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

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.

What You'll Do

You’ll lead a team focused on creating learning strategies for Commercial Lines Sales, Underwriting, and Safety Services across Direct Writer, Hortica, National Accounts, Regional, Transportation, and Safety Services.

Specifically, you will:

• 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.

What it Takes

• 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).

• Prior experience managing teams in a business environment is 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.

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.