Harrison Santiago is a Private Client Specialist with UWIB Risk & Insurance Solutions, focused on delivering clear, practical guidance in personal lines insurance. He works closely with clients to simplify complex coverage decisions and ensure they are properly protected, taking a client-first approach rooted in transparency and efficiency. Harrison began his career in client-facing roles where he developed a strong foundation in communication, problem-solving, and relationship management. Known for his ability to connect with clients and translate technical details into real-world understanding, he emphasizes clarity, responsiveness, and trust in every interaction. He takes pride in helping clients feel confident in their coverage decisions, especially in situations where thoughtful guidance can make a meaningful difference in both protection and long-term value. Outside of work, Harrison has a deep interest in music composition, personal style inspired by Italian sprezzatura, and horology. He also enjoys traveling and experiencing different cultures, which continues to shape his perspective both personally and professionally.
- Published on: July 14, 2026Education
Reality Hit, and I Was Caught Totally Off Guard
"That's not something you'd expect to hear from me. I'm usually one of those guys who's got it all together. I've thought everything through, planned for every possibility, crossed all my T's and dotted all my i's. But I never thought this would really happen to me. Reality hit, and I was caught totally off guard."Read More - Published on: July 10, 2026Education
Navigating Cyber Underwriting Questionnaires: A Guide to Success
In today's digital age, businesses face a multitude of cyber threats, making cybersecurity an essential concern. As such, cyber insurance has become a critical tool to help businesses guard against these risks...Read More - Published on: June 26, 2026Education
What We're Seeing in Small and Mid-Sized Businesses in 2026
After nearly five decades in business, and after working with family-owned companies, entrepreneurs, and organizations of every size, I've learned that every year brings a new set of challenges. Some years it's the economy. Some years it's technology. And some years it's simply uncertainty.Read More - Published on: June 26, 2026Education
Putting Our Strongest People in Positions to Win
Over the years, I've come to appreciate that one of the hardest parts of leadership is recognizing that not everyone contributes at the same level. I wish that weren't true, but experience has taught me otherwise. Some people consistently solve problems, take ownership, and move the organization forward. Others struggle, sometimes because they need coaching, and sometimes because they're simply in the wrong role. I've learned that pretending everyone performs equally isn't kindness. It usually creates frustration for the people carrying the heaviest load.Read More - Published on: June 23, 2026Education
What Happens When Technology Serves People Instead of the Other Way Around?
For much of my career, technology has promised to make work easier. Sometimes it has. Sometimes it has simply moved the work around. But over the past couple of years, we’ve been approaching artificial intelligence differently. Read More - Published on: June 17, 2026Education
Why Good Leaders Must Eventually Become Less Important
There’s a hard truth about business ownership that I’ve been working through personally over the past few years. If my company cannot grow without me being directly involved in most decisions, client relationships, and day-to-day execution, then I don’t really have a scalable organization. I’ve simply created a job. It may not even be a particularly good-paying one. It’s just a job that still depends on me for it to function. I know this because I’ve lived it. Read More - Published on: April 11, 2026Education
Cyber Incident Tabletop Exercise: A Comprehensive Outline
In today's digital landscape, organizations face an increasing number of cyber threats. Cyber incidents, ranging from data breaches to ransomware attacks, can disrupt operations, damage reputations, and lead to significant financial losses...Read More - Published on: March 31, 2026Education
Why Gig-Economy Businesses Still Need Workers’ Compensation Insurance (Even If You Only Hire Helpers “As Needed”)
If you run a small business that looks more like the gig economy than a traditional company, you’re probably thinking the same thing a lot of owners do: “I don’t have full-time W-2 employees, so why do I need workers’ comp?”Read More