Senior Delivery Manager

Robots and Pencils

12d

About The Position

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. Some engagements may also involve leading discovery and operational documentation initiatives for education clients. These initiatives focus on developing a clear understanding of how work is currently performed across organizations by mapping end-to-end operational and student journey processes. This foundational work helps support future transformation initiatives, including the responsible adoption of AI-enabled capabilities.

Requirements

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 projects in agile environments, meeting demanding timelines and quality expectations.
Deep understanding of the Software Development Lifecycle (SDLC), agile practices (Scrum, SAFe, Kanban), and modern cloud architectures.
Strong familiarity with common tools: Jira, Confluence, Trello, Git, CI/CD pipelines.
Ability to leverage delivery metrics and performance data to inform strategies and optimize outcomes.
Strong technical acumen, with the ability to contribute to architectural discussions and understand engineering constraints.
Exceptional interpersonal and stakeholder management skills; confident managing executive-level relationships and escalations.
Experience managing delivery teams across multiple time zones and geographies.

Nice To Haves

PMP, Scrum Master, or other relevant technical/project management certifications are highly desirable.
Experience working with education or higher education environments, or leading complex discovery and operational documentation engagements, is a strong plus.

Responsibilities

Lead high-performing distributed delivery teams, fostering a culture of excellence, accountability, and collaboration.
Act as the operational bridge between onshore stakeholders and offshore development teams, ensuring clear communication and cohesive execution.
Provide mentorship and guidance to delivery leaders, project managers, and engineers.
Own the end-to-end delivery of multiple concurrent client engagements, ensuring scope, budget, timeline, and quality benchmarks are consistently met.
Define and track delivery of KPIs, using data to drive decision-making and continuous improvement.
Manage project execution with a proactive risk management approach, resolving issues before impacting outcomes.
Lead discovery and process-mapping initiatives that document current operational workflows and end-to-end journeys, particularly in education environments where understanding student lifecycle processes is critical.
Serve as the primary client in contact for delivery-related matters, building trusted, long-term relationships through transparent communication and consistent results.
Conduct regular client check-ins and executive briefings to report on progress, blockers, and strategic opportunities.
Travel to client sites (minimum once per month) to align goals, gather feedback, and support project success.
Facilitate workshops and working sessions with stakeholders to gather insights, document operational processes, and align on delivery outcomes.
Partner with technical leads and architects to ensure alignment between delivery execution and technical vision.
Advocate for modern engineering practices, tooling, and automation strategies that improve delivery velocity and quality.
Support architecture and design discussions as needed to unblock teams and ensure sound decision-making.
Where applicable, leverage internal AI tools or models to support documentation, workflow analysis, and delivery efficiency.
Continuously improve agile processes and delivery frameworks to support distributed team dynamics.
Identify delivery bottlenecks and implement scalable solutions that enhance communication, accountability, and throughput.
Champion a culture of continuous improvement, innovation, and learning across all delivery teams.