Sentry · 12 hours ago
Learning & Performance Specialist - CL Sales, Underwriting, & Safety Services
Stevens Point, WI
Full-time
Hybrid
Senior Level
5+ years expSentry is one of the largest and financially strongest mutual insurance companies in the United States, recognized for its commitment to employee satisfaction. The Learning and Performance Specialist will design and deliver learning solutions to enhance performance in Commercial Lines, collaborating with various stakeholders to assess needs and develop effective training programs.
Insurance
Responsibilities
Create practical, business-focused learning and performance solutions aligned with Commercial Lines strategies and goals
Partner with SentryU, instructional designers, and business leaders to assess needs, identify performance gaps, recommend solutions, and develop learning experiences (classroom, eLearning, blended, performance support, etc.)
Deliver high-quality facilitation—virtual, in-person, and hybrid—for audiences from new hires to senior leaders
Lead and contribute to projects with clear objectives, timelines, and deliverables that support business priorities
Define and integrate performance metrics into solution design to measure impact and drive improvement
Build and deliver programs that engage learners, strengthen capability, and support both role-specific and enterprise-wide competencies
Qualification
Required
Bachelor's degree or equivalent experience, plus at least 5 years in an insurance or business learning role (Commercial Lines strongly preferred)
Strong communication, organization, and project management skills
Proven ability to assess learning needs and translate them into actionable development plans
Experience leading projects with defined scopes, milestones, and outcomes
Effective facilitation skills across multiple formats and diverse audiences
Working knowledge of adult learning principles and their application in business settings
Preferred
Professional designations such as CPCU, ATD, AU, CPIA, ASP, CSP, or related coursework
Experience developing employees at all organizational levels
Familiarity with instructional design concepts and blended learning strategies
Benefits
Flexibility through a scheduled Hybrid work model
In-office workspace and materials for your home office
Meal Subsidy
401(K) plan with a dollar-for-dollar match on your first eight percent
Tuition Reimbursement program
Generous Paid-Time Off plan
Volunteer-Time off
Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits
Well-being and Employee Assistance programs
Gift matching program to encourage charitable giving
Company
Sentry
In 1904, members of the Wisconsin Retail Hardware Association founded their own insurance company—one built on mutual support, shared strength, and a commitment to service.
5001-10000 employees
Funding
Current Stage
Late StageLeadership Team
Aaron Deering
Chief Technology Officer
Todd Schroeder
Chief Administrative Officer and Chief Financial Officer/Treasurer
Recent News
2025-07-11
2025-07-08
2025-05-05
Company data provided by crunchbase