Sr. Learning Specialist
As the Senior Learning Specialist, you will lead the modernization of PSO’s learning and knowledge strategy, leveraging AI and automation to make high-quality content accessible in the flow of work. Your main directive is to centralize, automate, and optimize learning and knowledge-management programs—previously fragmented across teams—so frontline support is empowered to deliver faster, more effective service. You’ll partner closely with cross-functional and AI platform teams to ensure knowledge and learning resources are surfaced contextually and remain ahead of the curve as business and user needs evolve.
What you’ll do:
AI-Driven Program Leadership: Design and drive initiatives to leverage AI and automation for learning and knowledge management, enabling content to surface contextually at the point of need for support agents and BPO partners.
Content Lifecycle Ownership: Own the end-to-end process for PSO learning and knowledge content—including the intake, prioritization, creation, continual evaluation, and sunsetting of materials—ensuring content stays accurate, useful, and aligned with PSO and policy updates.
Future-Ready Tools Implementation: Partner with product, data, and engineering teams to select, implement, and optimize learning and knowledge platforms that support AI-powered search, recommendations, and workflow integrations.
Data-Backed Continuous Improvement: Use analytics, stakeholder input, and AI-driven insights to identify areas for improvement, assess learning impact, and deliver actionable recommendations that drive both agent performance and customer satisfaction.
Cross-Functional Partnership: Build strong relationships with internal stakeholders (Support, Product,, IT, Data and Infrastructure, AI committees) and external vendors to ensure knowledge programs meet current and emerging needs in a rapidly changing environment.
Governance & Quality Standards: Implement quality assurance and governance for all learning and knowledge content to guarantee reliability, accuracy, and compliance with policy and enforcement changes.
Partner with internal stakeholders/subject matter experts to develop, facilitate and deliver training to ensure Business Process Outsourcing (BPO) vendor and Pinterest Support Operations employee knowledge management.
Work collaboratively with the Learning Experience manager and internal stakeholders to identify training needs, problems and suggest training solutions.
Own end-to-end creation and delivery of innovative training that is easily digestible for adult learners and applied across virtual, video and e-learning modalities.
Facilitate interactive training sessions, delivering an exceptional learning experience for participants.
Manage multiple projects and priorities simultaneously and mitigate risks to eliminate potential roadblocks in the design, development and implementation of training.
Assess the impact of training and measure knowledge retention in, identifying where knowledge and skills gaps remain.
What we’re looking for:
5+ years of experience in learning and knowledge program management, with hands-on work leveraging AI or automation in content, search, or learning systems.
5+ years of experience in developing and delivering adult learning programming and training.
2+ years of experience in Customer Support or User Support training management are highly preferred.
Deep expertise in the full content lifecycle—from needs analysis and prioritization, to development, measurement, and sunsetting.
Proven track record of leading cross-functional programs, especially involving tools/platforms at the intersection of customer support, AI, and knowledge management.
Advanced abilities with LMS, KB, and AI-driven learning technologies; excels at identifying, implementing, and optimizing new tools in partnership with technical teams.
Excellent verbal and written communicator and facilitator; can distill complex concepts and influence stakeholders at all levels.
Data-driven and business-minded; designs with the user experience in mind and ties work to business outcomes.
Instructional design knowledge and application with the ability to transform content into highly engaging and impactful learning experiences. Knowledge of instructional design tools (Articulate, Google slides etc.) and knowledge tools (Guru, Zendesk Guide).
Able to effectively engage with leadership, facilitate discussions about complex topics, influence, and reach agreements.
Self-motivated with a track record in stakeholder management, problem-solving skills and able to operate autonomously in an evolving and fast paced environment.
Relocation Statement:
This position is not eligible for relocation assistance. Visit our PinFlex page to learn more about our working model.
In-Office Requirement Statement:
We let the type of work you do guide the collaboration style. That means we're not always working in an office, but we continue to gather for key moments of collaboration and connection.
This role will need to be in the office for in-person collaboration 1-2 times/quarter and therefore can be situated anywhere in the country.
#LI-REMOTE
#LI-BD4
About the job
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Sr. Learning Specialist
As the Senior Learning Specialist, you will lead the modernization of PSO’s learning and knowledge strategy, leveraging AI and automation to make high-quality content accessible in the flow of work. Your main directive is to centralize, automate, and optimize learning and knowledge-management programs—previously fragmented across teams—so frontline support is empowered to deliver faster, more effective service. You’ll partner closely with cross-functional and AI platform teams to ensure knowledge and learning resources are surfaced contextually and remain ahead of the curve as business and user needs evolve.
What you’ll do:
AI-Driven Program Leadership: Design and drive initiatives to leverage AI and automation for learning and knowledge management, enabling content to surface contextually at the point of need for support agents and BPO partners.
Content Lifecycle Ownership: Own the end-to-end process for PSO learning and knowledge content—including the intake, prioritization, creation, continual evaluation, and sunsetting of materials—ensuring content stays accurate, useful, and aligned with PSO and policy updates.
Future-Ready Tools Implementation: Partner with product, data, and engineering teams to select, implement, and optimize learning and knowledge platforms that support AI-powered search, recommendations, and workflow integrations.
Data-Backed Continuous Improvement: Use analytics, stakeholder input, and AI-driven insights to identify areas for improvement, assess learning impact, and deliver actionable recommendations that drive both agent performance and customer satisfaction.
Cross-Functional Partnership: Build strong relationships with internal stakeholders (Support, Product,, IT, Data and Infrastructure, AI committees) and external vendors to ensure knowledge programs meet current and emerging needs in a rapidly changing environment.
Governance & Quality Standards: Implement quality assurance and governance for all learning and knowledge content to guarantee reliability, accuracy, and compliance with policy and enforcement changes.
Partner with internal stakeholders/subject matter experts to develop, facilitate and deliver training to ensure Business Process Outsourcing (BPO) vendor and Pinterest Support Operations employee knowledge management.
Work collaboratively with the Learning Experience manager and internal stakeholders to identify training needs, problems and suggest training solutions.
Own end-to-end creation and delivery of innovative training that is easily digestible for adult learners and applied across virtual, video and e-learning modalities.
Facilitate interactive training sessions, delivering an exceptional learning experience for participants.
Manage multiple projects and priorities simultaneously and mitigate risks to eliminate potential roadblocks in the design, development and implementation of training.
Assess the impact of training and measure knowledge retention in, identifying where knowledge and skills gaps remain.
What we’re looking for:
5+ years of experience in learning and knowledge program management, with hands-on work leveraging AI or automation in content, search, or learning systems.
5+ years of experience in developing and delivering adult learning programming and training.
2+ years of experience in Customer Support or User Support training management are highly preferred.
Deep expertise in the full content lifecycle—from needs analysis and prioritization, to development, measurement, and sunsetting.
Proven track record of leading cross-functional programs, especially involving tools/platforms at the intersection of customer support, AI, and knowledge management.
Advanced abilities with LMS, KB, and AI-driven learning technologies; excels at identifying, implementing, and optimizing new tools in partnership with technical teams.
Excellent verbal and written communicator and facilitator; can distill complex concepts and influence stakeholders at all levels.
Data-driven and business-minded; designs with the user experience in mind and ties work to business outcomes.
Instructional design knowledge and application with the ability to transform content into highly engaging and impactful learning experiences. Knowledge of instructional design tools (Articulate, Google slides etc.) and knowledge tools (Guru, Zendesk Guide).
Able to effectively engage with leadership, facilitate discussions about complex topics, influence, and reach agreements.
Self-motivated with a track record in stakeholder management, problem-solving skills and able to operate autonomously in an evolving and fast paced environment.
Relocation Statement:
This position is not eligible for relocation assistance. Visit our PinFlex page to learn more about our working model.
In-Office Requirement Statement:
We let the type of work you do guide the collaboration style. That means we're not always working in an office, but we continue to gather for key moments of collaboration and connection.
This role will need to be in the office for in-person collaboration 1-2 times/quarter and therefore can be situated anywhere in the country.
#LI-REMOTE
#LI-BD4