Who we help

For Businesses

Tax planning, structure, dispute resolution, and defense for businesses of every size.

Every business owes tax somewhere, and the exposure rarely sits in one place. Income tax filings, payroll withholding, state and sales tax, and the entity structure the company chose years ago all create obligations that can turn into a dispute.

Whiteford represents companies of every size, from a first-year startup to an established multistate operation. The work runs from choosing and maintaining an entity structure, through planning for changing tax rules, to defending the company when the IRS or a state tax authority questions a return.

When a dispute does arrive, the sequence matters. Getting representation in place early keeps an IRS audit inside its original scope, preserves privileged communications, and keeps a civil examination from drifting toward allegations of wrongdoing.

Where business tax exposure becomes personal

Payroll tax is the clearest example. Amounts withheld from employee wages are trust fund money, and when they are not paid over the IRS can assess the Trust Fund Recovery Penalty against the owners, officers, or managers it identifies as responsible persons. The company's problem becomes a personal one, collectible from personal accounts and property.

Common issues

Entity structure and tax planning

The structure a company files under drives its tax treatment, and the choice made at formation is rarely revisited as the business grows. We advise on structure and on planning for changing tax rules, so the position the company reports is one it can defend later.

Payroll taxes and the Trust Fund Recovery Penalty

Withheld Social Security and Medicare are trust fund money held for the government. If they are not paid over, the IRS can assess the penalty personally against owners, officers, and anyone else with control over which bills get paid, then levy their accounts and lien their property.

IRS audits of a business return

Most audits begin with a letter asking for proof of something the return reported. What the company hands over in the first weeks decides whether the examination stays narrow or expands into more years and more issues. We act as the point of contact and keep it in scope.

Delinquent filings and unpaid balances

Missed Forms 941, 940, 1120, or 1065, along with state sales and use tax returns, create two separate problems: the filing gap and the balance. They carry different deadlines, and the order in which they are addressed changes what relief is available.

State and local tax

Businesses pay income tax at the state level as well as the federal, plus payroll tax and sales tax on what they sell. State audits look back three years or more and ask for W-2s, 1099s, receipts, bills, and canceled checks. We handle those examinations and the appeals that follow.

Privilege and allegations of wrongdoing

Communications with a lawyer carry protection that communications with an accountant do not. When an examination starts probing intent rather than numbers, or a PPP or ERC claim is in question, that difference decides what can safely be put in writing and by whom.

Recommended next steps

  • Route the examiner's requests through counsel before the company answers them.
  • Confirm which payroll, income, and sales tax filings are actually missing before you file anything.
  • Identify everyone who decides which bills get paid, because those are the people the IRS will name as responsible persons.
  • Keep sensitive analysis in a privileged channel rather than in email to the bookkeeper.

How we help

Frequently asked questions

When does a business need a tax attorney rather than its accountant?
When the question stops being how to report something and starts being whether the company can defend it. An examination that probes intent, a payroll tax balance that could reach the owners personally, a matter heading to IRS Appeals or court, or any need for privileged advice are each points where an attorney belongs in the room.
Can the IRS collect the company's payroll taxes from me personally?
It can collect the trust fund portion, meaning the amounts withheld from employee wages. The IRS assesses the Trust Fund Recovery Penalty against people it identifies as responsible persons, which can include owners, officers, and managers who had control over company finances and decided which creditors were paid. Once assessed, it is collected like any personal tax debt.
The business has years of unfiled returns. Where do we start?
By separating the filing problem from the payment problem. Missing Forms 941, 940, 1120, or 1065 and state sales tax returns have to be identified and prepared first, because the balance is not final until they are in. Only then can a realistic resolution of what is owed be put in front of the IRS.
What does an audit of a business return usually focus on?
Most begin where the return conflicts with information the IRS already holds, or where it scores unusually against comparable filers. Deductions that are large relative to reported income, third-party 1099 income that does not appear on the return, missing years, cash-intensive operations, and related-party or pass-through transactions are the recurring triggers.

Where we work

All Whiteford offices where you can meet with an attorney

Maryland

Baltimore

7 St Paul Street
Suite 1500
Baltimore, MD 21202
(410) 498-6815
Maryland

Columbia

8830 Stanford Boulevard
Suite 400
Columbia, MD 21045
(410) 431-1954
Maryland

Ocean City

7408 Coastal Highway
Ocean City, MD 21842
(302) 829-3043
Maryland

Rockville

111 Rockville Pike
Suite 800
Rockville, MD 20850
(410) 347-8730
Maryland

Towson

Towson Commons, Suite 300
One West Pennsylvania Avenue
Towson, MD 21204-5025
(443) 278-2191
Colorado

Denver

2128 West 32nd Avenue
Denver, CO 80211
(720) 419-1296
Delaware

Bethany Beach

26 N. Pennsylvania Avenue
Bethany Beach, DE 19930
(302) 829-3043
Delaware

Rehoboth Beach

18949 Coastal Highway
Rehoboth Beach, DE 19971
(302) 829-3043
Delaware

Wilmington

600 North King Street
Suite 300
Wilmington, DE 19801
(302) 337-5359
District of Columbia

Washington, DC

1717 Pennsylvania Avenue NW
Suite 1300
Washington, DC 20006
(202) 972-6503
Florida

West Palm Beach

222 Lakeview Avenue, Suite 1550
West Palm Beach, FL 33401
(561) 282-9850
Kentucky

Lexington

250 West Main Street, Suite 1800
Lexington, KY 40507
(859) 687-6700
New Jersey

Fairfield

375 Passaic Avenue
Suite 100
Fairfield, NJ 07004
(973) 227-5900
New York

New York

444 Madison Avenue
4th Floor
New York, NY 10022
(646) 618-8660
New York

White Plains

1025 Westchester Avenue, Suite 106
White Plains, NY 10604
(914) 580-9176
North Carolina

Charlotte

4064 Colony Road
Suite 315
Charlotte, NC 28211
(980) 242-5001
Pennsylvania

Pittsburgh

11 Stanwix Street
Suite 1400
Pittsburgh, PA 15222
Virginia

Falls Church

3190 Fairview Park Drive
Suite 800
Falls Church, VA 22042
(703) 280-9260
Virginia

Richmond

Two James Center, 1021 E. Cary Street
Suite 2001
Richmond, VA 23219
(804) 485-1492
Virginia

Roanoke

10 S Jefferson Street
Suite 1110
Roanoke, VA 24011
(540) 759-3560
Virginia

Virginia Beach

249 Central Park Avenue
Suite 300-91
Virginia Beach, VA 23462
(757) 208-9512
Contact Michael March