Are you looking to make an impactful difference in your work, yourself, and your community? Why settle for just a job when you can land a career? At ICW Group, we are hiring team members who are ready to use their skills, curiosity, and drive to be part of our journey as we strive to transform the insurance carrier space. We’re proud to be in business for over 50 years, and its change agents like yourself that will help us continue to deliver our mission to create the best insurance experience possible.

Headquartered in San Diego with regional offices located throughout the United States, ICW Group has been named for ten consecutive years as a Top 50 performing P&C organization offering the stability of a large, profitable and growing company combined with a focus on all things people. It’s our team members who make us an employer of choice and the vibrant company we are today. We strive to make both our internal and external communities better everyday! Learn more about why you want to be here!

Job Summary

The Learning Academy Manager (LAM) for Digital Transformation serves as a strategic advisor, change enabler, and workforce capability architect for ICW Group’s IT and Analytics functions. This role is the architect of the Digital Transformation Academy, ensuring it provides skill development opportunities and professional development resources that align with documented career pathways for team members across IT and Analytics.

The LAM partners with leaders to identify capability gaps, co-create multi-year learning plans, embed adoption strategies, and integrate skills data into workforce planning. By developing and stewarding the Digital Transformation Academy, the LAM ensures that employees are equipped to meet both current and future business needs while enabling ICW Group’s Operation 2027 priorities.

This role is designed for a forward-thinking workforce enablement leader who combines business acumen with deep learning expertise, bringing proactive insight, digital fluency, and enterprise-level partnership to ICW Group’s transformation journey.

Key Responsibilities

Strategic Business Partnership

• Collaborate directly with the Human Resources Business Partners assigned to IT and Analytics to ensure alignment on all strategic initiatives.
• Partner with IT and Analytics leaders to co-create multi-year skill roadmaps and translate business objectives into learning strategies.
• Serve as a trusted advisor on workforce readiness in areas such as emerging technologies, data governance, cybersecurity, automation, and digital product development.
• Participate in the Learning Advisory Council, representing IT/Analytics needs in quarterly Portfolio Reviews.
• Shape demand upstream by advising leaders on departmental training needs before requests reach intake.
• Facilitate skill mapping workshops with stakeholders and Human Resources Business Partners as new roles are identified within their assigned department.
• Perform recurring reviews and maintenance of assigned departmental skill maps to ensure relevance to business need.

Digital Transformation Academy & Career Pathways

• Design, launch, and continuously evolve the Digital Transformation Academy, with dedicated tracks for IT Foundations, Cybersecurity, Analytics & Data Science, and Agile/Digital Ways of Working.
• Build structured career pathways that support professional growth, succession planning, and workforce readiness.
• Curate and integrate external certifications and vendor resources; manage budget allocations to ensure strategic alignment and cost-effectiveness.

Learning Roadmaps, Adoption & Development Models

• Develop 24–36 month workforce enablement roadmaps aligned to each department’s skill taxonomy and strategic business imperatives.
• Create 70-20-10 development pathways (on-the-job, mentoring, formal learning) for core digital and analytics skills.
• Ensure adoption and reinforcement strategies are embedded at Gate 2 (Solution Design Proposal), including communication, manager enablement, and reinforcement.
• Ensure academy programs prepare employees for future roles and evolving digital demands.

Learning Design & Facilitation

• Develop and deliver content across multiple modalities (eLearning, ILT, VILT, blended) while leveraging our suite of AI enablement tools.
• Facilitate training sessions, workshops, and communities of practice to strengthen enterprise digital literacy.
• Integrate LinkedIn Learning, vendor training, and industry certifications into the Academy experience.

Project & Portfolio Management

• Manage Academy initiatives through Cognota using the Stage Gate 1–5 process.
• Lead cross-functional project teams for Academy initiatives, serving as project manager for internal learning efforts. Coordinate workstreams across instructional designers, facilitators, learning technologists, communications specialists, and HRBPs.
• Set timelines, clarify deliverables, manage dependencies, and facilitate regular checkpoints to ensure projects stay on scope, on budget, and on schedule.
• Provide regular updates to stakeholders on Academy progress and outcomes.
• Contribute to quarterly Portfolio Reviews, ensuring Academy initiatives are prioritized against enterprise demand and resources.

Professional Development & Team Alignment

• Commit annually to professional growth through ATD certifications, industry conferences, and digital learning networks.
• Role-model Workforce Enablement team charter values of partnership, innovation, and accountability.
• Consistent collaboration with HRBPs and other Academy Managers to share best practices and contribute to cross-functional Academy initiatives.

AI Fluency & Digital Enablement

• Support responsible and safe use of AI in IT functions, contributing to the creation and communication of an AI Safe Use Charter while championing adoption of AI-powered learning tools to accelerate training design, personalization, and delivery.

Required Qualifications

• Bachelor’s degree in Learning & Development, Education, Human Resources, Information Technology, Data/Analytics, or related field; Master’s preferred.
• 7+ years of experience in learning and development, with direct exposure to IT, Analytics, or Digital Transformation.
• Demonstrated ability to design, implement, and manage functional academies or structured learning programs.
• Experience in instructional design, learning facilitation, and content development across multiple modalities.
• Familiarity with Agile/SAFe practices, IT service management, data governance, and cybersecurity frameworks preferred.
• Strong stakeholder management and consulting skills.
• Proficiency in structured project and portfolio management processes or platforms (e.g., Cognota, LMS).
• Commitment to professional development through ATD certifications, conferences, or industry credentials.

Required Core Skills

• Strategic Consulting & Business Partnering – Acting as trusted advisor to IT/Analytics leaders, shaping upstream demand.
• Instructional Design – Building learning solutions aligned to IT/Analytics skill needs.
• Training Delivery & Facilitation – Facilitating ILT, VILT, and blended sessions.
• Technology Application – Leveraging LMS platforms, eModules, AI-powered tools, and digital learning solutions.
• Performance & Adoption – Embedding adoption and reinforcement into design to close skill gaps and drive measurable impact.
• Business Insight – Understanding IT and Analytics strategy to align Academy solutions.
• Future Readiness – Anticipating digital trends, including AI, and embedding them into Academy roadmaps.
• Collaboration & Leadership – Leading cross-functional Academy pods with SMEs and stakeholders.
• Communication – Translating technical concepts into accessible learning experiences.
• Analytics Awareness – Connecting Academy outputs to workforce planning and talent reviews.
• Lifelong Learning – Continuously updating knowledge of digital transformation and L&D practices.

Physical Requirements

Office environment – no specific or unusual physical or environmental demands and employees are regularly required to sit, walk, stand, talk, and hear.

Work Environment

This position operates in an office environment and requires the frequent use of a computer, telephone, copier, and other standard office equipment. While performing the duties of this job, the employee is regularly required to sit. The employee is occasionally required to reach with hands and arms and climb or balance. The employee must frequently lift and/or move up to 5 pounds and occasionally lift and/or move up to 25 pounds. The noise level in the work environment is usually moderate. This position requires more than 80% computer use.

The current range for this position is

$104,125.20 – $175,599.98

This range is exclusive of fringe benefits and potential bonuses. If hired at ICW Group, your final base salary compensation will be determined by factors unique to each candidate, including experience, education and the location of the role and considers employees performing substantially similar work.

Why Join ICW Group?

• Challenging work and the ability to make a difference
• You will have a voice and feel a sense of belonging
• We offer a competitive benefits package, with generous medical, dental, and vision plans as well as 401K retirement plans and company match
• Bonus potential for all positions
• Paid Time Off with an accrual rate of 5.23 hours per pay period (equal to 17 days per year)
• 11 paid holidays throughout the calendar year
• Want to continue learning? We’ll support you 100%

ICW Group is committed to creating a diverse environment and is proud to be an Equal Opportunity Employer. ICW Group will not discriminate against an applicant or employee on the basis of race, color, religion, national origin, ancestry, sex/gender, age, physical or mental disability, military or veteran status, genetic information, sexual orientation, gender identity, gender expression, marital status, or any other characteristic protected by applicable federal, state or local law.

At ICW Group we offer a work environment that encourages entrepreneurialism and celebrates success. Our team members are hands-on contributors who are given the opportunity to make an impact. It’s our people who make us an employer of choice and the vibrant company we are today.

Job Category: Shared Services

Job Type: Full time

Req ID: JR100879