Obare has over 20 years of work experience, having worked for various organisations in various capacities relating to governance, strategy, leadership, financial management and talent management. Previously he has worked for MTN Business as the Quality Management Representative (QMR)and Head of Finance. He also worked at UUNET Kenya and at Strathmore University. 

Obare is the immediate former Chief Executive Officer at the Institute of Certified Secretaries (ICS).

As a scholar, he has publications in various international and local academic journals. He has lectured/lectures at various Universities and Colleges including Kenya School of Law (KSL).

He holds a Master of Laws (LL.M), a Master of Science (MSc) in Finance, a Bachelor of Law degree (LL.B), all from the University of Nairobi (UoN) and a Bachelor of Commerce from Strathmore University. He has completed the PMD course offered jointly by SBS Kenya & GIBS University, Pretoria South Africa.

He is a Lawyer, a Certified Information Systems Auditor (CISA), a Certified Secretary (CS), an Accountant (FCPA) - (a Fellow of the Institute and former Council member), a Certified Investment and Financial Analyst (FA), an Accredited Governance Auditor, a Certified Mediator, an International Coaching Federation (ICF) Certified Coach, a trained ISO 9001:2015 internal auditor, a trained trainer on Crucial Conversations by VitalSmarts USA and a trained trainer on Corporate Secretarial Toolkit by IFC & CSIA.

He has served/serves at various boards.