Learning & Performance Specialist - CL Sales, Underwriting, & Safety Services

Effective workplace learning is intentional—it requires strategy, insight, and leadership.

As a Learning and Performance Specialist, you’ll strengthen our culture of continuous development by designing and delivering solutions that elevate performance across Commercial Lines. You’ll use your insurance expertise, business acumen, and facilitation skills to equip associates with the knowledge and capabilities they need to excel.

This role supports Commercial Lines Sales, Underwriting, and Safety Services across Direct Writer, Life & Annuities, National Accounts, Regional, Transportation, and Safety Services.

What You’ll Do 

• 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.

What it Takes

• 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 Skills

• 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.

What You'll Receive

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.

• Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday you’ll work in office.
• As a Sentry associate, you will have an in-office workspace and materials for your home office. In addition to the laptop, you will receive prior to your start, Sentry will provide equipment for your home office. 
• Meal Subsidy available for associates who report to an office.
• 401(K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.
• Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program.
• Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off.
• Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle.
• Well-being and Employee Assistance programs.
• Sentry Foundation gift matching program to encourage charitable giving.

About Sentry

We take great pride in making Forbes’ list of America’s Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.

Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority.

Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.

Get ready to own your future at Sentry. Opportunities await!

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Katelynne Rivera

Katelynne.Rivera@Sentry.com

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.