Lisa A. Orro

Member, Director of Tax Services

Lisa serves as Tax Team Leader for Weiss Advisory Group, where she has been a valued member of the firm for more than a decade. She brings over twenty years of experience in tax and accounting, working closely with individuals and small business owners to provide thoughtful, detail-oriented guidance.

Lisa began her career as a staff accountant at Avon Products, Inc., gaining valuable experience in corporate accounting before transitioning into public accounting. Prior to joining Weiss Advisory Group, she worked with two local CPA firms based in Westchester County, where she further developed her expertise in tax compliance, planning, and small business accounting.

She holds a Bachelor’s Degree in Accounting from Pace University and is known for her practical, client-focused approach. Lisa works across all areas of accounting and tax planning, helping clients stay organized, compliant, and confident in their financial decisions.

In addition to her professional experience, Lisa is a licensed public notary and is currently pursuing her Enrolled Agent (EA) designation to further expand her ability to represent and support clients before the IRS.

Areas of Focus

• Small Business Accounting & Tax Planning
  • (including contractors in the trades such as HVAC, plumbing, landscaping, and electrical services)
• Real Estate Business Owners
  • (rental property owners, multi-entity structures, and cash flow–driven planning)
• Medical Professionals
  • (including physicians, dentists, and therapists)
• Legal Professionals
  • (solo practitioners and small law firms)
• Fiduciary & Wealth Transfer Tax Filings
  • (trust income tax returns, estate tax returns, and gift tax returns)
    
• Tax Compliance, Planning, and Ongoing Advisory Support

Richard F. Weiss, CFP®, CHFC®, CPA, PFS®, CEP®, CLU®

Founder

Richard brings more than four decades of experience in public accounting and financial services, providing clients and colleagues with seasoned perspective and trusted judgment. He is the founder of Weiss Advisory Group and continues to serve the firm as a senior consultant, offering strategic insight shaped by decades of client work and professional leadership.

Beyond his role at Weiss Advisory Group, Richard is actively engaged in the community. He served on the Board of Directors of PCSB Bank and Putnam County Housing Corporation, and Putnam County Development Corporation, reflecting his longstanding commitment to local economic stability and community development.

Richard holds a Bachelor of Business Administration in Accounting from the City University of New York. Over the course of his career, he has advised individuals, families, and business owners across a wide range of financial and tax matters, earning a reputation for thoughtful planning, technical expertise, and steady guidance.

His professional credentials include CERTIFIED FINANCIAL PLANNER® (CFP®), Chartered Financial Consultant® (ChFC®), Personal Financial Specialist (PFS®), Chartered Life Underwriter® (CLU®), Certified Estate Planner® (CEP®), and Certified Public Accountant (CPA)—a combination that reflects both depth and breadth across tax, financial planning, and advisory disciplines.

Keith D. Weiss, CFP®, MBA

Managing Member

Keith has been with Weiss Advisory Group for more than two decades, working closely with individuals and small business owners to help them navigate the U.S. tax code with clarity and confidence.

He specializes in tax planning and tax minimization strategies, focusing on legal and ethical methods that help clients reduce unnecessary tax exposure while staying compliant. Keith works with entrepreneurs and small business owners to address entity structure, retirement plans, and long-term tax efficiency.

In addition, Keith advises corporate and public-sector employees—including professionals at companies such as Regeneron, Pepsi, Amazon, Google, Mastercard, IBM, and Con Edison, as well as public service professionals (i.e. teachers, police officers, and firefighters)—on the tax implications of employer-sponsored benefits. His work includes guidance around retirement plans, pensions, and equity compensation, helping clients make informed decisions within an often complex benefits landscape.

Areas of Focus

• Qualified Retirement Plans (401(k), SEP-IRA, SIMPLE-IRA)
• Small Business Retirement Plan Design & Implementation
  • (including plan selection, contribution strategies, and tax-efficient structures)
• Equity Compensation (ISOs, NSOs, RSUs)
• Pensions and Deferred Compensation
• Retirement-Focused Tax Planning