Why Work at Oakleaf?

Our CEO and founder Chris Milner believes deeply in our vision: that as a services company, our greatest assets are our employees and our customer relationships. We succeed and grow when we can advance the interests and meet the needs of both of these stakeholders while making a profit. As an Oakleaf employee or contractor, we believe one of our main ways of achieving this is to challenge and reward our team.

We believe in having fun, too. We have company outings (like our crab-fest this last summer) and a holiday party at year-end. We also host regular company lunches and Town Halls, where Chris and the management team share their successes and challenges, and team members are encouraged to ask the toughest questions.

Above all, we are deeply committed to maintaining the highest levels of integrity and trust - with each other and with our clients. We believe this makes us better team members, and better people, and results in the delivery of the highest level of excellence to our clients.


As a condition of employment with The Oakleaf Group, any successful job applicant will be required to complete successfully a background investigation, which may also include a pre-employment drug screen and/or credit check for positions in some areas of our business.

The Oakleaf Group is an equal opportunity employer. Applicants are considered for positions without regard to race, religion, gender, native origin, age, disability, or any other category protected by applicable federal, state, or local laws.

The Oakleaf Group participates in the E-Verify program.

Working at Oakleaf

We pride ourselves on our enormous diversity - gender, age, race, creed, skillset, temperament - so working at Oakleaf, you’ll be striving and thriving alongside an impressive array of team members.

We value hard work, and most people work longer than a 40-hour week, but we also support flexibility, and have a lot of remote and flex-time team members.  We want to ensure that you work at maximum efficiency, so we have core hours, and care more about a job well done than facetime and lots of meetings.

As a services firm that works in the world of finance, we are constantly seeking the latest cutting edge technologies and methodologies, so you will have the opportunity to stretch and grow your skills.  We encourage an entrepreneurial approach, and reward innovation and creativity.

Although we have grown quickly, we have worked hard to keep our hierarchy flat, and focus our efforts on nimbleness and flexibility, not on bureaucracy and administration. 

But don’t take our word for it. Please watch our video, and listen to what some of our team members say about what it’s like to work at Oakleaf!


Oakleaf values the work and commitment of all of its employees.  We offer a comprehensive benefits package and are committed in making your health and wellness our number one priority.  We offer the following benefits:

  • Medical
  • Dental
  • Vision
  • Prescription Drug Program
  • Flexible Spending Accounts
  • Disability Insurance (Short-term and Long-term)
  • Group Life Insurance
  • Accidental Death & Dismemberment (AD&D) Insurance
  • Transportation Pre-Tax Benefits
  • Paid Time Off (for qualifying positions)
  • 10 Paid Holidays Per Year (for qualifying positions)
  • Professional Development Opportunities
  • Identity Theft Protection

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7315 Wisconsin Avenue, East Tower 10th Floor
Bethesda, MD 20814
P. (202) 684-2800 • F. (202) 684-2803

© 2018 The Oakleaf Group, All Rights Reserved.