Senior Delivery Manager (Remote)

Senior Delivery Manager

Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. With more than 20 years in FinTech, we've grown from start-up to industry leader by innovating, simplifying, and valuing people. We are a subsidiary of PROG Holdings (NYSE: PRG), a FinTech holding company with three business segments: Progressive Leasing, Purchasing Power (a leading employee purchase program for consumer products and services using payroll deduction), 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 one of our corporate locations in Utah, Arizona or Colorado

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.

YOU ARE: A technically fluent delivery manager who operates at the team level — close to the work, the risk, and the engineers doing both. You understand the full software development lifecycle, from planning through delivery. You build systems that create predictability, surface risk early, and protect delivery integrity. You influence engineers, product managers, and stakeholders through structure, data, and clear framing.

You are comfortable operating in ambiguity. When dependencies slip, scope pressure mounts, or execution variability surfaces, your instinct is to model the impact, structure the options, and reset expectations with clarity.

You are equally at home in flow-based, service-oriented environments where work is continuous and interrupt-driven as you are in iteration-based teams. You understand that delivery discipline looks different depending on the team operating model, and you adapt your approach accordingly without losing rigor.

You treat AI tools as force multipliers for delivery work by using them to draft communications, model trade-offs, accelerate backlog synthesis, and generate operational artifacts faster than manual methods allow. You have a point of view on where AI augments delivery rigor versus where it creates false confidence, and you apply that judgment deliberately.

YOUR DAY-TO-DAY:

• Delivery System Operations
• Influence and Stakeholder Management
• Technical Fluency
• Service-Oriented Team Operations
• Iteration-Based Team Operations

YOU'LL BRING:

• 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

YOU MIGHT ALSO HAVE:

• 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)

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.