Senior Technical Learning and Upskilling Lead (Contract)

Fearless Solutions; Baltimore (MD); Remote; USD 124,000 - 193,000; Part time

Job summary

Fearless is seeking a Technical Learning & Workforce Development Lead (1099) to build and lead a self-sustaining upskilling engine across engineering, data, IT, and business teams. You’ll diagnose skill gaps, design learning pathways, and enable hands-on capability with a focus on AI tools and modern instructional design.

You’ll stand up strategy, programs, and internal champions, while coaching internal SMEs and ensuring measurable adoption and ROI for client engagements.

Qualifications

• 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.
• 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.

Responsibilities

• Skills strategy and assessment: Build a technical taxonomy tied to business priorities and role families; Run skills-gap assessments; Set an upskilling roadmap with leadership.
• Program design and delivery: Design blended learning; Curate external content and vendors; Deliver select sessions and coach SMEs.
• Capability building and change management: Stand up champions network; Coach managers; Address adoption resistance with clear communication.
• Measurement and reporting: Define and track metrics; Report ROI to executives; document playbooks and hand off to internal owners.

Skills

Skills strategy

Assessment

Program design

Delivery

Change management

Metrics reporting

Executive comms

Independent work

Tools

LMS/LXP

Degreed

Workday Learning

Cornerstone

Pluralsight

Coursera

Job description

Fearless is seeking a Technical Learning & Workforce Development Lead (1099) to build and lead a self-sustaining upskilling engine across engineering, data, IT, and business teams. You’ll diagnose skill gaps, design learning pathways, and enable hands-on capability with a focus on AI tools and modern instructional design.

You’ll stand up strategy, programs, and internal champions, while coaching internal SMEs and ensuring measurable adoption and ROI for client engagements.