AI Engineering Trainer, (1099 Contractor)

AI Engineering Trainer (1099 Contractor)

At Fearless, we are seeking a 1099 contractor to serve as an AI Engineering Trainer for a 10-week intensive workforce development program focused on AI-enabled software engineering and modernization. The trainer will lead a cohort of 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. The trainer will help participants design, develop, integrate, test, troubleshoot, and securely deploy AI-enabled and agentic AI solutions within realistic enterprise environments. Training will 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. The curriculum is provided by Fearless; the trainer is not expected to develop the curriculum independently but may supplement it with additional examples, exercises, or resources that strengthen the learning experience. This is a fully remote 1099 contractor engagement requiring 40 hours per week for 10 weeks, with work performed between 9:00 a.m. and 5:00 p.m. EST

Your Responsibilities in this Role: 

●​Deliver live, instructor-led technical training focused on AI engineering, agentic AI, and AI-enabled software development. 

●​Lead hands-on labs, technical demonstrations, practical exercises, and collaborative projects that require participants to design, build, integrate, test, debug, and troubleshoot AI-enabled solutions. 

●​Teach and reinforce practical application of 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. 

●​Provide instruction and coaching on prompt engineering, Retrieval-Augmented Generation (RAG), AI orchestration patterns, and agentic AI concepts as applicable to the approved curriculum. 

●​Reinforce secure AI integration, responsible AI practices, data governance, privacy, security, and risk mitigation throughout technical exercises and projects. 

●​Provide real-time technical assistance during labs and project work, including troubleshooting, debugging, code review, and problem-solving support. 

●​Review participant technical work and provide individualized feedback, coaching, and remediation to strengthen identified skill gaps. 

●​Assess participant progress through labs, assignments, knowledge checks, technical demonstrations, and capstone activities. 

●​Support team-based capstone work requiring participants to demonstrate an AI-enabled or agentic solution within a realistic enterprise modernization scenario. 

●​Collaborate with program leadership and other instructors to monitor participant progress, identify areas requiring additional reinforcement, and maintain alignment with the approved training plan.

Project Specific Skill and Experience Requirements

●​Minimum of 5 years of professional experience in AI/ML engineering, software engineering, data engineering, or a closely related technical discipline. 

●​Demonstrated hands-on experience designing, developing, deploying, troubleshooting, optimizing, or maintaining AI and/or agentic AI solutions in production or comparable enterprise environments. 

●​Demonstrated 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 technical feedback. 

●​Experience teaching through hands-on labs, projects, demonstrations, and applied exercises rather than lecture-only instruction. 

●​Strong communication skills with the ability to explain complex AI and software engineering concepts to learners with varying levels of technical experience. 

Preferred Experience 

●​Experience developing or deploying AI solutions within 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. 

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 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.