Chief Delivery Officer (CDO)

SUMMARY:
Job Purpose:

• The Chief Delivery Officer (CDO) is a senior manager reporting to the Chief Operational Officer (COO)
• The CDO is responsible for leading the end-to-end implementation of the Company's Software Product for clients across South Africa, the United Kingdom, and all international markets
• The role is responsible for owning and professionalizing the company's customer delivery function, creating predictable, scalable delivery execution across the implementation portfolio. This role is accountable for implementation delivery performance, PMO leadership, programme governance, delivery risk management, and customer implementation confidence
• The role ensures that all software implementations, client onboarding, and platform deployments are executed with excellence, on time, and within scope. This role serves as the bridge between the company's Sales and Implementation, while also ensuring a smooth and effective handover from Implementation to The Company's Professional Services (post go-live support)
• The role is execution-focused, with responsibility for building delivery discipline, improving predictability and increasing organisational delivery maturity

POSITION INFO:
Key Responsibilities: Delivery Leadership: Own the end-to-end delivery execution across customer implementation programmes Drive a culture of accountability, predictability and execution excellence Be accountable for delivery performance across the implementation portfolio Ensure programme execution against agreed milestones Ensure implementation quality and predictability Oversee delivery risk identification and mitigation Ensure executive visibility of delivery health Oversee delivery resource planning and prioritization Provide oversight of all client implementation and onboarding, ensuring delivery consistency and quality across all regions PMO Leadership and Project Governance: Build and lead a robust, high-performing Programme Management Office (PMO) delivery function Implement and maintain standardized delivery governance structures, methodologies, and reporting cadences, with clear milestone management discipline Create a single operating model for delivery management Implement and maintain RAID Governance, dependency tracking, escalation protocols, portfolio reporting, executive dashboards, and delivery health visibility Direct leadership of Programme and Project Managers Champion the adoption of agile and hybrid delivery methodologies People Leadership and Capacity Development: Lead, mentor, and develop a high-performing delivery team comprising Project Delivery Managers, Project Managers, Implementation Consultants (Solution Developers), and Test Analysts Foster a delivery culture grounded in accountability, continuous improvement, and client-centricity. Set clear performance expectations, conduct regular performance reviews, and create development plans aligned to business needs Strengthen delivery capability across the organization, while building bench strength and resilience Customer Implementation Leadership and Client Partnership Management: Serve as senior delivery executive for major customer implementations and build confidence with strategic customers through credible delivery leadership Build trusted, strategic relationships with senior client stakeholders (C-suite and operational leads) Lead or oversee executive customer governance meetings and steering committees Lead escalation resolution for critical client delivery issues, balancing client expectations with internal capacity constraints Implementation of effective issue resolution and programme recovery where required Delivery Interface Management: Serve as senior delivery interface into Product and Innovation, Architecture, QA, BAU and Sales This role does not own Product or Engineering, but must ensure effective execution interfaces Responsible for ensuring that delivery dependencies are identified early and actively managed Coordinating delivery-critical work across functions. Ensuring that implementation commitments are operationally credible Supporting effective transition from sales\/discovery phase into delivery Support the Customer Support function (The Company's Professional Services) in ensuring smooth transitions from project delivery into business-as-usual operations Escalating structural blockers and trade-offs to the COO Commercial discipline: Partner with the Finance team, COO and broader commercial leadership to improve delivery economics Responsibilities include protecting implementation margins and reducing leakage from rework\/inefficiency Improving capacity utilisation and supporting realistic delivery commitments Ensuring that delivery execution supports long-term customer value Delivery Operational Excellence and Continuous Improvement: Improve the scalability and maturity of the delivery function Transition from reactive heroics towards repeatable operational discipline Identify and implement process improvements that increase delivery throughput, reduce time-to-value for clients, and lower delivery risk Monitor and report on key delivery metrics including on-time delivery rates, sprint throughput, time tracking compliance, defect rates, and client satisfaction scores Improve delivery workflows and implement lifecycle management Increase automation and reporting maturity where appropriate Strengthen governance disciplines Improve resource allocation discipline Reduce delivery inefficiency and rework Ensure delivery practices remain compliant with relevant regulatory and contractual obligations across all operating jurisdictions Qualifications and Experience: A relevant tertiary qualification in Business Management, Information Technology, or a similar field Significant senior leadership experience in enterprise software delivery, SaaS implementation, platform delivery or technology-enabled operations Demonstrated track record of successfully delivering complex, multi-stakeholder software implementation programmes in an insurance or financial services context Deep understanding of the insurance value chain, including policy administration, claims management, MGA structures, and regulatory frameworks across relevant markets (EAMA) Previous experience with the London Market or Specialty Insurance Proven experience leading and scaling delivery teams in a fast-growth technology environment Strong proficiency in agile and hybrid delivery methodologies Skills Required: Exceptional leadership and people management skills, with the ability to inspire, coach, and hold teams accountable Strong presence and stakeholder management skills, with the ability to engage credibly with senior customers and at C-suite Strong communication skills - written, verbal, and presentational - with the ability to distil complex delivery information into clear, actionable insights for varied audiences Analytical and commercially minded, with the ability to balance delivery quality, speed, and cost Structured and execution-orientated, with the ability to manage multiple concurrent programmes A strong operator rather than a conceptual strategist. Highly accountable, with low ego, high ownership Resilient under pressure with sound judgement and decision-making ability in ambiguous or high-stakes environments Collaborative and able to influence cross-functional teams without direct authority