Director of Employee Benefits Training & Development

Woodrow Cross•Portland, OR

8d•$100,000 - $125,000•Hybrid

About The Position

The Cross Family of Agencies welcomes you. We need your talent and expertise. Position title: Director of Employee Benefits Training and Development Location: Portland, ME or any other EB Office Reports to: President, Employee Benefits Role summary: Lead the design, delivery, and evaluation of learning, leadership development, and capability-building initiatives within the Employee Benefits division . This role supports the development of producers, account management teams, and operational staff by building programs that strengthen technical expertise, client service capabilities, and leadership readiness within the EB business. Key responsibilities: Strategy & planning — Develop and own a multi-year employee beneftis training and development strategy aligned with business goals, workforce plans, and operational effectiveness. Program design & delivery — Oversee creation and rollout of employee benefits focused leadership development, manager enablement, onboarding, technical upskilling, and compliance learning programs. Learning architecture — Define employee benefits career pathways, competency frameworks, and select and govern learning technologies (LMS, content platforms, assessment tools). Measurement & ROI — Establish KPIs, evaluate program effectiveness using qualitative and quantitative methods, and report impact to senior leadership. Stakeholder partnership — Collaborate with business leaders, Human Resources and subject-matter experts to prioritize capability gaps and co-create solutions. Innovation & continuous improvement — Champion modern learning practices (microlearning, blended learning, experiential programs, coaching, peer learning) and pilot new approaches. Compliance & governance — Ensure employee benefit specific training meets regulatory and internal policy requirements and that learning data is secure and auditable.

Requirements

Education: Bachelor’s degree in Organizational Development, Human Resources, Education, Business, or related field; Master’s preferred.
Experience: 5+ years in learning & development, organizational development, or talent management.
Technical skills: Familiarity with LMS platforms, learning analytics, instructional design methodologies, and virtual learning technologies.
Domain knowledge: Strong grounding in leadership development, change management, competency modeling, and performance consulting.
Strategic thinker — Translates business strategy into capability plans.
Influence & partnership — Builds credibility with senior leaders and cross-functional teams.
Program execution — Delivers complex, multi-channel learning initiatives on time and on budget.
Data-driven — Uses metrics to guide decisions and demonstrate ROI.
Coaching & facilitation — Skilled in executive coaching, group facilitation, and experiential learning design.
Change leadership — Leads organizational change with empathy and rigor.

Nice To Haves

Experience in fast-growing or matrixed organizations.
Certification in instructional design, change management (e.g., Prosci), or coaching credentials.
Track record of implementing learning technology and modern content strategies.
Comfort with ambiguity and rapid prioritization.

Responsibilities

Strategy & planning — Develop and own a multi-year employee beneftis training and development strategy aligned with business goals, workforce plans, and operational effectiveness.
Program design & delivery — Oversee creation and rollout of employee benefits focused leadership development, manager enablement, onboarding, technical upskilling, and compliance learning programs.
Learning architecture — Define employee benefits career pathways, competency frameworks, and select and govern learning technologies (LMS, content platforms, assessment tools).
Measurement & ROI — Establish KPIs, evaluate program effectiveness using qualitative and quantitative methods, and report impact to senior leadership.
Stakeholder partnership — Collaborate with business leaders, Human Resources and subject-matter experts to prioritize capability gaps and co-create solutions.
Innovation & continuous improvement — Champion modern learning practices (microlearning, blended learning, experiential programs, coaching, peer learning) and pilot new approaches.
Compliance & governance — Ensure employee benefit specific training meets regulatory and internal policy requirements and that learning data is secure and auditable.