Courageous Leadership Alliance, Inc Strategic Planner (Senior) Remote · Full time

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At Courageous Leadership Alliance, we empower organizations to achieve mission excellence through innovative training solutions, strategic organizational design, and data-driven performance improvement. With deep expertise in federal, Department of Defense, and Air Force operational environments, we specialize in transforming real-world requirements into effective learning systems that enhance readiness, decision-making, and team performance. Our approach blends mission focus, instructional rigor, and enterprise insight. We work collaboratively with government partners and subject matter experts to design scenario-based training, performance measurement frameworks, and scalable solutions that reflect how teams operate in complex, high-stakes environments. What sets us apart is our dedication to: 1. Operational realism: Our solutions mirror actual workplace challenges and decision points, preparing learners for performance under pressure. 2. Integrated systems thinking: We treat training as an enterprise information system—structured, measurable, and sustainable. 3. Continuous improvement: Through analytics, evaluation, and iterative design, we ensure solutions evolve with mission needs. 4. Federal and DoD expertise: With years of experience supporting readiness evaluations and organizational transformation, we deliver training that matters. At Courageous Leadership Alliance, we don’t just build training—we build capability. Our work ensures people aren’t just trained, but ready.

The Senior Strategic Planner provides high-level strategic planning, coordination, and advisory support to senior leadership within the Department of Defense (DoD) and Department of the Air Force (DAF). This role is responsible for developing and executing long-range strategic initiatives, facilitating executive-level engagements, and producing high-quality decision-support materials that enable effective leadership decision-making. The Senior Strategic Planner ensures alignment with federal financial management laws, regulations, and policy guidance while supporting mission priorities and organizational objectives.

The individual in this position leads and supports strategic planning efforts, including the development of long-range plans such as five-year strategic plans, and coordinates complex initiatives across multiple stakeholders. Responsibilities include preparing executive briefs, analytical reports, meeting minutes, and action tracking documentation for senior leadership forums, ensuring accurate follow-through on decisions and assigned tasks. The role also includes planning and facilitating executive-level events and leadership engagements, often involving large groups of senior leaders and stakeholders.

The Senior Strategic Planner must demonstrate strong expertise in DoD and DAF financial laws, regulations, and guidance, including a thorough understanding of statutory requirements such as 10 U.S.C. § 9022 related to financial management and the Chief Financial Officers (CFO) Act of 1990. This position requires the ability to analyze complex policy and financial management frameworks and translate them into actionable strategic initiatives.

Candidates must possess a Master’s degree in Strategic Planning, Public Policy, Business Administration, Financial Management, or a related field, along with an active Secret Security Clearance. The role requires a minimum of 10 years of relevant professional experience, including at least 5 years supporting the Department of Defense. Within that experience, the candidate must demonstrate:

• At least 2 years of experience developing executive-level briefs, reports, and meeting documentation, and coordinating actions and due-outs from senior leadership forums.
• At least 5 years supporting strategic-level planning and coordination efforts, including the development and execution of long-range strategic plans and facilitation of executive leadership engagements within DoD or DAF environments.
• At least 7 years of experience planning and facilitating executive or senior leadership events involving 70 or more participants.

The Senior Strategic Planner must possess strong analytical, organizational, and communication skills, with the ability to manage complex initiatives, coordinate across multiple leadership levels, and deliver high-quality strategic products in fast-paced, mission-driven environments.