careers @ westwood

Careers in insurance
A career in the insurance industry


what we do

Westwood Insurance Group is a Game Changing Reputable National Insurance Brokerage Leader. We are the boutique insurance broker of choice for commercial agents serving the healthcare industry. 


our values

We conduct ourselves with moral, ethical and intellectual excellence, serving our clients, prospects, partners, each other and community. We give our attention, time and resources freely to those in need.  In doing so, we create and nurture growth opportunities and embrace positive change, remaining grateful for the opportunity to serve with integrity.


our objectives

  • Client Centric – Client needs drive all behavior.
  • Exceptional – We Anticipate, Prepare and Execute better than anyone
  • Passionate – In our commitment to Excellence


insurance careers with a leader

When you work with Westwood, you will have an insurance career with an industry leader. Since 2001, Westwood has expanded from a local Cleveland, OH based company to one of the strongest national players in the wholesale insurance brokerage space. WIG has thousands of satisfied clients and is rapidly expanding its network in the healthcare and P&C verticals. For the past 20 years our clients have come to expect the unparalleled service and professionalism that Westwood has become nationally known for.

If you are an insurance agent, please fill out the agent’s application here.

current vacancies

Dynamic Superstars are Always Wanted

Check out the vacancies for insurance careers below. If a role with your specific skills is not available, but you are a dynamic superstar with awesome follow up skills and a never say die attitude, we’d love to have your resume on file. You never know when a role that suits you perfectly will come up.

Verifiable Superstar Broker/Producer

Are you a Verifiable Superstar Broker/Producer, serving the Healthcare industry?
Do you regularly target Whales in your marketplace?
If so, We Need to Talk!

Who are we?

We’re a fast-growing wholesaler serving the healthcare industry serving hundreds of satisfied commercial agents. We are looking for a highly qualified and experienced Commercial Broker/Producer to join our motivated team of superstars.

What is your background?

  • A minimum of 3 years of successful work experience in commercial insurance.
  • An active Property and Casualty Insurance License.
  • Demonstrated success in commercial insurance sales, preferably serving the healthcare industry.
  • A strong technical aptitude with computer programs such as Microsoft Office, Google, Adobe, and CRM software.

What skillsets should you have?

  • Persistence: Pit Bull mentality with awesome follow-up skills and a never say die attitude.
  • Network: Experience and expertise in their own area.
  • Communication: Strong communication skills both by phone and in writing.
  • Listener: Ability to hear, understand, and communicate complex business challenges.
  • Teacher and Mentor: Willingness to help others and share knowledge.
  • Strong Tech Skills: Ability to learn and continuously improve technical skills.
  • Carrier Network: Connections and relationships with multiple carriers.
  • Team Player: Gets along with everyone, exudes confidence, and is not condescending.

What do we bring to the table?

If you’re a Superstar Broker/Producer, we’ll offer you a role as either an independent contractor or an employee.

Our top independent broker/producers earn over $150,000/year in commissions, while employees enjoy many benefits, including:

  • 401(k) and 401(k) matching.
  • Health insurance, Dental insurance, Vision insurance.
  • A flexible schedule working remotely, with paid time off.
  • Supplemental commission earnings.
  • E&O insurance coverage.

What you must do right now

Write a cover letter, attach it to your resume and contact us immediately!
Email your resume and cover letter in MS Word or PDF format to:

Before you apply: We are only looking for serious applicants, who are verifiable Superstars.

Dynamic Commercial Underwriting Specialist

As we continue to expand our reach within the healthcare space, we are in need of a highly qualified and enthusiastic Commercial Underwriting Specialist to join our value driven team of champion insurance professionals.

If you have the passion, motivation, energy, humility, and entrepreneurial mind set to build a career and not just secure a job, then contact us immediately. DO NOT apply unless you are in the top 5% of candidates who qualify for this terrific career opportunity. Serious applicants send a Cover Letter and CV in MS Word.

Job Description

The Commercial Underwriting Specialist’s role is to effectively market insurance submissions to carriers, follow-up for requested information, negotiate terms with carriers, present terms to retail agents, and assist in sales and product development.

  • Minimum 3 years successful work experience in commercial insurance
  • Active Property and Casualty Insurance License
  • Demonstrated success in Client Management and Technical Knowledge sharing
  • Strong technical aptitude with computer programs like Microsoft Office, Google, Adobe, On-line software, etc.
  • Aptitude for underwriting and analyzing complex risks

Area of Responsibility

  • Gather information from agents, assess their client’s needs and build customized policies
  • Explain features, advantages, and disadvantages of various policies
  • Capture and provide accurate information to build winning quotations
  • Maintain strong knowledge of products, policy features and applicable premium levels
  • Complete follow-up as needed to ensure all correspondence and policy requirements are fulfilled and executed
  • Maintain historical records using supplied technologies to ensure information retrieval
  • Bring new and renewal business to closure
  • Meet activity and production goals to comply with client effective dates
  • Market submissions to insurance Carriers and negotiate best terms for Clients
  • Communicate submission/marketing status with sales teams as needed and in scheduled production meetings


  • Consultative approach
  • Excellent listening, comprehension, and communication ability
  • Sales and Customer Service
  • Positive Attitude
  • Self-motivated
  • Organized and able to Prioritize/Reprioritize
  • Accountable
  • Strong desire to help solve client needs
  • Confident
  • Ability to work in a fast-paced environment managing multiple competing priorities/demands
  • Ability to build rapport over the phone
  • Ability and willingness to discuss client needs and exposures
  • Insurance industry connections/network
  • Risk analysis and underwriting ability
  • Desire to exceed expectations
  • Able to act independently with minimal interaction

Remember, please respond ONLY if you are in the TOP 5% of candidates and are a verifiable true superstar Commercial Underwriting Specialist by sending your resume and Cover Letter ASAP!
Job Type: Full-time
Salary: $60,000.00 per year

  • 401(k)
  • 401(k) matching
  • Dental insurance
  • Flexible schedule
  • Health insurance
  • Paid time off
  • Vision insurance


• Monday to Friday

Supplemental pay types:

• Bonus pay

Apply for a position with Westwood

If you are monitoring insurance careers to find something suitable for your skillset, keep returning to this page or follow the Westwood Insurance Group on Linkedin, Facebook or Instagram. New insurance careers become available from time-to-time as we continue to expand, so if you are a self-starting achiever, we’d like to hear from you.

traditional insurance products

Westwood have fostered exceptional relationships with underwriters and we go to great lengths to keep abreast of their latest products, changes in requirements and restrictions, including having weekly calls with the carriers, which you can see here, by joining our insurance insider group.

    Insurance products at Westwood Insurance Group

    You can find more information on the Insurance Products main page.

    If you have any questions on the different policies, check out our Insurance FAQ’s

    alternative structures

    Westwood President, Michael Richards has extensive experience in setting up alternative structures for larger clients. Here are some examples:


    If you think your client could be large and stable enough to benefit from starting or participating in a captive or has a special need for another alternative structure, contact Michael Richards now by phone: 855 351 7487.