Navigation
Home About Process Reviews My Story Blog
Coverage
Personal Insurance Commercial Lines High-Value & Specialty Specialty & Niche Risks Get a Free Quote
Licensed P&C Broker · Oracle RMS · Ontario

Meet Chad Kless — Your Insurance Advocate

Hockey player. Marathon runner. Half Ironman-in-training. Chad brings the same relentless drive and endurance from sport to every client he serves across Ontario.

Chad Kless — P&C Insurance Broker, Oracle RMS Ontario
Chad Kless
P&C Insurance Broker · RIBO Licensed
Oracle Insurance Risk Management Services Inc.

From the Ice to the Open Road — and Everything In Between

Growing up in Ontario, sports were everything — and hockey was at the centre of it all. Whether it was early morning practices, intense playoff games, or pushing through adversity on the ice, those years shaped who I am. They taught me discipline, resilience, and above all, how to compete relentlessly on behalf of my team.

That competitive edge is exactly what I bring to insurance every single day. When I sit across from a client — whether it's a family protecting their home or a business owner managing complex commercial risks — I approach it the same way I approached every game: with full commitment to winning the best outcome for the people counting on me.

"In hockey, you don't settle for second best. I take that same mentality into every client conversation — I'm not done until I've found the right coverage at the right price."

But the athletic drive didn't stop at the rink. In recent years I've taken on a new challenge — long-distance running and triathlon. I've completed multiple marathons and am currently training for my first Half Ironman — a 1.9km swim, 90km bike, and a 21.1km run, back to back. It's the ultimate test of preparation, endurance, and mental toughness.

The parallel to insurance isn't lost on me. A Half Ironman isn't won on race day — it's won in the months of early mornings, careful planning, and refusal to quit when things get uncomfortable. That's exactly how I approach every client file. The preparation happens long before a claim does, and when it matters most, you want someone in your corner who doesn't stop until the job is done.

Over the past 5+ years in the insurance industry, I've developed deep expertise across personal lines, commercial insurance, and high-value specialty risks. I've had the privilege of working with homeowners, entrepreneurs, and high-net-worth individuals across Ontario — helping them navigate the complexities of insurance with clarity and confidence.

Today, I'm proud to be part of Oracle RMS, one of Canada's largest and most respected independent brokerages. When I'm not at my desk or on the phone for clients, you'll find me on the ice, logging kilometres on the road, or in the pool — preparing for the finish line.

Compete. Endure. Deliver.

Hockey, marathons, and Half Ironman training aren't hobbies — they're a mindset. Here's what a life of athletic competition brings to every client relationship:

Ontario General Insurance Hockey Tournament Champion
Marathon Runner · Half Ironman Athlete-in-Training
  • Competitive drive to find the best rate across every market
  • Ironman-level preparation — every policy detail reviewed, nothing left to chance
  • Marathon endurance — I stay with you through every step of the claims process
  • Team player — working with insurers, lawyers, and adjusters on your behalf
  • A winner's mindset — I'm only satisfied when you're fully protected
How I Work

Commitments to Every Client

These aren't just words — they're the principles I hold myself to on every file, every renewal, and every claim.

01

Transparency First

No jargon, no fine print surprises. I explain your coverage in plain language so you always know exactly what you're paying for and why.

02

Market-Wide Shopping

I'm not tied to any single insurer. I shop Intact, Aviva, Chubb, Unica, and more to find the policy that genuinely fits your life or business.

03

Responsive & Reliable

Insurance questions don't wait. I pride myself on being reachable, responsive, and ready — whether it's a quick question or a major claim.

04

Long-Term Relationships

My goal isn't a one-time transaction. I aim to be your broker for life — reviewing your coverage annually as your needs evolve.

Oracle RMS
Insurance Brokers · Ontario
60,000+
Clients Served
40+
Locations
300+
Professionals
2011
Founded
Visit Oracle RMS →

Backed by One of Canada's Best

I'm proud to be part of Oracle Insurance Risk Management Services Inc. — an award-winning, independent brokerage headquartered in Concord, Ontario, serving clients across the entire province.

Founded in 2011 and grown to over 40 locations, Oracle RMS was built on a simple belief: every client deserves a tailored insurance solution, not a generic policy. That philosophy aligns perfectly with how I work.

Being part of Oracle RMS means you get the best of both worlds — the personal attention of working directly with me, combined with the market access, resources, and backing of one of Ontario's largest independent brokerages.

📍 Head Office: 100 Drumlin Circle, Concord, ON L4K 3E5

Ready to Work with Chad?

Whether you need personal, commercial, or specialty coverage — I'm here to fight for the best protection at the best price. Let's talk.