DMS is committed to providing its employees with the resources, organizational support and professional opportunities necessary to realize their highest potential. This commitment, along with the hard work and dedication of highly capable and committed employees, has been the hallmark of the company’s success. DMS seeks employees who will accept challenges as opportunities and work to maintain the standard of excellence our clients expect.

Career Opportunities

DMS seeks individuals who excel at critical thinking, working collaboratively, communicating professionally, and attending to detail. DMS offers competitive salaries, comprehensive benefits, opportunities for advancement, and an environment that embraces diversity.

DMS has career opportunities in the following professions:

  • Disability Insurance Claims
  • Information Technology
  • Insurance Accounting
  • Corporate Accounting
  • Actuarial
  • Legal
  • Client Services
  • Underwriting
  • Administrative Resources
  • Operations
  • Human Resources

DMS is an Equal Opportunity Employer

Current Career Opportunities:

Chief Information Officer:

Reporting to the company’s Chief Executive Officer (CEO), the Chief Information Officer (CIO) oversees the company’s Information Technology Department consisting of IT Officers, Directors, System Application Developers, Business Analysts and Network Administrators to deliver reliable, high-performance information systems and infrastructure supporting all business operations while maintaining the integrity and security of the company’s IT environment.  Utilizing an evolving technology roadmap which guides the company’s long-range planning for technology investments, the CIO anticipates, plans and directs the implementation of systems upgrades, security protocols and maintenance activities.  As a member of the company’s senior leadership team, the CIO collaborates with executive team members to manage a queue of initiatives and projects, balancing business priorities, risks and cost, and supports the company’s business development initiatives, presenting DMS’ IT platform to prospective clients as a core strategic asset and differentiator.


Establish and operate a project portfolio and budget management process that deploys, tracks, and adjusts program and project resources.

Manage overall client implementations across the enterprise, including both technical and business process changes resulting from each implementation.

Develop security frameworks for IT assets and support an enterprise-wide IT security practice to ensure that all IT assets are protected.

Maintain electronic communication standards consistent with DMS’ documented information security practices.

Establish and maintain effective governance for IT controls as measured by outside SOCI/SOCII audits.

Manage technology obsolescence and vendor risks.

Identify opportunities to drive cost and productivity improvements.

Oversee disaster recovery planning and the implementation of emergency protocols.

Job Requirements:

Leadership and Communications

Ability to create and execute upon a clear strategic vision for information technology that supports the company’s business objectives.

Ability to communicate an IT vision and strategy across all levels of the organization and build consensus around key initiatives and projects.

Ability to work collaboratively with a diverse group of internal and external leaders.

Exceptional oral and written interpersonal and communication skills: the ability to articulate ideas to both technical and non-technical audiences.

Ability to recruit, hire and motivate a high-performance team that values transparency and accountability.

Exceptional business process acumen; strong analytical and problem-solving skills.

Comfortable with ambiguity; ability to respond to unexpected circumstances with flexibility.

A team player who collaborates effectively with internal and external partners.

A high energy executive; tenacious and passionate about achieving goals.


IT Operations

Knowledge of a range of vendor technology solutions; ability to select and integrate the most appropriate technologies supporting business initiatives.

Experience managing complex data conversions and system development projects.

Experience designing and managing an effective IT governance framework across the spectrum of IT service delivery.

Outstanding organizational skills, and the ability to manage multiple priorities in a fast paced, high pressure environment.

Strong background in IT budget development and an understanding of capital investment financing.

Professional Experience and Education

Minimum of ten years of experience in information technology, including a minimum of five years of experience in an IT management capacity; experience in a VP IT/CIO or equivalent position is preferred.

Insurance industry experience is required.

A bachelor’s degree is required; an advanced degree in a related field, such as computer science and/or business (MBA) is preferred.


Software Developer:

We are seeking a full time Software Developer to join our Springfield, MA office.  This position directly contributes to the development and maintenance of applications to support our business needs. Responsibilities include participating in the evaluation of business requirements; preparing application system specifications; developing, testing and implementing application solutions; performing maintenance and support tasks on existing systems and writing technical documentation in support of assigned projects.

The ideal candidate will be an avid learner and will have the ability to work with limited supervision as well as within a team.

Position Requirements include but are not limited to:

– One to three years software development; familiarity in developing object oriented systems using Visual Basic 6.0, Visual Basic.Net, Visual Studio, SQL Server and Crystal Reports

– Bachelor’s Degree in Computer Science or related field

– Candidate must be able to demonstrate effective communication, both orally and in writing

– Excellent problem solving skills are required

– Insurance Industry experience is preferred

Thank you for your interest in a career with DMS. Current job opportunities are updated on our website as they become available. Please check back soon.

Application submission requirements: 

If you are interested in a future position, please email your resume and cover letter to: