Employee Benefits Training & Development Specialist

HUB International•San Diego, CA

About The Position

In a rapidly changing world, HUB advises businesses and individuals on how to prepare for the unexpected. As one of the worlds' largest insurance brokers, our focus is dedicated to providing our customers with the peace of mind that what matters most will be protected-through unrelenting advocacy and tailored insurance solutions that put our clients in control. Our growing team of professionals across North America represents a broad, deep and one-of -a kind aggregation of entrepreneurs and leaders recognized for their excellence throughout the insurance community. THE OPPORTUNITY: Design, develop, and deliver comprehensive training programs that elevate service excellence across all Employee Benefits service team roles in the SoCal region. Build scalable training infrastructure that accelerates new hire productivity, ensures compliance, standardizes processes, and enables successful acquisition integration while supporting continuous professional development. Training programs serve 300+ service professionals across Account Manager (AM), Account Representative (AR), Benefits Analyst (BA), and Account Executive (AE) roles. This includes new hire onboarding, acquisition integration, and ongoing skill development. Strategic Context The SoCal region is positioned for significant growth through organic hiring and strategic acquisitions. This expansion, combined with increasing regulatory complexity in the employee benefits landscape, creates an urgent need for scalable training infrastructure that ensures consistent service excellence while accelerating team capability development. The role balances immediate training delivery needs (DELIVER mode) with building scalable, reusable training infrastructure (BUILD mode) that serves multiple audiences and use cases. Success is measured through quantifiable business impact: accelerating new hire productivity, protecting revenue through improved client retention, and streamlining acquisition integration timelines. This position requires a "build fast, learn faster" approach—delivering 80% good content today is better than 100% perfect content that never gets delivered. The focus is on creating practical, immediately applicable training that evolves through feedback and continuous improvement.

Requirements

Adult learning principles and instructional design expertise
Deep knowledge of employee benefits, group health insurance, and compliance (ERISA, HIPAA, ACA, state mandates)
Experience with benefits administration systems (Benefitpoint strongly preferred)
Excellent facilitation and presentation skills for diverse audiences
Strong written communication and materials development abilities
Project management skills to balance multiple priorities simultaneously
Proficiency in Microsoft Office Suite (PowerPoint, Word, Excel) for content creation
Ability to translate complex technical concepts into accessible training content
5+ years in employee benefits industry with client-facing or service team experience
Required Experience: 5-7 years of relevant experience
Required Education: Diploma

Nice To Haves

3+ years designing and delivering professional training programs
Experience with acquisition integration or change management
Background in developing onboarding programs and competency frameworks
Familiarity with learning management systems (LMS) and e-learning tools
Proven ability to measure training effectiveness and demonstrate business ROI
Self-directed and able to build infrastructure from the ground up
Strategic thinker who can see both big picture and tactical execution
Comfortable with ambiguity and able to prioritize effectively
Collaborative relationship-builder who engages stakeholders at all levels
Adaptable and responsive to changing business needs
Committed to continuous improvement and learning
Patient with results while maintaining urgency for progress

Responsibilities

Strategic Training Program Development Design and develop comprehensive training curricula for AM, AR, BA, and AE roles, covering compliance, insurance acumen, systems (Benefitpoint), client lifecycle processes, and professional soft skills.
Create modular, reusable training content that can serve multiple purposes (new hire onboarding, acquisition integration, and service team development).
Develop all training materials in HUB-branded PowerPoint, Word, and Excel formats ensuring brand consistency and professional quality. Each training will include a mix of job aids to assist with a smooth transfer of learning from training (Virtual or Brainshark) to the desk.
Build foundational content that forms the core of multiple training programs, maximizing efficiency through strategic content leverage.
Partner with Subject Matter Experts (SMEs) across compliance, systems, products, and operations to ensure technical accuracy and relevance.
Design assessment tools and competency validation methods to measure learning effectiveness.
Facilitate instructor-led training (ILT) sessions, virtual instructor-led training (VILT), and coordinate self-paced learning programs.
Execute new hire onboarding using structured 30-60-90-day learning pathways customized by role.
Deliver ongoing service team level-up training on priority skill gaps identified by managers and business needs.
Lead acquisition integration training to rapidly align acquired teams with HUB standards, processes, and culture.
Provide one-on-one coaching and support for team members requiring additional development.
Respond to urgent training needs while maintaining focus on strategic program development.
Partner with Regional Leadership on strategic training priorities, resource allocation, and business impact measurement.
Collaborate closely with Service Team Managers to identify performance gaps, training needs, and measure post-training application.
Work with Compliance, Systems, and Product SMEs to ensure training content accuracy and regulatory compliance.
Coordinate with HR and Talent Acquisition on new hire onboarding timelines and acquisition integration planning.
Engage with other Regional Training Directors to share best practices, leverage content, and ensure consistency in core training standards.
Maintain open communication with service team members through office hours, feedback collection, and responsive support.
Track and manage training development projects, delivery schedules, and stakeholder requests using Monday.com.
Collect and analyze feedback from training participants, managers, and leadership to continuously improve program quality.
Monitor training completion rates, assessment scores, and business impact metrics (time-to-productivity, error reduction, client satisfaction).
Maintain organized training resource library and documentation for scalability and knowledge transfer.
Communicate regular progress updates to stakeholders on program development, delivery metrics, and emerging needs.
Adapt training content based on regulatory changes, system updates, process improvements, and business strategy evolution.

Benefits

Throughout our network of more than 450 HUB offices in North America, we offer a competitive, exciting and friendly work environment that strategically positions our employees for longevity and success.
At HUB, we believe in investing in the future of our employees, and provide continuous opportunities for growth and development.
Our entrepreneurial culture fosters an environment that empowers our people to make the best decisions for our customers and organization, focusing on expanding the industry knowledge of our insurance professionals to better serve our valued clients.
We are committed to providing you with competitive and flexible benefits options that are rooted in your current needs, yet evolves as your needs change over time.
Join us in taking the first step toward creating a future that combines a diverse, challenging work environment with financial security and career satisfaction.
HUB International is proud to offer comprehensive benefit and total compensation packages which could include health/dental/vision/life/disability insurance, FSA, HSA and 401(k) accounts, paid-time-off benefits, and eligible bonuses, equity and commissions for some positions.

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