Senior Delivery Manager

At Robots & Pencils, we drive digital innovation by building meaningful, scalable software products for forward-thinking clients. We are seeking an experienced and strategic Senior Delivery Manager to lead complex, enterprise-grade programs involving AI-enabled automation, cloud-native platforms, and mobile-first experiences.

This role will lead distributed teams across North America and Eastern Europe and is responsible for aligning delivery execution with client expectations, regulatory constraints, and long-term business outcomes. You will play a critical role in high-impact engagements within highly regulated environments, including utilities and government-adjacent organizations.

This position includes monthly travel to client sites in the U.S. to support relationship building, delivery alignment, and strategic planning.

• Lead high-performing, distributed delivery teams across backend, mobile, web, data, and AI disciplines, fostering accountability, collaboration, and delivery excellence.
• Act as the operational bridge between onshore stakeholders and offshore development teams, ensuring clarity, alignment, and cohesive execution.
• Partner closely with client-side project managers and technical leads, operating as a trusted extension of the client team.
• Provide mentorship and delivery leadership across technologies including iOS (Swift), Android (Kotlin), React, Node.js, .NET, Python, and cloud-native services.
• Encourage cross-disciplinary collaboration and continuous learning across evolving technical stacks.

• Own end-to-end delivery of complex, multi-phase programs, ensuring scope, budget, timelines, quality, and operational readiness are consistently met.
• Lead delivery for systems involving:
  • AI-powered automation (e.g., voice AI, workflow automation)
  • Event-driven architectures
  • Mobile and web portals
  • Enterprise data integrations (e.g., SAP)
• Manage phased releases, production readiness, and transition into operations and maintenance (O&M) models.
• Define, track, and report delivery KPIs, leveraging data-driven insights to guide decision-making and continuous improvement.
• Apply proactive risk management, especially in environments with compliance, security, and operational reliability requirements.

• Serve as the primary delivery contact for clients, building trusted, long-term relationships through transparency, consistency, and strategic insight.
• Navigate complex stakeholder landscapes, including unionized work forces and operational teams that may be skeptical of automation.
• Lead executive-level status updates, roadmap discussions, and escalation management.
• Translate complex technical initiatives—such as AI-driven call automation and cloud modernization—into clear business value.
• Travel monthly to client sites to support relationship-building, alignment, and strategic planning.

• Partner with architects and technical leads to align delivery execution with AWS-first, cloud-native architectures.
• Oversee delivery of systems leveraging:
  • AWS Lambda, API Gateway, Dynamo
    
    DB (single-table design), Amazon Connect
  • Voice AI technologies (e.g., Amazon Nova 2 Sonic)
  • Web Socket APIs, AWS Cognito, and event-driven services
  • React-based web portals and mobile applications (React Native or native iOS)
• Ensure seamless integration with enterprise systems such as SAP and third-party services (e.g., Twilio).
• Support observability and monitoring strategies using tools such as Langfuse, logging, and metrics frameworks.
• Balance innovation with reliability, security, and compliance requirements.

• Continuously evolve agile delivery practices (Scrum, SAFe, Kanban) to support distributed teams and enterprise clients.
• Identify and remove delivery bottlenecks using tools such as Jira, Confluence, Git Hub, and Azure Dev Ops.
• Champion automation, CI/CD pipelines, and quality-first engineering practices.
• Foster a culture of transparency, accountability, and continuous improvement across Pods.

• 12+ years in software delivery,…