Philip A. K. Stiles

Senior Attorney

Philip A. K. Stiles focuses his practice on business litigation, commercial loan workouts and restructuring. The industries he serves range from real estate to healthcare, where he represents developers, small and medium
sized businesses, investors and high net-worth individuals.

Phil’s practice is concentrated in litigation that affects most small and medium sized businesses including: commercial loans/lender disputes, business disputes and commercial leases. Phil has deep litigation experience representing both borrowers and lenders in a wide assortment of workout matters as well as contractual disputes.

Prior to joining the Ioppolo Law Group, Phil managed the Complex Litigation practice for a medium- sized, Florida law firm. He provided strategic legal advice with regard to the successful operation of client companies, litigation, negotiated settlement agreements, complex debt resolution and restructuring, and contract origination.

In addition to his previous legal experience, Mr. Stiles was Vice President and Corporate Counsel to a global software provider, where he managed all transactional work and outside counsel on litigation and intellectual property.

With more than 20 years experience in management and C-level support, Phil is able to counsel his clients as both an executive and a seasoned litigator. His deep understanding of business provides him unique insight into client issues as he tackles their legal challenges in a constantly changing marketplace. Having owned his own company, Mr. Stiles understands the unique challenges of business ownership He also understands the need to evaluate risk versus reward in making business decisions. Phil’s business background includes business ownership, business development, management, hiring/firing, P&L responsibility, budgeting and financial forecasting.

Phil’s corporate experience includes working with a variety of industry leaders, small businesses and start-up ventures. Phil worked in sales and business development for industry leaders such as American Express, and Cendant, earning numerous awards including Presidents Club Awards for business productivity, all of which required a broad knowledge of technical products and capabilities.

Phil graduated with Honors from Rollins College with a Bachelor of Science degree in Business Administration and Management, with a minor in Economics. He then attended Florida A&M University College of Law where he earned his Juris Doctor and was later admitted to The Florida Bar.

Growing up in Central Florida, Mr. Stiles has maintained strong ties to the local community having attended Trinity Preparatory School, Winter Park High School, Rollins College and Florida A&M University College of Law.

  • Civil Litigation
  • Commercial/Business Litigation
  • Banking Litigation
  • Debtor/Creditor’s Rights
  • Commercial Foreclosure
  • Contract and Corporate Disputes
  • Commercial Landlord Tenant Disputes

  • Represented major real estate developer in multiple commercial loan modifications and workouts in excess of $10,000,000.00.
  • Represented buyer/venture capitalist in misrepresentation litigation against seller by challenging business valuation.
  • Counseled commercial property investor in limiting loan exposure and settled loan deficiencies related to loans in excess of $5,000,000.00.
  • Represented national retailer in an enforcement action related to an employee’s covenant not to compete and obtained judgment in favor of the retailer.


Vice President and General Counsel for a global software provider where Phil managed all in-house legal work and oversight of outside counsel for contracts, intellectual property, mergers and acquisitions, compliance and litigation.

  • Responsible for the launch and ongoing operation of the U.S. office.
  • Managed a broad range of legal issues including contract negotiation, drafting and review; supervision of outside litigating counsel and negotiating pricing and details.
  • Responsible for all Human Resource functions of the company.

Mergers and Acquisitions Specialist where he performed due diligence, researched and analyzed financial statements and tax filings, as well as making recommendations on acquisition decisions to the company’s senior leadership.

  • Conducted comprehensive computerized business evaluations and prepared confidential company and financial analyses for business owners preparing to sell.
  • Interviewed and qualified potential purchasers as well as negotiating offers for the purchase of businesses.
  • Consistently ranked in the top 5% in sales nationally.

Manager of Business Development for Cendant, and American Express where Phil sold Sale of software connectivity and web-based self-booking tools to the travel industry.

  • Worked with large travel agencies as well as major corporations.
  • Necessitated a broad knowledge of technical products and capabilities.
  • Accountable for negotiating transactions, responding to RFP’s and financial analysis.
  • Negotiated with Chief Financial Officers and Attorneys, as well as Procurement and Travel Managers.
  • Responsible for securing contracts which met sales goals and profitability margins.
  • Multiple Presidents Club Award winner.

Director of Sales for various medical service providers where he was responsible for client located throughout the US. Phil evaluated a client’s present configuration and future technical needs, configuring the hardware and/or software solutions and presenting proposals to physician groups.

  • Interacted with Administrators and Physicians in medical groups.
  • Responsible for developing and working my own leads to closure, as well as maintaining profit margins and quotas.

  • Florida
  • United States District Court, Middle District of Florida