From 2000 to 2008, Mr. Umar Sheikh held the position of the Director of Strategic Negotiations at International Machinery. While in this role, he was responsible for mergers and acquisitions in the U.S. and Europe.

From 2008 to 2012, Mr. Sheikh worked for the Ministry of Health in the last role of Director of Labour Relations at British Columbia's Ministry of Health. He provided strategic advice and oversight on provincial labour relations matters, and represented the Ministry of Health at health benefit provider contract negotiations.

From 2014 to 2017 Mr. Sheikh served as General Counsel and Director, Legal Services of the British Columbia Nurses' Union (BCNU) – responsible for providing strategic and legal advice to the BCNU as well as litigating and negotiating grievances and collective agreements for unions and employees. In September, 2017 he was appointed Chief Executive Officer, Negotiations and Strategic Development, of the BCNU. He held this position until 2020 when he was elected to the board of Directors of NAV Canada where Mr. Sheikh continued to utilize his extensive bargaining, negotiations and labour relations experience.

After returning to Victoria to join the firm of Crease Harman LLP., Mr. Sheikh decided to break out on his own with Sheikh Law.