Job Spec: Executive Assistant / Junior Chief of Staff (CEO Office)
Location: Stellenbosch – Cape Town (Hybrid)
Reports To: CEO and C-Suite team
Who we are
Pinotage Health Corporation is building a US healthcare agentic workflow platform that transforms doctor and patient encounters. Our mission is to reduce the administrative burden on physicians through agentic AI systems that are safe, reliable, and clinically correct — so doctors can spend more time with patients, not paperwork.
We are a small, high-calibre team of experienced operators, based in Stellenbosch, working closely together to build and scale a global product.
The company is entering a phase of rapid growth, where execution, alignment, and clear operating structure are critical.
Role Purpose / Mission
This role sits at the intersection of Executive Assistant and Junior Chief of Staff, acting as a high-trust partner to the CEO while also supporting execution across the business.
You will focus on maximising CEO effectiveness, driving follow-through on priorities, and stepping into operational gaps, helping ensure the company runs smoothly and key initiatives move forward.
Core Responsibilities
CEO Enablement & Executive Support
• Own and manage the CEO’s calendar, inbox, and key communications • Prioritise time and commitments to maximise focus and impact • Ensure meetings are well-prepared, structured, and followed through • Act as a gatekeeper and facilitator across internal and external stakeholders
Coordination & Stakeholder Management
• Act as a central coordination point across leadership and teams • Schedule, prepare, and track key meetings and actions • Maintain visibility on commitments and ensure accountability
Execution & Follow-Through
• Track and drive progress on key priorities and projects • Ensure decisions translate into clear next steps and delivery • Step in to support execution where needed
Operational & Project Support
• Assist with cross-functional initiatives and ad hoc projects • Help structure workflows, priorities, and reporting • Improve organisation and reduce reactive workload for the CEO
Travel & Logistics
• Manage local and international travel and itineraries • Ensure seamless execution across time zones
Required Experience
• 3–6 years experience in an Executive Assistant, Operations, or similar role • Experience supporting a CEO, founder, or senior executive preferred • Exposure to startup, scale-up, or high-performance environments • Strong organisational skills with the ability to manage competing priorities • Experience working across international teams/time zones
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
Ideal Candidate Traits
• Early-stage operator who wants exposure to leadership and company-building • Highly organised executor with strong attention to detail • Comfortable switching between admin, coordination, and light operational work • Ambitious and eager to grow into a broader operations or Chief of Staff role over time • Comfortable working in a small, fast-growing team
Why This Role Matters As Pinotage scales, complexity increases rapidly.
This role ensures:
• The CEO is focused on the highest-impact work • Priorities are clearly tracked and delivered • The business operates with structure and momentum
Why Join Pinotage Health? Work directly with the CEO, and others team members, to help scale an AI-driven healthcare platform, and play a central role in a high-growth company.