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Sentry Insurance Jobs in Chicago, IL (NOW HIRING)

Apex Systems

Hadoop Admin

Chicago, IL · On-site

$70 - $73.68/hr

Expert-level knowledge of Cloudera Hadoop components such as HDFS, Sentry, HBase, Kafka, Impala ... other insurance plans that offer an optional layer of financial protection. We offer an ESPP ...

Innovizant LLC

Java Developer/Architect

Schaumburg, IL

$61.75 - $83.50/hr

... Insurance and credit union business in achieve their business goals. Innovizant made up of ... Sentry etc. Good experience with databases and SQL Good experience with at least one programming ...

Innovizant LLC

Java Developer/Architect

Schaumburg, IL · On-site

$61.75 - $83.50/hr

... Insurance and credit union business in achieve their business goals. Innovizant made up of ... Sentry etc. • Good experience with databases and SQL • Good experience with at least one ...

All JobsSentry Insurance JobsSentry Insurance Jobs in Chicago, IL

Sentry Insurance information

See Chicago, IL salary details

$31.9K

$67.8K

$85.5K

How much do sentry insurance jobs pay per year?

As of Jul 28, 2026, the average yearly pay for sentry insurance in Chicago, IL is $67,833.00, according to ZipRecruiter salary data. Most workers in this role earn between $61,800.00 and $77,300.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an Insurance Agent at Sentry Insurance, and why are they important?

To thrive as an Insurance Agent at Sentry Insurance, you need strong sales abilities, knowledge of insurance products, relevant state licensure, and often a bachelor’s degree or equivalent experience. Familiarity with customer relationship management (CRM) software and quoting systems is typically required. Outstanding interpersonal skills, active listening, and problem-solving abilities help agents build trust and address client needs effectively. These skills are vital for meeting sales targets, ensuring customer satisfaction, and maintaining compliance in a competitive insurance market.

What is the difference between Sentry Insurance vs Claims Adjuster?

AspectSentry InsuranceClaims Adjuster
CredentialsLicenses, insurance certificationsLicenses, insurance certifications
Work EnvironmentOffice, remote, fieldOffice, remote, field
Industry UsageInsurance provider, underwritingInsurance, claims processing
Primary RoleInsurance provider, risk assessmentEvaluate and settle insurance claims

While Sentry Insurance is a provider offering various insurance products, a Claims Adjuster is a professional who evaluates insurance claims on behalf of insurers like Sentry. Claims Adjusters work directly with policyholders to assess damages and determine payouts, whereas Sentry Insurance manages the overall insurance policies and underwriting processes.

What opportunities for professional development and advancement are typically available to employees at Sentry Insurance?

At Sentry Insurance, employees often benefit from a range of professional development opportunities, including ongoing training, mentorship programs, and support for industry certifications. The company encourages internal mobility, allowing employees to explore different roles or departments based on their interests and performance. Advancement is typically based on a combination of demonstrated skills, leadership potential, and contributions to team goals. Employees are also supported through structured performance reviews and clear career pathways, helping them to grow within the organization.

What kind of insurance company is Sentry?

Sentry Insurance is a mutual insurance company that provides a range of insurance products, including business, personal, and specialty coverage. It operates as a provider of property and casualty insurance and emphasizes customer service and risk management solutions.

How much does Sentry Insurance pay?

Sentry Insurance offers competitive salaries that vary depending on the role, experience, and location. Entry-level positions typically start around $40,000 to $60,000 annually, while more experienced roles can pay upwards of $80,000 or more. Compensation may also include benefits such as health insurance, retirement plans, and performance bonuses.

What is the highest paying insurance agent job?

The highest paying insurance agent roles are typically senior or specialized positions such as captive agents working for large insurance companies or those with extensive experience and a strong client base. These roles often offer higher commissions, bonuses, and incentives, with top earners making six figures annually. Advanced certifications and a proven sales record can also contribute to higher compensation levels.

What is Sentry Insurance?

Sentry Insurance is a mutual insurance company that provides a variety of insurance products, including business insurance, personal auto insurance, and life insurance. Founded in 1904 and headquartered in Stevens Point, Wisconsin, Sentry serves policyholders across the United States. The company is known for its strong financial stability and focus on customer service, offering solutions for businesses of all sizes as well as individuals seeking personal coverage.

Is Sentry Insurance a good company to work for?

Sentry Insurance is generally regarded as a stable employer with a focus on employee benefits and a collaborative work environment. Employees often cite opportunities for professional development and a positive company culture, though experiences can vary by role and location.
What are popular job titles related to Sentry Insurance jobs in Chicago, IL? For Sentry Insurance jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Sentry Insurance jobs in Chicago, IL look for? The top searched job categories for Sentry Insurance jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Sentry Insurance jobs? Cities near Chicago, IL with the most Sentry Insurance job openings:
Sentry Insurance jobs near you
Infographic showing various Sentry Insurance job openings in Chicago, IL as of July 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 95% Physical, 2% Hybrid, and 3% Remote job distribution, with an average salary of $67,833 per year, or $32.6 per hour.
Software Engineer (Cloud, Cross-Platform & .NET Systems)

Software Engineer (Cloud, Cross-Platform & .NET Systems)

Altom Transport

Chicago, IL

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 21 days ago

Altom Transport rating

7.4

Company rating: 7.4 out of 10

Based on 8 frontline employees who took The Breakroom Quiz

Job description

We're seeking an experienced Software Engineer to maintain, enhance, and modernize a suite of .NET-based applications while developing new cross-platform, mobile, and distributed systems. This role bridges legacy modernization with next-generation engineering, spanning .NET, Flutter, Go, Docker, Linux, and private-cloud services.

A central component of this position involves integrating several independent internal applications to create a seamless, cohesive ecosystem across operational, logistics, compliance, and internal systems. The role also includes transforming a legacy Windows application into a modernized, forward-compatible software architecture.

The ideal candidate is comfortable working across Microsoft and non-Microsoft stacks, private cloud environments, Linux-based microservices, modern front-end development, and mobile applications. Familiarity with AI-assisted development tools (Cursor, Copilot, etc.) is highly valued to improve both speed and quality.

Key Responsibilities

  • Maintain, troubleshoot, refactor/modernize, and enhance existing .NET Framework / .NET Core applications.
  • Architect and develop APIs, microservices, event-driven components, and back-end systems for portals, dashboards, and enterprise workflows.
  • Build new back-end services using Go, .NET Core, Node.js, or Python for scalability and cross-platform compatibility.
  • Build cross-platform mobile and embedded applications using Flutter.
  • Develop lightweight, modern web interfaces using JavaScript/TypeScript with a strong focus on UX/UI design principles.
  • Integrate internal applications and data flows to improve cohesion across multiple sovereign systems, unifying workflows and reducing operational silos.
  • Plan and execute migration and modernization strategies to the organization's private cloud environment.
  • Deploy and manage Linux-based services and containerized workloads (Docker).
  • Design and manage CI/CD deployments using Docker, GitHub Actions, or GitLab CI.
  • Manage relational databases (SQL Server, Postgres, MySQL), including schema design and performance tuning.
  • Utilize AI-assisted tools (Cursor AI, GitHub Copilot) to enforce quality and accelerate delivery.
  • Collaborate with IT, engineering, and operations teams to ensure seamless integration and interoperability across business systems.
  • Participate in Agile ceremonies, structured change workflows, code reviews, and automated testing.

Requirements

Required Qualifications

  • 3+ years of hands-on experience with .NET Framework / .NET Core development.
  • Experience building cross-platform mobile applications using Flutter (Dart).
  • Proficiency with Go or another compiled back-end language (Rust, Java, etc.).
  • Practical experience with Linux service deployment, CLI workflows, and diagnostics.
  • Solid understanding of Docker and containerization concepts.
  • Experience deploying applications into private cloud or on-premises virtualized environments.
  • Strong experience with SQL Server; additional experience with Postgres/MySQL is a plus.
  • Ability to support and modernize legacy on-premise applications while designing new cloud-hosted replacements.
  • Working knowledge of API design, REST, GraphQL, microservices, and distributed systems.
  • Hands-on experience with AI-assisted development tools.
  • Familiarity with Git, GitHub, Bitbucket, or Atlassian

Preferred Skills

  • Experience converting monolithic applications into microservice or container-based architectures.
  • CI/CD engineering with GitHub Actions, GitLab CI, or Jenkins.
  • Strong UX/UI fundamentals, wireframing, and component-driven design.
  • Familiarity with authentication systems (OAuth2, SAML, JWT).
  • Exposure to distributed logging and monitoring platforms such as Sentry.
  • Experience working with Atlassian tools (Jira, Confluence) and formal change-order or ticket-based development workflows (helpful but not require)
  • Background in logistics, ERP, or enterprise operational platforms is a strong plus.

Soft Skills

  • Excellent communication and cross-team collaboration abilities.
  • Strong analytical and problem-solving mindset.
  • Adaptable, self-directed, and eager to adopt new technologies.
  • Strong sense of ownership, accountability, and architectural quality.
  • Passionate about automation, UX/UI consistency, performance, and clean engineering principles.

Benefits

  • 401(K) with company match from Day 1 
  • Blue Cross Blue Shield health insurance - medical, dental, vision, prescription 
  • Paid vacation, holidays, and personal time 
  • Optional life and disability insurance 
  • Safety bonuses for clean roadside inspections and safe driving records 
  • Paid training, PPE, and late-model, well-maintained trucks 
  • Boot reimbursement program 
  • Up to $2,400 company contribution to Health Savings Account (HSA) 

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