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Progressive

Software Developer Lead - AI

United States

Job at a glance

Pay
$128,000 – $150,000
Workplace
On-site
Sector
Engineering & Technology
Posted
Oct 15, 2026
First found
Oct 16, 2026, 12:44 PM ET

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About the job


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 a lead software developer – AI within the Enterprise Development Capabilities and Services (EDCS) organization, you will shape the future of AI in software development at Progressive. In this role, you’ll influence organizational strategy and contribute to the implementation of AI-enabled solutions through cross-functional collaboration that transform our Software Development Life Cycle (SDLC). You’ll also build and advance Maestro, Progressive’s internal AI-native platform for software development, to deliver enterprise-scale capabilities for engineering teams.

This is a remote position for US based work only.

Must-have qualifications

  • Bachelor's degree or higher in an Information Technology discipline or related field of study and minimum of six years of work experience designing, programming, and supporting software programs or applications
  • In lieu of the above, a high school diploma or GED or higher, the completion of a technical training program, and a minimum of six years related work experience
  • In lieu of the above, a high school diploma or GED or higher and a minimum of eight years related work experience designing, programming, and supporting software programs and applications

Preferred skills

  • Hands-on experience developing generative AI solutions, including MCP clients/servers and AI agents.
  • Versatile programming expertise across multiple languages; experience with Typescript and Go.
  • Broad technical fluency across infrastructure, networking, security, cloud, and CI/CD systems.
  • Strong communication skills and the ability to adapt in a dynamic environment.
  • Proven ability to mentor and enable other engineers through strong engineering practices.

Compensation

  • $128,000-$150,000/year
  • 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 2024 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.

Equal Opportunity Employer

*Sponsorship for work authorization for foreign national candidates is not available for this position. *

*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/ *

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