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 team supports through a solid  understanding of integration surfaces, API dependencies, and release risk in context

• Coordinate across engineering, QE, architecture, and platform teams to manage cross-functional dependencies and resolve blockers at the right level

• Apply delivery metrics (i.e. cycle time, throughput, carryover, predictability) as operational signals that drive structural change in how the team works

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 by maintaining flow efficiency while protecting planned delivery commitments from reactive work pressure

• Model WIP impact and context-switching costs to protect team throughput and focus

• Maintain and improve intake and triage processes that bring structure to interrupt-driven work without creating bureaucratic overhead

• Monitor Kanban flow metrics (i.e. lead time, cycle time, and queue depth) to identify bottlenecks and maintain healthy throughput

• Coordinate with dependent teams and platform consumers to maintain demand visibility and set clear expectations proactively

Iteration-Based Team Operations

• Manage sprint cadence and iteration health across one or more engineering teams with a focus on commitment reliability and sprint goal integrity

• Enforce sprint entry discipline by ensuring stories meet sizing and readiness standards before planning begins, and holding the line when they don’t

• Track and improve sprint predictability using carryover, velocity trends, and planning accuracy as signals to adjust how the team operates

• Manage scope pressure during active sprints through modeling the impact of additions or changes and presenting clear trade-off options to the Product Manager before commitments shift

• Maintain cross-sprint dependency visibility across teams or workstreams, identifying what is at risk and when

• Run retrospectives as structured operational reviews by identifying systemic delivery friction and driving follow-through on changes

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

• AI‑enabled tools are already part of how work gets done across our organization, and their use will continue to expand over time. We value people who are curious, adaptable, and open to learning as roles and workflows evolve.

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.