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 ColoradoEmployee 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 AreA 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-dayDelivery System OperationsMaintain and improve delivery visibility across complex, dependency-heavy work by tracking cross-team blockers, integration risks, and upstream/downstream exposureModel the impact of scope changes, timeline shifts, and capacity constraints by presenting structured options with clear trade-offs to decision-makersDrive backlog readiness discipline, ensuring work entering execution is well-defined and dependency-mapped before it startsIdentify and actively manage delivery risk through surfacing issues proactively, quantifying impact, and framing resolution paths for engineering and product leadershipMaintain and improve delivery operating norms that reduce rework, carryover, and execution variability over timeLeverage 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 ManagementInfluence engineer and product manager behavior through structure and data by driving accountability and shared clarity on delivery commitmentsFrame delivery trade-offs clearly by presenting structured options with explicit implications on timeline, quality, and capacityPartner with Product Managers to enforce readiness standards and protect delivery integrity when scope pressure mountsCommunicate 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 doSocialize production release schedules in advance with the development team, Product Manager, and relevant change advisory processes ensuring the team is prepared for releasesTechnical FluencyMaintain working fluency in the technical systems your team supports through a solid understanding of integration surfaces, API dependencies, and release risk in contextCoordinate across engineering, QE, architecture, and platform teams to manage cross-functional dependencies and resolve blockers at the right levelApply delivery metrics (i.e. cycle time, throughput, carryover, predictability) as operational signals that drive structural change in how the team worksService-Oriented Team OperationsManage a Kanban-based delivery system for a team handling a mix of planned work and high-priority operational demandBalance intake discipline with responsiveness by maintaining flow efficiency while protecting planned delivery commitments from reactive work pressureModel WIP impact and context-switching costs to protect team throughput and focusMaintain and improve intake and triage processes that bring structure to interrupt-driven work without creating bureaucratic overheadMonitor Kanban flow metrics (i.e. lead time, cycle time, and queue depth) to identify bottlenecks and maintain healthy throughputCoordinate with dependent teams and platform consumers to maintain demand visibility and set clear expectations proactivelyIteration-Based Team OperationsManage sprint cadence and iteration health across one or more engineering teams with a focus on commitment reliability and sprint goal integrityEnforce sprint entry discipline by ensuring stories meet sizing and readiness standards before planning begins, and holding the line when they don’tTrack and improve sprint predictability using carryover, velocity trends, and planning accuracy as signals to adjust how the team operatesManage 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 shiftMaintain cross-sprint dependency visibility across teams or workstreams, identifying what is at risk and whenRun retrospectives as structured operational reviews by identifying systemic delivery friction and driving follow-through on changesYou’ll Bring5 to 7 years of delivery management experience embedded within software engineering teams in a fintech or similarly regulated, technically complex environmentDemonstrated ability to influence engineer and product manager behavior through structure, data, and clear framingProven experience building or materially improving delivery systems: reducing carryover, improving commitment reliability, or increasing planning quality through structural changesExperience modeling delivery trade-offs and presenting structured options to leadershipDeep SDLC fluency, including integration complexity, release management, dependency modeling, and cross-team coordinationStrong working knowledge of Jira for dependency tracking, delivery modeling, and operational insightComfort operating in API-heavy, integration-dependent backend environments where delivery risk lives in the connections between systemsPrior experience managing Kanban-based teams in service-oriented or platform engineering environmentsDemonstrated use of flow metrics (i.e. lead time, cycle time, WIP) as day-to-day operational tools for managing team health and throughputDemonstrated 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 changeStrong written and verbal communication skills, including the ability to frame engineering consequences clearly for non-technical stakeholdersBachelor’s degree or equivalent experienceYou Might Also HavePrior experience managing sprint-based teams, including planning discipline, Definition of Ready enforcement, and iteration health managementWorking knowledge of CI/CD pipelines, deployment infrastructure, or cloud services sufficiently enough to understand release risk and coordinate across platform teamsExperience coordinating across both iterative (sprint-based) and continuous-flow (Kanban) teams within the same organizationFamiliarity with ServiceNow or similar change management tooling in a governed release environmentExperience supporting offshore or distributed engineering teams with uneven execution maturityAgile, Scrum, or Kanban certification (CSM, PSM, KMP, or equivalent)We OfferCompetitive CompensationFull Health Benefits; Medical/Dental/Vision/Life Insurance + Paid Parental LeaveCompany Matched 401kPaid Time Off + Paid Holidays + Paid Volunteer HoursEmployee Resource Groups (Black Inclusion Group, Women in Leadership, PRIDE, Adelante)Employee Stock Purchase ProgramTuition ReimbursementCharitable Gift MatchingJob required equipment and servicesProgressive 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.