Senior Delivery Manager (Remote)

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

• 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 by presenting structured options with clear trade-offs to decision-makers

• Drive backlog readiness discipline, ensuring work entering execution is well-defined and dependency-mapped before it starts

• Identify and actively manage delivery risk through surfacing issues proactively, quantifying impact, and framing resolution paths for engineering and product leadership

• Maintain and improve delivery operating norms that reduce rework, carryover, and execution variability over time

• Leverage AI tooling to accelerate operational work, including status synthesis, risk narrative generation, and backlog readiness summarization, while maintaining human judgment on prioritization and stakeholder framing decisions.

Influence and Stakeholder Management

• Influence engineer and product manager behavior through structure and data by driving accountability and shared clarity on delivery commitments

• Frame delivery trade-offs clearly by presenting structured options with explicit implications on timeline, quality, and capacity

• Partner with Product Managers to enforce readiness standards and protect delivery integrity when scope pressure mounts

• Communicate delivery feasibility and confidence clearly to the engineering team and partnering Project Managers by providing early warning when assumptions change and surfacing recovery options when they do

• Socialize production release schedules in advance with the development team, Product Manager, and relevant change advisory processes ensuring the team is prepared for releases

Technical Fluency

• Maintain working fluency in the technical systems your