Cybersecurity Trainer

At Fearless, we are seeking a 1099 contractor to serve as a Cybersecurity Trainer for a 24-week, hands‑on workforce development program designed to advance federal cybersecurity personnel from foundational knowledge through operational proficiency. The program focuses on enterprise identity and access management, privileged access management, and continuous security monitoring platforms. The trainer will deliver live, instructor‑led sessions using a pre‑designed curriculum, translating complex cybersecurity technologies into structured learning experiences through hands‑on labs, scenario‑based exercises, and practical skills validation.

This is a fully remote 1099 contractor engagement requiring approximately 15–20 hours per week, with work performed between 9:00 a.m. and 5:00 p.m. EST.

• Deliver engaging instructor‑led virtual cybersecurity training sessions aligned to Government‑approved curriculum, learning objectives, and proficiency requirements.
• Develop and maintain course materials including instructor guides, student guides, presentations, demonstrations, lab exercises, assessments, and technical documentation.
• Configure, validate, and test training lab environments and sandbox systems before each cohort to ensure successful hands‑on exercise completion.
• Facilitate realistic operational scenarios involving administration, configuration, troubleshooting, security operations, integration, and recovery activities.
• Provide instruction supporting Qmulos Q‑Compliance and Q‑BA², Cyber Ark Privileged Access Management, and SailPoint Identity IQ platforms.
• Administer baseline, formative, and post‑training assessments and evaluate participant performance against defined learning objectives and competency thresholds.
• Monitor attendance, participation, lab completion, assessment results, and skill progression and provide required information for LMS and program reporting.
• Identify participants requiring additional assistance and provide targeted coaching, remediation, office hours, or supplemental exercises as appropriate.
• Coordinate with the Program Manager, stakeholders, technical SMEs, LMS personnel, and other instructors to maintain consistent delivery across cohorts.
• Capture lessons learned and participant feedback and recommend curriculum, lab, pacing, or instructional improvements for subsequent cohorts.
• Ensure instructional materials and delivery comply with applicable security, privacy, accessibility, and Section 508 requirements.

• Minimum of 5 years of experience in cybersecurity engineering, administration, operations, technical training, or closely related discipline.
• Demonstrated experience explaining complex technical concepts to audiences with varying levels of technical proficiency.
• Practical experience administering, engineering, implementing, or supporting enterprise cybersecurity technologies.
• Proven capability independently conducting technical demonstrations, facilitating hands‑on labs, diagnosing student lab issues, and evaluating practical competency.
• Strong knowledge in Identity and Access Management, Identity Governance and Administration, Privileged Access Management, or security compliance and continuous monitoring.
• Strong knowledge in NIST Risk Management Framework, security control implementation and assessment, logging and SIEM, or cloud security.
• Strong knowledge in AWS, APIs, system integration, automation, troubleshooting, or Dev Sec Ops  and security operations.

• Experience supporting cybersecurity systems in federal or other highly regulated environments.
• Vendor certifications in Qmulos, Cyber Ark, or SailPoint.

• Ability to sit for extended periods while…