Learning Leader - CL Insurance (Sales, Underwriting, and Safety Services)

Sentry Insurance•Stevens Point, WI

52d•Hybrid

About The Position

Lasting, meaningful learning in the workplace doesn't happen by chance - it's intentional. It takes strategy, insight, and leadership to create experiences that help people perform at their best. That's where you come in. As a Learning Leader in SentryU, you'll partner with senior leaders and key stakeholders to shape a learning portfolio that drives business results and makes work easier for our associates. Your role is about more than delivering learning - it's about understanding the business, identifying performance needs, and creating solutions that strengthen skills, build confidence, and connect people to our culture.

Requirements

Bachelors Degree or equivalent work experience and a minimum of 5 years of experience in an insurance role or business learning professional (commercial lines preferred).
Proven ability to align learning initiatives with business outcomes and performance metrics.
Strong portfolio and project management, performance consulting, and facilitation skills.
Proficiency in Microsoft Suite, including SharePoint, teams, Word, Excel, and PowerPoint.

Nice To Haves

Prior experience managing teams in a business environment is preferred.

Responsibilities

Coach and develop others: Lead a team of learning professionals, fostering a culture of trust, growth, and high performance.
Partner for impact: Work with senior leaders and steering committees to define learning strategies that align with business priorities and performance outcomes.
Design for results: Manage a learning portfolio and create new learning solutions that blend formal and informal approaches-classroom, digital, social, experiential, and microlearning.
Measure and improve: Evaluate effectiveness, monitor costs, and ensure initiatives deliver measurable value.

Benefits

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.

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