Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun. Apply today and take the first step to Destination: Progress.

As an IT systems engineer lead at Level20, you’ll join a team responsible for the creation of new products and capabilities. In this role, you’ll support technology platforms, devices, and infrastructure that power our organization. You’ll play a key part in improving technology servicing and support, coordinating activities, and contributing to engineering initiatives that support more than 100 team members. You’ll partner with operations, security, and technical stakeholders on roadmap development and efficiency-focused initiatives.

At Level20 (https://www.progressive.com/careers/our-teams/level20/), Progressive’s growth incubator, we fuel growth for the company through the exploration and development of new-to-market products and services beyond Property and Casualty Insurance. Our team has the backing of Progressive, which gives us access to a larger resource pool than a traditional start-up.

This is a hybrid role in downtown Cleveland, OH (Office Location: 800 W St Clair Ave STE 200, Cleveland, OH 44113) with free parking. Work-from-home days are possible for this position (Monday and Friday).

This is a remote position for US based work only.

Must-have qualifications

• A minimum of nine years related experience working with operating system hardware and/or software components in a large IT environment with many categories of devices, infrastructures, and operating systems
• {OR} Associate's degree or higher in an Information Technology discipline, Math or other related field of study and a minimum of eight years working with operating system hardware and/or software components in a large IT environment with many categories of devices, infrastructures and operating systems.

Preferred skills

• Knowledge of IT operations supporting a variety of SaaS-based capabilities, including Microsoft Entra, AWS, Atlassian, and similar platforms
• Experience with Microsoft Active Directory/Entra administration
• Applied experience in Tier 2 and above support and advanced technical troubleshooting, diagnosing, and problem-solving skills issues for Macintosh and Windows platforms
• Scripting and general software development knowledge (i.e. Linux Bash, PowerShell, Python, Azure, GitHub, JSON, and or YAML)
• Possesses excellent verbal and written skills and consistently demonstrates the aptitude and passion to learn new skills

Compensation

• $132,000-$147,000/year depending on experience
• Gainshare annual cash incentive payment up to 40% of your eligible earnings based on company performance

Benefits

• 401(k) with dollar-for-dollar company match up to 6%
• Medical, dental & vision, including free preventative care
• Wellness & mental health programs
• Health care flexible spending accounts, health savings accounts, & life insurance
• Paid time off, including volunteer time off
• Paid & unpaid sick leave where applicable, as well as short & long-term disability
• Parental & family leave; military leave & pay
• Diverse, inclusive & welcoming culture with Employee Resource Groups
• Career development & tuition assistance
• Onsite gym & healthcare at large locations

Energage recognizes Progressive as a 2025 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.

Equal Opportunity Employer

Applicants must be authorized to work for any employer in the U.S. without the need or potential need, of current or future sponsorship for employment. Progressive does not hire candidates with (e.g., F-1 CPT, OPT, or STEM OPT, H-1B, O-1, E-3, TN) statuses for this role.

For ideas about how you might be able to protect yourself from job scams, visit our scam-awareness page at https://www.progressive.com/careers/how-we-hire/faq/job-scams/

#LI-CL1