Chief Delivery Officer (CDO)

Overview

Amazing chance to join a Software Development company that develops software for the insurance industry. They are a medium size company that look after their staff and give recognition. They have been around for over 25 years and have an international footprint in London. They have a branch in London, Stellenbosch and Rosebank. They are extremely people orientated and offer a fun dynamic working environment.

No. of Vacancies

Specific Skills

• Exceptional leadership and people management skills, with the ability to inspire, coach and hold teams accounta-ble
• Strong presence and stakeholder management skills, with the ability to engage credibly with senior customers and C-suite stakeholders
• Strong communication skills, written, verbal and presentational, with the ability to distil complex delivery infor-mation into clear, actionable insights for varied audiences
• Analytical and commercially minded, with the ability to balance delivery quality, speed and cost
• Structured and execution-oriented, with the ability to manage multiple concurrent programs
• A strong operator rather than a conceptual strategist
• Highly accountable, with low ego and high ownership
• Resilient under pressure with sound judgement and decision-making ability in ambiguous or high-stakes environ-ments
• Collaborative and able to influence cross-functional teams without direct authority
• Able to create calm, clarity and control in complex delivery environments
• Strong enough to hold teams accountable without creating unnecessary escalation or fear
• Comfortable operating close to the detail while still communicating at executive level
• Able to build trust with PMs, technical teams, senior stakeholders and customers
• Strong dependency management skills across Product, Engineering, Architecture, BAU, Sales and Finance
• Able to distinguish between useful governance and process noise
• Commercially alert to margin leakage, underbilling, scope creep and revenue risk
• Strong judgement on when to solve within the delivery function and when to escalate structural trade-offs

SUCCESS MEASURES FOR THE POSITION

• Improved delivery predictability across the implementation portfolio
• Stronger PMO governance, cadence and portfolio visibility
• Reduced reliance on ExCo intervention in day-to-day project detail
• Clearer, more concise executive reporting on delivery health, risk and decisions required
• Improved PM ownership, communication and accountability
• Better visibility and management of Core Dev / Architecture / Product dependencies
• Stronger handoffs from Sales to Discovery, Discovery to Delivery, and Delivery to BAU
• Improved customer implementation confidence and reduced escalations
• Improved delivery efficiency, implementation margin and utilization
• Reduced rework, scope leakage and avoidable delivery noise
• More resilient delivery function with reduced single-person dependency
• Scalable delivery operating model capable of supporting growth

Responsible For

KEY RESPONSIBILITIES

• Delivery leadership
• Own end-to-end delivery execution across customer implementation programs
• Build a delivery culture grounded in accountability, clarity, predictability and customer confidence
• Be accountable for delivery performance across the implementation portfolio
• Ensure program execution against agreed milestones, scope and commercial assumptions
• Improve delivery predictability through clear planning, dependency management and escalation discipline
• Oversee delivery risk identification, mitigation and recovery planning
• Ensure executive visibility of delivery health through concise, exception-based reporting
• Oversee delivery resource planning, prioritization and capacity visibility
• Ensure delivery commitments are operationally credible before they are made to customers
• Reduce reliance on informal escalation and senior executive intervention in day-to-day delivery detail
• PMO leadership and project governance
• Build and lead a robust, high-performing PMO and delivery management function
• Create a single operating rhythm for delivery management across the implementation portfolio
• Establish clear project control standards, including consistent RAG reporting, milestone tracking, blocker owner-ship, dependency tracking, people risk, commercial risk and client sentiment
• Ensure PMO meetings operate as effective project control forums, focused on risks, blockers, decisions, ownership and support required
• Separate internal PMO control from ExCo-level exception reporting, ensuring senior leaders receive the right visibil-ity without being pulled into unnecessary project detail
• Implement and maintain RAID governance, dependency management, escalation protocols, portfolio reporting, executive dashboards and delivery health visibility
• Ensure project managers provide concise, consistent and decision-ready updates
• Strengthen project manager ownership, judgement and communication capability
• Build resilience in the PMO model so that delivery visibility and control are not dependent on any single individual
• Champion pragmatic agile and hybrid delivery methodologies appropriate to client, project and product context
• Ensure delivery governance is useful, proportionate and commercially relevant, not process for its own sake
• People leadership and capacity development
• Lead, mentor and develop a high-performing delivery team comprising Project Delivery Managers, Project Manag-ers, Implementation Consultants / Solution Developers and Test Analysts
• Set clear expectations around ownership, communication, risk escalation and delivery discipline
• Coach PMs to communicate clearly with senior stakeholders, distilling complex project detail into actionable up-dates
• Build bench strength and succession within the delivery function, reducing single points of failure
• Create a delivery environment where teams can surface risk early without fear, while still being held accountable for delivery outcomes
• Identify capability gaps and work with the COO / People team on targeted development, recruitment or perfor-mance interventions
• Support sustainable delivery practices that reduce burnout risk and improve resilience across the team
• Customer implementation leadership and client partnership management
• Serve as senior delivery executive for major customer implementations and build confidence with strategic cus-tomers through credible delivery leadership
• Lead or support senior customer delivery governance where delivery risk, program recovery or material implemen-tation decisions require senior involvement
• Build trusted relationships with senior client stakeholders, while ensuring day-to-day ownership remains clear within the project team
• Lead escalation resolution for critical implementation issues, balancing client expectations with the company delivery capacity and commercial constraints
• Ensure project teams identify customer risk early and escalate with clear mitigation options
• Support effective program recovery where required
• Ensure implementation handover into BAU / Support is clear, documented and operationally ready
• Delivery interface management
• Serve as the senior delivery interface into Product, Architecture, Core Development, QA, BAU / Support, Sales and Finance
• This role does not own Product, Architecture or Engineering, but is accountable for ensuring delivery dependencies into those functions are visible, prioritized, tracked and escalated appropriately
• Ensure delivery-critical Product / Core Dev / Architecture dependencies are identified early and linked to project milestones, client commitments and commercial risk
• Establish a regular operating cadence between PMO, Product, Architecture and Core Dev to manage delivery de-pendencies
• Ensure implementation commitments are operationally credible before they are made to customers
• Support effective transition from Sales / Discovery into Delivery, ensuring assumptions, scope, dependencies and customer responsibilities are clear
• Support effective transition from Delivery into BAU / Support, ensuring known issues, commitments, documenta-tion and support arrangements are clear
• Escalate structural blockers, capacity conflicts and trade-offs to the COO with options and recommendations
• Commercial discipline
• Partner with Finance, the COO and commercial leadership to improve delivery economics
• Protect implementation margin by improving estimation, delivery control, scope discipline and change-control management
• Reduce leakage from rework, unclear scope, unmanaged dependencies and inefficient delivery practices
• Improve capacity utilization and resource planning across the implementation portfolio
• Ensure delivery reporting highlights revenue at risk, billing milestone risk, unpaid scope, margin pressure and cus-tomer confidence risk
• Ensure project delivery supports long-term customer value and does not rely on unsustainable over-servicing
• Support realistic delivery commitments during Sales, Discovery and contracting
• Delivery operational excellence and continuous improvement
• Improve the scalability and maturity of the delivery function through practical, sequenced operating improve-ments
• Move the delivery function from reactive heroics towards repeatable operational discipline
• Identify and implement process improvements that increase delivery throughput, reduce time-to-value and lower delivery risk
• Develop a clear delivery roadmap using a practical Step / Hop / Leap approach: immediate control, stronger oper-ating discipline and scalable delivery model
• Monitor and report on key delivery metrics, including delivery confidence, milestone adherence, sprint throughput, blocker ageing, time tracking compliance, defect rates, revenue at risk, implementation margin and client satisfac-tion
• Work with Finance, Data and operational teams to improve delivery dashboards and reduce manual reporting bur-den over time
• Strengthen governance disciplines without creating unnecessary bureaucracy
• Improve resource allocation discipline across delivery teams and delivery-critical dependencies
• Reduce delivery inefficiency, rework and avoidable escalation
• Ensure delivery practices remain compliant with relevant contractual and regulatory obligations
• Technical Delivery Literacy and Core Dev Interface
• Work closely with the Delivery Core Dev leadership to ensure delivery-critical technical work is clearly understood, prioritised, tracked and escalated where required
• Maintain sufficient technical literacy to engage credibly with Core Development, Architecture, Product and QA teams on delivery dependencies, blockers, estimates and delivery risk
• Understand the operational impact of technical dependencies on customer milestones, implementation plans, commercial commitments and client confidence
• Ensure Core Dev dependencies are visible within delivery governance, portfolio reporting and executive dash-boards
• Work with the Core Dev delivery team to ensure sprint commitments, delivery risks and technical blockers are com-municated clearly to PMO and delivery stakeholders
• Support effective prioritisation between implementation commitments, BAU, roadmap, defects, upgrades and ur-gent customer needs where these affect delivery execution
• Escalate structural blockers, capacity conflicts and technical delivery trade-offs to the COO with clear options and recommendations
• The CDO is not expected to make technical architecture decisions but must be able to create delivery discipline around technical work so that PMO, Core Dev, Product and Architecture are operating from a shared view of prior-ity, risk, capacity and commitment

PRIORITY FOCUS FOR THE FIRST 6 MONTHS

• The initial priority for the CDO will be to stabilize and professionalize the delivery operating rhythm, including:
• Resetting PMO governance so project reviews are focused, consistent and action-oriented
• Establishing clear ExCo exception reporting across delivery health, client risk, commercial risk and support needed
• Improving delivery dependency visibility across Product, Architecture, Core Dev, BAU and Finance
• Strengthening PM capability, ownership and concise stakeholder communication
• Improving handoffs from Sales to Discovery, Discovery to Delivery, and Delivery to BAU
• Creating clearer delivery controls around scope, change, milestones, client responsibilities and billing risk
• Supporting recovery and active control of priority projects where required
• Reducing single points of failure and improving resilience across the delivery team
• Building a practical delivery roadmap to support scale without creating a large transformation program

Additional Requirements

PARAMETERS OF THE POSITION

• This is a full-time, permanent role
• Flexibility to work extended hours and across time zones is required
• Regular national and international travel to client sites and the company offices will be required
• The CDO will be expected to participate in senior leadership forums and committees

Job Nature

Full Time, Hybrid work model

Educational Requirements

• 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 pro-grams in an insurance or financial services context
• Deep understanding of the insurance value chain, including policy administration, claims management, MGA struc-tures and relevant regulatory frameworks across EMEA and other international markets
• Previous experience with London Market or Specialty Insurance is desirable
• Proven experience leading and scaling delivery teams in a fast-growth technology environment
• Strong proficiency in agile and hybrid delivery methodologies
• Experience building or professionalizing a PMO or delivery management function

Experience Requirements

5+

Job Location

Rosebank, Stellenbosch

Salary

• Medical aid
• Pension
• Group Life
• Group Trauma
• Income protector
• Funeral Policy
• 20 Annual Leave days
• Performance bonus
• Pay for studies with work back agreement
• Hybrid working model (3 days a week from home and 2 days a week at the office)

Job Level

Senior Position

Interested candidates can send their resumes to [email protected] mentioning "Job Title" in the subject line.