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IT Systems Engineer Sr or Lead

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60601, USA
Listing for: Progressive
Full Time, Remote/Work from Home position Listed on 2026-11-06
Job specializations:
  • IT/Tech
    Systems Engineer, IT Support, Cybersecurity, Unix/Linux
Salary/Wage Range or Industry Benchmark: 98400 - 146900 USD Yearly USD 98400.00 146900.00 YEAR

Job Description & How to Apply Below

Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun.

As an IT systems engineer senior or lead on the Managed File Transfer (MFT) Team, you’ll help ensure the secure, reliable movement of files between Progressive and its external trading partners. In this role, you’ll set up, maintain, and troubleshoot file transfers while supporting the systems, tools, and environments that enable activities ranging from project integration testing to critical business operations.

You’ll collaborate with peers, internal customers, and external trading partners, requiring strong communication and documentation skills to support accurate record-keeping, reporting, and audit compliance. You’ll participate in a required on-call rotation and contribute to a variety of projects based on business needs and your expertise.

This an remote position with occasional travel to an office for an meeting/and or training.

Minimum qualifications
  • Minimum of 5 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 minimum of 4 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 FTP protocols (SFTP, FTPS, HTTPS, etc.).
  • Experience supporting distributed systems, with Linux highly preferred.
  • Demonstrable experience with scripting and automating processes in support of continuous improvements.
  • Experience with infrastructure support (including application upgrades and configurations) and Cloud/containers.
  • Strong communication skills to collaborate with peers, internal customers, and external trading partners and strong documentation skills.
Compensation
  • $98,400 - $146,900
  • Gainshare annual cash incentive payment up to 30% 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

Energage recognizes Progressive as a 2026 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.

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