Legal - Rules Analyst 2 with Security Clearance

Job Description Step into the center of the mission. Oak Leaf Solutions is seeking a Rules Analyst Level 2 to transform complex legal and policy documents into clear, actionable rules that power compliance and automation for a critical national security customer in Hanover, MD. In this role, you’ll be the bridge between law, policy, and technology—extracting key requirements, shaping controls and system behaviors, and helping mission teams operate with confidence and precision. If you love diving into dense material, spotting patterns, and turning “legalese” into rules that real systems can use, this is where your expertise will truly matter. A current and active TS/SCI Clearance with a Polygraph is required to be considered. The ideal candidate will be responsible for the following: Responsible for analyzing legal and policy documents to extract key information from the documents in accordance with established guides and procedures. Responsible for identifying compliance obligations in legal and policy documents in accordance with established procedures. The Level 2 Rules Analyst shall possess the following capabilities: Use multiple word processing and presentation tools (e.g., MS Word, PowerPoint, Adobe Pro).

Use task tracking and documentation software (e.g., Confluence and JIRA).

Engage with customers to understand problems and determine solutions based on existing documentation and guidance.

Prepare reports, responses, and briefings targeted to a wide range of audiences.

Analyze compliance obligations to identify, design, and maintain controls, system requirements, and/or machine-readable rules that enable compliance automation.

Provide subject matter expertise to the development of mission compliance-related policy and guidance.

Create and maintain user guide documentation for analyzing legal and policy documents.

Familiarity With Customer Authorities Demonstrated With Practical Experience. Requirements

• Education Requirement: Bachelor’s Degree in a relevant discipline (e.g., Legal, Technical Field, Library Science) from an accredited college or university is required. b. Experience Requirement: Ten (10) years of relevant experience in programs involving Customer authorities, and a Bachelor’s Degree in a relevant discipline (e.g., Legal, Technical Field, Library Science) from an accredited college or university is required. A Master’s degree or J.D. may be substituted for Two (2) years of experience, reducing the requirement to Eight (8) years of experience. Four (4) additional years of experience may be substituted for a Bachelor’s degree for a total of Fourteen (14) years. Benefits
  
  

About Oak Leaf Solutions Founded in 2008, Oak Leaf Solutions is a mission-driven small business delivering advanced systems engineering, cybersecurity, and technical operations to U.S. Government customers. We specialize in high-impact work that supports national security, while cultivating a culture that values innovation, integrity, and employee well-being. At Oak Leaf, you’ll find a place where your skills make a difference—and where your compensation reflects your value. We offer highly competitive salaries, exceptional benefits, and meaningful opportunities for professional growth. Veterans, reservists, and cleared professionals are strongly encouraged to apply. Learn more at www.oakleafsolutions.net. Benefits Our benefits are designed to take care of you—at work, at home, and everywhere in between: Premium Medical Coverage

Tricare Supplement Plan – 100% employer-paid for employees, 80% for dependents

Dental & Vision Insurance – 100% employer-paid

Disability Insurance – 100% employer-paid

Life Insurance – $100,000 policy, 100% employer-paid

401(k) with Company Contribution – Pre-tax or Roth, with up to $5,000/year in contributions

Generous Paid Leave – 15 PTO days 11 federal holidays up to 12 weeks parental leave

Professional Development – Up to $5,250/year for certifications, training, and education

Wellness Perks – Gym membership reimbursement (up to $50/month) CareFirst Blue365 discounts

Support for Military Families – Pay differential for active duty reserve service

…and more.