Carex is partnering with a Insurance industry partner to hire a Technical Transformation Lead for a 1-year contract who will independently drive cross-functional delivery, operational alignment, and portfolio visibility across complex technology initiatives. This role leads medium to large programs spanning multiple teams and domains, ensuring operational leaders are embedded in technology decision-making and that process impacts, dependencies, transition needs, and readiness requirements are effectively addressed. The Technical Transformation Lead will contribute to portfolio governance by surfacing risks, interdependencies, and capacity constraints while maintaining alignment with strategic outcomes. This role requires the ability to flex across predictive, agile, and hybrid delivery practices while providing clear, data-driven insights to senior leadership. Hybrid in Madison, WI.
What You’ll Do
- Lead medium to large cross-functional programs using predictive, agile, and hybrid delivery methodologies.
- Ensure operational leaders are appropriately represented in technology decisions involving continuity, risk, cost, compliance, and other key trade-offs.
- Facilitate the identification of operational impacts resulting from technology decisions and partner with teams to establish efficient transition approaches.
- Manage cross-team dependencies, integration points, resource constraints, and competing priorities across multiple workstreams.
- Lead transition planning activities, including roadmaps, readiness assessments, testing cycles, and implementation planning.
- Facilitate workshops and working sessions across technical, operational, product, and compliance teams.
- Contribute to portfolio governance by escalating risks, increasing dependency visibility, and supporting alignment with prioritization decisions.
- Track program budgets, forecasts, burn rates, and overall financial performance while identifying opportunities for optimization.
- Deliver clear, data-driven reporting on program health, milestones, risks, dependencies, and outcomes to senior leadership.
- Establish and maintain structured risk management and change control processes across programs.
- Support scaled agile planning activities as needed.
- Identify and document post-go-live improvement opportunities and incorporate insights into long-term roadmap planning.
- Build strong cross-functional relationships that promote collaboration, trust, accountability, and effective decision-making.
- Support continuous improvement initiatives designed to increase flow efficiency, predictability, and delivery momentum.
- Collaborate closely with key stakeholders and partners throughout program planning and execution.
- Perform additional responsibilities as needed to support successful program outcomes.
What You’ll Bring
- Bachelor’s degree in Computer Science, Business, a related field, or equivalent professional experience.
- 8–10 years of program or project management experience, including experience leading complex, cross-functional initiatives.
- Strong experience coordinating technical and operational stakeholders across multiple teams and domains.
- Proficiency with Agile methodologies and working familiarity with scaled Agile frameworks.
- PMP, CSM, SAFe, LeSS, PgMP, or PfMP certification preferred.
- Strong capabilities in risk management, dependency orchestration, change control, and transition planning.
- Excellent communication, facilitation, and negotiation skills across diverse stakeholder groups and levels of leadership.
- Demonstrated ability to lead teams through ambiguity, organizational change, and complex transformation environments.
- Solid financial management experience across multi-team programs, including budgeting, forecasting, and financial tracking.
- Ability to synthesize complex program information into concise, data-driven reporting and actionable insights for senior leadership.
Carex Consulting Group is an equal opportunity employer. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, marital status, disability, gender identity, or Veteran status.
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