Online Learning Lead (11-12-month Fixed-term/Remote)

ABOUT GENERATION: At Generation, we believe in the power of employment to change lives. We are a global nonprofit organization that supports adults to achieve economic mobility through employment. Generation trains and places adult learners of all ages into careers that are otherwise inaccessible, working in partnership with governments, employers, and other system actors. We also conduct original research and share data insights on high-priority global workforce transition topics to inform decision-making by workforce system stakeholders. Launched in 2015, Generation comprises a global hub (Generation You Employed, or GYE) and a network of in-country affiliates. To date, the network has 150,000+ graduates and 23,000+ employers across 50 professions and 17 countries. When learners join Generation, 91% are unemployed, of which nearly half are long-term unemployed. Three months after completing our program, graduates have a 78% job placement rate, rising to 88% within six months. Of our employed graduates, 79% are hired by repeat employers who have previously hired Generation graduates, and 89% are in jobs directly related to the profession for which we have trained them. Employed graduates immediately earn an average of 3-4X their previous earnings. Two to five years after graduation, 77% of our alumni from upper-middle income countries continue to meet their daily financial needs and 63% can save for the future. To date, Generation’s global graduates have earned more than $1.9 billion in wages. Generation graduates typically have a secondary school background, 52% are female, 28% have dependents, and the majority identify with underrepresented communities in their country. Position Overview: This role will lead the testing, evaluation, implementation, and scaling of AI-enabled learning and instructor-facing tools across Generation's LATAM and Europe regions. The role will be responsible for identifying high-impact opportunities for AI-enabled learning, establishing pilot hypotheses and success measures, generating evidence on effectiveness, and translating successful interventions into scalable learning models. The role will support the Online Team's broader AI and learning technology agenda, including the effective adoption, implementation, and evolution of Canvas and other learning technologies across the region. Working closely with country teams, implementation teams, vendors, and technical stakeholders, the role will ensure AI-enabled learning solutions are effectively embedded into learner and instructor experiences and continuously improved through evidence, feedback, and iteration. Operating at the intersection of curriculum design, learning science, instructional delivery, and applied AI, the role will help shape the evolution of Generation's AI-enabled learning strategy through regional implementation, pilot outcomes, learner and instructor insights, and recommendations for future product enhancements and scaling decisions. The role will also act as a key partner to external AI and learning technology providers, helping identify opportunities for product improvements, influencing feature development, and ensuring solutions continue to meet the needs of learners, instructors, and country teams. Location: This role is remote, with preference given to candidates based in Chile. Working hours must overlap with CET by at least 4 hours and candidates must be flexible in adjusting their schedule when required to support collaboration across Europe and the Americas. Generation is an equal opportunity employer and actively encourages applications from people of all backgrounds. Key Accountabilities & Responsibilities: Lead AI Pilots and Learning Innovation - Lead the testing, evaluation, implementation, and scaling of AI-enabled learning and instructor-facing tools across LATAM and Europe. - Define pilot hypotheses, success measures, and evidence requirements aligned to Generation’s AI learning priorities. - Design and execute pilots that generate robust evidence on learner outcomes, instructor effectiveness, learner engagement, and operational efficiency. - Identify opportunities to reduce reliance on synchronous instruction through the use of AI-enabled learning experiences while maintaining or improving learning quality. - Translate pilot findings into clear recommendations regarding scaling, iteration, further development, or discontinuation. Accelerate AI-Enabled Learning Models - Explore how AI tools can transform learner and instructor experiences across programmes and geographies. - Identify moments in the learner journey where AI can appropriately support or augment learning, feedback, assessment, revision, practice, and coaching activities. - Map learner and instructor journeys to identify opportunities for greater efficiency, engagement, and learning impact. - Work with country teams to identify programmes, cohorts, and learner populations best suited for AI-supported delivery. - Ensure local delivery realities, learner needs, and operational constraints are incorporated into solution design and implementation planning. Shape Product Evolution and Vendor Partnerships - Act as a key partner to AI and learning technology vendors throughout piloting, implementation, and scale. - Gather and synthesize learner, instructor, and country feedback to identify opportunities for product enhancements and new functionality. - Influence vendor roadmaps by advocating for improvements aligned with Generation’s learning model and regional needs. - Partner with the Learning Technology & AI Innovation Lead to identify opportunities for future pilots, feature development, and learning innovation. - Support decisions regarding future investment, rollout, and scaling of AI-enabled learning solutions. Canvas and Learning Technology Leadership - Lead the effective adoption, implementation, and continuous improvement of Canvas and related learning technologies across LATAM and Europe. - Partner with country teams to ensure learning technologies are embedded effectively within learner and instructor experiences. - Support the implementation and adoption of new learning technologies and AI-enabled tools introduced by the Online Team. - Identify opportunities to improve learner and instructor experiences through more effective use of Canvas and the wider learning technology ecosystem. - Work closely with Digital and Learning Technology colleagues to ensure technology solutions align with learning needs and operational realities. Evidence, Measurement and Regional Leadership - Define and monitor key measures of success, including learner outcomes, instructor effort reduction, learner engagement, AI adoption, and satisfaction. - Support the collection and analysis of pilot evidence, including learner feedback, instructor feedback, performance data, and operational insights. - Communicate findings and recommendations clearly to senior stakeholders to inform regional and global decision-making. - Contribute to the evolution of Generation’s AI-enabled learning strategy through regional implementation insights, pilot outcomes, and learner and instructor feedback. - Manage the regional AI Pilots Delivery Manager, providing direction, coaching, prioritization, and support. Required Experience And Skills: Required - Minimum 5 years’ experience in online or blended learning design and delivery - Minimum 5 years’ experience rolling out digital learning tools across multiple countries - 1–2 years’ exposure to AI tools, AI‑enabled workflows, or AI experimentation - Working hours that overlap with CET by at least 4 hours - Fluent English (written and spoken) Strongly preferred - Deep understanding of learner journeys, assessment design, and learning science - Experience designing or evaluating asynchronous learning at scale - Comfort working with experimentation frameworks, pilots, and evidence‑based decision‑making - Ability to translate between instructional, curriculum, and technical teams - Pragmatic mindset: comfortable testing, learning, iterating, and stopping what doesn’t work ***Please apply with your English resume, thank you***