Cybersecurity Trainer, (1099 Contractor)

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

Your Responsibilities in this Role:

●​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, CyberArk Privileged Access Management, and SailPoint IdentityIQ 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.

Project Skill and Experience 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 DevSecOps and security operations.

Preferred Experience

●​Experience supporting cybersecurity systems in federal or other highly regulated

environments.

●​Vendor certifications in Qmulos, CyberArk, or SailPoint.

Physical Requirements:

• Ability to sit for extended periods while working on a computer or during meetings.
• Must be able to travel occasionally to client sites or company meetings, which may involve driving or flying.
• Ability to communicate effectively via phone, email, and in-person, requiring clear speech, listening, and written communication skills.
• Ability to move within an office environment, including reaching for files, using office equipment, and occasional light lifting (up to 10 pounds).

Life at Fearless

We're a digital integration consultancy on a mission to build a better tomorrow. At Fearless, we combine technology, people, and organizational development to solve meaningful problems. Through iterative development, we deliver smart, user-friendly solutions that make technology work better—for everyone.

But great technology is only part of the story. What truly sets Fearless apart is our Purple Culture and our commitment to building meaningful partnerships with the people who help us deliver exceptional results.

What Makes Us Purple?

Whether you're a team member, contractor, or partner, our Purple Culture influences how we collaborate, communicate, and solve problems together.

Being Purple means you:

• Contribute to work that creates meaningful impact
• Collaborate with people who value curiosity, innovation, and continuous improvement
• Bring your expertise to challenging and rewarding projects
• Work with transparency, trust, and mutual respect
• Help create solutions that improve the lives of the people who use them
• Join a community committed to equity, inclusion, and belonging

We're proud to be an equal opportunity organization. We believe diverse perspectives make us stronger, and we welcome individuals from all backgrounds, experiences, and identities.

Compensation & Engagement Details

Fearless is committed to offering competitive contract rates that reflect the expertise, experience, and value our independent contractors bring to client engagements.

Final rates are determined based on experience, qualifications, project requirements, and market considerations.

This position is structured as an independent contractor (1099) engagement and is not eligible for employee compensation programs or benefits.

Why Partner with Fearless?

When you partner with Fearless, you'll have the opportunity to:

• Contribute to mission-driven work that delivers meaningful outcomes
• Collaborate alongside experienced professionals across technology, delivery, design, and organizational development
• Apply your expertise to impactful client engagements
• Build relationships with a values-driven organization committed to excellence
• Work with a team that values autonomy, accountability, and results
• While independent contractors are not eligible for employee benefits, we strive to create strong partnerships that support successful outcomes for both our clients and our contractor community.

Independent Contractor Requirements

To engage with Fearless as an independent contractor, the following documentation must be provided prior to the start of work:

• Completed Form W-9
• Proof of General Liability Insurance
• Certificate of Insurance (COI)
• Compliance with any project-specific customer requirements, including background checks or security clearances, when applicable

Additional documentation may be required depending on the nature of the engagement.

Reasonable Accommodations

Fearless is committed to providing reasonable accommodations for applicants and candidates with disabilities. If a reasonable accommodation is needed to participate in the application or interview process, please contact the Human Resources Department at hr@fearless.tech.

So, What's Next?

We've refined our engagement process to ensure alignment between Fearless, our clients, and our contractor partners.

If there's mutual alignment, we'll reach out to begin the interview and evaluation process. Depending on the role or project, the process may vary slightly, but typically includes:

1. Introductory Conversation

We'll connect to:

• Learn more about your experience and expertise
• Discuss project requirements and expectations
• Review rate expectations and engagement details
• Answer any questions about Fearless and the opportunity

2. Skills Assessment (If Applicable)

For some engagements, we'll ask you to complete a role-specific assessment or work sample to better understand your capabilities and approach.

3. Skills & Business Fit Conversation

This conversation allows us to:

• Discuss relevant experience and project examples
• Explore your approach to problem-solving and collaboration
• Ensure alignment between your expertise and the engagement's needs
• Some engagements may also require customer interviews, background checks, or security clearance verification based on project requirements.

Where You Can Partner with Fearless

At Fearless, we’re proud to partner with talented independent contractors across the United States. We are currently able to engage 1099 contractors residing in all 50 states. For contractors who may be interested in future full-time employment opportunities with Fearless, please note that our current W-2 employment footprint includes the following 15 states:

Alabama, California, Delaware, District of Columbia, Florida, Georgia, Maryland, New Jersey, New York, North Carolina, Ohio, Pennsylvania, South Carolina, Tennessee, Texas, and Virginia. While contractor engagements are available nationwide, eligibility for future W-2 opportunities is contingent upon residing in one of our approved employment states at the time of consideration.

#LI-Remote