History
Eras
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Singing my Song
100

What was Progressive's innovative business philosophy for approaching auto insurance?


What is approaching auto insurance in an innovative way, unlike any other company?  

100

During the Manufacturer/Wholesale Era in the 1980s-1990s, Progressive focused on establishing its product portfolio. What was the key need for growth during this era?

What is growing with more preferred customers to expand the total addressable market?

100

Tricia Griffith was appointed CEO of Progressive in July 2016. What role did she hold immediately prior to becoming CEO?

What is Personal Lines Chief Operating Officer?

100

Since 2013, Progressive’s Keys to Progress® program has donated vehicles to veterans facing tough circumstances. How many veterans and veteran organizations have been helped by this program so far?

What is more than 1,000?

100

This person's favorite song suggests they are a thoughtful, grounded, and optimistic person who prioritizes gratitude and connection in their life.

Who is Tara?

200

Progressive introduced the industry's first drive-in claims location in its founding year. What year was this groundbreaking service launched?

What is 1937?

200

In the Retail Era of the 1990s-2000s, Progressive shifted its focus toward building its consumer brand. What California proposition influenced this era?

What is Proposition 103?

200

Karen Bailo, Progressive's Commercial Lines Group President, began her career at Progressive in 1990. What was her first role at the company?

What is Customer Service as a Management Trainee?

200

In 2023, Progressive entered into a companywide relationship with which nonprofit organization to help address family homelessness?

What is Family Promise?

200

This person's choice of song suggests they’re a passionate, energetic, and community-driven individual who finds joy in the shared excitement of sports and music.

Who is Tracy

300

In 1956, Progressive Casualty Insurance Company was founded to specialize in what type of insurance?

What is nonstandard insurance?

300

In the Destination Insurer Era of the 2000s-2010s, Progressive aimed to grow market share in a specific bundled segment. What is the name of this segment?

What is "Robinsons" (auto and home bundled segment)?

300

John Murphy, Progressive’s Claims President, joined the company in 1992. What degree did he earn, and from which university?

What is a bachelor's degree in psychology from the State University of New York at Albany?

300

Progressive employees present lessons to students through an internally developed curriculum. What is this curriculum called?

What are Crash Courses?

300

This person's favorite song suggests that they prioritize love, gratitude, and meaningful connections in their life. They might hold onto the belief that certain people or moments are irreplaceable and one-of-a-kind. They are likely someone who values authenticity, emotional depth, and the beauty of human relationships.

 

Who is Derrick

400

In 2004, Progressive piloted a usage-based insurance program to research driving habits. What was this program called?

What is TripSense®?

400

In the Destination Company Era beginning in 2020, Progressive explored new products to increase its addressable market. What global event created extreme volatility in loss costs and the work environment during this time?

What is the COVID-19 pandemic?

400

Mari Pumarejo was named Chief Marketing Officer in June 2025. Before joining Progressive, she collaborated with several major brands. Name two brands she worked with prior to Progressive.

What are Glidden and Ralph Lauren Paints?

400

In 2020, Progressive officially partnered with which organization to donate computer equipment and electronics to underserved communities?

What is PCs for People?

400

This person's favorite song suggests they are a thoughtful, empathetic, and spiritually attuned person who values depth, beauty, and connection in all its forms. 

Who is Kaliyah

500

In 2008, Progressive debuted a new brand icon, Flo, in the "Superstore" campaign. What phrase from Flo became a pop-culture phenomenon?

What is "Wow! I say it louder."?

500

During the Destination Insurer Era, Progressive identified a lack of three specific types of insurance products. What were they?

What are Home, Condo, and Renters insurance?

500

Andrew Quigg, Progressive’s Chief Strategy Officer, joined the company in 2007. What was his first role at Progressive?

What is Agency Auto Product Manager?

500

Progressive’s IT Educational Partnership Program (PEPP) offers high school students internship opportunities in which two areas?

What are Cleveland, OH, and Colorado Springs, CO?

500

This choice of song suggests they are a thoughtful, faith-driven, and emotionally grounded individual who prioritizes gratitude, hope, and connection in their life.

Who is Tiffany

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