Delivery lead /Product Delivery Lead AI

DELIVERY LEAD — AI PRODUCT DELIVERY

Remote/Hybrid 

Contract

 ABOUT THE OPPORTUNITY

 We are seeking an experienced Delivery Lead to serve as the single point of accountability for partner-side delivery efforts across multiple AI product initiatives. This is a senior program management role providing unified delivery oversight, status visibility, and risk management across distributed development teams and workstreams.

The Delivery Lead owns delivery health holistically: release predictability, proactive risk management, resource optimization, and executive-ready reporting. This role coordinates above individual project managers, synthesizes delivery information across all teams, and serves as the primary interface for program-level delivery accountability.

ROLE SUMMARY

As Delivery Lead, you will:

• Manage end-to-end delivery across multiple AI product workstreams involving distributed onsite and offshore teams

• Provide consolidated program status, risk visibility, and decision support to executive stakeholders

• Own release planning, capacity management, and dependency coordination across multiple Azure DevOps boards

• Proactively identify and resolve delivery risks before they impact commitments

• Produce executive-ready artifacts including status reports, RAID logs, release plans, and burn-down analyses

• Coordinate with technical leads, project managers, and product owners to ensure aligned execution

This role requires a proactive, ownership-driven leader who operates independently, anticipates issues before they materialize, and presents solutions—not just problems—to stakeholders.

KEY RESPONSIBILITIES

1. Program Status Reporting & Executive Communication

• Produce weekly written status updates per product: RAG status, key decisions needed, blockers, sprint progress

• Synthesize consolidated status across all workstreams—delivering executive-ready summaries, not raw data

• Draft escalation memos within 24 hours of critical issues, including situation analysis, impact assessment, options, and recommendations

• Create and maintain program dashboards providing real-time visibility into delivery health

• Manage stakeholder expectations proactively with data-driven insights and trade-off analysis

2. RAID Log & Decision Management

• Own and maintain comprehensive RAID (Risks, Assumptions, Issues, Dependencies) log across all workstreams

• Update RAID log continuously and deliver to stakeholders before weekly reviews—proactively, not on request

• Maintain decision log documenting context, options considered, decisions made, and rationale

• Flag decisions requiring stakeholder input with sufficient lead time and supporting analysis

• Track risk mitigation actions to closure with accountability and deadlines

3. Release Planning & Multi-Sprint Forecasting

• Maintain rolling release plans per product with all requirements allocated to sprints

• Produce weekly multi-sprint burn-down reports showing projected completion at actual velocity

• Provide explicit RAG assessment on release targets with quantitative supporting data

• When targets are at risk (Amber/Red), present options (scope, capacity, timeline) with recommendations—before being asked

• Confirm resource capacity at least 2 sprints forward; re-project forecasts within 48 hours of material changes

4. Resource, Capacity & Workstream Management

• Maintain living register of all team resources: assignments, workstreams, allocation percentages, confirmed capacity

• Track demand vs. capacity per workstream; surface imbalances and context-switching risks proactively

• Provide unified view of resource allocation across all teams—eliminating need for stakeholder triangulation

• Flag resource conflicts and skill gaps at least 2 sprints ahead with proposed mitigation

• Optimize resource allocation across onsite and offshore delivery teams

5. Proactive Risk Management & Dependency Resolution

• Identify and flag stories with unclear acceptance criteria, missing dependencies, or capacity risks before sprint start

• Own cross-team dependency resolution with defined SLAs and escalation paths

• Anticipate delivery risks through forward-looking analysis and trend identification

• Conduct post-mortems on significant delivery misses; share findings and corrective actions

• Build mitigation plans for identified risks with clear ownership and timelines

6. Delivery Artifact Production

• Serve as first-draft owner of: sprint plans, release notes, RAID logs, dependency registers, decision logs, status reports

• Ensure all artifacts are polished, complete, and executive-ready before stakeholder review

• Maintain documentation standards ensuring consistency across all workstreams

• Produce handover documentation for production releases and major milestones

7. Program Governance & Quality Assurance

• Establish and maintain program execution standards and risk management frameworks

• Ensure adherence to Agile delivery practices: sprint planning, backlog grooming, reviews, retrospectives

• Partner with technical leads to validate feasibility, assess risks, and challenge delivery assumptions

• Drive delivery discipline and accountability across distributed teams

• Monitor velocity trends and quality metrics; recommend process improvements

REQUIRED QUALIFICATIONS

Experience & Background

• 8+ years of program/project management experience in enterprise technology delivery

• Proven track record managing complex, multi-workstream programs with distributed teams

• Strong experience with AI, cloud-native applications, or enterprise software delivery

• Demonstrated ability to consolidate delivery information across multiple teams and tools (Azure DevOps, Jira, etc.)

• Experience working with onsite/offshore delivery models and multi-vendor coordination

• History of proactive risk management and issue prevention—not reactive firefighting

Technical Knowledge

• Working knowledge of AI/ML technologies, LLM-based architectures, and AI orchestration frameworks (LangChain, AutoGen, LlamaIndex, Semantic Kernel)

• Familiarity with modern development stacks: Python, .NET (C#, .NET Core), Azure cloud platform

• Understanding of Agile/Scrum methodologies, CI/CD pipelines, and DevOps practices

• Experience with Azure DevOps, Jira, or similar project management and tracking tools

• Ability to engage in technical discussions with architects and engineers to assess delivery feasibility

Communication & Leadership Skills

• Exceptional written communication—capable of producing executive-ready documents without iteration

• Strong stakeholder management and executive presentation skills

• Proven ability to present options and recommendations with every issue—not just identify problems

• Experience facilitating cross-functional workshops, prioritization sessions, and alignment meetings

• Skilled at managing expectations and navigating scope/timeline/resource trade-offs

Delivery Excellence Attributes

• Proactive ownership mentality—operates independently and doesn''''''''''''''''t wait to be asked

• Strong analytical skills: velocity tracking, capacity planning, burn-down forecasting, trend analysis

• Experience maintaining RAID logs, capacity maps, and dependency registers continuously—not periodically

• Pattern recognition: ability to anticipate delivery challenges before they materialize

• High accountability with minimal supervision; thrives in fast-paced, dynamic environments

• Data-driven decision making with strong attention to detail

ROLE CHARACTERISTICS

What This Role IS:

Single point of delivery accountability for partner-side execution

Proactive program leader who anticipates risks and presents solutions

Executive interface providing consolidated delivery visibility

First-draft owner of all program artifacts and documentation

Coordinator above project managers—consolidating the complete picture

What This Role Is NOT:

 Scrum master focused on team-level sprint execution

 Technical architect or hands-on developer

 Replacement for existing project managers—coordinates above them

 Reactive reporter waiting to be asked for status

 Problem identifier without solutions—always presents options and recommendations

SUCCESS METRICS

• Stakeholders have complete delivery visibility through single consolidated view

• Risks and issues are identified and escalated proactively—before impacting commitments

• Release targets are met or, when at risk, options are presented with sufficient lead time for decision-making

• Resource capacity and allocation are transparent, balanced, and optimized

• All delivery artifacts are complete, accurate, and require minimal stakeholder rework

• Stakeholders can focus on strategic decisions rather than information gathering

WORKING ENVIRONMENT

• Remote/hybrid work arrangement with core business hours overlap required

• Coordination across multiple time zones (onsite and offshore teams)

• Fast-paced environment with high expectations for delivery excellence

• Direct interface with executive stakeholders and technical leadership

• Ownership-driven culture with high accountability and minimal micromanagement