Careers

Woman in pink sweater collaborating with male colleague at computer workstation in modern office environment

Life at DSS

At DSS, we engineer smarter workflows and boost provider performance to improve patient outcomes. We help health care organizations work better and care better.

Our people are our greatest asset. We grow by investing in their growth – encouraging ambition and nurturing talent.

Founded by three brothers with a bold vision for health care, DSS is a place for those who share that vision and want to drive real innovation.

Join Our Talent Pool – Shape the Future with Us.

Current Opportunities Career for Military Veterans
Featured Position

Automation Engineer I

Kickstart your career in automation engineering! As an Automation Engineer I, you’ll help ensure our platforms run smoothly, securely, and at scale. Working alongside senior engineers, you’ll gain hands-on experience with CI/CD pipelines, cloud environments, and deployment automation. You’ll collaborate with cross-functional teams, troubleshoot challenges, and contribute to platform improvements—all while learning modern technologies and best practices.

Employee Growth and Benefits

At DSS, our employees are more than just team members – they're the driving force behind our success. Our excellence is rooted in our dedicated people, and we recognize and celebrate their contributions through meaningful rewards, growth opportunities, and a culture that values every voice.

Health & Well-Being

Coverage to suit family needs includes medical, dental and vision insurance and telehealth. Mental health: EAP program, virtual therapy.

Life Balance Program 

Gym membership rewards, digital wellness program (online coaching), weight management tools, quit smoking program, Will preparation, travel assistance, identity theft protection.

Tuition Assistance

We’re invested in you and your future. Develop personally and professionally.

Retirement Plan

401K: 100% match first 3% of annual salary. No vesting schedule. Free Online Advice.

Pet Insurance

Up to 20% discount for caring for your furry friends.

Our People

Behind every breakthrough in Veteran health care is our team's unwavering dedication to succeed.

AnnMarie employee photo
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Stepping into my first QA team was both exciting and a little nerve-wracking, but the support I received made all the difference.

AnnMarie L.
Quality Assurance Analyst I
David employee photo
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There’s a real emphasis on growth here. When I have questions, someone is always there with the answer, including peers. We’re all in this together.

David G.
Senior Software Engineer
Jocelyne employee photo
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What immediately stood out to me about DSS was its deeply rooted family-oriented culture—and the opportunity to contribute to something greater: the well-being of our Veterans.

Jocelyne S.
Manager, Travel

Go beyond a fulfilling career.Engage in a fulfilling lifestyle.

At DSS, we build careers – and communities. As part of our family, employees have meaningful opportunities to give back and make a diference.