Delivery Lead – AI-Native Platforms & Operations
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Key skills for this role
About the Role
Olive Green Holding is seeking a Delivery Lead to act as the CTO's second-in-command, driving execution across AI-native platforms, technology operations, and product delivery. The role requires strong experience in delivery, program management, and technology operations, with hands-on AI tool usage.
Key Skills for This Role
Responsibilities
- Act as the operational right hand person to the CTO across technology, product, and delivery activities
- Coordinate initiatives across product, engineering, support, infrastructure, vendors, and business stakeholders
- Translate strategic objectives into executable plans
- Own delivery governance across multiple concurrent projects and workstreams
- Track dependencies, risks, issues, decisions, and delivery milestones
- Help define and improve delivery frameworks, standards, and ways of working
- Facilitate workshops, planning sessions, reviews, and stakeholder updates
- Support product discovery, requirements gathering, and roadmap development
- Review user journeys and operational workflows to identify improvement opportunities
- Use AI tools to automate delivery activities, documentation, reporting, testing, and operational processes
- Assist in vendor management, procurement, and technology evaluations where required
- Build reporting, dashboards, and management visibility across technology initiatives
Requirements
- Strong experience and exposure across delivery, programme management, product management, technology operations, cyber security infrastructure and business systems leadership
- Proven ability to coordinate multiple stakeholders and drive complex initiatives to completion
- Comfortable operating across product, engineering, operations, and support functions
- Hands on experience using AI tools to improve productivity and accelerate delivery
- Strong problem solving ability with a bias toward action
- Excellent written and verbal communication skills
Full Job Posting
About the role
- We are building a portfolio of AI native platforms, internal operational systems, enterprise technology services, and venture stage digital products.
- We are looking for a highly capable generalist who can operate as the CTO's second in command across multiple business units and technical teams including delivery, technology operations, product execution, and organisational enablement.
- This role offers significant visibility, influence, and responsibility, with ownership over delivery outcomes rather than simply managing tasks.
What you’ll own
- Support the evolution of IT operations into an AI enabled support model
- Improve service management, operational processes, and support capabilities
- Coordinate infrastructure, security, access management, and operational readiness activities
- Help standardise tools, platforms, and ways of working across the organisation
- Ensure technology teams have the foundations required to scale effectively
- Work alongside Product Owners and Platform Owners to convert ideas into deliverable outcomes
- Coordinate platform launches, releases, testing, and go live activities
- Support production readiness including authentication, app store publication, infrastructure readiness, monitoring, and documentation
- Identify delivery risks, dependencies, bottlenecks, and mitigation plans
- Support the creation and growth of new digital ventures and internal platforms
- Work directly with stakeholders to define requirements and shape solutions
- Take ownership of smaller products and initiatives where appropriate
What you’ll do
- Act as the operational right hand person to the CTO across technology, product, and delivery activities
- Coordinate initiatives across product, engineering, support, infrastructure, vendors, and business stakeholders
- Translate strategic objectives into executable plans
- Own delivery governance across multiple concurrent projects and workstreams
- Track dependencies, risks, issues, decisions, and delivery milestones
- Help define and improve delivery frameworks, standards, and ways of working
- Facilitate workshops, planning sessions, reviews, and stakeholder updates
- Support product discovery, requirements gathering, and roadmap development
- Review user journeys and operational workflows to identify improvement opportunities
- Use AI tools to automate delivery activities, documentation, reporting, testing, and operational processes
- Assist in vendor management, procurement, and technology evaluations where required
- Build reporting, dashboards, and management visibility across technology initiatives
What we’re looking for
- Strong experience and exposure across delivery, programme management, product management, technology operations, cyber security infrastructure and business systems leadership
- Proven ability to coordinate multiple stakeholders and drive complex initiatives to completion
- Comfortable operating across product, engineering, operations, and support functions
- Strong organisational skills without becoming process heavy or bureaucratic
- Commercially minded and focused on business outcomes rather than activity metrics
- Hands on experience using AI tools to improve productivity and accelerate delivery
- Strong problem solving ability with a bias toward action
- Comfortable working in ambiguity and helping create structure where it does not yet exist
- Able to balance strategic thinking with practical execution
- Excellent written and verbal communication skills
- Able to challenge constructively while maintaining strong stakeholder relationships
- Comfortable switching between executive conversations and detailed operational discussions
Bonus experience
- Product Management experience
- IT Service Management (ITIL or equivalent)
- AI coding tools such as Cursor, Claude, Codex, Replit, Copilot, or ChatGPT
- Workflow automation platforms including n8n, Zapier, or Make
- Azure, AWS, or cloud infrastructure platforms
- Authentication platforms and identity management
- SaaS platform implementation and administration
- Vendor and third party supplier management
- Agile delivery methodologies
- SQL, APIs, integrations, and automation
- SAP/Salesforce/ODOO experience
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