Built for Those Who
Think Strategically.

Kieffer Insurance Group serves entrepreneurs, 1099 professionals, growing businesses, and families who want more than a quote — they want a strategy.

Freelancers, Consultants & Independent Contractors

1099 Professionals

When you work for yourself, you're responsible for your own health coverage — and the stakes are high. A gap in coverage, a poor plan selection, or a missed tax strategy can cost thousands. Kieffer Insurance Group designs comprehensive coverage strategies for 1099 professionals that protect your income, optimize your tax position, and give you access to the same quality of coverage as corporate employees.

Book a Strategy Session

Common Challenges

  • Paying full retail premiums without employer contribution
  • Coverage that lapses when income fluctuates
  • No guidance on how to make premiums tax-deductible
  • Overwhelmed by plan options with no strategic context

How KIG Helps

  • Coverage that travels with your contracts and clients
  • Premium tax deduction strategies for self-employed individuals
  • Private PPO and marketplace plan optimization
  • Annual strategy reviews as your income changes

Business Owners Building Something Significant

Entrepreneurs

You've built something worth protecting. Kieffer Insurance Group works with entrepreneurs who want health coverage that scales with their business — not just a plan that checks a box. We design benefit strategies that align with your revenue structure, your tax position, and your long-term financial goals.

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Common Challenges

  • Coverage that doesn't scale with business growth
  • Missed opportunities to use health benefits for tax efficiency
  • No strategic integration between health coverage and financial planning
  • Reactive decisions made during open enrollment without a plan

How KIG Helps

  • Revenue-aware benefit strategy design
  • SIMRP and advanced reimbursement arrangements
  • Coverage that adapts as your business grows
  • Strategic integration with your overall financial plan

Companies with 2–200 Employees

Small to Mid-Sized Businesses

Your team is your greatest asset. Kieffer Insurance Group designs group benefit strategies that help you attract and retain top talent, reduce your tax liability, and build a benefit package that reflects the quality of your company — without breaking your budget.

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Common Challenges

  • High group premium costs without strategic cost-sharing design
  • Benefits packages that don't differentiate you from competitors
  • No guidance on Section 125 or SIMRP tax advantages
  • Annual renewals handled reactively without market benchmarking

How KIG Helps

  • Group health benefit architecture and design
  • Employer contribution strategy and tax optimization
  • Employee benefit communication and education
  • Annual plan review and renewal strategy

Protecting What Matters Most

Families

Health coverage decisions affect every member of your family. Kieffer Insurance Group helps families navigate the complexity of marketplace plans, private options, and supplemental coverage — ensuring every family member is protected without overpaying for coverage you don't need.

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Common Challenges

  • Confusion about which plan tier is right for the family's health needs
  • Gaps in coverage for children's preventive and specialty care
  • Dental and vision coverage that doesn't integrate with medical
  • Coverage decisions made under time pressure without full information

How KIG Helps

  • Family plan optimization and cost analysis
  • Marketplace plan navigation and premium tax credit strategy
  • Coverage transition support (job change, retirement, divorce)
  • Dental, vision, and supplemental coverage integration

Who We May Not
Be the Right Fit For.

Kieffer Insurance Group operates at a concierge, strategic level. We are not the right fit for every client — and we believe in being honest about that. Our approach requires engagement, openness to education, and a commitment to long-term thinking.

Clients who want the cheapest plan regardless of coverage quality
Those who prefer a transactional, one-time interaction
Businesses unwilling to invest in strategic benefit planning
Individuals who are not open to education-based decision making

Ready to Work with
Kieffer Insurance Group?

Book a complimentary strategy session. We'll assess your current situation and show you what a strategic approach to health coverage looks like for your specific circumstances.

Book Your Strategy Session