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Progressive LeasingPosted 1 month ago

Senior Delivery Manager (Remote)

On-siteFlorida, United States

Full TimeSenior LevelLarge

Job Summary

Maintain and improve delivery visibility across complex, dependency-heavy work by tracking cross-team blockers, integration risks, and upstream/downstream exposure. Model the impact of scope changes and capacity constraints to present structured trade-offs to decision-makers while enforcing backlog readiness discipline. Drive accountability through data, socialize production release schedules, and coordinate across engineering, QE, and platform teams to resolve blockers. Manage both Kanban-based flow systems and sprint cadences, utilizing flow metrics and AI-assisted tooling to optimize throughput and reduce execution variability. Protect delivery integrity by surfacing risks proactively and resetting expectations with clarity when assumptions change.

Required Qualifications

  • 5 to 7 years of delivery management experience embedded within software engineering teams in a fintech or similarly regulated, technically complex environment
  • Demonstrated ability to influence engineer and product manager behavior through structure, data, and clear framing
  • Proven experience building or materially improving delivery systems: reducing carryover, improving commitment reliability, or increasing planning quality through structural changes
  • Experience modeling delivery trade-offs and presenting structured options to leadership
  • Deep SDLC fluency, including integration complexity, release management, dependency modeling, and cross-team coordination
  • Strong working knowledge of Jira for dependency tracking, delivery modeling, and operational insight
  • Comfort operating in API-heavy, integration-dependent backend environments where delivery risk lives in the connections between systems
  • Prior experience managing Kanban-based teams in service-oriented or platform engineering environments
  • Demonstrated use of flow metrics (i.e. lead time, cycle time, WIP) as day-to-day operational tools for managing team health and throughput
  • Demonstrated use of AI-assisted tooling (LLMs, AI-augmented Jira workflows, or similar) to improve delivery throughput, reduce coordination overhead, or accelerate artifact generation with the discernment to know when AI output requires human review before it reaches stakeholders
  • Calm, structured approach to ambiguity and able to reset expectations and protect delivery integrity when plans change
  • Strong written and verbal communication skills, including the ability to frame engineering consequences clearly for non-technical stakeholders
  • Bachelor's degree or equivalent experience

Desired Qualifications

  • Prior experience managing sprint-based teams, including planning discipline, Definition of Ready enforcement, and iteration health management
  • Working knowledge of CI/CD pipelines, deployment infrastructure, or cloud services sufficiently enough to understand release risk and coordinate across platform teams
  • Experience coordinating across both iterative (sprint-based) and continuous-flow (Kanban) teams within the same organization
  • Familiarity with ServiceNow or similar change management tooling in a governed release environment
  • Experience supporting offshore or distributed engineering teams with uneven execution maturity
  • Agile, Scrum, or Kanban certification (CSM, PSM, KMP, or equivalent)

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