Head of Organizational Readiness - Finance & Risk Transformation

Software Guidance & Assistance, Inc., (SGA), is searching for a Head of Organizational Readiness - Finance & Risk Transformation for a contract assignment with one of our premier Insurance services clients in New York, NY or Stamford, CT .

Responsibilities :

• Accountable for the operational plan, including communications, change management, and training strategy that enables successful adoption of technology solutions across the Finance & Risk organization.
• The initial focus will be the deployment of the Oracle Planning and Expense Management optimization solutions for the FP&A organization.
• Ensures Finance & Risk leaders and teams are informed, prepared, and capable of operating new planning, forecasting, and expense management processes at go-live and beyond.
• partners closely with Finance Transformation, FP&A, Technology, Risk, HR Business Partner and Communications teams to translate Oracle Planning implementation into sustained behavior change, role clarity, and embedded ways of working.
• Cross-Functional Leadership & Governance
• Serve as the single point of accountability for Communications, Change Management, and Training within the E2E Planning & Expense Management Operational Readiness workstream.
• De ne and own the Operational Readiness framework for Finance & Risk.
• Establish readiness governance, milestones, and success criteria aligned to program delivery timelines and business outcomes.
• Drive alignment across Finance, Technology, Risk, and Transformation teams to ensure consistent messaging, change reinforcement, and user enablement.
• Provide clear, concise readiness updates to Finance & Risk leadership, highlighting adoption risks, dependencies, and required decisions.
• Partner with program leadership to inform go-live readiness decisions from a people-readiness perspective.
• Finance Communications Leadership (in partnership with Communications Business Partner)
• Drive the Finance & Risk Operational Readiness communications strategy for Oracle Planning, ensuring consistent, timely, and targeted messaging across all impacted Finance stakeholders.
• Identify stakeholder groups (FP&A, Business Finance, Controllership, leaders) and tailor communication approaches based on level of impact and readiness.
• Develop and govern Finance & Risk communications artifacts, including key messages, FAQs, leader talking points, walkthrough decks, and milestone updates.
• Coordinate phased communications (leadership, managers, end users) to support awareness, engagement, and readiness ahead of key milestones and go-live.
• Gather feedback on communication effectiveness and continuously re ne messaging based on adoption signals and readiness insights.
• Change Management (in partnership with HR Business Partner)
• Lead the change management approach for Oracle Planning, aligned to enterprise change standards and the Finance & Risk transformation objectives.
• Conduct change impact assessments in partnership with our implementation partner to understand how Oracle Planning affects roles, processes, decision-making, and performance expectations.
• Partner with FP&A leaders to prepare them to lead their teams through change, reinforcing new planning behaviors and retiring legacy tools and shadow processes.
• Establish change checkpoints and readiness pulse checks to assess adoption risks and drive mitigation actions.
• Ensure change activities are tightly integrated with program milestones, communications, and training delivery.
• De ne and track readiness and adoption metrics, including operational performance indicators, user readiness, and stabilization outcomes.
• Training & Enablement for Oracle Planning
• Own the training and enablement strategy for Oracle Planning, ensuring users are prepared to execute their roles effectively at go-live.
• Partner with FP&A, Technology, and SMEs to de ne role-based training curricula aligned to Oracle Planning work fl ows and Finance processes.
• Oversee development of Finance job aids, process guides, simulations, and on-demand learning assets.
• Ensure training delivery is sequenced appropriately (pre-go-live, go-live, post-go-live reinforcement) to support sustained adoption.
• Track training completion, pro fi ciency, and readiness metrics and escalate risks where gaps remain.

Required Skills:

• Senior experience leading communications, change management, and training for enterprise transformation initiatives.
• Demonstrated success leading readiness for large-scale business or technology transformations.
• Strong understanding of operating models, end-to-end processes, risk and controls, and enterprise change dynamics.
• Proven ability to in fl uence executive stakeholders and drive alignment across functions.
• Experience designing and executing communications, training, and adoption strategies in partnership with specialized teams.
• Strong executive communication and stakeholder engagement skills.
• Key Skill and Competencies:
• Transformation change leadership
• Executive and stakeholder communications
• Training strategy and learning enablement
• Oracle Planning adoption and readiness
• Organizational change management
• Data-driven readiness assessment

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