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, 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 also lectured at various Universities and Colleges.

He holds a Master of Science (MSc) in Finance, a Bachelor of Law degree (LL.B) both from the University of Nairobi (UoN), a Bachelor of Commerce 1st Class Honours from Strathmore University. He completed the Program for Management Development (PMD) course offered jointly by SBS Kenya & GIBS University of Pretoria South Africa.

He is a Lawyer, a Certified Information Systems Auditor (CISA), a Certified Secretary, an Accountant, a Certified Investment and Financial Analyst (FA), an Accredited Governance Auditor, 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 in various boards.