Rules Analyst - Level 2 (Security Clearance Reqd)

Oak Leaf Solutions is seeking a sharp, detail-driven Rules Analyst who is passionate about transforming complex legal and policy requirements into clear, actionable guidance. In this role, you’ll work at the intersection of compliance, technology, and mission support-helping U.S. Government customers understand their obligations and enabling automated solutions that strengthen national security. If you excel at making sense of intricate documents, enjoy collaborating with stakeholders, and thrive in an environment where your expertise has real impact, we’d love to meet you., 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.

• Requires 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.
• 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 14 years.

• 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.

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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.