Senior Executive Oracle Advisor

Redress Compliance is an independent enterprise software licensing advisory firm that works exclusively on the buy side. We help the world's largest organizations navigate Oracle licensing, negotiate from a position of strength, and eliminate unnecessary spend. We cover 11 enterprise vendors, have completed 500 engagements, and are recognised by Gartner. We don't resell. We don't take vendor commissions. We sit on your side of the table.

The Role

We're hiring a Senior Executive Oracle Advisor to lead our most high-profile Oracle engagements. This is not a back-office compliance role. You will be in the room with CIOs, CFOs, and procurement leaders at Fortune 500 companies — presenting strategies, challenging assumptions, and driving outcomes that save millions.

You'll operate as the lead advisor on complex, multi-workstream Oracle engagements and manage a virtual team of subject matter experts across licensing, technical, and commercial disciplines.

What You'll Do

• Lead end-to-end Oracle advisory engagements independently, from scoping through final negotiation and contract execution
• Present strategic recommendations directly to C-suite executives and senior procurement stakeholders
• Advise on Oracle ULA strategy — including certification, renewal, renegotiation, and exit planning
• Develop and execute Oracle Cloud Infrastructure optimization strategies, including cost modelling, commitment structuring, and migration planning
• Lead Oracle support reduction initiatives, including Third Party Support transitions and de-support strategies
• Advise on Exadata Cloud@Customer deployments — commercial structuring, licensing implications, and negotiation positioning
• Drive Oracle contract negotiations, leveraging deep knowledge of Oracle's internal pricing, discount structures, approval processes, and deal mechanics
• Manage virtual teams of technical and licensing SMEs, ensuring quality delivery across concurrent engagements
• Contribute to thought leadership, client proposals, and business development as a visible senior member of the firm

What You Bring

• Deep, demonstrable experience with Oracle's internal commercial operations — ideally from time spent inside Oracle in a sales, deal management, pricing, or licensing capacity
• Thorough understanding of how Oracle's sales organisation works: territory structures, approval chains, discount authority, quarter-end dynamics, and deal tactics
• Proven track record advising enterprise buyers on Oracle licensing, ULA strategy, cloud migration, and contract negotiation
• Experience leading consulting engagements autonomously, including managing client relationships at the executive level
• Strong commercial acumen — you understand enterprise procurement, contract law fundamentals, and multi-year deal structuring
• Experience with Oracle Cloud Infrastructure and Exadata Cloud@Customer from a commercial and architectural standpoint
• Ability to manage and coordinate a virtual team of specialists across time zones
• Excellent written and verbal communication skills, including executive-level presentation ability
• Based in the United States (preferred); must be available to work across US time zones

Nice to Have

• Experience across adjacent vendors (Microsoft, SAP, Salesforce, Broadcom/VMware) is a plus but not required
• Existing relationships in enterprise procurement or IT leadership
• Experience in or familiarity with the independent advisory space

Why Redress

• Work with a firm that has genuine insider credibility and a reputation for delivering hard results
• Lead engagements where your expertise directly moves the needle — no bureaucracy, no bench time
• Collaborate with a lean, senior team that punches well above its weight
• Competitive compensation with performance-based upside
• Remote-first, US-based, with flexibility to manage your own schedule