Senior Delivery Manager - Remote

Overview

Join to apply for the Senior Delivery Manager - Remote role at Progressive Leasing

Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. As an almost 20-year-old Fin Tech company, we innovate, simplify, and value all people. We are a subsidiary of PROG Holdings (NYSE: PRG), with three business segments including Progressive, Vive Financial, and Four, a Buy Now Pay Later (BNPL) platform. This role is work from home and can be performed remotely anywhere in the continental US or at our corporate office in Utah.

Employee Value Proposition (EVP): PROG is dedicated to providing people with opportunity — opportunity for inclusive collaboration, opportunity for innovation, and opportunity for development.

Prog Tech is the driving force behind our company’s technological evolution. We are problem solvers and technical experts who deliver meaningful outcomes. We value craftsmanship, continuous improvement, and collaboration, and we encourage experimentation and learning from failures.

• Oversee end-to-end delivery of technology initiatives across multiple teams, ensuring successful execution.
• Work with Product Managers and Engineering Leaders to define roadmaps, set expectations, and track progress.
• Create and maintain delivery plans, capturing dependencies, risks, and blockers.
• Support teams in managing work within Jira and other project tracking tools.

• Facilitation of Key Team Ceremonies

• Daily Stand-ups — Ensure visibility into work-in-progress and unblock teams as needed.
• Sprint Planning — Help teams scope and prioritize upcoming work for the next sprint.
• Backlog Refinement — Collaborate with Product Managers and Engineering to ensure work is well-defined and estimated.
• Sprint Retrospectives — Guide teams in reviewing and improving delivery processes over time.

• Process Optimization & Continuous Improvement

• Ensure teams follow structured planning, execution, and tracking processes, adjusting approaches as needed.
• Leverage a mix of iterative (Agile) and structured (Waterfall) methodologies, tailoring processes to fit project complexity.
• Help teams break down work into manageable increments and track deliverables against business objectives.
• Identify and drive opportunities for efficiency improvements across teams and functions.

• Stakeholder Communication & Reporting

• Provide weekly status updates to leadership on key initiatives, highlighting progress, risks, and mitigation plans.
• Act as the point of contact between technical teams and business stakeholders, ensuring alignment and expectation-setting.
• Manage cross-team dependencies and proactively remove blockers that could impact delivery timelines.

• Performance & Metrics Tracking

• Track and report on KPIs to measure delivery success, including:
  Completion vs Commitment (%), Cycle Time (days), Sprint Backlog Horizon, On-Time Vulnerability Remediation.
• Use data and insights to identify trends, gaps, and areas for improvement.

• 3+ years of experience in project delivery, program management, or related roles in a technology-driven organization.
• Experience with cloud and on-prem infrastructure management teams.
• Experience managing multiple teams and cross-functional projects using a mix of Agile, iterative, and structured delivery approaches.
• Strong ability to facilitate key team ceremonies, track dependencies, and mitigate risks in complex technology initiatives.
• Hands-on experience with Jira, Confluence, or other project management tools.
• Excellent stakeholder management, problem-solving, and communication skills.
• Preferred: PMP, PMI-ACP, or Certified Scrum Master (CSM); not required.

• Work on high-impact technology initiatives in a growing fintech organization.
• Opportunities for career…