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System Administrator(2720-INS)

June 30, 2026

Who We Are Insurity empowers insurance organizations to quickly capitalize on new opportunities by delivering the world’s most configurable, cloud-native, easy-to-use, and intuitively analytical insurance software. Just as importantly, we empower our people—providing the tools, support, and opportunities they need to grow and succeed. We don’t just make bold promises—we deliver results. As the largest cloud-based software provider for the Property & Casualty market, Insurity is trusted by 22 of the top 25 P&C carriers and 7 of the top 10 wholesale brokers in the MGA space. Behind that trust is a team that delivers exceptional value and deep industry expertise. While our technology sets us apart, it’s our people who truly make the difference. At Insurity, you’ll collaborate with some of the most creative and knowledgeable minds in insurance tech—in a culture that fosters innovation, teamwork, and continuous learning. Our award-winning onboarding experience welcomes and supports you from the moment you accept our offer. Ready to grow your career with an industry leader? Apply today—we’re excited to welcome you. #UatInsurity What’s In It For U <ul><li>Work Where You Thrive: Find a hybrid work environment that allows you to enjoy great work life balance, stay connected and collaborative </li><li>Generous Time Off: Our leadership believes in taking the time you need when you need it. </li><li>Day One Health Benefits + Employer-Matched Retirement Savings: You might think these are table stakes, but we know these matter to you. </li><li>More Than Just Core Values: Our values are fundamental in how we attract, train, and retain top talent. </li><li>Award-Winning Onboarding Program: We set you up from the get-go to make a significant impact from Day One and follow you through your entire first year. </li><li>Real Career Growth Opportunities: We love to promote from within with over 25% of our open roles filled through internal applicants on average. </li><li>Mentorship Program: We support a champion culture and growth mindset by pairing you with experienced, talented leaders to help you grow personally and professionally. </li><li>Insurity Podcasts: Explore podcasts from our Learning & Development team for deeper insight into Insurity products, company innovation, and the business as a whole. </li><li>Continuous Learning Opportunities: Own your development with your own LinkedIn Learning and Kaplan licenses. </li><li>Employee Referral Bonus: Once you come onboard, give Insurity the biggest compliment you can give by referring someone to work here and earn a referral bonus. </li></ul>Insurity’s Next System Administrator The System Administrator will support and optimize Insurity’s public and private cloud environments, helping maintain performance, reliability, and security across daily operations. The role includes system administration, application support, automation, troubleshooting production and infrastructure issues, and contributing to platform stability and continuous improvement. The ideal candidate is a proactive, detail-oriented professional with experience in Windows Server, cloud platforms, networking, and scripting, who thrives in a collaborative, fast-paced environment and is comfortable using modern AI-assisted tools to improve day-to-day efficiency What Our System Administrator Will Do <ul><li>Work with senior level administrators in troubleshooting and triaging activities.</li><li>Contribute to changes in host and guest configurations.</li><li>Help diagnose system performance problems with senior level administrators.</li><li>Assist senior level administrators with monitoring and capacity planning activities.</li><li>Recommend best practices for solutions and help to identify operational gaps.</li><li>Assist in managing individual projects including private cloud initiatives.</li><li>Be flexible to work across various areas of technology to support the operations team application and infrastructure.</li><li>Use modern AI assistants and operational tools, where appropriate, to support day-to-day troubleshooting, analysis, and team efficiency.</li><li>Participate in rotating team oncall support for hosted and nonhosted customers.</li><li>Stay up to date on industry and job-related trends and best practices, including reading relevant publications, articles, blogs, etc.</li><li>Other duties as assigned </li></ul>Technical Skills Who We’re Looking For <ul><li>Good hands-on experience in IIS (Internet Information Services) configuration, application deployment, and understanding of end-to-end application flow across environments.</li><li>Good proficiency in Windows Server administration (2008 and above).</li><li>Exposure to Cloud platforms such as AWS or Azure.</li><li>Working knowledge of application lifecycle and CI/CD pipelines (e.g., Jenkins, Azure DevOps).</li><li>Exposure to monitoring tools such as Dynatrace, Nagios, or AppDynamics.</li><li>Good understanding of HTTP/S protocols, load balancing, DNS, and network security concepts.</li><li>Hands-on experience with PowerShell scripting and process automation.</li><li>Familiarity with SQL Server and backend database connectivity.</li><li>Understanding of system performance tuning, capacity planning, and root cause analysis. Soft Skills:</li><li>Exposure to modern operational practices, including the use of AI-assisted tools or automation helpers for troubleshooting, analysis, and day-to-day administration tasks. </li><li>Excellent analytical and problem-solving ability.</li><li>Strong time management, organization, and multitasking skills.</li><li>Self-starter with a collaborative approach and a willingness to mentor others.</li><li>Adaptable to changing priorities and evolving technologies. </li></ul>Certifications (Preferred): <ul><li></li><li>AWS or Azure Administrator Associate Certification</li><li>Microsoft Certified Solutions Expert (MCSE)</li><li>VMware Certified Professional (VCP)</li><li>Experience: 2-4 years of hands-on experience in system administration, infrastructure management, or cloud operations (public/private cloud environments) and Application Configuration.</li><li>Education: Bachelor's degree in computer science, Information Technology, or a related field — or equivalent practical experience.</li><li>Travel required - Minimal, limited to training, team collaboration, or data center requirements. </li></ul>Thank you for your interest in Insurity! Please understand that due to the volume of applicants we receive, only selected candidates will be contacted.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...