Working at Oakleaf

Why work at Oakleaf?

What is it like working at Oakleaf?


Why Work at Oakleaf?

Our CEO and founder Chris Milner believes deeply that 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. The Oakleaf family is large and diverse with people joining us as full-time employees, independent contractors, and consulting advisors. We speak many languages and come from many backgrounds but we all come together as Team Oakleaf. We are particularly proud to say that more than a few consultants have left and returned within a few years to bring their new experiences back to Oakleaf.


We have the privilege of working with some of the smartest people in the industry who are working on cutting edge and transformative projects. We work to bring those experiences home so we can all learn and grow. We encourage cross-training and continuous learning. In some cases we have set up mentor programs so that those who are strong in one skill can help others who are working to expand their skills. We also arrange for our people to support a variety of client projects whenever practical. Learning from new environments is critical to building a strong and multi-faceted career.


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, better people, and results in the delivery of the highest level of excellence to our clients.


Working at Oakleaf

The Oakleaf Group is boutique consulting firm specializing in the mortgage industry. Our clients include the GSE firms, banking clients, law firms, investment firms, federal government clients, and credit unions. We have Oakleaf consultants working at client sites under the client's direction and delivery teams working at our Bethesda headquarters or remotely delivering services to clients. 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.


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 Benefits:

  • United Healthcare medical insurance with options including a Choice Plus plan and Health Saving Account plan options.
  • Prescription Drug program administered through United Healthcare which includes options for both retail pharmacy and mail-order.
  • United Healthcare Dental PPO
  • United Healthcare Vision with two plan options depending on your needs.
  • Health care spending accounts
  • Dependent care spending accounts
  • Disability Insurance (Short-term and Long-term)
  • Group Life Insurance
  • Accidental Death & Dismemberment (AD&D) Insurance
  • 401(k) retirement savings plans
  • Commuter Benefits Program (pre-tax options for parking/metro)
  • Paid Time Off (vacation/sick leave)
  • 10 Paid Holidays Per Year
  • Professional Development Opportunities
  • Identity Theft Protection
  • Annual social events including the famous Oakleaf Summer Crab Feast


Headquarters Building Benefits:

  • Free access to the building gym.
  • Building sponsored picnics, ice cream socials, and social events.
  • Coffee, snacks and frequent group lunches in the office.
  • Farmers market every Thursday in the Spring and Summer.
  • Easy access to the metro.
  • Direct access to the parking garage (monthly passes available)
  • Two deli's in the building and a plethora of Bethesda restaurants within walking distance

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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.