The team at Waldman Accounting is excited to announce an expansion to our services. We are now licensed to help individuals, families, self-employed professionals, and businesses navigate health and life insurance options. This milestone represents our ongoing commitment to providing holistic guidance that goes beyond traditional bookkeeping, accounting and tax services.
For individuals and self-employed folks, we now offer enhanced guidance for necessary insurance coverage that seamlessly integrates with your tax strategy. No more juggling multiple advisors or dealing with potential cost-saving oversights.
For businesses, we can design, implement, and manage complete employee benefits packages—including group health insurance, SHOP Marketplace plans, ICHRA, QSEHRA, and ancillary benefits—all with tax optimization built into every recommendation.
“There is a major gap in how most insurance agents understand the tax implications tied to insurance decisions for self-employed individuals and small businesses. Many agents overlook the complex tax laws and strategies that can significantly impact their clients, especially when it comes to maximizing benefits and savings. With my tax background, I saw an opportunity to bridge that gap and provide more informed, strategic guidance. As a new father, I also have a personal appreciation for the peace of mind that life insurance provides, knowing my family is financially protected no matter what happens.” – Diego Prieto, Accountant, Waldman Accounting
Why a tax-focused benefits approach delivers better results
Integrated tax and benefits planning
Health insurance decisions create ripple effects throughout your tax situation—from Marketplace subsidies and S Corp shareholder rules to HSA eligibility and payroll withholding strategies. We align your benefits choices with your business entity type and overall tax plan, ensuring you keep more of what you earn.
Avoid costly ACA compliance mistakes
We’ve witnessed clients receive inadequate guidance during Marketplace enrollment —particularly around income estimates— only to face unexpected tax bills when advance premium tax credits are reconciled at filing time. Our proactive approach includes accurate income estimation, timely Marketplace updates when circumstances change, and strategic planning to minimize year-end subsidy repayments.
“We will help bridge the gap between what’s reported on the tax return and what’s reported for healthcare, so clients don’t fall into the common pitfalls we see at tax time—such as unexpectedly having to repay money to the government.” – Ian Waldman, Founder, Waldman Accounting
Comprehensive company benefits we manage
Traditional group health insurance (including SHOP)
- Group medical, dental, and vision plans designed for small teams
- Complete SHOP Marketplace eligibility assessment and enrollment support
- Detailed payroll and contribution modeling (employer percentage vs. employee cost sharing) to align with your budget
Individual Coverage Health Reimbursement Arrangement (ICHRA)
- Employer-funded monthly allowance system where employees purchase individual coverage that meets their specific needs
- Flexible employee classifications (full-time, part-time, salary vs. hourly) with customized contribution structures
- Ideal solution for distributed teams or businesses with variable scheduling requirements
Qualified Small Employer Health Reimbursement Arrangement (QSEHRA)
- Simplified, budget-friendly allowance system for medical premiums and qualified expenses
- Designed for employers with fewer than 50 full-time equivalent employees who don’t offer traditional group health coverage
- Perfect when headcount is small and group plan pricing is budget-prohibitive
Voluntary benefits
- Comprehensive life insurance options (both individual and group coverage)
- Disability insurance, supplemental dental/vision, critical illness coverage
- Modern perks, including telemedicine access, Employee Assistance Programs (EAPs), and wellness benefits
- Strategic benefit packaging to maximize perceived employee value while maintaining cost control
Our tax-smart benefits implementation process
Marketplace accuracy and compliance
We ensure precise household Modified Adjusted Gross Income (MAGI) estimation, coordinate with your existing bookkeeping and payroll systems, and implement rapid updates for life changes to prevent subsidy clawbacks during tax season.
Self-employed health insurance deduction optimization
We conduct eligibility evaluations for the self-employed health insurance deduction (including Form 8962 considerations), coordinate strategically with premium tax credits, and optimize cash flow planning.
S Corporation shareholder compliance
For S Corp owners, we establish proper W-2 reporting protocols so 2% shareholders can potentially claim the Section 162(l) deduction correctly while maintaining IRS compliance.
Strategic HSA planning
When HSA-eligible, high-deductible health plans align with your situation, we model contribution strategies versus premium costs to optimize both current tax savings and long-term wealth accumulation.
Tax credit maximization
For qualifying small businesses, we assess eligibility for the Small Business Health Care Tax Credit through SHOP Marketplace participation and handle all necessary documentation.
Specialized services for every business
Self-employed individuals: confident coverage decisions
- Easy-to-understand plan comparisons analyzing premiums, provider networks, prescription drug coverage, deductibles, and out-of-pocket maximums
- Expert guidance on qualifying life events (marriage, childbirth, relocation, income changes), including proper reporting timelines and procedures
- Life insurance integration with your broader financial planning and wealth-building strategy
Business owners: compliant, strategic benefits selection
Discovery and budget planning
We conduct in-depth analysis of your workforce composition, compensation philosophy, and financial objectives to establish realistic total benefit costs that protect your profit margins.
Custom benefits design
We provide detailed comparisons of group health insurance, ICHRA, and QSEHRA options with multiple contribution scenarios, plus strategic layering of ancillary benefits that resonate with your team (dental/vision coverage, EAP services, telemedicine access).
Seamless enrollment management
Clear, professional employee communications with defined deadlines and comprehensive support throughout the process. We manage all aspects of Marketplace, SHOP, or insurance carrier onboarding, plus establish efficient new hire enrollment workflows.
Payroll integration and reporting
We configure contribution structures, ensure compliance with owner-specific tax rules, and coordinate directly with your accounting team (that’s us!) for seamless year-end tax preparation.
Ongoing Administrative Support
Life changes are inevitable. We help employees update coverage correctly and maintain vigilant oversight of compliance deadlines and renewal requirements.
Why employee benefits matter more than ever
Offering employer-sponsored health insurance and benefits isn’t just a nice-to-have — it’s essential for competing in today’s talent market. Employees prioritize comprehensive health coverage when selecting an employer. A well-designed benefits package can help employers attract and retain top talent without dramatically increasing payroll expenses.
Businesses that offer health insurance benefits see significantly higher employee retention rates and can attract quality candidates who might otherwise choose larger competitors.
Schedule a free benefits consultation
Whether you’re purchasing your first business health insurance policy, approaching renewal season, or building a comprehensive benefits package from the ground up, we’re here to simplify the process and eliminate costly surprises.
In your complimentary 20-minute consultation, we’ll:
- Review your specific goals, budget parameters, and current headcount
- Map the optimal path forward (group insurance vs. ICHRA vs. QSEHRA)
- Identify available tax credits and deductions you could be missing
- Outline next steps for implementation and ongoing management
Contact us today to schedule your free benefits consultation: info@waldmanaccounting.com
This post is for general education and marketing purposes and isn’t tax, legal, or insurance advice. Eligibility and amounts depend on your specific facts and current law. Always consult with a licensed professional.