Craig is a lawyer and the Chief Executive Officer of Legal Aid Saskatchewan, having held the position since 2012.

The organization offers legal representation and duty counsel services to low income individuals for adult and youth criminal charges and family matters. Such services are provided by nearly 80 lawyers and paralegals, supported by about 65 staff, in 13 offices throughout the province.

Prior to holding this office, he worked for the Legal Services Society of BC; before that, he was Chief Executive Officer of the Law Society of Nunavut and a senior manager with the Insurance Corporation of British Columbia responsible for supervising outside defence lawyers.

During his time in private practice he has undertaken criminal defence and legal aid, worked as a prosecutor and done civil and commercial and insurance litigation.

Craig has long been active in extracurricular endeavours that support the profession, mostly through service with the Canadian Bar Association and being active in Pro Bono work.