A full-service agency helping you find the right coverage at the right price for

every policy you need.

 
Our experienced team does the hard work of comparing coverages so you don’t have to.

We’re looking forward to serving you!

 

Talk To Our Advisors

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Stephen Ross
CEO of Ross Insurance Brokers, Inc

Stephen Ross is originally from New Zealand, where he began his insurance career more than 25 years ago. For the past 15 years, he has served as a Dave Ramsey Trusted Provider, helping individuals, families, and business owners protect what matters most through sound insurance strategies

 

Stephen and his wife, Lois, now call Honolulu, Hawaii home. They have two adult children and enjoy the island lifestyle, including Hawaii’s beautiful beaches, outdoor adventures, and vibrant local community. They are actively involved in their church and are passionate about building meaningful relationships both personally and professionally.

 

Known for his genuine care for people, Stephen believes insurance is about more than policies—it’s about helping families create security, confidence, and peace of mind. Whether working with retirees, families, or business owners, his goal is to provide trusted guidance, exceptional service, and long-term relationships built on integrity and trust.

 

SCHEDULE AN APPOINTMENT

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Grace Ross

Life and Health Insurance Advisor – Small Group

 

Grace Ross believes that genuine care is the key to helping people succeed. She enjoys taking the time to understand each person’s situation, listening to their needs, and helping them find solutions that bring peace of mind and confidence for the future. Her goal is not only to build meaningful relationships with her clients but also to help them achieve lasting results that positively impact their lives.

 

With over seven years of customer service and insurance experience, Grace has developed a strong ability to communicate effectively and connect with people from all walks of life. She studied Intercultural Business Communications and Theology in college, which helped shape her passion for serving others and understanding diverse perspectives.

 

Grace especially enjoys working with business owners to build comprehensive employee benefits packages that help strengthen employee retention, engagement, and overall well-being. She looks forward to serving clients with genuine care and helping them navigate their insurance needs with confidence

 

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Caroline

Caroline Cauldwell

Life and Health Insurance Advisor

 

Caroline is passionate about helping clients find insurance solutions that provide clarity, confidence, and peace of mind. With six years of customer relations experience and eight years in various business roles, she has developed a strong ability to understand people’s needs and guide them toward the right coverage.

 

Raised in the close-knit community of Washington Island, Wisconsin, Caroline values trust, relationships, and exceptional service. She enjoys building meaningful connections with clients and helping them protect what matters most.

 

Outside of work, Caroline enjoys staying active, discovering great food, and exploring the beauty of the Rocky Mountains.

 

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ratho

Ratho Reis

Home and Auto Insurance Advisor

 

Ratho has spent his entire life in the Pacific Northwest, where he developed a strong appreciation for family, community, and serving others. As a devoted husband and father of five, he understands the importance of protecting what matters most and helping families build a secure future.

 

Having taught Financial Peace University multiple times, Ratho has seen firsthand the impact that sound financial planning and proper protection can have on a family’s life. After several years in the home and auto insurance industry, he is excited to continue serving clients with a focus on putting families first.

 

Outside of work, Ratho enjoys spending time with his family, exploring the outdoors, and creating lasting memories with his 5 children.

 

 

Meet Our Customer
Service Team

 


Life & Health

Our Life & Health Customer Service Team is here to support you with compassion and clarity. Whether you need help understanding your policy, updating coverage, or managing claims, they’re committed to making the process smooth and stress-free. Their goal? To ensure you feel confident and cared for, every step of the way.

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Shawn Sato

Senior Client Services Asisstant

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Charmaine Sato

Client Service Assistant

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Tracii Verdejo

Client Service Assistant


Home & Auto

Our Home & Auto Customer Service Team is here to help you feel secure  whether you’re protecting your house, your car, or both. From updating your coverage to guiding you through claims after unexpected events, they’re your reliable partners in staying protected on the road and at home.

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Margarita Simeros

Senior Client Services Assistant

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Anna Lhea Julian

Client Services Assistant


Client Communication

Our Client communication supports the agency’s connection with policy holders through clear, thoughtful messaging. From everyday updates to broader campaigns, the focus is on making information easy to understand, timely, and aligned with client needs.

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Jasmine Khokhar

Agent Coordinator


Executive Team

Our Executive Team brings experience, heart, and leadership to everything we do. They guide our mission with a focus on trust, innovation, and putting people first.

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Josh Ross

Chief Financial Officer

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Alexa Umali – Panagsagan

Head of Operations and HR. CPHR ®

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Sheryll Monzon

Operations Supervisor

Our Story

Guided by Faith.

Grounded in Family.

Committed to Financial Peace.

Aloha, and welcome to Ross Insurance Brokers.

 

I’m Stephen Ross, Founder and CEO of Ross Insurance Brokers. Our company was built on a simple belief: people deserve honest advice, genuine care, and insurance solutions that help protect what matters most.

 

My journey began in New Zealand, where I was born and raised. Later, I attended Bible college in Singapore with a focus on World Missions. While I originally believed my future would be in ministry, I discovered another calling—helping families build security and peace of mind through insurance.

 

In 1998, I entered the insurance industry and quickly realized that insurance is about much more than policies. It’s about people, relationships, and helping families navigate life’s most important decisions.

 

After moving to Portland, Oregon in 2002, my wife Lois and I attended Dave Ramsey’s Financial Peace University through our local church. The experience transformed the way I viewed both money and insurance. Seeing many families confused by their options, I set out to build an agency focused on education, transparency, and trusted guidance.

 

That vision led to the launch of Ross Insurance Brokers from our family garage in 2003.

 

Since then, we have had the privilege of serving more than 16,000 Ramsey families and helping clients across 24 states. What began as a small family business has grown into a trusted agency built on long-term relationships and a commitment to doing what’s right for our clients.

One of the greatest joys has been seeing our children join the mission. Our daughter Grace joined the company in 2021, followed by our son Joshua in 2022. Today, Ross Insurance Brokers is proudly family-owned and family-operated.

 

Our family now calls Honolulu, Hawaii home. With roots in New Zealand, Singapore, and the Pacific Northwest, we feel deeply connected to Hawaii’s values of aloha, ohana, faith, and community. Those values shape how we serve our clients every day.

 

Whether we’re helping someone navigate Medicare, protect a home, insure a business, or prepare for retirement, our goal remains the same: to provide trusted guidance, personalized solutions, and genuine care.

 

Insurance has never been just about policies for me. It’s about helping families protect what matters most and achieve greater financial peace.

 

Thank you for taking the time to learn about our story. We look forward to serving you and welcoming you into the Ross Insurance Brokers ohana.

 

With gratitude,

 

Stephen Ross
Founder & CEO

Stephen Ross - At a Glance

• Born and raised in New Zealand, with a heart for missions and service.

• Completed Bible college in Singapore with a focus on World Missions.

• Entered the insurance industry in 1998, discovering a passion for helping families protect what matters most.

• Moved to Portland, Oregon in 2002 and worked with New York Life.

• Took Dave Ramsey's Financial Peace University, which transformed his business philosophy.

• Founded Ross Insurance Brokers in 2003 from his garage-guided by Ramsey principles.

• Incorporated the business in 2007 and expanded product offerings with a growing team.

• Became a Dave Ramsey Health Endorsed Local Provider (ELP) in 2011-now serving clients in 24 states.

• Relocated to Denver, Colorado in 2018 and transitioned to a fully remote team model.

• Grace (2021) and Joshua (2022) joined the company-making it a family-run mission.

• Operates a remote team in the U.S. and the Philippines, focused on excellence and outreach.

• Company mission: Protecting families first-with personalized, honest insurance solutions.

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Our Core Values

At Ross Insurance Brokers, our culture is built on five key values that reflect both our faith and our approach to business:

• Fun - We celebrate life together.

• Innovative - We don't just react-we anticipate.

• Value - People before profit, always.

• Excellence - We charge ahead like rhinos-focused and resilient.

• Synergy - We know more together than we do alone.

 

These values guide how we care for our clients, lead our team, and make decisions every day.

 

We've now been in business for over 22 years, and even through the challenges of COVID-19, we've adapted and grown. Our remote-first model allows us to operate with excellence from locations across the U.S. and in the Philippines, where we're proud to also give back through job creation.

 

With my wife Lois, originally from Singapore, our heart for missions continues-both in how we serve families here and how we support causes abroad. At the end of the day, this business has always been about people, purpose, and peace of mind.

 

Whether you're shopping for health insurance, life protection, Medicare plans, or home and auto coverage, we're here to simplify the process and help you make wise decisions-just like we'd do for our own family.

 

We are grateful for your trust and look forward to walking this journey with you.