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 

• 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. 

Process Optimization & Delivery Excellence 

• 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, GitHub, and Azure DevOps. 

• Champion automation, CI/CD pipelines, and quality-first engineering practices. 

• Foster a culture of transparency, accountability, and continuous improvement across Pods. 

Required Skills & Experience 

• 12 years in software delivery, technical program management, or engineering leadership. 

• 5 years managing distributed teams across onshore and offshore locations (Eastern Europe experience preferred). 

• Proven success delivering complex, regulated, multi-platform systems in agile environments. 

• Strong understanding of: 

• Cloud-native architectures (AWS preferred) 

• AI-enabled workflows and automation 

• Enterprise integrations and data systems 

• Hands-on familiarity with delivery tooling including Jira, GitHub, Azure DevOps, CI/CD pipelines, and cloud observability tools. 

• Exceptional client-facing communication skills with experience working in high-stakes, compliance-oriented environments. 

• Ability to operate consultatively thinking beyond immediate deliverables to long-term client outcomes. 

• PMP, Scrum Master, SAFe, or equivalent certifications are strongly preferred. 

Personal Attributes 

• Client-Centric & Strategic: Builds trust and aligns delivery to real business and operational outcomes. 

• Calm Under Pressure: Comfortable leading through ambiguity, scrutiny, and high-impact decision-making. 

• Collaborative & Empathetic: Effective working across cultures, time zones, and diverse stakeholder groups. 

• Outcome-Oriented: Holds teams accountable while enabling sustainable delivery. 

• Consultative Leader: Thinks beyond “what to build” to “why it matters” and “how it lands.” 

• Adaptable & Proactive: Anticipates risk, navigates resistance, and leads to change thoughtfully. 

Why Join Robots & Pencils? 

We blend strategy, design, and engineering to craft technology that transforms businesses and improves human experiences. As a Senior Delivery Manager, you’ll lead high-impact AI and cloud transformation programs, work alongside world-class technologists, and help clients modernize critical systems with confidence, clarity, and care.