Cutover Lead

    Highlights

    They need someone who has personally authored minute-by-minute cutover runbooks, led mock cutovers/rehearsals, and managed production weekend war rooms specifically for Source-to-Pay (S2P/P2P) and Contract Lifecycle Management (CLM) platform integrations into financial/ERP backends. • Cross-System Technical Coordination: Oversee and connect cutover activities across three core applications (Contract Life Cycle Management [CLM/Icertis], Source-to-Pay [S2P/Ivalua], and an Agentic AI solution) and their integration points with the backend financial system (Deltek Costpoint).

    Numbers & Facts

    LocationMclean, VA

    Description

    Need someone who has led Source to Pay and Contract Lifecycle Management system cutover efforts."
    They need someone who has personally authored minute-by-minute cutover runbooks, led mock cutovers/rehearsals, and managed production weekend war rooms specifically for Source-to-Pay (S2P/P2P) and Contract Lifecycle Management (CLM) platform integrations into financial/ERP backends.
    Key Responsibilities
    • Cutover Planning & Ownership: Lead, complete, and take full accountability for the end-to-end cutover plan. Coordinate task sequencing, system dependencies, readiness checks, transaction freezes, data migration, and go/no-go criteria across all systems.
    • Cross-System Technical Coordination: Oversee and connect cutover activities across three core applications (Contract Life Cycle Management [CLM/Icertis], Source-to-Pay [S2P/Ivalua], and an Agentic AI solution) and their integration points with the backend financial system (Deltek Costpoint).
    • Process Leadership: Direct ad-hoc process management (rather than supervising direct reports) to ensure all vendor and internal functional/technical teams execute on target cutover tasks.
    • Cutover Execution & Command Center: Lead cutover rehearsals and run the production cutover command center over a planned weekend execution window (target date: April).
    • Downstream & Hypercare Oversight: Evaluate downstream impacts across financial, contract, and S2P workflows during transition. Oversee hypercare post-go-live, including issue triage, system stability, batch schedules, and initial month-end reconciliation.
    • AI Tooling & Troubleshooting: Leverage AI tools and LLMs as support mechanisms to proactively query technical documentation and resolve cross-functional dependencies rather than waiting on team members.

    Candidate Must-Haves (Qualifications & Requirements)
    1. Technical & Domain Expertise
    • Technical System Transition Knowledge: Demonstrated experience leading cutovers or major transitions across Source-to-Pay (S2P), Contracts/CLM, and Financial Systems/ERP.
    • COTS / SaaS Experience: Strong experience working with commercial off-the-shelf (COTS) or SaaS environments (such as Costpoint, SAP, Oracle, Icertis, or Ivalua) rather than custom-developed solutions.
    • Cross-Functional System Aptitude: Ability to trace and understand end-to-end technical task dependencies and downstream impacts across integrated ERP/SaaS environments.
    • Leveraging AI Support: Practical experience using AI/LLM tools as daily productivity/problem-solving tools to analyze documentation and accelerate decision-making.

    2. Soft Skills & Execution Style
    • Technical Aptitude + Process Focus: Hands-on technical understanding paired with rigorous organization skills—not just a high-level Project Manager.
    • Extreme Organization & Communication: Highly detail-oriented with the clear communication needed to align vendors, technical teams, functional SMEs, and executive leadership.

    3. Location, Logistics & Work Schedule
    • Hybrid Schedule Commitment: Willingness to work in-person 4 days/week (Mon–Thurs) split between McLean, VA and Bethesda, MD based on team needs.
    • Weekend Execution Flexibility: Ability to work extended hours and full weekend coverage during the primary cutover window.
    • Legal Status: Preference for U.S. Citizen (Green Card holders will also be considered).

    Key "Nice to Haves"
    • Experience in government contracting or project-based accounting environments.
    • Direct experience with Deltek Costpoint processing, Icertis, or Ivalua.
    • Prior experience running war rooms/command centers for production cutovers.
    • Proficiency with scheduling software such as Microsoft Project or Smartsheet.
    Key Responsibilities
    Collaborate, develop, and manage the cutover plan, including task sequencing, dependencies, readiness checks, and go or no go criteria. Coordinate activities across CLM such as Icertis, S2P such as Ivalua, Agentic AI, Costpoint, integrations, data migration, and finance. Lead cutover rehearsals, capturing and applying lessons learned. Manage cutover execution, including transaction freeze, data extraction, reconciliation, deployment steps, and integration activation. Run the cutover command center, overseeing issue triage, escalation, and checkpoint validation. Ensure financial, data, and transaction integrity during migration and system startup. Oversee hypercare activities including daily monitoring, issue resolution, integration stability, and first month reconciliation. Communicate cutover status, risks, and decisions to program leadership and executive stakeholders.

    Qualifications
    • 5+ years of experience supporting or leading system cutovers, go lives, or major operational transitions
    • Experience with ERP, SaaS, or financial systems such as Costpoint, SAP, Oracle, Icertis, or Ivalua
    • Experience with data migration, integrations, batch schedules, and reconciliation processes
    • Ability to organize and manage complex task sequencing
    • Ability to communicate clearly with technical teams, functional SMEs, and leadership
    • Ability to work during extended hours, weekends, and time sensitive execution windows
    • Bachelors degree

    Nice to Have Skills
    • Experience with Deltek Costpoint processing, integrations, and accounting period management
    • Experience with Icertis Contract Intelligence or Ivalua Source to Pay platforms
    • Experience in government contracting or project based accounting environments
    • Experience running command centers or war rooms during production cutovers
    • Knowledge of AI/ML driven automation and parallel-run validation
    • Knowledge of Smartsheet or Microsoft Project
    • PMP or SAFe certification

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