Before joining Torys, Jacob volunteered as a junior legal associate for B'nai Brith Canada and was a research assistant at Schulich School of Business. Prior to entering law school, Jacob worked as a senior financial analyst for Unilever Canada and as a treasury intern for Nestle Canada.

Jacob acted as vice-president of finance for Big Brothers and Big Sisters of York University and volunteered as a Big Brother mentor. In addition, Jacob acted as duty counsel at Osgoode Hall Law School's Community and Legal Aid Service Program.