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 buildcapabilities, strengthen commitment, and connect people to each other and our culture.

What You'll Do 

You’ll lead a team focused on creating learning strategies for our professional and leadership development programs, as well as for our corporate functions.

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 a P&Cinsurance role or business learning professional position. 7 or more years of experience preferred.

• Prior experience managing teams in a business environment is strongly preferred.

• Proven ability to align learning initiatives with business outcomes and performance metrics. 

• Strong portfolio and project management, performance consulting, learning design, and facilitation skills. 

• Proficiency in Microsoft Suite, including SharePoint, teams, Word, Excel, and PowerPoint. 

• Experience with learning technologies and learning management systems a plus.

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.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Katelynne Rivera