Working at The Oakleaf Group | Glassdoor

The Oakleaf Group Overview

Chevy Chase, MD
51 to 200 employees
Company - Private
$25 to $50 million (USD) per year
The Oakleaf Group is a Risk, Finance and Compliance advisory firm serving banks, GSEs, regulators, law firms, and asset managers. Our team consists of industry subject matter experts, bank regulatory reporting practitioners, risk management professionals, and technologists who ... Read more

Mission: To serve the greater good by advancing fairness, integrity, transparency and efficiency in financial markets.

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 ... Read more

The Oakleaf Group – Why Work For Us?

The Oakleaf Group is a Washington, DC based risk analytics, finance and technology advisory firm.  Our business model is simple and effective:  We listen to our clients and respond with advisory and consulting solutions tailored to their specific needs.  We earn customers’ trust by delivering on our commitments.  And we price our services competitively.

The Oakleaf Group brings broad quantitative, technology, regulatory, and operations expertise to bear in developing practical yet robust strategies for our financial institution clients.  Our deep domain expertise enables us to assist our clients in addressing industry specific challenges in mortgage finance, portfolio analytics and strategy.

As one of Oakleaf’s business and technology consultants, you are part of a team that drives client success—through focus, insight and determination to overcome complexity and remove obstacles. From Day One at Oakleaf, you help our clients realize their potential for greater success. As practitioners, we understand the challenges our clients face because we’ve faced them ourselves. 

It’s our people who make the Oakleaf difference. Our talented people develop and deliver solutions to help some of the biggest names become better at what they do. Our people thrive in a non-hierarchical, team-driven and entrepreneurial culture of a company that is big enough to matter and small enough to care.

Oakleaf celebrates individuality, integrity and transparency in our work environment and we provide our employees with the freedom to realize their aspirations.

We support and encourage an entrepreneurial outlook and independent thinking.  Oakleaf is not about organizational charts and layers — we operate with minimal hierarchy because we want all employees to contribute to continued growth of Oakleaf's brand and reputation. Everyone's ideas are heard.

The size of Oakleaf offers our employees unlimited access to senior management.  Little bureaucracy means plenty of cross-learning opportunities to work on projects and make a real contribution to developing the business. We know that the more successful our employees are, the more successful our clients are.

We actively encourage learning, whether through formal classroom-based training, learning on the job or networking. We give our employees the tools they need to develop their passion and tackle whatever challenges come their way. We recognize and reward people who deliver and are reliable, adaptive and innovative.

The Oakleaf Group Reviews

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Chris Milner
8 Ratings
  • Featured Review

    "Great Place To Work!"

    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Current Employee - Anonymous Employee in Chevy Chase, MD
    Current Employee - Anonymous Employee in Chevy Chase, MD
    Positive Outlook
    Approves of CEO

    I have been working at The Oakleaf Group full-time (More than 3 years)


    Ownership change few years ago, amazing people, interesting work, growing fast, Management truly cares about employees, great benefits, good compensation package, very innovative place; Management invests a lot into employees and the company


    Growing and running out of space, need additional office

    Advice to Management

    Continue doing what you are doing!

See All 26 Reviews

The Oakleaf Group Interviews



Getting an Interview

Getting an Interview





    Executive Assistant to Chief Executive Officer Interview

    Anonymous Interview Candidate in Bethesda, MD
    No Offer
    Negative Experience
    Easy Interview


    I applied through other source. I interviewed at The Oakleaf Group (Bethesda, MD) in April 2017.


    Submitted a CV to the company's website, as well as directly to the CEO. The HR emailed me that they would have "boxed" (deleted) my CV because only she sees incoming resumes and only she decides who works at the company but that the CEO liked my background.

    She setup calls that were suppose to go an hour but then in 20 minutes into the first call she ends it. Explaining she has another appointment, but 40 minutes later calls me again and states this is her only free time to talk.

    A meeting with the CEO/COO was setup and I went into the office. HR explained that these meetings were basic that it did not matter what they thought of my candidacy it was HR's decision.

    I chatted with the COO and CEO for almost an hour and then departed. I was later called and told that my experiences were great but that, as she had said a week before, that HR wants a young female in the role. After that call, your standard blow-off email came into my Inbox.``

    Interview Questions

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