Senior Project Manager

OverviewOur client, a Fortune 100 insurance organization, is looking for a Senior Project Manager to support a large-scale digital transformation initiative. This role sits within a high-impact program focused on building a unified internal platform that enables agents and advisors to access and manage client engagement in a centralized experience.As a Senior Project Manager, you will operate as a senior individual contributor responsible for driving delivery across multiple workstreams in a complex, fast-paced environment. This is an opportunity to lead highly visible initiatives while gaining access to DRUM’s Upskill Program, which provides ongoing professional development, industry exposure, and executive mentorship.ResponsibilitiesOwn end-to-end delivery of large-scale, cross-functional programs within a complex enterprise environmentDefine and drive program roadmaps, milestones, and execution strategy across multiple workstreamsPartner with business, product, and engineering stakeholders to align priorities and ensure successful deliveryLead Agile ceremonies and ensure consistent execution across 1–2 week sprint cyclesManage risks, dependencies, and blockers; proactively escalate and drive resolutionCoordinate across multiple vendors and internal teams to ensure alignment and accountabilityProvide clear, concise communication to senior leadership and executive stakeholdersEstablish and maintain program governance, reporting, and documentation using tools like JiraOperate effectively in an evolving, early-stage environment with shifting prioritiesQualifications7–12+ years of experience in project or program management within enterprise technology environmentsProven experience owning and delivering large-scale, cross-functional IT initiatives end-to-endExperience working in Agile environments with strong proficiency in Jira and related toolsDemonstrated ability to manage multiple workstreams, stakeholders, and competing prioritiesStrong executive communication and stakeholder management skillsExperience working in fast-paced, ambiguous environments, ideally supporting early-stage or MVP product buildsBackground in insurance or financial services is a plusBachelor’s degree requiredAbout the DRUM Upskill ProgramThe DRUM Upskill Program provides full-time employment with DRUM while you work on impactful initiatives with leading organizations. In addition to hands-on experience, you will gain access to:Executive-level mentorship and coachingIndustry-specific advisors and technical guidanceOngoing professional development and upskilling opportunitiesA pathway to long-term career growth and potential conversion opportunities