Executive Enterprise Transformation Leader

Jobtailor; Reston (VA); On-site; USD 180,000 - 240,000; Full time

Job summary

Jobtailor is seeking a Senior Transformation Leader to drive enterprise-wide programs from concept through execution in Reston, VA. You will partner with C-suite and cross-functional leaders to deliver measurable business outcomes, govern complex portfolios, and guide multi-year roadmaps using AI-enabled process improvements.

The role emphasizes data-driven decision making, executive presence, and proven ability to lead high-performing teams, with a focus on governance, benefits realization, and

Qualifications

• 12+ years of progressive experience in business transformation or enterprise-wide program delivery.
• Proven track record leading complex transformation initiatives with measurable outcomes.
• Experience guiding multi-year, cross-functional transformation projects with quantified benefits and KPI attainment.
• Expertise in portfolio governance, benefits realization, KPI/OKR design, and executive stakeholder management.
• Hands-on experience with Microsoft Project/Planner, Power BI, Azure DevOps/Jira, Mural/Miro, and Teams.
• Experience facilitating current-state and future-state process mapping with diverse stakeholder groups for business process reengineering.
• Skill applying AI and automation tools to process efficiency, decision support, analytics, and workflow optimization responsibly.
• Strategic thinking and systems orientation.
• Data-driven decision-making using dashboards, KPIs, and advanced analytics.
• Executive presence and ability to influence at C-suite level.
• Track record of building and leading high-performing cross-functional teams.

Responsibilities

• Lead complex, enterprise-wide transformation initiatives from conception to completion.
• Partner with executives to align initiatives with strategic goals and deliver measurable results.
• Facilitate problem-solving sessions using human-centered design and systems thinking.
• Lead software transformation projects involving governance, workflow redesigns, and data integrations.
• Represent transformation portfolio in executive forums and steering committees.
• Define KPIs/OKRs and benefits realization plans; baseline, track, and achieve targets.
• Establish governance structures, stage gates, and sponsor cadence.
• Develop delivery standards, tools, playbooks, and templates.
• Run project performance reviews, risk management, and dependencies coordination.
• Own portfolio budget management, forecasting, and ROI tracking.
• Define sustainability plans covering ownership, operating model updates, and training.
• Govern transitions to business-as-usual with SLAs and handoffs.
• Embed changes into policies, roles, incentives, and systems.
• Help develop rolling multi-year transformation roadmap.
• Provide guidance and coaching to junior staff; support resource forecasting and vendor augmentation.
• Foster accountability, psychological safety, and continuous improvement.

Skills

Business transformation leadership

KPI/OKR design

Portfolio governance

Microsoft Project/Planner

Change management

Education

PMP

Agile

Prosci

Lean Six Sigma

Tools

Power BI

Azure DevOps

Jira

Mural

Miro

Microsoft Teams

Job description

Jobtailor is seeking a Senior Transformation Leader to drive enterprise-wide programs from concept through execution in Reston, VA. You will partner with C-suite and cross-functional leaders to deliver measurable business outcomes, govern complex portfolios, and guide multi-year roadmaps using AI-enabled process improvements.

The role emphasizes data-driven decision making, executive presence, and proven ability to lead high-performing teams, with a focus on governance, benefits realization, and