Technical Learning & Workforce Development Lead, (1099 Contractor)

Technical Learning & Workforce Development Lead(1099 Contractor)

We're looking for a technical practitioner turned workforce developer to build our technical and digital skills across our core practice areas. You'll diagnose skill gaps, design learning pathways, and lead hands-on capability enablement so that our engineers, analysts and business teams can quickly use new capabilities in their real work with success.  

This is a fractional role because we need senior expertise to stand up the strategy, programs and internal capability. A full-time leader may not be needed for the long term. Success means leaving behind a self-sustaining upskilling engine: trained internal champions, reusable curricula and clear skill metrics.

Your Responsibilities in this Role:  

Skills strategy and assessment

• Build a technical taxonomy tied to business priorities and role families (engineering, data, IT, product, business users).
• Run skills-gap assessments using surveys, hands-on evaluations, manager input and HRIS/LMS data.
• Set an upskilling roadmap with leadership, prioritizing high-impact roles and use cases.

Program design and delivery

• Design blended learning: workshops, cohort programs, self-paced content, mentoring and on-the-job projects.
• Curate and evaluate external content, certifications and vendors (cloud, data, AI platforms) and make budget recommendations.
• Deliver select sessions personally and coach internal subject-matter experts to teach.

Capability building and change management

• Stand up champions / community-of-practice network to sustain adoption.
• Coach managers to support skill growth, career mobility and new ways of working.
• Address adoption resistance and role anxiety with clear communication and change practices.

Measurement and reporting

• Define and track metrics: skill proficiency gains, tool adoption, productivity impact, internal mobility and retention.
• Report progress and ROI to executives; adjust programs based on data.
• Document playbooks and hand off to internal owners before the engagement ends.

Project skill and experience requirements:

• 10+ years total experience, including 4+ years hands-on in a technical role (software engineering, data/analytics, cloud, IT or solutions architecture).
• Proven record (2+ years) designing and delivering upskilling, with measurable adoption or productivity results. Expect to share examples.
• Hands-on fluency with current generative AI tools (e.g., Claude, ChatGPT, Copilot, Gemini), AI-assisted development and core concepts like LLMs, RAG, agents and evaluation.
• Grounding in adult learning and instructional design (ADDIE, SAM, 70-20-10) and skills-based talent practices.
• Experience building skills frameworks or competency models and running gap assessments.
• Working knowledge of responsible AI, data privacy and security considerations.
• Strong facilitation and executive communication; credible with both engineers and executives.
• Comfort working independently across multiple stakeholders with limited hours.

Preferred qualifications

• Background in organizational development, I/O psychology, HRD or a related field (degree or certification).
• Certifications such as ATD CPTD, SHRM, Prosci change management, or cloud/AI credentials (AWS, Azure, Google Cloud).
• Experience with LMS/LXP and skills platforms (e.g., Degreed, Workday Learning, Cornerstone, Pluralsight, Coursera).
• Prior fractional, consulting or interim leadership engagements.
• Experience in regulated or government-contracting environments, if relevant to your organization.
• Has built an internal champions network or community of practice.

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.

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