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Associate Director - Learning

Sentry Insurance
life insurance, parental leave, tuition reimbursement, 401(k), remote work
United States, Wisconsin, Stevens Point
1800 North Point Drive (Show on map)
Feb 14, 2026
You'll lead teams responsible for creating & executing learning strategies for our associates in our Commercial Lines, Personal Lines, and Customer Service & Operations business units.

We believe learning and development is essential to individual and organizational growth and fully understand that it doesn't just happen by accident. In fact, it requires a strong strategic plan partnered with individuals and leaders who understand the complexities of performance-based learning.

Is that you? Do you have the experience and desire to work collaboratively to assess, plan, design, implement and evaluate performance-based learning and development initiatives? As the Associate Director of Learning, you'll be part of the SentryU team, whose mission is to build capabilities, connections, culture, and commitment for all associates at Sentry, and have the opportunity to make a positive difference for others every day.

What You'll Do

As an Associate Director - Learning, you will:

  • Partner with Sentry leadership to assess and understand learning and performance needs/gaps in relationship to business strategies and goals.

  • Collaborate with your teams on the design, development, and delivery of performance-based learning programs and solutions that positively impact business objectives.

  • Oversee and ensure the effectiveness of technical learning programs in underwriting, sales, safety services, and operations, as well as support other assigned learning portfolios.

  • Serve as a member of SentryU's leadership team, contributing to enterprise-wide decisions related to learning and talent development at Sentry.

  • Implement, monitor and analyze business metrics to ensure learning effectiveness while tracking and managing expenses.

  • Manage a learning team, creating an inclusive, engaging and motivating work environment and providing ongoing coaching and support.

What it Takes

  • Bachelor's Degree or equivalent work experience.

  • Minimum of 8 years of previous work experience in P&C insurance.

  • Prior experience leading a business learning and development team and cultivating relationships with senior executives.

  • Demonstrated performance consulting, workplace learning design, presentation, and facilitation skills and experience.

  • Previous experience managing people; managing managers a plus.

  • Strong project management and organization skills.

  • Experience linking learning and development initiatives to business outcomes and performance metrics.

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.

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