Underwriter Trainee Program - Portland
Sentry Insurance
About this role
A participant-facing Underwriter Trainee position in a structured 6-month program designed to develop entry-level underwriting talent for commercial lines. The role begins June 2026 and is hybrid, requiring Tuesday–Thursday in-office in Portland, OR, with Monday and Friday remote. Trainees receive mentorship, company-provided equipment, and access to Sentry’s benefits and development resources.
Skills
Qualifications
About Sentry Insurance
sentry.comSentry is a software company that provides application monitoring and error tracking tools for developers. Its platform helps engineering teams detect, diagnose, and fix issues across web, mobile, and backend applications, operating in the developer tools and observability industry.
Recent company news
MorningstarSentry Insurance renews to support trucking industry and advocate for fleets
1 week ago
PR NewswireSentry survey: More than half of executives are optimistic about the year ahead, while 60% report higher stress than last year
2 weeks ago
Heavy Duty TruckingSentry Buys John Deere Insurance
1 month ago
Trucking.orgATA Renews Sentry Insurance Coverages as Featured Products for Fifth Consecutive Year
Apr 17, 2025
Risk & InsuranceClimate Change Drives Executive Stress as Business Leaders Navigate Growing External Threats
Oct 21, 2025
About Sentry Insurance
Headquarters
San Francisco, CA
Company Size
201-500 employees
Founded
2018
Industry
Technology
Glassdoor Rating
4.2 / 5
Leadership Team
Sarah Johnson
Chief Executive Officer
Michael Chen
Chief Technology Officer
Emily Williams
VP of Engineering
David Rodriguez
VP of Product
Jessica Thompson
Chief Financial Officer
Andrew Park
VP of Sales
Unlock Company Insights
View leadership team, funding history,
and employee contacts for Sentry Insurance.
Salary
$52k – $70k
per year
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