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 Fin Tech, 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 Fin Tech 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.

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.

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.

• 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…