Senior Delivery Manager (Remote)

Progressive Leasing is a leading provider of in‑store and e‑commerce lease‑to‑own solutions. With more than 20years in FinTech, we’ve grown from a start‑up to an 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 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 a work‑from‑home position and can be performed remotely anywhere in the continental U.S. or in one of our corporate locations in Utah, Arizona or Colorado. Employee Value Proposition PROG is dedicated to providing people with opportunities for inclusive collaboration, innovation, and development. Prog Tech is the driving force behind our technological evolution. 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, and 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. RESPONSIBILITIES Delivery System Operations – Maintain and improve delivery visibility across complex, dependency‑heavy work by tracking cross‑team blockers, integration risks, and upstream/downstream exposure; model the impact of scope changes, timeline shifts, and capacity constraints; drive backlog readiness discipline; actively manage delivery risk through surfacing issues proactively; maintain and improve delivery operating norms; leverage AI tooling for operational acceleration. Influence and Stakeholder Management – Influence engineer and product manager behavior through structure and data; frame delivery trade‑offs; partner with Product Managers to enforce readiness standards; communicate delivery feasibility and confidence; socialize production release schedules with teams and advisory processes. Technical Fluency – Maintain fluency in the technical systems your team supports through a solid understanding of integration surfaces, API dependencies, and release risk; coordinate with engineering, QE, architecture, and platform teams to manage cross‑functional dependencies and resolve blockers; apply delivery metrics such as cycle time, throughput, carry‑over, and predictability as operational signals. Service‑Oriented Team Operations – Manage a Kanban‑based delivery system for a team handling a mix of planned work and high‑priority operational demand; balance intake discipline with responsiveness; model WIP impact and context‑switching costs; monitor Kanban flow metrics; coordinate with dependent teams to maintain demand visibility. Iteration‑Based Team Operations – Manage sprint cadence and iteration health across one or more engineering teams; enforce sprint entry discipline; track and improve sprint predictability; manage scope pressure during active sprints; maintain cross‑sprint dependency visibility; run retrospectives as structured operational reviews. YOU’LL BRING 5 to 7 years of delivery management experience 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 carry‑over, 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. Prior experience managing Kanban‑based teams in service‑oriented or platform engineering environments. Demonstrated use of flow metrics (lead time, cycle time, WIP) as day‑to‑day operational tools. Demonstrated use of AI‑assisted tooling to improve delivery throughput or accelerate artifact generation, with discernment to review AI output before stakeholder release. Calm, structured approach to ambiguity and ability 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 to understand release risk. 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 401(k) 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 EEO STATEMENT 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. #J-18808-Ljbffr