Len may be regarded as a "captain of industry" in Trinidad.  He started his business career more than 40 years ago. In 1965 he joined the Neal & Massy Group of companies, the largest local business conglomerate.  In the course of his career there he was appointed as a Director of several subsidiaries, including Crown Life Insurance, and his last position was that of Group Corporate Secretary.  Since 1987 he has been Executive Chairman of his own investment company.

Len's career as an entrepreneur in his own right started in 1973, when together with several business partners he founded Prestige Holdings Limited.  This company obtained the Kentucky Fried Chicken franchise for Trinidad and has been very successful in expanding that.  Len served as Chairman from 1973 to 1991.  The company was floated on the Trinidad & Tobago Stock Exchange at the start of 1999.

Len is a Fellow of the Institute of Directors and a Fellow of the Institute of Management of the United Kingdom.  He has been a member of committees and trade delegations appointed by successive Governments, and has represented Trinidad & Tobago at international conferences within and outside the Caribbean region.  He has been elected as Vice President of the Caribbean Chamber of Industry and Commerce, and has been Director of the Dispute Resolution Centre and President of the Trinidad & Tobago Chamber of Industry and Commerce.