VP, Delivery Lead

Job Summary

We are seeking a seasoned VP, Delivery Lead to own and optimize Agile delivery across a large portfolio of software initiatives. Reporting directly to the CTO, this role is responsible for leading a team of Scrum Masters, managing delivery operations, and ensuring that planning, staffing, and execution align with business and technical priorities.

 

This is a senior leadership role with responsibility for portfolio planning, team resourcing, and budget oversight, requiring deep delivery experience, operational rigor, and strong cross-functional coordination.

 

Responsibilities

• Lead, coach, and develop a team of Scrum Masters who support multiple engineering teams across high-impact software initiatives.
• Partner with the CTO and engineering/product leadership to translate strategic priorities into structured delivery plans, with clear timelines, milestones, and resource allocations.
• Manage delivery team staffing and capacity planning, ensuring alignment between business goals and available talent.
• Oversee and optimize the portfolio delivery budget, including headcount, vendor resources, tooling, and operational costs.
• Drive portfolio-level planning and tracking, including quarterly/annual roadmaps, sprint metrics, and milestone tracking.
• Standardize and scale Agile delivery practices across teams using frameworks like Scrum, SAFe, LeSS, or custom Agile-at-scale approaches.
• Provide executive-level reporting on delivery status, risk, capacity, and forecasted outcomes; communicate clearly with technical and non-technical stakeholders.
• Identify and address cross-team dependencies, risks, and delivery blockers to maintain momentum across all initiatives.
• Foster a culture of continuous improvement, supporting retrospectives, delivery reviews, and performance optimization across teams.
• Support talent planning, performance management, and recruitment efforts for delivery roles in alignment with CTO objectives.

 

Qualifications

• 20+ years of experience in software delivery, program management, or engineering leadership roles, with a strong track record in Agile environments.
• At least 5 years leading a team of Scrum Masters or Agile delivery managers in a complex, multi-team setup.
• Strong experience in portfolio planning, budget ownership, and staffing strategy within a technology organization.
• Deep understanding of Agile delivery frameworks and best practices (Scrum, SAFe, Kanban, Agile at Scale).
• Proven ability to drive operational efficiency and delivery predictability through metrics, tooling (e.g., Jira, Aha!, Confluence), and governance.
• Comfortable working closely with C-level executives and cross-functional leaders.
• Excellent communication, facilitation, and stakeholder management skills.

 

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