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60 Progressive Insurance Director Of Insurance Operations Jobs Hiring Near You

Progressive

Insurance Defense Attorney

Sterling Heights, MI · Hybrid

$145K - $161K/yr

Progress. As an insurance defense attorney within our No-Fault litigation team, you'll be a part of our motor vehicle insurance defense litigation team, providing legal representation to Progressive ...

Progressive

Insurance Defense Attorney

Minneapolis, MN · Hybrid

$97K - $108K/yr

Progress. As an insurance defense attorney within our Bodily Injury/No-Fault litigation team, you'll be a part of our motor vehicle insurance defense litigation team, providing legal representation ...

Progressive

Insurance Defense Attorney

Saint Paul, MN · Hybrid

$97K - $108K/yr

Progress. As an insurance defense attorney within our Bodily Injury/No-Fault litigation team, you'll be a part of our motor vehicle insurance defense litigation team, providing legal representation ...

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Progressive Jobs Information

Do workers at Progressive Insurance get paid breaks?

Yes. Most people get paid breaks.
71% of people say they get paid breaks.
Based on data from 122 people who took the Breakroom Quiz between July 2025 and July 2026.

Does Progressive Insurance pay people when they’re sick?

Yes. Most people get paid when they’re sick.
78% of people say they would get paid if they were sick but scheduled to work.
Based on data from 86 people who took the Breakroom Quiz between February 2026 and August 2026.

At Progressive Insurance, are sick days and vacation days separate paid time off?

Sick days and vacation days are used from the same paid time off.
78% of people say they have to use vacation days when they’re out sick.
Based on data from 88 people who took the Breakroom Quiz between February 2026 and August 2026.

Is the health insurance from Progressive Insurance affordable enough for their workers?

Most people say the health insurance costs are okay.
94% of people say the health insurance costs are okay
Based on data from 81 people who took the Breakroom Quiz between February 2026 and August 2026.

Do people get paid time off at Progressive Insurance?

Most people get paid time off work.
100% of people say they get paid time off.
Based on data from 89 people who took the Breakroom Quiz between February 2026 and August 2026.

How far ahead of time do people find out their work schedule?

Only some people find out their schedule four weeks ahead of time.
  • 45% of people with changing schedules find out their shifts one week or less ahead of time.
  • 15% of people with changing schedules find out their shifts two weeks ahead of time.
  • 5% of people with changing schedules find out their shifts three weeks ahead of time.
  • 35% of people with changing schedules find out their shifts four weeks or more ahead of time.

Based on data from 55 people who took the Breakroom Quiz between December 2024 and May 2026.

Do workers at Progressive Insurance worry about hours?

Most people don’t worry about getting enough hours.
98% of people report they don’t worry about getting enough hours.
Based on data from 53 people who took the Breakroom Quiz between July 2025 and July 2026.

Do Progressive Insurance workers get to choose the shifts they work?

Most people get to choose which shifts they work.
68% report that they have enough control over which shifts they work.
Based on data from 57 people who took the Breakroom Quiz between May 2025 and May 2026.

How easy is it for Progressive Insurance workers to change shifts?

Most people find it easy to change shifts.
72% of people report that it’s easy to change shifts if they need to.
Based on data from 60 people who took the Breakroom Quiz between May 2025 and May 2026.

How easy is it to get time off at Progressive Insurance?

Most people find it easy to get time off.
83% of people report it’s easy to get time off.
Based on data from 84 people who took the Breakroom Quiz between February 2026 and August 2026.

Do Progressive Insurance managers change schedules at the last minute?

Most managers don’t change people’s schedules at the last minute.
98% of people say their manager doesn’t change their shift schedule at the last minute.
Based on data from 54 people who took the Breakroom Quiz between July 2025 and July 2026.

Do jobs at Progressive Insurance spill into time workers aren’t paid for?

Rarely. The job doesn't usually spill into unpaid time.
7% of people report that their job takes up time that they don’t get paid for.
Based on data from 84 people who took the Breakroom Quiz between May 2025 and May 2026.

How easy is it to take sick days at Progressive Insurance?

Most people find it easy to take sick days.
85% of people report that it’s easy to take time off if they are sick.
Based on data from 86 people who took the Breakroom Quiz between February 2026 and August 2026.

Is a Progressive Insurance job good for students?

Most students say this is a good place to work if you’re studying.
81% of students report this is a good place to work if you’re studying.
Based on data from 26 people who took the Breakroom Quiz between November 2024 and May 2026.

Is working at Progressive Insurance good if you’re a parent or caregiver?

Most parents and caregivers say this is a good place to work.
91% of people who care for a child or other relative report this is a good place to work.
Based on data from 132 people who took the Breakroom Quiz between August 2025 and August 2026.

Do people at Progressive Insurance feel treated with respect by their managers?

Most people feel treated with respect by their managers.
88% of people say they’re treated with respect by their managers.
Based on data from 84 people who took the Breakroom Quiz between February 2026 and August 2026.

Do people at Progressive Insurance get to take their breaks without interruption?

Most people get breaks without interruption.
91% of people report that they get to take their breaks without interruption.
Based on data from 85 people who took the Breakroom Quiz between February 2026 and July 2026.

Is it stressful to work at Progressive Insurance?

Most people feel stressed out here.
71% of people say they often feel stressed out at work.
Based on data from 84 people who took the Breakroom Quiz between February 2026 and August 2026.

Do people at Progressive Insurance enjoy their jobs?

Most people enjoy their job.
70% of people report they enjoy their job.
Based on data from 77 people who took the Breakroom Quiz between February 2026 and August 2026.

Do people at Progressive Insurance recommend working with their team?

Only some people recommend working with their team.
39% of people report that they wouldn’t recommend working with their immediate team to a friend.
Based on data from 89 people who took the Breakroom Quiz between February 2026 and August 2026.

Do people get enough training when they start at Progressive Insurance?

Most people got enough training when they started.
83% of people report they got enough training when they started working here.
Based on data from 87 people who took the Breakroom Quiz between February 2026 and August 2026.

Do people get support to advance at Progressive Insurance?

Most people are given support to advance their career here.
In the last year, 79% of people report being given support to advance their career here.
Based on data from 86 people who took the Breakroom Quiz between February 2026 and August 2026.

Do people think Progressive Insurance’s headquarters understands what’s happening where they work?

Some people think headquarters doesn’t understand what’s happening where they work.
51% of people think that this employer’s headquarters or owners don’t have a good understanding of what’s really happening where they work.
Based on data from 78 people who took the Breakroom Quiz between February 2026 and August 2026.

Do workers feel well informed about how Progressive Insurance is doing?

Most people feel well informed about how the company is doing.
87% of people feel that they are kept well informed about how the company is doing as a whole.
Based on data from 84 people who took the Breakroom Quiz between February 2026 and August 2026.

What other companies are hiring for Director Of Insurance Operations jobs?

What are the most popular jobs at Progressive Insurance?

Senior Corporate Attorney

Progressive Casualty Insurance Company

Remote

$168K - $184K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 16 days ago

Progressive Insurance rating

8.7

Company rating: 8.7 out of 10

Based on 596 frontline employees who took The Breakroom Quiz

70th of 308 rated insurance

Job description

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 asenior corporate attorney in Entity Management & Regulatory Reinsurance, within Progressive's Business Law Group, you'll serve as a trusted legal and strategic advisor on complex reinsurance, regulatory, and corporate matters. You'll support the business's reinsurance and subsidiary entity management functions, including licensing initiatives, legislative and statutory analysis, and cross-functional initiatives. By providing legal counsel, you'll advance organizational objectives while managing legal, regulatory, and operational risk.
This is a remote position with a preferred location in Cleveland, Ohio. The role requires quarterly travel to Progressive Corporate Headquarters in Cleveland as needed.
Must-have qualifications
  • Juris doctorate or Master of Laws (LLM) and a minimum of five years of post-degree legal practice experience
  • Active license to practice law in at least one state; Active or Corporate license in state where working (or eligible to be)

Preferred skills
  • Significant experience in entity management and corporate governance (formations, reorganizations, dissolutions, maintenance) within complex insurance organizations, including stock and mutual companies, and Lloyds organizations
  • Experience drafting and negotiating complex reinsurance contracts, including quota share agreements and catastrophe bonds
  • Extensive knowledge of insurance holding company regulations, including licensing, required filings, and financial examination
  • Ability to work collaboratively with internal and external partners, including legal team members, Financial Reporting, and Risk Management, as well as outside counsel and various regulators
  • Experience with legislative and statutory research, monitoring, and creating or revising correspondence compliance processes and procedures

Compensation
  • Base: $168,500 - $184,500/year
  • Gainshare annual cash incentive payment up to 40% of your eligible earnings based on company performance
  • Participation in our restricted stock units plan

Benefits
  • 401(k) with a 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 2025 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.
Equal Opportunity Employer
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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