AI Engineering Trainer, (1099 Contractor)

Fearless•Baltimore, MD

5d•Remote

About The Position

Fearless is seeking 1099 contractors to serve as AI Engineering Trainers for cohort-based workforce development programs focused on AI-enabled software engineering and modernization. Qualified candidates may be matched to training opportunities as they open. Trainers lead experienced technical professionals through a structured curriculum developed by Team Fearless, using live instruction, hands-on labs, technical demonstrations, collaborative projects, and individualized coaching. Trainers need hands-on AI engineering experience and the ability to translate complex technical concepts into practical skills. They help participants design, develop, integrate, test, troubleshoot, and securely deploy AI-enabled and agentic AI solutions in realistic enterprise environments. Topics include AI engineering fundamentals, agentic AI, AI-assisted software development, Python, data and integration patterns, secure software delivery, responsible AI, and legacy-system modernization. Fearless provides the curriculum; trainers are not expected to create it independently, though they may supplement it with examples, exercises, or resources. This is a fully remote, 1099 independent-contractor engagement. Programs run 8 to 10 weeks and require approximately 4 to 40 hours per week, depending on the opportunity. Work is performed on Eastern Time, with the specific schedule shared for each opportunity. Occasional travel to client sites or company meetings may be required. The role is not eligible for employee compensation programs or benefits. Rates are determined based on experience, qualifications, project requirements, and market considerations.

Requirements

At least 5 years of professional experience in AI/ML engineering, software engineering, data engineering, or a closely related technical discipline.
Hands-on experience designing, developing, deploying, troubleshooting, optimizing, or maintaining AI and/or agentic AI solutions in production or comparable enterprise environments.
Experience delivering technical instruction, hands-on training, developer enablement, mentoring, coaching, or workforce development for adult technical learners.
Strong working knowledge of Python and modern AI/LLM development tools, frameworks, and engineering workflows.
Experience with AI-enabled application development, including APIs, data integration, testing, debugging, and secure software development practices.
Experience with generative AI and modern AI engineering patterns such as prompt engineering, RAG, AI orchestration, and/or agentic AI frameworks.
Ability to review participant code and technical artifacts, diagnose implementation challenges, and provide actionable feedback.
Experience teaching through hands-on labs, projects, demonstrations, and applied exercises rather than lecture alone.
Strong communication skills and ability to explain complex AI and software engineering concepts to learners with varying levels of technical experience.
Ability to sit for extended periods while working on a computer or during meetings.
Ability to travel occasionally to client sites or company meetings, which may involve driving or flying.
Ability to communicate effectively by phone, email, and in person, including clear speech, listening, and written communication.
Ability to move within an office environment, reach for files, use office equipment, and occasionally lift up to 10 pounds.
Provide a completed Form W-9, proof of General Liability Insurance, and a Certificate of Insurance (COI) before work begins.
Comply with project-specific customer requirements, including background checks or security clearances when applicable.

Nice To Haves

Experience developing or deploying AI solutions in federal, financial, tax-processing, or similarly regulated enterprise environments.
Experience applying AI-assisted engineering techniques to legacy application modernization.
Experience with enterprise data platforms, cloud environments, CI/CD, DevSecOps, or secure AI deployment.
Familiarity with Databricks, Pega, Salesforce, Palantir, or comparable enterprise platforms.
Experience with AI governance, responsible AI, data governance, security, privacy, and compliance requirements.
Experience supporting team-based technical capstones, bootcamps, apprenticeships, or accelerated workforce development programs.
Familiarity with Learning Management Systems (LMS) and participant progress tracking.

Responsibilities

Deliver live, instructor-led technical training on AI engineering, agentic AI, and AI-enabled software development.
Lead hands-on labs, technical demonstrations, practical exercises, and collaborative projects in which participants design, build, integrate, test, debug, and troubleshoot AI-enabled solutions.
Teach and reinforce Python, AI/LLM tools and frameworks, APIs, data engineering concepts, source control, testing, and modern software delivery practices.
Guide participants through AI-assisted engineering workflows, including code generation, testing, automation, debugging, and legacy application modernization.
Coach participants on prompt engineering, Retrieval-Augmented Generation (RAG), AI orchestration patterns, and agentic AI concepts covered in the approved curriculum.
Reinforce secure AI integration, responsible AI, data governance, privacy, security, and risk mitigation throughout exercises and projects.
Provide real-time technical assistance during labs and project work, including troubleshooting, debugging, code review, and problem-solving support.
Review participant work and provide individualized feedback, coaching, and remediation to close skill gaps.
Assess participant progress through labs, assignments, knowledge checks, technical demonstrations, and capstone activities.
Support team-based capstone work in which participants demonstrate an AI-enabled or agentic solution in a realistic enterprise modernization scenario.
Collaborate with program leadership and other instructors to monitor participant progress, identify areas needing reinforcement, and stay aligned with the approved training plan.