Vacancies at Masters Insurance Company USA


The history of Masters Insurance Company began in 1966, about 50 or more years ago, when two brothers, Frank (1936 – 2020) and Sam Ciccolini, came into partnership. Later, they were joined by a third brother Max and bondsmen Gary Corby. The company was built up from scratch with several years of commitment, hard work, strong values of family and dedication.

Over the years, Masters Insurance Company, which started as a family business, has cemented its name down the line of history to become a top-notch insurance provider making it one of the largest, most trusted and reliable independently owned insurance and bonding brokerages in Ontario. Masters Insurance has since then grown to have several branches in the US, including Toronto, Hamilton, Ottawa, Windsor, New York and Florida.

Specializing in several insurance solutions, including; realty, health care, insurance program management, claims management, surety, tarion & subdivision bonds, deposit insurance, investments, life insurance & real estate, financial planning, builders risk program, commercial insurance and lots more.

Careers Available At Masters Insurance Company

If you are interested in working as an employee at Masters Insurance Company, you are in the right place. Here we will list some available job options you can choose from, including their roles and annual salaries.

List of Jobs Available At Masters Insurance Company

Job Roles & Responsibilities

Annual Salary

Insurance Retention Specialist

As an Insurance Retention Specialist, your primary responsibility is to ensure existing clients renew their insurance policies. You’ll develop strong relationships with clients, addressing their concerns and providing personalized solutions to maximize policy retention rates.


Insurance Sales Representative

As an Insurance Sales Representative, you’ll seek out potential clients, present insurance products, and tailor coverage options to meet individual needs. Building and maintaining client relationships is crucial, along with meeting sales targets to drive business growth.


Management Trainee

As a Management Trainee, you’ll undergo comprehensive training to understand various company operations aspects. Your role involves learning different managerial functions, assisting teams, and working on projects to prepare for higher-level leadership positions.


Customer Service Representative

As a Customer Service Representative, your main duty is to provide exceptional customer service. Handling inquiries, resolving issues, and maintaining a positive customer experience is vital to ensure client satisfaction and promote loyalty to the company.


Lawn Care Specialist

As a Lawn Care Specialist, you’ll be responsible for maintaining and improving the health and appearance of clients’ lawns. This includes mowing, fertilizing, weed control, and pest management, using your expertise to create lush and vibrant outdoor spaces.


Operations Manager

As an Operations Manager, you oversee the day-to-day functioning of a business or department. Your role involves optimizing processes, managing resources, coordinating teams, and implementing strategies to enhance efficiency and achieve organizational objectives.


Private Client Insurance Advisor

As a Private Client Insurance Advisor, you cater to high-net-worth individuals or exclusive clientele. Your focus is on providing personalized insurance solutions, risk management advice, and exceptional service tailored to the unique needs and assets of affluent clients.


Lawn Care Technician

As a Lawn Care Technician, you execute the practical aspects of lawn care services. Your tasks include applying fertilizers, pesticides, and herbicides, diagnosing lawn issues, performing aeration, and ensuring the proper care and maintenance of clients’ lawns.


Skills And Requirements Needed to Work At Masters Insurance Company

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Working at one of the biggest insurance companies in Canada, Masters Insurance Company, can be a fulfilling dream. However, it comes with a lot of work, and one must be ready to meet certain requirements to be considered worthy of any position in the company.

Skill Requirements

  • Communication Skills: You need strong communication skills to interact freely with clients, explain policies, and handle claims effectively.
  • Analytical Skills: Insurance professionals must be able to analyze complex data, assess risks, and make informed decisions.
  • Customer Service: Excellent customer service is crucial for building client relationships and addressing their needs and concerns.
  • Sales and Negotiation: Sales skills are important for selling insurance policies, and negotiation skills are helpful when settling claims or dealing with other parties.
  • Attention to Detail: Attention to detail is vital to accurately assess risks, calculate premiums, and avoid errors in policy documentation.
  • Problem-Solving: Insurance professionals need to be adept at identifying and resolving issues related to policies, claims, and customer inquiries.
  • IT and Digital Literacy: Familiarity with insurance software, online platforms, and digital tools is increasingly important in the modern insurance industry.

Educational Requirements

  • High School Diploma/GED: Many entry-level positions in insurance may require a high school diploma or equivalent.
  • Bachelor’s Degree: For more specialized roles and career advancement opportunities, a bachelor’s degree in insurance, finance, business administration, or related fields can be advantageous.
  • Industry Certifications: Obtaining relevant certifications like Chartered Property Casualty Underwriter (CPCU), Associate in Insurance Services (AIS), or others can enhance job prospects.

Other Basic Requirements

  • Licensing: Masters Insurance Company often require employees to obtain appropriate licenses to sell insurance in their specific region. The type of license depends on the insurance products being offered.
  • Ethical Standards: Insurance professionals must adhere to high ethical standards to protect the interests of clients and the company.
  • Regulatory Knowledge: Familiarity with insurance laws and regulations is essential to comply with legal requirements.
  • Teamwork: Working collaboratively with colleagues, agents, and other departments is common in insurance companies.
  • Sales Targets: Some positions may have sales targets that employees are expected to achieve.
  • Industry Knowledge: Keeping up-to-date with industry trends, new products, and regulation changes is advantageous.
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How to Apply for a Job at Masters Insurance Company

Are you confused about how to go about securing a spot at Masters Insurance Company? Kindly follow these simple step-by-step guide:

1. Research the Company
2. Identify Job Openings Available
3. Prepare Your Resume
4. Write a Compelling Cover Letter Seeking Employment
5. Complete the Application Form.
6. Follow Instructions Carefully to Avoid Making Unnecessary Mistakes that Can Hinder You
7. Be Clear and Concise
8. Proofread Your Application Thoroughly to Avoid Rejection or Denial
9. Avoid Generic Applications It Is Not Advisable by Big Companies
10. Showcase Relevant Skills You Possess In Your Application
11. Use a Professional Email Address that Is Active
12. Include References (if needed)
13. Be Honest and Truthful with Every Information You Provide on Your Application
14. Submit Before the Deadline, as It Can Increase Your Chances of Employment
15. Follow Up Politely (if necessary)

What You Shouldn’t Do?

Here are things you shouldn’t do when seeking employment at Masters Insurance Company:

1. Don’t Lie or Exaggerate
2. Avoid Unprofessional Email Addresses
3. Don’t Use Generic Cover Letters.
4. Don’t Ignore Instructions, as You Never Can Tell Which May be More Important
5. Avoid Errors and Typos In Your Application to Avoid Disappointment
  • Don’t Be Unprofessional in Tone
  • Don’t Overshare Personal Information.
  • Don’t Be Pushy in Follow-ups.

Keep it simple, precise, and good luck with your application!

Benefits of Working at Masters Insurance Company

Working at Masters Insurance Company can come with lots of benefits. Here is a list of some of the benefits you stand to enjoy working at Masters Insurance, one of Ontario’s most reliable insurance companies:

  1. Masters Insurance Company provides various job options, including finance, sales, marketing, claims, administration, legal services, human resources, technology etc.
  2. Masters Insurance offers employees a flexible work schedule. In other words, employees can decide to work on shifts that are best preferable to them, likewise other big insurance companies in the industry.
  3. Masters Insurance provides healthcare services to its full-time workers, which can help them maintain good health and boost their morale and productivity.
  4. Insurance companies like Masters have various job opportunities with high-paying potentials. On average, at Masters Insurance Company, one can earn $38,537 working as a Customer Service Representative.
  5. Working at Masters Insurance allows you to learn useful skills that can help you advance in your career and probably create better opportunities in the future. These skills may include; customer service, active listening, problem-solving, technical thinking, time management, and communication.
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Key Points About Masters Insurance Company

Here are some major key points you need to know about Masters Insurance Company:

1. Masters Insurance Company was founded by Frank, Sam Ciccolini, Max and Gary Corby.
2. Masters Insurance Company was established in 1966 and has been in business for over five decades and has expanded to a company size of 200 employees.
3. Masters Insurance Company has its headquarters in Vaughan, Ontario, United States.
4. Masters Insurance Company carry along other companies to better enable them to give its customers the best services by providing them with excellent home coverage for a great affordable price.
5. Masters Insurance Company understands how hard it can be to build, manage or own a business. Hence they show interest in protecting their customers’ businesses from risks and uncertainties.
6. Masters Insurance Company also offers life insurance coverage to help protect the lives of its customers and their loved ones and families.
7. Apart from providing great insurance services, Masters Insurance Company also help its customers create a well-designed plan on how they should live, including the things they want to do and the things that haven’t been thought of yet.

Masters Insurance Company Contact Info

For any complaint or query, you can contact Masters Insurance using the following options:

  • You can contact Masters Insurance using this telephone number – 1 888 673 6495
  • Or you can reach out directly through their website page –

Final Thought

Getting a job at Masters Insurance Company opens up numerous rewarding career opportunities. With various roles available, applicants can find positions that suit their skills and aspirations. The company’s commitment to excellence, employee growth, and supportive work environment make it an ideal choice for job seekers.

Masters Insurance Company values diversity and fosters an inclusive culture that promotes collaboration and innovation. Joining the company means becoming part of a dynamic team dedicated to providing top-notch insurance solutions. Whether starting or advancing a career, Masters Insurance Company offers a pathway to success, making it a desirable destination for ambitious professionals.


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