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 distributed teams across North America and Eastern Europe. This role requires a strong command of agile delivery practices, cross-cultural collaboration, and technical program leadership. You will be responsible for ensuring successful outcomes across complex engagements by aligning delivery execution with client expectations, business objectives, and quality standards.

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 teams spanning mobile, backend, data, and AI disciplines, fostering a culture of excellence, accountability, and collaboration.
• Act as the operational bridge between onshore stakeholders and offshore development teams, ensuring clear communication, alignment, and cohesive execution.
• Provide mentorship and strategic guidance to delivery leaders, project managers, and engineers across iOS (Swift), Android (Kotlin), .NET, and technologies.
• Encourage continuous learning and cross-disciplinary collaboration to maintain cutting-edge technical delivery across evolving tech stacks.

Project & Program Delivery

• Own end-to-end delivery of multiple concurrent client engagements, ensuring scope, budget, timeline, and quality benchmarks are consistently met.
• Oversee integration of complex systems leveraging SQL Server, Oracle, Azure DevOps, GitHub, and CI/CD pipelines.
• Define and track delivery KPIs, using data-driven insights to inform strategy and continuous improvement.
• Apply proactive risk management and scenario planning to anticipate and resolve delivery challenges before they impact outcomes.

Client Engagement & Relationship Management

• Serve as the primary client contact for delivery matters, building trusted, long-term relationships through transparent communication, strategic insight, and consistent execution.
• Lead regular client check-ins and executive briefings to communicate progress, surface opportunities, and align roadmaps.
• Translate complex technical details into clear business value, ensuring clients understand how technical delivery supports strategic objectives.
• Travel monthly to client sites to strengthen relationships, align expectations, and drive partnership success.

Technical Oversight & Strategic Enablement

• Partner with technical leads and architects to align engineering decisions with business goals and scalable architecture strategies.
• Provide oversight for technical initiatives involving modern mobile development, .NET and microservices, and AI-driven enhancements built with Python, TypeScript, and Azure OpenAI.
• Advocate for the use of Figma for product design collaboration, Radar/GeoMoby for geofencing, and Oracle Recruiting Booster and Dropbox Sign for enterprise integrations.
• Support architecture and design reviews, ensuring decisions balance innovation, performance, and maintainability.

Process Optimization & Delivery Excellence

• Continuously improve agile frameworks and delivery methodologies (Scrum, SAFe, Kanban) to maximize distributed team performance.
• Identify and address delivery bottlenecks using tools such as Jira, Confluence, and Azure DevOps to optimize throughput and accountability.
• Champion automation, CI/CD adoption, and quality-first engineering principles.
• Foster a culture of continuous improvement, transparency, and cross-team collaboration.

Required Skills & Experience

• 12+ years in software development or technical delivery, including 5+ years managing distributed teams across onshore/offshore locations (Eastern Europe experience preferred).
• Proven success delivering complex, multi-platform projects in agile environments.
• Deep understanding of the SDLC, agile practices, cloud architecture (Azure preferred), and enterprise integrations.
• Hands-on familiarity with tools such as Azure DevOps, GitHub, Jira, Confluence, SQL Server, Oracle, and modern mobile development frameworks.
• Ability to leverage data, delivery metrics, and performance dashboards to guide decisions and improve delivery health.
• Strong technical acumen with an ability to contribute meaningfully to architecture discussions.
• Excellent communication and stakeholder management skills; comfortable engaging at executive and engineering levels.
• PMP, Scrum Master, or equivalent certifications are highly desirable.

Personal Attributes

• Client-Centric & Strategic: Builds trusted partnerships, aligning technical execution with business impact.
• Accountable & Outcome-Focused: Owns delivery success and drives measurable results.
• Calm Under Pressure: Maintains composure and clarity in complex, high-stakes environments.
• Collaborative Leader: Inspires confidence and unites cross-functional teams around shared goals.
• Adaptive & Proactive: Anticipates challenges, adjusts quickly, and leads through ambiguity.
• Communicative & Empathetic: Excels in transparent, human-centered communication across time zones and cultures.
• Innovative Problem-Solver: Brings creative, data-informed solutions that balance technology, design, and business needs.

Why Join Robots & Pencils?
We blend strategy, design, and engineering to craft technology that transforms businesses and enriches human experiences. As a Senior Delivery Manager, you'll play a pivotal role in delivering impactful digital products that redefine success for our clients. You'll collaborate with global experts across mobile, web, AI, and enterprise systems—turning bold ideas into real-world innovation with speed, precision, and excellence.