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Howard Simon

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Tax Preparation Services

Riverwoods, IL

Additional Information

HowardSimon Retirement is a retirement consulting firm based in Chicago providing retirement planning expertise and tech-forward service since 1981. The firm specializes in designing and administering retirement plans for employers and individuals, with a team of nearly 50 experts including Retirement Consultants, Administrators, and Recordkeepers.

Specializes in

Retirement plan designSmall business retirement solutionsProfessional retirement plans (dentists, attorneys, physicians)Employee benefit strategyDOL and IRS compliance

Services

401(k) plan designCash Balance Plan designRetirement plan administrationPlan recordkeepingACP/ADP testing5500 filingFiduciary oversightTax planningCompliance consulting

Established 1981 · Team of almost 50 experts · Serving Chicago

Additional information extracted from the firm's public website. Last updated: August 8, 2026

Contact Information

Phone: 8479450340

Website: www.hsimon.com

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Frequently Asked Questions

How much does a bookkeeper cost in Riverwoods?

Freelance bookkeepers: $25–$50/hour. Professional bookkeeping firms: $40–$80/hour. Monthly packages for small businesses: $300–$800/month depending on transaction volume. Payroll add-on: $50–$150/month. Year-end prep: $500–$1,500 one-time. Always ask what's included.

What's the difference between a bookkeeper and an accountant?

Bookkeepers handle daily financial records: data entry, reconciliation, invoicing, payroll. Accountants provide higher-level services: tax strategy, financial statements, CRA audits, business advice. Most small businesses need a bookkeeper year-round and an accountant for tax season.

When should I hire a bookkeeper?

Hire a bookkeeper when: you're spending 5+ hours/month on books, you've missed a tax deadline, your records are behind, you're hiring employees (payroll), or your business revenue exceeds $50K. The cost of a bookkeeper is almost always less than the cost of mistakes.

Do bookkeepers need certification?

No certification is legally required, but look for CPB (Certified Professional Bookkeeper) from the Canadian Institute of Bookkeeping, or QuickBooks ProAdvisor / Xero Certified. These demonstrate training and competency. Always ask about their experience with businesses like yours.

Can a bookkeeper do my taxes?

Bookkeepers can prepare and file simple tax returns (T1, T2, HST/GST). For complex tax situations — corporate restructuring, tax planning, CRA audits, international tax — you need a CPA. Many bookkeepers partner with accountants and can coordinate your year-end seamlessly.