Senior Operational Planner

Cayuse Holdings•Honolulu, HI

1d•$105,000 - $115,000•Onsite

About The Position

The Senior Operational Planner is responsible for developing, writing, and maintaining detailed operational plans, providing expert staff planning, and ensuring effective integration across multiple domains to strengthen organizational initiatives. The planner collaborates with subject matter experts, coordinates complex schedules, participates in important planning meetings, and sustains the alignment of operational efforts with established organizational and regional priorities. This position aligns with Cayuse’s core values of Innovation, Excellence, Collaboration, Adaptability, and Integrity by fostering technical solutions that meet customer needs, promoting teamwork, and prioritizing quality in deliverables

Requirements

Bachelor’s degree in Operations Research, Military Science, National Security, Engineering, or related discipline.
Minimum five (5) years of direct operational or strategic planning experience in a military, government, or defense contractor environment.
Must be able to pass a background check. May require additional background checks as required by projects and/or clients at any time during employment.
Secret Clearance required.
Demonstrated expertise in exercise and experimentation design, airlift and mobility planning, operational analytics, and after-action reporting, with a strong record of compliance with relevant industry standards and best practices.
Strong written and verbal communication skills, coupled with advanced problem-solving abilities and a proven track record of successful cross-functional team collaboration.
Exceptional interpersonal skills and ability to build productive working relationships.
Outstanding organizational, analytical, and problem-solving skills, with keen attention to detail.
Proven ability to multitask and prioritize effectively in fast-paced environments with shifting priorities; adaptable and a rapid learner.
Self-motivated with the ability to work independently and as part of a multi-disciplinary team.
Skilled in handling sensitive and confidential information with integrity and discretion.
Proficient in MS Office suite, with strong analytical, organizational, and time-management capabilities.
Established relationships with potential clients and teaming partners, enabling immediate and effective contribution.
Willingness to travel for short-term assignments as required.
Highly motivated and comfortable managing multiple concurrent tasks.
Demonstrated business acumen and strong understanding of industry practices.
Ability to develop new relationships, both individually and in team contexts.
Exceptional written and oral communication skills, with demonstrated ability to facilitate meetings, coordinate schedules, and synthesize complex information.
Proficient in the use of virtual meeting platforms and in hosting virtual and hybrid meetings (including Webex, Teams, and similar technologies).

Nice To Haves

Master’s degree in operations, strategic studies, or a closely related field.
Experience supporting complex organizational or multinational planning initiatives.
Familiarity with structured planning and operational analysis processes, such as comprehensive decision-making methodologies and contingency or crisis management planning.
Demonstrated expertise in multi-domain operations or key functional areas within large organizations.
Experience in support roles on large-scale projects or contracts, including participation in and reporting on high-level meetings.
Prior military service is desirable.
Experience with market and business development.
Proficiency in account management.

Responsibilities

Develop, implement, and manage operational plans and supporting documentation—including foundational plans, annexes, and appendices—for exercises, contingency scenarios, and multidomain integration initiatives.
Support the articulation of organizational strategic vision, goals, and operational intent; ensure plans align with broader strategies and priorities.
Participate in high-level planning conferences; coordinate meeting schedules and facilitate subject matter expert engagement at these events.
Structured Decision-Making: Lead or support planning teams in framing complex challenges using recognized decision-making methodologies, including the preparation and delivery of detailed briefings to senior leadership.
Integrate threat analysis and intelligence assessments to inform simulations, advise on competitor/adversary courses of action, and enhance operational strategies.
Plan Maintenance and Documentation: Prepare, maintain, and update foundational plans and related documents to ensure they remain current and compliant with relevant industry guidance and best practices.
Conduct feasibility studies and integrated planning development to advance operational effectiveness, including assessment of key activities, resource allocation, task organization, pre-positioned assets, and priority lists.
Adapt contingency and operational plans to accommodate evolving scenarios and emerging requirements.
Provide expert planning and advisory support across a range of operational functions, such as space operations, information operations, asset protection, air and missile defense, CBRN, health and safety, physical security, personnel recovery, explosive ordnance management, operational security, cybersecurity, risk assessment, infrastructure protection, continuity of operations, and biometrics.
Contribute to updates and enhancements of organizational plans and policies; inform and support processes for reception, staging, onward movement, and integration (RSOI) as required.