Senior Delivery Manager

About Robots & Pencils

Robots & Pencils is a cutting-edge applied AI engineering company focused on transforming business architectures by creating AI co-workers seamlessly integrated into enterprise workflows, yielding tangible client outcomes. They leverage AWS deeply, combining user experience expertise with seasoned engineering talent to rapidly deploy AI solutions and ensure their sustained operation. With a reputation as a nimble alternative to large traditional integrators, the firm has gained trust across industries including Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, and Manufacturing. Established in 2009, with delivery centers in Canada, the US, Eastern Europe, and Latin America, their teams average over 15 years of experience, moving swiftly and focusing on delivering actual shipped products.

Position Overview

The Senior Delivery Manager acts as the principal delivery lead for multi-disciplinary engagements, overseeing the complete project lifecycle from initiation to release. This role requires managing cross-continental teams, ensuring alignment on objectives, and serving as the key delivery liaison for clients. The individual provides decisive leadership to steer projects amidst uncertainty, maintain rigorous program governance, and foster continuous client engagement.

Key Importance of the Role

As the steward of the company’s commitment to producing “production-ready AI within 30 to 45 days,” the Senior Delivery Manager sets the rhythm and discipline of delivery, cultivating trust that encourages client retention and expansion. The pace and success of projects hinge on proactive ownership of plans, early identification and communication of trade-offs, and unifying distributed teams toward shared goals.

Primary Responsibilities

• Direct the full lifecycle management of intricate, multi-phase projects ensuring scope, budget, timelines, and quality meet defined delivery success criteria.
• Facilitate agile ceremonies such as sprint planning, backlog grooming, and oversee delivery activities for one or multiple cross-functional teams.
• Coordinate phased product releases, ensure readiness for production, and manage smooth transitions into operations and support.
• Proactively identify and mitigate dependencies, risks, scope alterations, and escalations before they hinder progress.
• Establish, monitor, and communicate key delivery performance indicators, leveraging data to steer decision-making and balance trade-offs among scope, schedule, and resources.
• Support quality assurance and user acceptance testing, confirming acceptance criteria are achieved.
• Utilize AI-enhanced tools like Claude to improve delivery planning, reporting accuracy, and communication with stakeholders.
• Serve as the central delivery contact for clients, cultivating transparent, consistent communication and building trust while uncovering new value opportunities.
• Lead stakeholder workshops, roadmap alignments, and delivery meetings confidently.
• Translate delivery status, risks, and trade-offs clearly for both technical and executive audiences.
• Collaborate with Client Partners to identify engagement expansion opportunities and contribute to strategic proposals for future work.
• Guide distributed delivery teams across onshore and offshore locations by encouraging accountability, teamwork, and excellence in delivery.
• Mentor junior delivery managers providing constructive feedback and growth opportunities.
• Promote a culture of openness, continuous improvement, and high performance throughout the engagement.
• Participate in enhancing company-wide delivery practices, tools, and methodologies.
• Assess team composition and alert Client Partners to staffing needs and identify top talent.
• Conduct executive-level interviews for engineering, design, and other roles and contribute significantly to hiring decisions.

Candidate Profile

• Minimum 5 years’ experience in software delivery leadership, technical project management, or engineering team leadership roles.
• Solid expertise in agile methodologies across complex, multi-team projects such as Scrum, SAFe, or Kanban.
• Proven track record managing geographically distributed teams across onshore and offshore sites.
• Demonstrated ability to deliver complex, multi-platform digital solutions in agile settings.
• Exceptional client communication and relationship management capabilities.
• Familiarity with delivery tools including Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines.
• Knowledge of cloud-native systems and AI-powered platforms.
• Experience leveraging AI tools (e.g., Claude) to optimize delivery workflows and documentation.
• Preferred certifications such as PMP, Scrum Master, or SAFe.
• Experience in regulated sectors like utilities, government, or finance is advantageous.
• Keen insight to identify engagement growth opportunities and ability to proactively engage clients alongside Client Partners.

Desirable Additional Expertise

• Domain experience in Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing.
• Background in implementing agentic AI coworkers or applied AI initiatives within enterprises.
• Prior roles with client engagement, consulting, or account leadership experience enhancing ability to manage growth conversations.

Ideal Traits

• Proactive problem solver who acts decisively to fix issues and maintain momentum.
• Rapid learner willing to adapt in the evolving AI landscape.
• Candid communicator who provides honest feedback to improve work quality.
• High standards for quality and ownership, committed to delivering exceptional results.
• Ownership-driven with accountability for commitments and team support.
• Fully immersed in clients’ businesses while maintaining a balanced approach.
• Resourceful under constraints, using tight budgets or timelines to sharpen focus.
• Calm and deliberate decision maker amid competing pressures.
• Appreciates collaboration with highly experienced and dedicated colleagues.