Enterprise Agility Leader – Fleet Ecosystem (FELT)

ZipStaff Inc.; Washington (District of Columbia); On-site; USD 207,000 - 289,000; Part time

Benefits offered by this job

Health Insurance

Dental Insurance

Vision Insurance

401(k) + 401(k) matching

Paid time off

Referral Program

Job summary

ZipStaff seeks an Enterprise Agility Leader to guide the Fleet Ecosystem Leadership Team (FELT) at a major transportation organization in Washington, DC. This on-site, contract role combines strategic coaching with operating model stewardship across Product, Architecture, OCM, SRE, and Operations.

You will drive portfolio governance, translate roadmaps into backlogs, and establish health metrics while partnering with senior leaders to remove bottlenecks and enable continuous lean‑agile delivery.

Qualifications

• 8+ years of experience leading enterprise agile transformations in regulated environments.
• 6+ years in IT, systems engineering, or enterprise delivery disciplines.
• Experience moving from Waterfall/PMLC to Lean-Agile and Agile product delivery.
• Deep knowledge of SAFe, Scrum, Kanban, DevSecOps, Lean Portfolio Management.
• Active SAFe SPC certification or equivalent.
• Hands-on experience with Jira Align, Jira Software, Confluence, and analytics tools.
• Strong communication and stakeholder facilitation across Director/VP levels.

Responsibilities

• Define and sustain cross-portfolio Fleet operating model and working cadence.
• Facilitate alignment sessions across Product, Architecture, SRE, Tech, and OCM leaders.
• Translate roadmaps and funding priorities into coordinated backlogs.
• Manage cadences and dependencies across value streams with Jira Align.
• Establish health metrics and governance forums for transparency.
• Coach leaders on flow metrics, capacity planning, and lean-agile practices.

Skills

Executive stakeholder facilitation

Cross-functional leadership

Strategic coaching

Lean-Agile portfolio practices

Jira Align proficiency

Travel readiness

On-site collaboration

Education

SAFe SPC Certification

Tools

Jira Align

Jira Software

Confluence

AgilityInsights

Job description

Job Title: Enterprise Agility Leader – Fleet Ecosystem (FELT)

Location: Washington, DC (On-site)

Employment Type: Contract (W2 through ZipStaff — No C2C or 1099)

About the Opportunity

ZipStaff is seeking an Enterprise Agility Leader to serve as the primary strategic coach, facilitator, and operating model steward for the Fleet Ecosystem Leadership Team (FELT) at a leading transportation organization.

This critical oversight body sits above individual Fleet portfolios to align overarching vision with measurable execution. Working as an influential peer among cross-functional leaders in Product, Architecture, Organizational Change Management (OCM), Operations Technology, Site Reliability Engineering (SRE), and Field Operations, this role drives operating model evolution, cross-portfolio synchronization, and strategy-to-execution cadence. The ideal leader bridges high-level strategic planning with pragmatic portfolio governance, resolving systemic dependencies and fostering shared accountability across large, highly regulated enterprise operations. This is an on-site role in Washington, DC.

What You’ll Do:

• Define, evolve, and sustain the cross-portfolio Fleet operating model, embedding consistent ways of working, collaborative decision-making, and continuous improvement across the enterprise.
• Facilitate high-impact alignment sessions, strategic planning forums, and retrospectives for the FELT, ensuring active collaboration among Product, Architecture, SRE, Tech, and OCM leaders.
• Lead the translation of enterprise-level Fleet roadmaps, strategic outcomes, and funding priorities into coordinated execution backlogs across multiple delivery portfolios.
• Manage organizational cadences, monitor flow across value streams, eliminate systemic delivery bottlenecks, and maintain clear cross-portfolio dependency mapping using Jira Align and modern agility tooling.
• Establish objective health assessments, execution metrics, and governance forums to provide executive transparency into team performance, delivery commitments, and organizational risks.
• Coach senior leaders, program teams, and delivery partners on flow metrics, capacity planning, lean-agile portfolio practices, and change enablement in complex operating environments.

Required Qualifications:

• 8+ years of experience leading complex enterprise agile modernizations, operating model transformations, and value stream enablements across large-scale, highly regulated organizations.
• 6+ years of foundational experience working in IT, systems engineering, operations technology, or related enterprise delivery disciplines.
• Proven track record guiding organizations through transitions from traditional Waterfall/Project Management Lifecycles (PMLC) to Lean-Agile and Agile Product Delivery models.
• Deep, practical command of enterprise scaling frameworks and methodologies (SAFe, Scrum, Kanban, DevSecOps, Lean Portfolio Management), with the ability to balance framework theory with pragmatic business needs.
• Active SAFe Practice Consultant (SPC) certification (SAFe 6.0 preferred) or equivalent advanced enterprise-level coaching credentials.
• Direct hands-on experience utilizing enterprise agile management suites, specifically Jira Align, Jira Software, Confluence, and AgilityInsights (or comparable analytics tools).
• Exceptional communication, stakeholder engagement, and facilitation skills, capable of influencing Director- and VP-level stakeholders to drive consensus and strategic accountability.
• Ability to participate actively in virtual collaboration environments (camera-on culture) and travel quarterly along the Northeast corridor for in-person PI Planning and executive leadership alignment events.
• Ability to work on-site in Washington, DC.

Preferred Qualifications:

• Experience leading agile operating model transformations in transportation, rail, or highly regulated operational environments.
• Strong track record of executive-level facilitation and driving strategy-to-execution alignment across multiple portfolios.
• Hands-on experience establishing portfolio flow metrics, dependency management, and continuous improvement practices at the enterprise level.

Benefits:

• Health Insurance.
• Dental Insurance.
• Vision Insurance.
• 401(k) + 401(k) matching.
• Paid time off.
• Referral Program.

About ZipStaff:

ZipStaff partners with leading organizations to connect skilled technology professionals with high-impact contract opportunities. We focus on quality matches, clear communication, and long-term success for candidates and clients.