---
title: 'Learning Designer & Content Developer, OpenAI Academy (Contract) at GreenLight Workforce Solutions Inc'
canonical: 'https://feeny.ai/job/learning-designer-content-developer-openai-academy-contract-greenlight-t3dwrma392q2'
type: 'job'
last_seen: '2026-09-26'
---

# Learning Designer & Content Developer, OpenAI Academy (Contract) at GreenLight Workforce Solutions Inc

- **Company:** GreenLight Workforce Solutions Inc
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Posted:** 2026-09-25
- **Last confirmed live:** 2026-09-26
- **Apply:** https://jobs.ashbyhq.com/greenlight-workforce-solutions/62e046f6-3adc-47cf-a490-594295399b00

## Job description

## About the Team

OpenAI Academy is an AI literacy initiative dedicated to ensuring the benefits of AI are widely shared. Our programs help individuals and organizations build AI fluency, explore real-world applications, and use AI responsibly to solve problems.

Academy delivers in-person and virtual learning experiences in partnership with mission-aligned organizations. We create hands-on, accessible programs for audiences with different goals, contexts, and levels of experience. To date, over 4 million people worldwide have engaged with our content online, and thousands have attended our in-person events.

## About the Role

We’re seeking an experienced, highly self directed Learning Designer & Content Developer to create and test AI training for OpenAI Academy’s in-person and virtual programs. You’ll work with Academy leads and subject-matter experts to produce training packages from agreed-upon briefs, incorporate feedback, and meet delivery timelines. OpenAI will set program priorities and retain final approval of curriculum, content, and delivery standards. This is a contractor position.

In this role, you will:

Learning Design & Content Development

- Personally develop complete training packages, including polished, brand-aligned slide decks; speaker notes and concise live facilitation cues; demonstration scripts and prompts; realistic sample files; participant exercises and handouts; and facilitator preparation materials.
- Design practical learning experiences for virtual and in-person delivery, with clear learning objectives, realistic timing, transitions, prompts, participant practice, and fallback plans.
- Adapt examples, language, pacing, setup instructions, and practice activities to participants’ roles, goals, digital confidence, and AI experience. Design clear support for beginners and meaningful extensions for experienced participants, with useful outcomes learners can apply to their own lives or work.
- Work with subject-matter experts and Academy leads to turn complex product and policy concepts into clear, accurate, and usable instruction.

Curriculum Development & Maintenance

- Create reusable templates and document agreed design standards and production practices. Keep source materials organized, current, and clearly versioned so facilitators and partners can find approved materials.
- Develop agreed training packages from initial brief through review, rehearsal, final handoff, and subsequent updates. Keep slides, guides, prompts, exercises, and supporting assets aligned as the training evolves.
- Keep assigned training materials up to date as product capabilities, interfaces, and access requirements change. Update affected slides, prompts, demos, exercises, and facilitator guides, and retest workflows before delivery.

Facilitation & Trainer Support

- Pilot new trainings, lead rehearsals, and facilitate selected sessions to test materials and model effective delivery.
- Develop materials and support pilots to extend and improve Academy’s existing facilitator training pathway under the Academy team’s direction.
- Prepare and coach Academy and partner facilitators to use the materials through rehearsal and feedback, following OpenAI-approved guidance on accuracy, inclusion, safety, and participant experience.

Instructional Quality & Continuous Improvement

- Create lightweight learning-assessment and participant-feedback approaches that reveal whether programs are understandable, relevant, and actionable.
- Use rehearsal findings and participant and facilitator feedback to recommend and implement revisions to materials and delivery guidance.
- Build and rehearse demonstrations in the intended delivery environment. Verify prompts, outputs, timing, account and feature requirements, and screen readability; prepare realistic sample data, setup and reset instructions, and fallback outputs where needed.

Cross-Functional Collaboration

- Work closely with Academy program leads, trainers, subject-matter experts, and relevant Global Affairs, Product, Customer Education, Communications, and partner teams.
- Coordinate reviews at agreed milestones, resolve content and usability issues, and submit materials for OpenAI’s final approval.

What Success Looks Like

- Complete, tested training packages are delivered on schedule, meet Academy’s requirements, and enable facilitators to run engaging sessions without extensive clarification or undocumented knowledge.
- Participants can complete the intended activities and apply what they learned; audience adaptations reflect their needs while preserving the agreed learning objectives.
- Academy leads can delegate training development from an agreed brief, with focused review at key milestones and final approval by OpenAI.
- Rehearsal observations and participant and facilitator feedback lead to specific improvements, and materials remain current as products and audience needs change.

We’re Looking For

- Demonstrated experience in learning design, instructional design, adult learning, customer education, educator development, or a closely related field.
- A portfolio of complete training programs you personally designed and produced, including presentation materials, facilitator guidance, practical exercises, and demonstrations. Be prepared to explain your contribution, what changed after testing, and how other facilitators used the materials.
- Strong live facilitation skills and the ability to rehearse and deliver practical learning sessions for audiences with different levels of experience, confidence, and familiarity with AI.
- Strong hands-on proficiency with ChatGPT and AI-assisted workflows, including the ability to independently build, troubleshoot, and explain practical demonstrations for nontechnical audiences.
- Strong writing, editing, and slide-development skills: you make complex material clear, accurate, and actionable, and create polished, accessible materials that follow brand guidelines.
- Experience verifying product claims and updating instructional materials as capabilities, interfaces, and access requirements change.
- Experience managing content versions, incorporating stakeholder feedback, and delivering multiple training projects against agreed briefs and timelines.
- Sound judgment, attention to detail, and comfort operating in a fast-moving environment with evolving priorities.
- A commitment to accessible, inclusive learning and enthusiasm for OpenAI Academy’s mission.

## Preferred Experience

- Designing AI literacy, digital-skills, workforce, public-interest, or technology-learning programs.
- Adapting learning experiences for different communities, sectors, languages, or cultural contexts.
- Coaching facilitators, developing train-the-trainer resources, or supporting delivery through partners at scale.
- Using lightweight assessment, field observation, or performance evidence to improve instruction.

Potential Expansion Areas Additional work may be agreed upon with Academy leads based on program needs and contractor capacity, including:

- Translation and localization systems for Academy materials.
- Support for facilitator assessments, field observation, and quality sampling using OpenAI-approved readiness criteria, with qualification decisions retained by OpenAI.
- Additional learning-assessment tools and impact-measurement support.

## About GreenLight Workforce Solutions Inc

## Company Overview
- **One-liner**: GreenLight.ai is an AI-powered Freelancer Management System (FMS) that helps businesses compliantly hire, manage, and pay freelancers and contractors globally.
- **Entity Type**: Private (Pre-Seed stage)
- **Headquarters**: Palo Alto, California, United States
- **Founded**: 2018
- **Founders**: Jason Posel, Spencer Greene

## Core Business
- **Primary industries**: Human Resources, Artificial Intelligence, Software, InsurTech
- **Target customers**: B2B – enterprises, staffing firms, talent marketplaces, and companies managing contingent workforces
- **Mission / purpose**: “Making it easy to hire, organize, and pay contractors – anywhere.”

## Products & Services
- **Global Workforce Management System**: A single platform for onboarding, time tracking, billing, and reporting across more than 25 countries.
- **AI-Powered Worker Classification**: An AI engine that determines correct worker classification to mitigate misclassification risk.
- **Global Workforce Payments & Benefits**: Handles payroll and benefits for freelancers and contractors worldwide.
- **Regulatory & Tax Compliance**: Automates identity verification, background checks, and compliance with local tax and employment laws.
- **Automation & Analytics**: Automates paperwork and provides workforce analytics to stakeholders.
- **World‑Class API Integrations**: APIs that connect the platform with existing HR, payroll, and marketplace tools.
- **White‑Label & Embedded Solutions**: Custom configurations for staffing firms and marketplaces to offer the platform under their own brand.

## Market Standing
- **Valuation / Market Cap**: Not disclosed
- **Key Metric**: Funding – Closed an undisclosed Pre-Seed round on March 31, 2020.
- **Notable Investors / Partners**: Matt Mickiewicz, Blackhorn Ventures
- **Growth Signals**: Headcount estimated at 11–50 employees; active hiring for remote and hybrid roles across the US and UK; offers an API‑first approach to embed compliance and payments into client systems.

## Competitive Advantages
- Combines EOR (Employer of Record), AOR (Agent of Record), and worker classification into one integrated FMS platform.
- Proprietary AI‑driven classification engine reduces legal risk for companies using freelancers and contractors.
- Built with top employment law and compliance experts, enabling clients to scale quickly without expanding their back office.

## Strategic Focus
- Deepening global coverage (currently 25+ countries) and expanding white‑label/embedded offerings for talent marketplaces and staffing firms.
- Using AI and automation to further streamline contractor onboarding, compliance, and payment workflows.
- Prioritizing API integrations to embed compliance into customers’ existing tech stacks.

## Why Work Here
- **Work policy**: Offers remote, hybrid, and in‑office options; offices in Southport, FL (USA) and the United Kingdom.
- **Engineering culture**: Currently hiring a Full‑Stack AI Engineer / Workflow Automation Lead, indicating a focus on AI and automation.
- **Perks**: Not publicly described, but as an early‑stage VC‑backed startup, likely offers equity, flexible work, and direct impact on product direction.

## Sources
1. [greenlight.ai](https://www.greenlight.ai/)
2. [greenlight.ai/careers](https://www.greenlight.ai/careers/)
3. [Built In – GreenLight Workforce Solutions Inc.](https://builtin.com/company/greenlight-workforce-solutions-inc)
4. [Crunchbase – GreenLight Workforce Solutions](https://www.crunchbase.com/organization/greenlight-workforce-solutions)
5. [Ashby Jobs – GreenLight Workforce Solutions](https://jobs.ashbyhq.com/greenlight-workforce-solutions)

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