Doelie Lessing is a Director and Head of the Tax Practice Area with over 20 years of experience in tax law. 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.
PRACTICE AREAS
- 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)
- Chartered Tax Adviser at SAIT (2024)
- Ranked as a leading Partner by Legal 500: ‒ 2025 | Tax
- Ranked lawyer (Band 1) by Chambers High Net Worth Guide | 2017 - 2024 | Private Wealth Law
- Ranked lawyer (Band 2) by Chambers Global | 2013 – 2022, 2024, 2025 | Tax
- Ranked as a leading practitioner by Legal 500: ‒ 2011, 2018, 2020 and 2024 | Tax
- Ranked as a recommended lawyer by Legal 500 | 2015 - 2024 | Investment Funds
- Ranked by ITR World Tax as a Notable Practitioner | 2024, 2025
- Recognised as a Tax Expert | Tax Expert Guide 2022
- Named as a leading practitioner by Euromoney's Expert Guide to the World's Leading Women in Business Law | 2013 – 2022 | Tax
- 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 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
- Previously acted as 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
