The Skyscraper BLOG

February Wrap-Up: Are You Positioned for Q2?

As the final days of February 2026 wind down, many business owners are finally catching their breath after the “New...

Harry Baker/

February 27, 2026

Careers / Life at Skyscrapers, Claims, Insurance-technology, News

Why Q1 Sets the Tone for the Entire Year

The first quarter isn’t just the start of the calendar year — it’s where risk decisions quietly shape outcomes for...

Harry Baker/

January 30, 2026

Grocery / Supermarkets, Hiring, Multifamily Insurance, News, Technology

Closing the Year Protected

As the year comes to a close, it’s a moment to pause, reflect, and take stock of what has been...

Harry Baker/

January 26, 2026

Hiring, Technology, Trucking, Workers' Comp

Experience Mods: Why December Still Has a Major Impact

Many employers assume their Workers Compensation experience modifier is already “locked in” by December. In reality, late-year activity can still...

Harry Baker/

December 22, 2025

Insurance-technology, Staffing agencies

Thanksgiving Message: A Season of Gratitude and Care

Thanksgiving is a time to pause, reflect, and appreciate the people and communities that make our work meaningful. In business,...

Harry Baker/

December 9, 2025

Careers, Public Entities, Technology, Trucking

Gratitude in Business: Why People Come Before Profit

Successful businesses are not built on numbers alone. They are built on people. When leadership prioritizes gratitude, respect, and genuine...

Harry Baker/

December 5, 2025

Insurance-technology

Veteran-Owned Businesses: Specialized Insurance Programs and Credits

Veteran-owned businesses play a vital role in the economy, bringing leadership, discipline, and operational excellence into the private sector. Many...

Harry Baker/

November 17, 2025

Cannabis Insurance, Claims, Construction, Disability-PFL, Grocery / Supermarkets, Healthcare, Insurance-technology, Staffing agencies, Technology, Trucking

Building Trust with Bonds: Strengthening the Foundation for Contractors

In the world of construction, trust is built before the first brick is laid — and at Skyscraper Insurance, we...

Harry Baker/

October 13, 2025

Insurance-technology, Technology

Complex Claims & AI Future: How Technology Is Transforming Claims Management

In today’s insurance landscape, claims have become more than a routine process—they are complex, data-heavy, and time-sensitive events that shape...

Harry Baker/

September 5, 2025

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