively multitask and prioritize client needs.
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Proficiency in Microsoft Word, Excel, and Outlook.
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Property & Casualty (P&C) License required.
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Minimum of 2 years of experience in commercial account management, sales, insurance servicing, or a related role.
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Proven track record of managing and growing commercial accounts.
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Strong analytical, problem-solving, and decision-making abilities.
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Ability to work independently and collaboratively within a team environment.
Benefits & Perks
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Employer-paid life insurance
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Employer-supported disability insurance
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Paid time off (PTO)
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Closed on weekends
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Positive and collaborative work environment
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401(k) plan with company matching up to 6%
Equal Opportunity Employer
We are committed to creating a diverse and inclusive workplace and welcome applicants from all backgrounds and experiences.