Senior Delivery Manager - Remote

Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. As an almost 20+ year old FinTech company that has gone from start-up to industry leader, we know how to innovate, simplify, and value all people. We are a company founded on our grit and we are constantly looking to the future. As an ever-evolving group of entrepreneurs and technologists, we strive to do the right thing period in all aspects of our work. We are a subsidiary of PROG Holdings (NYSE: PRG), an exciting FinTech holding company, with three business segments including Progressive, Vive Financial, and Four, a Buy Now Pay Later (BNPL) platform.

We are currently hiring a Senior Delivery Manager to help grow our company and ensure our mission is achieved!     

This role is work from home position and can be performed remotely anywhere in the continental US or in 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. 

WE ARE: Prog Tech is the driving force behind our company’s technological evolution. We are passionate problem solvers and technical experts, working together to deliver impactful solutions. We pride ourselves on craftsmanship, continuous improvement, and collaboration. Our culture encourages experimentation, learning from failures, and delivering meaningful outcomes. 

We are seeking a Delivery Manager to drive the successful execution of technology initiatives across multiple software development teams within our organization. This role is responsible for coordinating project execution, tracking progress, managing dependencies, and ensuring the efficient delivery of software solutions. The Delivery Manager will work closely with Product, Engineering, Enterprise Technology, and Business stakeholders to support teams in structured planning, execution, and continuous improvement. While we do not operate in a traditional Agile-only environment, we leverage two-week sprint cycles and a Scrum team structure. The ideal candidate will be able to facilitate key team ceremonies while ensuring overall delivery excellence.

YOUR KEY RESPONSIBILITIES: 

Delivery Management

• Oversee end-to-end delivery of technology initiatives, ensuring successful execution across multiple teams.
• 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 that 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 key performance indicators (KPIs) to measure delivery success, including:
• Completion vs Commitment % (Target: ≥80%)
• Cycle Time Average (Target: <10 workdays)
• Sprint Backlog Horizon (Target: ≥3 sprints of ready work)
• On-Time Vulnerability Remediation (Target: 100%)
• Use data and insights to identify trends, gaps, and areas for improvement.

QUALIFICATIONS: 

• 3+ years of experience in project delivery, program management, or related roles in a technology-driven organization.
• Experience working with both 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) certification, but not required.

WHY JOIN US?

• Work on high-impact technology initiatives in a growing fintech organization.
• Opportunities for career growth within a publicly traded company.
• Flexible work options, including remote/hybrid work.
• Influence key projects and drive meaningful change.

WE OFFER:     

• Competitive Compensation 

• Full Health Benefits; Medical/Dental/Vision/Life Insurance + Paid Parental Leave 

• Company Matched 401k 

• Paid Time Off + Paid Holidays + Paid Volunteer Hours 

• Employee Resource Groups (Black Inclusion Group, Women in Leadership, PRIDE, Adelante) 

• Employee Stock Purchase Program 

• Tuition Reimbursement 

• Charitable Gift Matching 

• Job required equipment and services 

Progressive Leasing welcomes and encourages diversity in the workplace. We do not discriminate in any aspect of employment on the basis of race, color, religion, national origin, ancestry, gender, sexual orientation, gender identity and/or expression, age, veteran status, disability, or any other characteristic protected by federal, state, or local employment discrimination laws where Progressive Leasing does business.