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. 

 

Key Responsibilities 

Team Leadership & Coordination 

• 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. 

 

Project & Program Delivery 

• 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. 

 

Client Engagement & Stakeholder Management 

• 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 workforces 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. 

 

Technical Oversight & Strategic Enablement 

• 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, DynamoDB (single-table design), Amazon Connect 

• Voice AI technologies (e.g., Amazon Nova 2 Sonic) 

• WebSocket APIs, AWS Cognito, and event-driven services