Join Our Team

Thank you for your interest in becoming part of the Freedom Quest Family!


Trucking Specialist



We are always looking for people that can master their craft, who enjoy serving others, and who are capable of providing consistently superior customer service. While this is definitely a rewarding place to work, there are demands that go along with a position here, so we tend to be selective. After all we want good people to join us, stay with us, and grow with us.

Are you right for Freedom Quest? Is Freedom Quest right for you? Test yourself with these questions:


Are you always focused on finding solutions?


Our clients appreciate expertise… from guidance on how to meet the FMCSA’s compliance guidelines to getting a load from a broker. You should be comfortable (even excited!) about providing the resources, guidance, and expertise to keeps our truckers on the road.


Are you good at explaining things?


We have clients with diverse backgrounds, goals, business structure, and years of experience. A conversation may lead you to educate an insured about physical damage coverage on a truck and another about the radius requirements on a policy. The effort it takes to connect with a client with ten years of experience may be very different than a client that is just starting their new venture.


Can you stay calm and friendly under pressure?


Working in a remote team environment can be a very different experience than what was considered “normal.” Consider a new client being pressured by a broker for a certificate of insurance before releasing a load, your system is down, and the responsible person for sending the certificate has seven certificates in their queue.


Are you a team player?


Like in any sport, a superstar team has the advantage over a team of superstars. We want to give you the tools and resources for you to succeed at your craft with the expectation that instead of holding your teammates accountable, you’re going to hold them capable. At Freedom Quest we are best when everyone can count on one another to reach our goals together. Truly, Freedom Quest is bigger than the sum of its parts.


Are you willing to learn new things?


We’re all about evolving! Our goal this year is bigger than our goal last year. And guess what? Our goal next year is bigger than our goal this year. In order to accomplish our goals every year we have to become a bigger version of ourselves. The more you become, the more you can give.


Do you pay attention to the little things?


In this remote environment we are highly encouraged to utilize some skills that in the past may not have had the same level of emphasis. Listening for instance; we had the luxury of capturing what was said in body language to compensate on what we missed with our ears. Now we get to carefully listen to our team and our clients to be better equipped to provide solutions to challenges that may arise.


Are you patient and willing to serve people?


A man asked the master teacher, “how do you become great amongst the people?” The master teacher replied, “service to many leads to greatness.” Put another way, the more people you help, the greater you will become. And as it may apply to this position, we are privileged to serve.


Underwriting Analyst

Role and Responsibilities

Primary Duties

The Underwriting Analyst is responsible for understanding all the elements taken into consideration by the insurance company’s underwriters when considering insuring a trucking operation. This person must acquire a thorough understanding of what affects a trucking operation and what may harm it as it relates to insurance.



  1. Know how to read underwriting analysis report

These reports contain detailed information regarding a trucking company. It includes inspection history, record of violations, indication of drivers and/or trucks harming the operation, and much more.


  1. Quarterly review of report with each trucking client

The Underwriting Analyst must review the report with each client with the goal of educating the client on the items that are harming the business and may abet the increase in premium at renewal.


  1. Strategize with the client to determine most suitable practices to benefit the operation with the goal of premium reduction by the time renewal date approaches.


Daily Check List


  • Review reports
  • Write down personalized strategies that may help the insured
  • Consult with the insured to review reports and action steps for improvement.