AI Engineering Trainer, (1099 Contractor)
fearless.com· enterprise· Oct 23, 2026 · 5d ago
Baltimore, Maryland
In office
Contract
Senior
$120K–$176K est.
5+ years exp
Job description
Job Requirements
AI Engineering Trainer (1099 Contractor)
At Fearless, we are seeking 1099 contractors to serve as AI Engineering Trainers for intensive workforce development programs focused on AI-enabled software engineering and modernization. We have multiple training opportunities, and qualified candidates will be matched to them as they open.
Each program is a cohort-based training focused on AI-enabled software engineering and modernization. Trainers lead experienced technical professionals through a structured curriculum designed by Team Fearless, combining live instruction, hands-on labs, technical demonstrations, collaborative projects, and individualized coaching. This role requires both hands-on AI engineering experience and the ability to translate complex technical concepts into practical skills. Trainers 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 modernization of legacy systems. Fearless provides the curriculum. Trainers are not expected to build it independently, but are encouraged to supplement it with additional examples, exercises, or resources that strengthen the learning experience.
This is a fully remote 1099 contractor engagement. Training opportunities run 8 to 10 weeks and require approximately 4 to 40 hours per week, depending on the program. Work is performed on Eastern Time, and the specific schedule is shared with each opportunity.
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 where 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, as 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 give 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.
Work Experience
Required Experience
• 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 give actionable feedback.
• Experience teaching through hands-on labs, projects, demonstrations, and applied exercises rather than lecture alone.
• Strong communication skills, with the ability to explain complex AI and software engineering concepts to learners with varying levels of technical experience.
Preferred Experience
• Developing or deploying AI solutions in federal, financial, tax-processing, or similarly regulated enterprise environments.
• Applying AI-assisted engineering techniques to legacy application modernization.
• Enterprise data platforms, cloud environments, CI/CD, DevSecOps, or secure AI deployment.
• Familiarity with Databricks, Pega, Salesforce, Palantir, or comparable enterprise
• platforms.
• AI governance, responsible AI, data governance, security, privacy, and compliance requirements.
• Supporting team-based technical capstones, bootcamps, apprenticeships, or accelerated workforce development programs.
• Familiarity with Learning Management Systems (LMS) and participant progress tracking.
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).
Benefits
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 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
Application prep
Use the role’s language and application details while tailoring your materials.
Keywords to mirror
aipythonllmmlci/cd
- Platform
- phenom
- Effort
- medium