Senior Director, Digital Transformation (Remote) @ Progressive Leasing - Philadelphia, PA

Job Overview

2 months ago

Senior Director, Digital Transformation (Remote)

Progressive Leasing - Philadelphia, PA

Job Description:
Progressive Leasing is hiring a Senior Director of Software Engineering (Remote) to lead our Digital Transformation. Reporting to the Chief Information Officer, you will be a critical member of the development team. This role is responsible for strategic transformation plan design, tactical execution, and implementation of the company-wide digital solutions to improve employee and customer experiences, operational efficiency, and productivity.

This role can be worked remotely anywhere in the US, or work out of either of our 2 office locations which are located in Draper, UT and Glendale, AZ.

The Sr. Director role is accountable for the realization of all tactical and strategic engineering initiatives within their specialized area of focus. They implement contingency and redundancy plans for resources within their purview and align with Governance teams. They oversee the resolution of production issues, follow-on root cause analysis and remediation, ensure quality integration and collaborate with other senior leaders to devise project prioritization strategies. They operate in a hybrid environment, including on-prem, public cloud (i.e. AWS, Azure, GCP, etc.), and SaaS/PaaS partners. The Sr. Director will partner and work closely with leaders to ensure alignment with Company, Product and Technology OKRs. As a Director, they are accountable for the consistency in quality, overall performance, engineering soundness, security, execution of sprints, support, and maintenance of all software engineering initiatives and projects. They participate in scrum ceremonies, project design discussions, business discussions, code reviews, and even the hands-on creation or modification of software.

Above all, this position is a leadership role. They directly lead software engineering teams and collaborate with leaders from other teams (e.g., Product Management, Security, Infrastructure, Accounting and Operations), to make engineering decisions, work through issues, and set strategy.

  • Create and implement digital transformation roadmap and strategy
  • Own the vendor landscape and the relationships across the digital ecosystem. This individual is responsible for ensuring we have the right vendors, at the right time, and the strategic partnerships are assessed on a regular basis. When priorities need to be made across projects, the digital transformation leader will lead the process
  • Balance approaches in the context of performance, stability and business value/impact and determine the best course forward
  • Foster the development and maintenance of common engineering approaches consistent with organizational standards and industry best practices
  • Establish and maintain a balanced iteration cadence with a professional level of quality across all sprints
  • Ensure that software engineering team leaders and team members have the resources necessary to be productive and effective
  • Establish and manage team budget, proactively escalating exceptions as necessary
  • Understand cloud product development, managed cloud services, and able to provide technical and strategic feedback on improvements to the cloud product strategy total cost of ownership
  • Continually improve cloud deployment practices to enable shorter release cycles
  • Work side by side with technology leaders to keep the software engineering roadmap aligned to company goals
  • Work with other technology and business leaders to plan and execute skills training, team development or other enrichment for the team
  • Ensure that incident and change management, security, and engineering policies, standards, and procedures are followed
  • Set and manage team and individual goals as required
  • Maintain the integrity and efficiency of software engineering processes
  • Prepare and conduct performance reviews
  • All duties required related to hiring, coaching and separation of team members
  • Ensure laws, company policies, practices and procedures are followed by team members
  • All other duties as required
  • 10+ years of experience in leading problem resolution, issue remediation, and IT deployments
  • 10+ years of experience working with senior business leaders on a daily/weekly basis
  • 10+ years of experience in hands-on software development or engineering
  • 8+ years of senior leadership experience in the fields of Software Engineering, Enterprise Software Architecture, or Software Project Management, leading a team of 30 or more team
  • 8+ years of experience performing performance reviews
  • 4+ years working in a cloud-first environment, including experience with AWS, Azure, GCP or similar
  • 4+ years of experience in modern software practices like agile or scrum
  • Digital transformation experience
  • Authentication, React and Microservices experience
  • Experience integrating SaaS solutions into product pipelines
  • Experience with cloud-based API management
  • Hands-on experience in a multitude of domains, including agile development, business analysis, software engineering, database design, enterprise software architecture, technology leadership, and software quality assurance
  • Extensive and relevant experience prioritizing the work of others, challenging and resolving interruptions to prioritized work, resolving interpersonal conflict, and motivating and organizing teams
  • Hands-on technical experience solving business problems in, but not limited to one or more of the following business areas: Operations, Accounting and Finance, Sales, Order Management, Payment Processing, Back Office Systems, and/or Business Process Re-Engineering or Development
  • Demonstrated solid understanding of scalable technology architectures
  • Master’s degree or equivalent documented experience is required
  • Competitive Compensation; Eligible for STI + LTI
  • Full Health Benefits; Medical/Dental/Vision/Life Insurance + Paid Parental Leave
  • Company Matched 401k
  • Paid Time Off + Paid Holidays + Paid Volunteer Hours
  • Diversity Alliance Resource Groups
  • Employee Stock Purchase Program
  • Tuition Reimbursement
  • Charitable Gift Matching
  • Job required equipment and services


Progressive Leasing (NYSE: PRG) is the largest and longest-tenured virtual lease-to-own provider in the United States. The Company’s mission is to provide simple and affordable purchase options for credit challenged consumers. Over the last 20+ years, Progressive Leasing’s alternative lease-purchase options have helped millions of customers with less than perfect credit acquire needed items with ease. Progressive partners with 30,000 retail stores, helping to drive increased revenue and improve customer satisfaction. Learn more at

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.

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