Implementation Project Manager-Enterprise Project Rollout (Chicago)

Employment Type: 3 Month contract About Jobba At Jobba Trade Technologies, we build purpose-built software solutions that power the roofing and specialty construction industries. We operate as an agile, fast-paced technology company where every team member has a direct, visible impact on the growth of our platform and the success of our contractors. Role Overview We are seeking a dedicated, highly organized Implementation Project Manager to take sole operational ownership of our high-priority enterprise project. This is a 3 month contractor role. Currently, key project deliverables are distributed across distinct functional groups—including Engineering, DevOps, Product, and Customer Success. In this role, you will centralize project command—unifying departmental workflows, tracking milestone progress, eliminating operational bottlenecks, and ensuring seamless execution leading up to and beyond cutover. Key Responsibilities Centralized Project Command : Consolidate deliverables across Engineering, DevOps, Product, Customer Success, and client stakeholders into a single, authoritative master project plan. Milestone & Deliverable Tracking : Actively manage workstreams for core Jobba platform rollouts, business unit configurations, customer/property data imports, and document template generation. Integration Oversight : Drive progress on critical technical workstreams, including REST APIs, CRM triggers, Accounting integration, and Enterprise Data Warehouse (EDW) reporting pipelines. Risk Mitigation & Escalation : Identify operational dependencies, technical blockers, and capacity constraints across teams early; implement mitigation strategies to protect target launch timelines. Cross-Departmental Governance : Facilitate regular cross-functional syncs, sprint alignment sessions, and executive status reviews to ensure full organizational clarity. Go-Live Cutover & Transition : Coordinate final production cutover activities, User Acceptance Training (UAT), user profile provisioning, and post-launch support handoffs. Qualifications & Requirements Experience : 3–5+ years of experience managing complex SaaS implementations, enterprise software rollouts, or technical customer onboarding lifecycles. Cross-Functional Leadership : Proven success in bringing together disparate technical and business teams (Product, Engineering, DevOps, CS) under a single project structure. Technical Aptitude : Solid understanding of B2B SaaS architecture, API integration workflows, data migration pipelines, and enterprise software release cycles. Tools & Methodologies : Strong background in Agile/Scrum methodologies and hands-on experience with project management tools Industry Background (Preferred) : Experience in construction technology, commercial trades, field service management software, or ERP integrations (e.g., Viewpoint Vista) is a major plus. Communication Skills : Outstanding verbal and written communication skills, with the ability to lead technical deep-dives as well as deliver concise executive status reports. Jobba Trade Technologies