Job Spec: Chief of Staff / Chief Operations Officer (COO)
Building the Operating Model for an AI-Native Healthcare Company
Location: Stellenbosch – Cape Town (Hybrid)
Reports To: CEO
Who we are
Pinotage Health Corporation is building a next-generation, AI-native healthcare platform that transforms doctor and patient interactions.
Our mission is to reduce the administrative burden on physicians through safe, reliable, and clinically accurate AI systems, allowing doctors to spend more time with patients and less time on paperwork.
Based in Stellenbosch, we are a high-calibre team of experienced operators, technologists, and entrepreneurs building a global healthcare platform with the ambition to redefine how healthcare is delivered.
As we enter an exciting phase of growth, execution, alignment, and operational excellence have become critical to our success.
Your Mission
We are looking for a COO / Chief of Staff to help build the operational foundation of the business and partner closely with the CEO as we scale.
This is not a traditional COO role focused on managing large teams and established functions.
Nor is it a conventional Chief of Staff role centred on executive administration.
Instead, you will operate at the intersection of strategy, execution, technology, people, and organisational design, helping shape how a modern AI-enabled company operates.
You will work directly with the CEO and leadership team to translate strategy into action, create alignment across the business, establish operating rhythms, and ensure key initiatives are delivered.
As AI fundamentally changes how work gets done, we believe the organisations that thrive will be those that thoughtfully design how people, technology, processes, and data work together.
The successful candidate will not simply manage an existing operating model.
You will help build it.
Core Responsibilities
Strategy to Execution
• Partner closely with the CEO to translate company strategy into executable priorities • Drive strategic initiatives and ensure key objectives are delivered
• Establish operating cadences, planning rhythms, and accountability mechanisms
• Monitor progress against company goals and proactively remove obstacles
Organisational Design & Operations
• Help design and evolve the company's operating model as the business scales • Create clarity around ownership, decision-making, and accountability • Improve organisational efficiency through systems, process improvement, and technology • Identify opportunities to leverage AI and automation across the business
Cross-Functional Leadership
• Align teams around shared priorities and outcomes • Facilitate effective communication and decision-making across the organisation • Ensure information moves quickly and accurately between stakeholders • Act as a force multiplier for the CEO and leadership team
Executive Partnership
• Serve as a trusted advisor and thought partner to the CEO • Prepare strategic discussions, board materials, investor updates, and business reviews where
required • Provide visibility across critical initiatives, risks, and dependencies • Ensure leadership focus remains on the highest-value priorities
Scaling Capability
• Build systems that allow organisational knowledge to be captured, shared, and retained • Create operating structures that enable growth without unnecessary complexity • Foster a culture of accountability, ownership, and execution excellence
Experience & Background
We're less concerned with job titles and more interested in capability.
You may have experience in:
• Chief of Staff
• COO
• Business Operations
• Strategy & Operations
• Management Consulting
• Startup or Scale-Up Operations
• Founder Associate
• Commercial Operations
• Product or Technology Operations
Ideal candidates will typically have:
• 5+ years of experience in high-performance growth environments
• Experience working directly with founders, executives, or leadership teams
• Exposure to technology, SaaS, AI, healthcare, or high-growth businesses
• A demonstrated ability to move between strategic thinking and hands-on execution
• Strong commercial judgement and operational problem-solving capability
Core Competencies
• Organisation & Planning: Structured, detail-oriented, and reliable • Communication: Clear, professional, and concise • Proactivity: Anticipates needs and drives follow-through • Execution Focus: Gets things done and closes loops • Judgement & Discretion: Handles sensitive matters with care • Stakeholder Management: Confident working with senior individuals • Adaptability: Thrives in a fast-paced, evolving environment
Why This Role Matters As Pinotage scales, complexity increases rapidly.
This role is suited to
• Thrives in ambiguity and enjoys building from scratch • Thinks in systems, not silos • Naturally creates structure, clarity, and momentum • Is highly organised without becoming bureaucratic
• Can move comfortably between strategy discussions and operational execution • Has strong business judgement and exceptional follow-through • Is excited by the opportunity to help shape how a modern AI-enabled company operates
Why Join Pinotage Health? This is a rare opportunity to help build a global AI healthcare company from the inside.
You will work directly with the CEO and leadership team, influence how the organisation scales, and play a central role in designing the way the business operates in an AI-first world.
The opportunity is not simply to manage operations. The opportunity is to help define what operations look like in the next generation of healthcare technology companies.