Customer Experience Strategy Manager – AI & Automation

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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 customer experience strategy manager within the Commercial Lines Customer & Agent Experience organization, you will own our Automation & AI portfolio, helping identify opportunities to simplify work, improve customer and agent experiences, and deliver measurable business value through automation, AI, and operational improvements. You’ll lead a team of three individual contributors to execute the team's roadmap and partner across Commercial Lines Customer & Agent Servicing (CAS), Customer Relationship Management (CRM), IT, Data Science, Product, and Experience teams to prioritize and deliver high-value solutions. Additionally, you will be responsible for building business cases, defining success measures, and monitoring outcomes to ensure value delivery.

This is a remote position with occasional travel for meetings and/or training.

Must-have qualifications

  • A minimum of 9 years of related professional work experience (e.g., definition and delivery of products through digital, voice, and agent channel experiences) and at least 2 years of leadership experience (e.g., directly managing or mentoring).
  • {OR} Bachelor's degree or higher and a minimum of 6 years of related professional work experience (e.g., definition and delivery of products through digital, voice, and agent channel experiences) and at least 2 years of leadership experience (e.g., directly managing or mentoring).

Preferred skills

  • Demonstrated strategic and analytical leadership with the ability to solve complex business problems
  • Strong influencing skills across teams and organizational boundaries
  • Experience leading initiatives related to process improvement and automation-related initiatives
  • Ability to translate ideas and strategies into action and results
  • Experience with AI-related work
  • Experience leading technology, digital experience, operations, product management, or business strategy initiatives

Compensation

  • $102,800 - $146,900/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 2025 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.

Equal Opportunity Employer

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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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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...

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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?...

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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...

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