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Click here to check out our open positions.
Where Innovation
Meets Intelligence
A new approach to your software needs. Design-led. People first.

We create software that

users love.

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Strategy
At Flipside, we specialize in crafting custom software solutions tailored to your unique business needs and requirements.
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User Experience & Design
Our team is dedicated to creating user-centric designs that enhance the overall experience and usability of software.
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Development
We optimize the development process through agile methodologies, ensuring flexibility and efficiency in delivering top-notch software products.
Our strategic, human-centered design approach is driven by deep insights and understanding of our users across government and industry, and led by innovative and passionate individuals.

People are our product.

Check out the Values

that drive us.

1
Craftmanship
We are life long learners devoted to our craft. We strive to better ourselves so that we may produce better and better solutions
2
Inquisitiveness
Our inquisitiveness leads us to finding inspiration in unique places. When coupled with the freedom to challenge existing assumptions even when it's not the popular thing to do, we create conditions for bold and innovative solutions to arise.
3
Conviction
Above all else, we strive to help and protect people by serving our fellow citizens and our communities.
4
Humility
We listen to others. In order to actualize true change, we must build and grow our coalition of those who recognize the same problems.
5
Authenticity
We are what we do, not what we say we do.
6
Family
When you work for Flipside, we are invested in you. We endeavor to create strong bonds between our employees, partners, and everyone we work with.
Passion starts at the top. Meet our leadership.
Christopher Gross headshot
Chief Executive Officer
Christopher Gross
Marisa Beard headshot
Chief Operating Officer
Marisa Beard
Matt Shoemaker headshot
Chief Design Officer
Matt Shoemaker
Patrick Sharkey headshot
Chief Technology Officer
Patrick Sharkey
Life on the Flipside
We have benefits to brag about.

25 Days of PTO + 12 Holidays

We believe in work-life balance and encourage you to take time off and recharge. In addition to annual leave, we offer parental and bereavement leave.

10% 401K Contribution

Your retirement is important to us. We offer a full 10% contribution, no match or vesting required.

$1,000 Yearly Vacation Stipend

We believe when you work hard, you should play hard.

100% Paid Health Insurance Premiums

Flipside offers comprehensive medical (United Healthcare Choice Plus and HSA), with dental and vision plans included.

Additional Insurance Coverage

Flipside pays 100% of the premium for long term disability, short term disability, and life insurance plans.

Continuous Learning Opportunities

We offer professional development and educational reimbursements because your growth is our growth!

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Flipside is based in the DC Metro area and focuses on serving clients to better ives and protect our country. For many of our government customer-related positions, a TS/SCI clearance with polygraph is required.

Let's Chat