Senior Project 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 seeking a Senior Project Manager to drive the successful execution of high-impact, cross-functional technology initiatives. This role will be responsible for managing complex projects that span multiple teams, business units, and systems, ensuring structured planning, efficient execution, and successful delivery. The Project Manager will work closely with Product, Engineering, and Business stakeholders to define project scope, establish clear deliverables, and proactively mitigate risks. While not all projects require an Agile approach, familiarity with Agile and hybrid methodologies will be essential for success. The ideal candidate thrives in complexity, enjoys managing dependencies, and has a proven track record of successfully leading initiatives that involve intricate technical landscapes, regulatory considerations, and multiple stakeholder groups.

Your Day To Day

• Lead the planning, execution, and delivery of technology-driven projects, ensuring successful completion within scope, schedule, and budget.
• Manage multiple workstreams with interdependencies, navigating competing priorities and complex stakeholder landscapes.
• Develop and maintain project plans, tracking key milestones, risks, and constraints.
• Ensure teams follow structured project governance and decision-making frameworks.
  
  

Stakeholder Alignment & Communication

• Act as the primary liaison between technology and business stakeholders, ensuring alignment on objectives, timelines, and resource needs.
• Provide clear and concise project updates, including risk assessments and issue escalations, to senior leadership.
• Facilitate cross-functional collaboration between Engineering, Product, Compliance, Finance, and Operations teams.
  
  

Risk & Change Management

• Proactively identify project risks, dependencies, and constraints, implementing mitigation strategies before they become blockers.
• Ensure structured change control processes are followed to manage scope adjustments and business-critical changes effectively.
• Work closely with regulatory, security, and compliance teams to ensure adherence to required standards.
  
  

Process Optimization & Continuous Improvement

• Implement best practices in project management, leveraging both Agile and structured delivery methodologies.
• Continuously assess and refine project management processes to drive efficiency, visibility, and predictability.
• Champion documentation and knowledge-sharing practices to improve future project execution.
  
  

Project Governance & Reporting

• Track and report on project performance using key metrics, ensuring transparency in progress, risks, and outcomes.
• Ensure adherence to the company’s Project Management Lifecycle (PMLC) and governance frameworks.
• Partner with Finance to ensure accurate project forecasting and financial tracking.
  
  

You'll Bring

• 5 years of experience managing complex technical projects in a technology-driven environment, with a focus on enterprise-scale systems, platforms, or integrations.
• Experience managing cross-functional initiatives with multiple dependencies, including software development, infrastructure, security, and business process changes.
• Strong ability to manage competing priorities in a fast-paced environment, balancing short-term tactical needs with long-term strategic objectives.
• Hands-on experience with Jira, Confluence, or other project management tools to track project execution, dependencies, and risks.
• Excellent problem-solving, communication, and negotiation skills, with the ability to build trust with both technical and business stakeholders.
• Strong preference for candidates with experience managing large-scale technology implementations such as enterprise software, cloud migrations, data platform transformations, or regulatory-driven initiatives.
• Preferred: PMP, PMI-ACP, or Certified Scrum Master (CSM) certification, but not required.
  
  

What We Offer

• Competitive Compensation
• Full Health Benefits; Medical/Dental/Vision/Lif 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
  
  

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.