CSSP Operations Training Lead

Guidehouse • Honolulu, HI

9d • Hybrid

About The Position

As a Cybersecurity Service Provider CSSP Operations Training Lead, you will develop, manage, and continuously improve comprehensive training programs that directly support CSSP mission needs. You will incorporate analyst TIER requirements across different teams and skill levels, along with tool updates, operational lessons learned, and the evolving threat landscape, into all training content. This role is pivotal in coordinating training sessions, tracking completions, integrating learner feedback, and ensuring the workforce remains technically proficient and operationally ready. You will serve as the primary SME for CSSP training development, with strong project management skills, technical expertise, and a genuine passion for learning. You will promote a culture of individual and team development while tailoring training agendas and materials to the unique needs of each operational team, ultimately closing capability gaps and driving measurable improvements in CSSP performance.

Requirements

• Minimum of FIVE (5) years of experience in training program development, instructional design, or technical training delivery within cybersecurity operations, IT, or DoD environments.
• An ACTIVE and MAINTAINED "SECRET" Federal or DoD security clearance
• Demonstrated experience developing and managing training agendas, custom training modules, and role-based curricula.
• Hold a Bachelor’s Degree in Education, Instructional Design, Cybersecurity, Information Technology, or a related field.
• Demonstrate strong project management skills with proven ability to coordinate multiple training initiatives simultaneously.
• Possess strong technical skills and working knowledge of cybersecurity tools, processes, and operational workflows.
• Show a passion for learning and a proven track record of promoting an environment of individual and team development.
• Demonstrate excellent communication, presentation, and facilitation skills.
• Meet DoD 8570/8140 Level II or III certification and CSSP Compliant Certifications Required.

Nice To Haves

• Experience with adult learning principles, instructional design methodologies (ADDIE, etc.), and modern training delivery platforms.
• Passion for learning and a proven track record of promoting an environment of individual and team development.
• Experience tailoring training content to incorporate real-world operational lessons learned and specific capability gaps.
• Proficiency in tracking training completions, maintaining training records and requirements, and generating compliance reports.
• Knowledge of CSSP operations, TIER requirements, and continuous improvement frameworks.
• Excellent communication, presentation, and facilitation skills.
• Familiarity with process improvement methodologies and knowledge management systems.
• Ability to work independently with minimal guidance and oversight.
• Demonstrated experience in cybersecurity or DoD training environments.

Responsibilities

• Serve as the central point of accountability for all CSSP training activities, developing and managing training programs that are fully aligned with mission needs, analyst TIER requirements, tool updates, and operational lessons learned.
• Create and maintain a rolling CSSP training agenda, designing and delivering both baseline and progressive training sessions while ensuring training content remains current and relevant to evolving operational demands and threat landscapes.
• Coordinate training sessions across multiple teams and locations, tracking completion status, maintaining accurate training records, and integrating learner and stakeholder feedback to continuously enhance program quality and workforce readiness.
• Develop custom training materials based on specific tools, processes, and identified capability gaps across service areas while tailoring delivery methods to the unique requirements of individual teams and service areas.
• Collaborate closely with operational leads, technical SMEs, and the broader CSSP leadership team to ensure training directly supports mission objectives and closes performance gaps.
• Identify training needs through analysis of operational data, after-action reviews, and capability assessments, then design and execute responsive training solutions that improve overall CSSP effectiveness.
• Promote a culture of continuous learning and professional development, mentoring personnel and fostering an environment where individual and team growth is prioritized.
• Periodically evaluate training effectiveness through assessments, surveys, and performance metrics, making data-driven adjustments as needed.

Benefits

• Medical, Rx, Dental & Vision Insurance
• Personal and Family Sick Time & Company Paid Holidays
• Parental Leave
• 401(k) Retirement Plan
• Group Term Life and Travel Assistance
• Voluntary Life and AD&D Insurance
• Health Savings Account, Health Care & Dependent Care Flexible Spending Accounts
• Transit and Parking Commuter Benefits
• Short-Term & Long-Term Disability
• Tuition Reimbursement, Personal Development, Certifications & Learning Opportunities
• Employee Referral Program
• Corporate Sponsored Events & Community Outreach
• Care.com annual membership
• Employee Assistance Program
• Supplemental Benefits via Corestream (Critical Care, Hospital Indemnity, Accident Insurance, Legal Assistance and ID theft protection, etc.)

What This Job Offers

• Job Type: Full-time
• Career Level: Senior