Principal Learning Strategist

Job Description

Learning Strategist – Expert Learning & Development

Location

• Hybrid in San Diego, CA

Overview

We are seeking an experienced Learning Strategist to lead the planning, design, and evaluation of learning programs supporting its Expert workforce.

This role is responsible for determining what Experts need to learn, how learning should be delivered, and how learning effectiveness will be measured.

The Learning Strategist will own the learning strategy, instructional approach, content structure, assessment design, and quality standards for assigned lines of business.

Working closely with Learning Capability Partners, Program Management Office (PMO), Instructional Designers, and Subject Matter Experts (SMEs), this individual will translate business requirements into actionable learning plans that support Expert readiness and performance.

The ideal candidate has extensive experience in learning strategy, instructional design, adult learning principles, and large-scale training programs, with strong judgment around scope, stakeholder alignment, and measurable learning outcomes.

Responsibilities

Learning Strategy & Needs Assessment

• Participate in project kickoff meetings and lead the learning intake process.
• Gather and evaluate critical learning requirements, including:
• Business goals and objectives
• Success metrics and expected outcomes
• Target Expert audiences
• Current learner knowledge and skill levels
• Launch dates and timelines
• Training needs and performance gaps
• Determine whether training is the appropriate solution to address identified business challenges.
• Translate business requirements into clear learning objectives and strategies.
• Develop learning approaches aligned with Expert performance expectations.
• Support learning initiatives across one or more assigned lines of business.

Learning Content Audit & Gap Analysis

• Review existing learning materials against established skills rubrics.
• Evaluate content relevance, quality, and alignment with learning objectives.
• Categorize existing content based on required actions:
• Carry over existing content
• Adapt or update content
• Build new content
• Defer content for future development
• Identify learning gaps and opportunities to improve existing materials.
• Recommend content updates based on business requirements and learner needs.
• Leverage Generative AI tools to support content audits and maintenance activities.

Learning Program Scoping & Planning

• Partner with Learning Capability Partners and PMO to define learning project scope.
• Develop detailed learning build plans and supporting documentation.
• Create deliverables including:
• Learning build maps
• Development hour estimates
• Resource and capacity estimates
• Risk assessments
• Build briefs aligned with business requirements
• Evaluate project feasibility, resource requirements, and delivery timelines.
• Identify scope limitations and communicate potential trade-offs.
• Provide recommendations on what can realistically be delivered within established constraints.
• Communicate project risks and dependencies before launch dates are committed.
• Manage scope changes through agreed-upon processes.

Instructional Design & Learning Architecture

• Design comprehensive learning plans aligned with business objectives and learner needs.
• Determine appropriate instructional formats and delivery methods.
• Establish learning module sequencing and overall program structure.
• Design learning experiences that incorporate:
• Digital learning modules
• Live training sessions
• Practical exercises
• Skills practice
• Knowledge assessments
• Certification requirements
• Ensure individual learning components support the broader learner journey.
• Create clear instructional outlines and build specifications for Instructional Designers.
• Ensure learning content is structured to support assessment and certification.
• Apply adult learning principles to create effective learning experiences for diverse audiences.

Assessment, Certification & Learning Effectiveness

• Design assessments to measure learner knowledge and skill development.
• Establish certification requirements aligned with learning objectives.
• Define measurable criteria for evaluating training effectiveness.
• Determine whether learning initiatives have improved Expert performance.
• Align assessments with established skills rubrics and business expectations.
• Evaluate learning outcomes and identify opportunities for continuous improvement.
• Ensure learning programs support measurable business and performance results.

Cross-Functional Collaboration & Content Development Oversight

• Partner with Learning Capability Partners, PMO, Instructional Designers, and SMEs throughout the learning development lifecycle.
• Obtain SME approval on all learning outlines before content development begins.
• Provide strategic direction and guidance to Instructional Designers responsible for building learning materials.
• Monitor content development to ensure alignment with approved learning plans and outlines.
• Review learning deliverables for quality, consistency, and instructional effectiveness.
• Identify and escalate risks, blockers, and deviations from approved plans.
• Maintain oversight of learning quality without directly managing day-to-day content production.
• Ensure clear communication and alignment across project stakeholders.

Business Partnership & Stakeholder Management

• Serve as a learning strategy partner for one or more assigned lines of business.
• Develop a strong understanding of:
• Business operations
• Expert responsibilities
• Target learner audiences
• Current and future learning needs
• Advise business partners on learning strategy, scope, and delivery feasibility.
• Communicate project constraints, priorities, and trade-offs to senior stakeholders.
• Support effective decision-making around learning investments and program priorities.
• Maintain alignment between business requirements and learning solutions.
• Coach business partners on foundational learning design and project scoping principles.

Generative AI & Learning Process Improvement

• Apply Generative AI (GenAI) tools to improve learning workflows.
• Use AI to support activities such as:
• Learning content audits
• Content maintenance
• Identification of content gaps
• Learning documentation
• Identify opportunities to improve learning development efficiency.
• Support consistent and scalable learning design processes.

Required Qualifications

• 8+ years of experience in Learning Strategy, Instructional Design, or Learning Program Leadership.
• Demonstrated experience owning learning programs from initial intake through launch.
• Experience developing learning strategies for large and diverse audiences.
• Strong understanding of adult learning principles and instructional design methodologies.
• Experience designing comprehensive learning programs, including learning pathways, module sequencing, and delivery formats.
• Strong experience with assessment and certification design.
• Ability to measure learning effectiveness and evaluate impact on performance.
• Experience conducting learning needs assessments and content gap analyses.
• Strong project scoping skills, including:
• Resource estimation
• Capacity planning
• Risk identification
• Scope management
• Stakeholder alignment
• Demonstrated ability to make strategic decisions regarding project feasibility, priorities, and trade-offs.
• Experience collaborating with SMEs, Instructional Designers, PMO, and business stakeholders.
• Strong stakeholder management skills, including the ability to influence senior leaders.
• Excellent written communication skills with experience creating actionable learning briefs, outlines, and documentation.
• Strong organizational and analytical skills.
• Ability to manage multiple learning initiatives across business functions.
• Practical experience using Generative AI tools to support learning development, content audits, or maintenance.
• Ability to provide strategic direction and quality oversight without directly managing every development activity.

Preferred Qualifications

• Experience designing learning programs for:
• Frontline employees
• Contact center teams
• Tax professionals
• Accounting professionals
• Experience supporting large-scale Expert training or workforce readiness programs.
• Experience working across multiple lines of business with diverse learning requirements.

Education

• Master's degree in Adult Education, Instructional Design, Learning and Organizational Development, or a related field, or equivalent experience.