For insurance executives, where you base your career significantly impacts your future course. Many find themselves in a toss-up between Los Angeles and Chicago. Both cities offer distinct advantages based on their unique insurance landscapes, with LA’s fast-evolving, tech-driven market versus the legacy-rich environment in Chicago. But which is better? 

As we discuss what sets these major insurance hubs apart, it’s essential to simultaneously assess your career goals, the market trends in each city and which landscape best aligns with the skills and expertise you bring to the table. 

Los Angeles: The land of tech-driven innovation 

Los Angeles is a crucial part of the US’ rapidly expanding insurtech market, which is projected to reach $66.66 bn by 2029. LA has seen a growing focus on digitization, particularly in niche markets like cyber, real estate or, thanks to Hollywood, entertainment insurance. This makes LA the go-to city for specialists in these fields.  

For executives looking to push boundaries, LA offers a forward-thinking environment with opportunities to lead groundbreaking projects. Leading insurance companies in the city are investing heavily in cutting-edge technologies like artificial intelligence (AI) and blockchain to streamline processes, offer personalized insurance products and automate claims management.

More good news – California is the leading state in insurtech, accounting for 28.3% of the US’ total insurtech deals. LA is a vital cog in this machine, making it a safe bet for executives eager to lead in this fast-evolving sector.

Chicago: Legacy-driven, but steadily resilient

In contrast, Chicago’s insurance industry is deeply rooted in traditional sectors like life insurance, reinsurance, property and casualty insurance. Home to large, established players such as Aon and Arthur J. Gallagher, Chicago has built its reputation as a stable and reliable insurance market.

The Windy City’s strength lies in its legacy-driven institutions, which offer executives the chance to oversee substantial portfolios in long-standing insurance sectors. Chicago’s financial landscape is marked by an emphasis on managing large-scale risks, which requires deep expertise in risk management, underwriting and compliance.

While not as aggressively innovative as LA, Chicago is certainly not lagging behind when it comes to technological adoption. The city’s insurance firms are beginning to embrace automation, data-driven insights and even AI solutions, particularly in areas like claims processing and customer relationship management.

However, the pace of adoption is slower than in LA, making it a city better suited for executives seeking to modernize existing frameworks rather than create entirely new ones.

Working as an insurance executive in LA vs. Chicago: What you need to know

First things first – compensation. Both cities offer similar salaries for insurance executives. LA comes out on top, averaging $142,194 while Chicago averages $133,897. But there are a few more things to consider:

• LA’s insurance sector is heavily influenced by insurtech and niche markets, creating a strong demand for forward-thinking executives who are tech-savvy. Its diverse workforce is also welcoming to those who have had unconventional career paths

• Chicago’s talent is more aligned with legacy sectors. Executives from non-traditional backgrounds may face hurdles due to a preference for candidates with experience in established companies

It’s also important to consider the competitiveness of each city’s talent landscape:

• LA attracts executive talent from diverse industries and backgrounds, leading to intense competition for executive roles. That being said, the vibrant startup scene and host of industry events means there’s no shortage of networking opportunities

• Chicago’s insurance market benefits from long-standing relationships, making it easier for local talent to find opportunities, but harder for newcomers. The growing trend of M&As in the city does create opportunities as firms look for experienced leaders

Insurtech is another critical factor that could tip the scales depending on your priorities as an executive.

• LA’s vibrant and tech-driven market is perfect for executives looking to spearhead projects that embrace digital transformation

• Chicago, while slower to adopt insurtech at scale, offers a different kind of challenge: integrating these technologies into established sectors while honoring a legacy that’s built on stability and reliability

Finally, a few words on the quality of life each city has in store for insurance executives:

• Cultural scene: While LA has a vibrant entertainment industry, Chicago is hailed for its rich history and diverse cultural offerings, including museums and theaters

• Cost of living: Housing in Chicago is more affordable than in LA, allowing for more financial stability and freedom

• Work flexibility: Many tech-driven LA companies emphasize flexible working arrangements, while Chicago’s traditional corporate culture often means less flexibility

The verdict: Which city should you choose?

The decision comes down to your career aspirations and where you see yourself making the biggest impact.

LA’s dynamic, tech-focused landscape is ideal if you want to be at the forefront of innovation. On the other hand, if you prefer a stable environment where you can modernize long-established processes and oversee substantial portfolios, Chicago is likely a better fit.

Both cities have their strengths, but understanding your own leadership style, expertise and where you can create the most value will be key in making the right choice.

For all their bonuses and drawbacks, both cities are magnets for new waves of executive talent. If you’re an insurance firm in LA or Chicago, and you want to capitalize on this talent, Hanover can help you find, attract and secure it.

Contact us today to find out how we can support your talent needs.