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.