Bob Crossland

"The Benefits Guy"

Chartered Benefit Consultant (CBC)

Life Underwriters Training Council Fellow (LUTCF)


"I help small companies - and individuals - have big company benefits"
Serving the Washington, DC metro area's insurance and benefits needs since 1991

Products Offered for Companies and Individuals

  • Employer-provided health insurance, including the Small Business Exchange (SHOP)
  • Health insurance for families and individuals - both On Exchange and Off Exchange
  • Life Insurance
  • Business Life Insurance
  • Dental Insurance
  • Short and Long Term Disability Insurance
  • Long Term Care Insurance
  • Health Reimbursement Accounts (HRAs)
  • Health Savings Accounts (HSAs)
  • Supplemental Benefits
  • Medicare Solutions

What people are saying...

Katie Harvey
New Business Coordinator at Capital Group Benefits
"Bob is phenomenal to say the least! He has such a big heart and will spend countless hours with clients to ensure they understand what their needs are. He's a great friend and I am so glad to know him personally and professionally! I always refer Bob when I can."
John T. Wilkins
Assistant Vice President, Main Street Bank
"I have had the pleasure of knowing Bob for about a year and half. While he has always been a great resource for my personal benefits questions, he's also been fantastic with the people I have advised to work with him. When Bob provided some quotes to the president of an organization I belong to, not only did he wow her with his knowledge, he wowed me with the thousands of dollars we were able to save over the year. I would not hesitate in the future to recommend Bob's services to my clients, friends, and family. It's so refreshing to work with someone that cares about his profession and his customers as much as Bob does."
Juli Lieberman Clifford
Real Estate Consultant at Keller Williams Tyson's/Vienna
"I recently worked with Bob to find affordable health/medical insurance. Bob was able to provide me with estimates from several companies so that I could compare rates and plans. He was able to answer a number of questions I had about coverage, etc. To me, health insurance is a maze of confusing information, Bob was able to sort the information for me and we came up with a policy that both meets my needs and budget. Top Qualities: Great Results, Expert, High Integrity."
Paulina Stowell
Long and Foster, Realtors
"Artie and I wanted to thank you again for helping us with our health insurance needs. You took the time to meet with us in person to find out what we were looking for in our new health insurance plan. You thoroughly explained the differences between different providers and process we highly recommend you to our friends and co-workers. Thanks Bob!"
Chau Tran
CEO, APS Pest Services, LLC
"In the practice of health and life insurance, Bob is to be commended for his commitment to excellence. He is more than just focused, but also diligent and quite resourceful in his profession. His personality alongside his tenacity gives him an edge in all endeavors. Without hesitation, I recommend Bob Crossland."
Phil Canada
President, Lansdowne Real Estate Company
"Bob Crossland demonstrates a thorough knowledge of the intricacies of health insurance for individuals and businesses and he was able to shop and compare plans to provide a quality solution that was optimal for our budget. I am a self employed small-businessman and Bob’s professionalism and responsiveness to the health insurance needs of my wife and I are greatly appreciated."
Bob Crossland

About Bob

Bob Crossland has lived and worked in Northern Virginia since 1980. For more than 20 years, he’s specialized in selling insurance and financial products. His resume includes working for major insurance companies and agencies, running his own property & casualty agency, and working for a well-known Wall Street brokerage firm. Now totally independent, he founded Crossland Insurance to provide benefit solutions – health, life, disability, dental and long term care insurance – to companies and individuals & families, placing an emphasis on containing costs while enhancing value. Bob has also been certified for several years by AHIP (America’s Health Insurance Plans, our trade association) to market Medicare supplemental products, Medicare Advantage, and Part D Plans to the senior markets and is often asked to speak publicly about Medicare and the Affordable Care Act. He often partners with other local insurance agencies and financial advisors as a resource to provide expertise, advice and solutions for benefit needs. With a reputation as a problem solver, Bob states, “I help small companies - and individuals - have big company benefits.”


Bob Crossland, CBC, LUTCF
3360 Post Office Rd #6231
Woodbridge, VA 22195
Phone: (703) 283-7240
Fax: (703) 791-4546