Sentry

60 Sentry Jobs Hiring Near You

Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today ...

Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today ...

At Sentry, your total rewards go beyond competitive compensation. We're committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both ...

Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today ...

Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today ...

Security Engineer, IAM

San Francisco, CA · On-site

$155K - $400K/yr

Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today ...

Security Engineer, IAM

Toronto, ON · On-site

CA$162K - CA$420K/yr

Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today ...

Fitness Attendant

Stevens Point, WI · On-site

$13.25 - $15.50/hr

As a Fitness Attendant at Sentry's Wellness Center, you will play a critical part in providing health and wellness service to other Sentry Insurance associates. Hours for this on-call role vary by ...

Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today ...

Premium Audit Technician

Madison, WI · On-site

$49K - $61K/yr

This position can be located in our Stevens Point, or Madison, WI office(s) and will follow Sentry's current hybrid model of 3 days in-office. Entry level role focused on supporting the premium audit ...

Showing results 41-60

Sentry Jobs Information

What is it like to work at Sentry?

Sentry is a remote-first company that prioritizes flexibility, autonomy, and collaboration, fostering a culture that values open communication and mutual support among team members.

The company's structure is organized into small, cross-functional teams that work together to achieve shared goals, with a focus on delivering high-quality products and services. Sentry's mission is to empower developers to write better code by providing a comprehensive error tracking platform.

Working at Sentry may appeal to candidates who value remote work flexibility, are passionate about software development and error tracking, and are looking for a company that prioritizes employee well-being and growth opportunities.

What makes Sentry an attractive place to work?

Sentry is a leading provider of error tracking and monitoring solutions for software applications, with a strong reputation for delivering reliable and efficient tools to the developer community. The company fosters a collaborative and innovative work environment, where employees can engage in open-source projects, participate in hackathons, and contribute to the development of its flagship product. By joining Sentry, individuals can leverage opportunities for professional growth, contribute to the success of a rapidly growing company, and make a meaningful impact on the software development ecosystem.
Infographic showing various job openings at Sentry in the United States as of August 2026, with employment types broken down into 96% Full Time, and 4% Part Time. Highlights an 99% Physical, and 1% Remote job distribution.

Underwriting Manager - Middle Market

Sentry

Madison, WI • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 22 days ago


Job description

Manages a group of associates who have underwriting responsibility for all middle market lines, responsibly growing strategy, talent, and business.
This position will be located in our Madison, WI Regional office under a hybrid work model.
What You'll Do:
As an Underwriting Manager - Commercial Lines, you will oversee and guide the implementation and successful execution of our business strategy and uphold continuous improvement through leadership focused on process, problem solving, performance, partnering, purpose and people. In addition, you will:
  • Manage the day-to-day underwriting operations while providing technical guidance to a team of underwriters.
  • Recommend and implement changes to improve productivity, growth, profitability, and quality, as well as monitor effectiveness of these policies and procedures.
  • Interpret underwriting guidelines for larger or more complex files.
  • Handle difficult underwriting inquiries through direct personal action.
  • Coordinate and participate in underwriting training programs
  • Attend cross functional team meetings, present and work with other teams in pursuing new accounts, as well as agencies/insureds to develop and maintain effective business relationships.

What it Takes:
  • Bachelor's degree or equivalent work experience
  • Minimum 2 years of related work experience, with experience in middle market underwriting preferred
  • Completion of insurance courses such as IIA and CPCU preferred
  • Previous courses in management or management experience preferred
  • Thorough knowledge of specific insurance concepts and terminology
  • Effective analytical, human relations and communications skills
  • Ability to meet travel requirements of the job

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 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 since 2017. 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!
Joe Larsen
Senior Talent Acquisition Specialist
Joe.larsen@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.