Senior Delivery Manager

Robots and Pencils; Remote; CAD 120,000 - 150,000; Full time

Job summary

A technology firm in Canada seeks an experienced Senior Delivery Manager to lead enterprise-grade programs focusing on AI and cloud transformation. This role involves managing distributed teams, ensuring strategic alignment, and fostering client relationships. Candidates should have over 12 years of software delivery experience, strong capabilities in cloud-native architectures, and exceptional communication skills. Join to influence high-impact projects and drive business results with technology.

Benefits

Professional development opportunities

Flexible work arrangements

Health and wellness benefits

Qualifications

• 12+ years in software delivery, technical program management, or engineering leadership.
• 5+ years managing distributed teams across onshore and offshore locations.
• Strong understanding of cloud-native architectures and AI-enabled workflows.
• Hands-on familiarity with delivery tooling like Jira and GitHub.

Responsibilities

• Lead high-performing, distributed delivery teams across various disciplines.
• Own end-to-end delivery of complex, multi-phase programs.
• Serve as the primary delivery contact for clients.
• Partner with architects and technical leads for delivery execution.

Skills

Cloud-native architectures

AI-enabled workflows and automation

Exceptional client-facing communication

Managing distributed teams

Agile delivery practices

Education

PMP, Scrum Master, SAFe, or equivalent certifications

Tools

Jira

GitHub

Azure DevOps

Job description

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

• 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
• 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:
• 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).
• 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 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.

Note: This description excludes application form prompts and unrelated postings.