Robert Mulcare, RSSA, REBC, FPQP
VP, Client Development
Highstreet Insurance & Financial Services
320 SW Ct Ave
Pendleton, OR 97801, US
Affiliations
Professional Details
Hey there, my name is Robert. I am a licensed insurance advisor with Highstreet Insurance & Financial Services, specializing in Medicare and retirement income planning. Licensed in 27 states, I work with clients nationwide, meeting in person when possible and utilizing secure technology to serve clients virtually—ensuring access to knowledgeable guidance regardless of location.
I entered the insurance industry in 2018 following five years in nonprofits and public policy, bringing a strong foundation in advocacy, systems navigation, and client-centered service. I began my career with a small, local agency in Southern Oregon, focusing on individual health insurance and Medicare, and have since expanded my practice to include Social Security planning, retirement income strategies, life insurance, disability coverage, and long-term financial protection. My work is grounded in a singular priority: protecting clients’ most valuable asset—their ability to live with security, dignity, and independence.
I am actively engaged in industry leadership and policy advocacy. Since 2020, I have served on the Northwest Medicare Summit Committee and currently serve on the Board of Directors for the Oregon Chapter of the National Association of Benefits and Insurance Professionals (NABIP). I completed my second term as President of NABIP-Oregon in January 2026 and continue to contribute at the national level through NABIP’s Legislative Groups, including the Individual Market and Single Payer Working Groups.
Community service has been a defining part of my professional life. I previously served on the board of Friends of the Children – Klamath Basin, an organization dedicated to breaking cycles of generational poverty through long-term professional mentorship. In 2025, I was asked to help launch Friends of the Children – Eastern Oregon, where I currently serve as Board Chair. In addition, I served the City of Klamath Falls as a Reserve Police Officer from 2015 through 2023, advancing to the rank of Reserve Lieutenant.
I am committed to using my experience, leadership, and expertise to help individuals, families, and communities plan with confidence and see possible.
Areas of Expertise
- Insurance Agent
- Medicare Advisor
- Retirement Specialist
Real Stories from Real People
Most People Leave Money on the Table
96% Don't Optimize
Very few people get all the Social Security they’re entitled to.
$111,000 Average Lost
The average household is losing $111,000 in potential income.
1 Chance To Claim
Social Security gives you one chance to get it right – forever.
Maximize Your Benefits
Discover important information for your situation.
Married
If you are married, you may be able to collect up to one-half of your spouse’s Social Security benefit. This won’t affect your spouse’s checks. Ask an RSSA® for details.
Divorced
If you are divorced and 62 or older, you may qualify to receive Social Security benefits from your ex-spouse — in addition to your own Social Security payments. Ask an RSSA® for details.
Widowed
If your spouse has passed away, you may be eligible for a survivor benefit. The extra money may be essential for you. Ask an RSSA® for details.
Single
If you are single, and solely responsible for your retirement, making the optimal Social Security claiming decision is particularly important. Ask an RSSA® about your options.
Self-Employed
As a self-employed person, you may be able to decrease your payroll taxes — yet still receive the maximum income from Social Security. Ask an RSSA® for details.
Disability
Social Security can provide valuable disability benefits if you qualify, but these benefits — and how you qualify for them — are often misunderstood. Ask an RSSA® for details.
Immigrant
If you are a lawful permanent resident, but not yet a citizen, you may still qualify for Social Security benefits. Ask an RSSA® for details.


