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Sentry Logo Sentry · Human Resources

Associate Director - Learning

United States, Stevens Point · Job Posted February 20, 2026
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Job Description

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. 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.

Job Responsibility

  • 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

Requirements

  • Bachelor’s Degree or equivalent work experience
  • Minimum of 8 years of previous work experience
  • Experience in P&C insurance strongly preferred
  • 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

Nice to have

  • Experience in P&C insurance
  • managing managers

What we offer

  • Hybrid work model (Monday and Friday work from home)
  • In-office workspace and materials 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
  • Continue your education and career development through Sentry University (SentryU) and utilize our 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
  • Sentry Foundation gift matching program
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