Doelie Lessing

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Location: Stellenbosch

Tel: +27 21 809 6147

Fax: +27 11 535 8532



Director Doelie Lessing has over 20 years’ experience in tax law, advising in the Tax and Investment Funds & Private Equity practice areas. She is deeply experienced in tax considerations as relates to mergers; corporate reorganisations; funding and financial services; local and foreign investment fund and deal structuring; and multi-jurisdictional investments and structures. She is particularly skilled in matters relating to high-net-worth and multinational families and their businesses; private equity; international trust and estate planning; and cross-border and local executive share incentive arrangements. Doelie is frequently named in global publications as a top-ranked tax lawyer.

  • Investment Funds & Private Equity
  • Tax
  • Mergers, acquisitions and reorganisations of corporate entities
  • International tax planning for corporates and  wealthy individuals and families, including:
    • controlled foreign companies
    • foreign trusts
    • transfer pricing and thin capitalisation
    • settlor and beneficiary charges
    • double tax agreements
  • Financial services
  • Tax structuring for local and international investment funds
  • Private equity deal structuring
  • Black economic empowerment transactions
  • Africa-specific investments
  • Tax litigation, alternative dispute resolution and settlements
  • Employee incentive plans
  • International tax planning for executives and mobile employees
  • VAT


  • Advising a multinational private equity group in relation to a structure for investment fund with a focus on African infrastructure
  • Tax considerations relevant to a transfer of foreign currency loans to a listed group's domestic treasury company
  • Restructuring a multinational incentive plan following changes to SA tax law involving foreign dividends
  • Tax advice regarding the restructuring of insurance arrangements for a retirement fund's obligations through a Collective Investment Scheme in Securities
  • VAT treatment of sale of book debts
  • Transfer pricing tax litigation
  • Incentive plan for an investment advisory team rendering services to multijurisdictional entities
  • Structuring advice regarding a European property fund with SA investors
  • Total return swap referencing listed instruments with significant differences in value
  • Advising a short-term insurance company in relation to its proposed expansion abroad
  • Advising on the acquisition by international investor of an interest in Nigerian manufacturing operation and the expansion of the operation to SA
  • B Com: Stellenbosch University (1991)
  • LLB: Stellenbosch University (1993)
  • M Com (Tax) (cum laude): Stellenbosch University (1999)
  • Director: Werksmans (2009)


  • Named as a leading lawyer in Tax: The World's Leading Lawyers for Business Chambers Global (2013 – 2020);
  • Ranked as a leading lawyer in Private Wealth Law Chambers High Net Worth Guide (2017-2020);
  • Named as a leading practitioner in Tax field by Euromoney’s Expert Guide to the World’s Leading Women in Business Law (2013 – 2019);
  • Nominated by in-house counsel and peers as a pre-eminent practitioner in Euromoney's Guide to the World's Leading Tax Advisers (2018);
  • Named as a highly-regarded practitioner in The International Who’s Who of Corporate Tax Lawyers (2013);
  • Named as a recommended lawyer in Tax (2011 – 2018) and Investment Funds (2015) in The Legal500;
  • Named amongst the world’s leading private client lawyers in Who’s Who Legal: Private Client 2014 - 2015 and Who’s Who Legal 2015 – Compendium Edition;
  • Named as a recommended South African Tax Lawyer in the PLC Tax on Transactions Multi-jurisdictional guide (2012);
  • External examiner for the University of Cape Town’s Tax Masters Degree;
  • Member of the International Tax Planning Association and the South African Institute of Tax Practitioners;
  • Co-founder, past chairman and member of STEP (Society of Trust and Estate Practitioners), Cape Town;
  • Co-author of the South African chapter of the Practical Law Private Client Multi-jurisdictional Guide, 2014 edition;
  • Co-author of the South African chapter in the treatise International Estate Planning.