Caldwell Insurance Services provides…
Simple guidance. Powerful coverage. Personal support.

Employee Benefits Programs

Helping you attract and retain top talent — while protecting your bottom line.

We specialize in building flexible, affordable employee benefits packages for small to mid-size businesses. Whether you’re looking for medical, dental, vision, 401(k), or voluntary benefits, we tailor a strategy that fits your business — and your budget.

✅ Plans that scale with your team
✅ Streamlined onboarding and renewals
✅ Full broker support year-round
✅ Competitive pricing from trusted carriers

We focus on what matters: retaining your workforce, staying compliant, and keeping costs under control — without sacrificing care.

Individual and Family Coverage

We offer a wide range of individual and family plans through top carriers:

  • Anthem Blue Cross

  • Blue Shield of California

  • Covered California

  • Kaiser Permanente

  • Health Net

  • And more…

We’ll help you compare plans, understand your network, and enroll confidently.

✅ Premium assistance guidance
✅ Direct enrollment or Covered CA help
✅ Plan reviews and renewals

Medicare Plans

Navigating Medicare doesn't have to be confusing. We guide you through:

Original Medicare (Parts A & B)

Part D prescription plans

Medicare Advantage (Part C)

Medicare Supplement (Medigap) plans

Whether you're turning 65 or helping a loved one through the transition, we’ll walk you through every step — and be here year after year for reviews and plan changes.

✅ No cost for our services
✅ Personalized advice, not call center scripts
✅ Access to major Medicare-approved carriers

401(k) Plan Setup & Support

We help small businesses offer retirement benefits that attract and retain top talent — without the confusion or high costs.

From choosing the right provider to ensuring compliance and ease of administration, we guide employers through the setup and management of 401(k) plans that work for both the company and its employees.

✅ Personalized guidance through setup and onboarding
✅ Access to trusted 401(k) plan administrators
✅ Flexible contribution options for both employer and employee
✅ Ongoing support to keep your plan compliant and competitive

Offering a retirement plan isn’t just a perk — it’s a smart investment in your team’s future. We’ll help you get it right, every step of the way.