Steven Kelley

Background

About Steven Kelley

Redefining how organizations buy and negotiate cloud and enterprise software. Enterprise technology and licensing advisor focused on helping organizations reduce software and cloud costs, mitigate compliance exposure, and create leverage in complex vendor negotiations. Background includes enterprise licensing and sales roles at Microsoft, followed by founding Software Licensing Advisors in 2012. In 2019, the business was merged into Directions on Microsoft to support the expansion of its Microsoft EA advisory services. Across these efforts, delivered over $2B in client savings through strategic deal structuring, negotiation, and license optimization. Known for operating where most organizations struggle—at the intersection of IT operations, cloud engineering, software asset management (SAM), sourcing, and executive leadership—aligning technical, financial, and strategic priorities into clear, executable licensing and cloud strategies. Founder of LicenseBids, a marketplace platform redefining how organizations source cloud and software. Introduces a competitive, RFQ-driven model for Microsoft 365, Azure, AWS, and Google environments—enabling blind bidding from CSPs and channel partners, as well as curated, advisor-led sourcing for complex enterprise requirements. Core Expertise Microsoft & Cloud Licensing Strategy (M365, Azure, AWS, GCP) Contract Negotiation & Commercial Structuring Software Asset Management (SAM) & Compliance Risk Cost Optimization & Vendor Strategy Cross-Functional Alignment Across IT, Cloud, SAM, Sourcing & Executive Leadership