Executive Assistant / Junior Chief of Staff (CEO Office)

Job Spec: Job Spec: Chief of Staff

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.

Your Mission

Act as a force multiplier to the team, driving execution, alignment, and operating discipline across the business.

Translate strategy into action, ensure leadership alignment, and help build the operating system required to scale a high-growth company.

Core Responsibilities

Executive Execution

• Drive execution of the company’s highest-priority initiatives
• Ensure decisions translate into clear actions and outcomes
• Support the team on strategic projects and follow-through

 

 

Leadership Alignment

• Work closely with CEO, CTO, and Chief Product Officer
• Align priorities across product, engineering, and operations
• Facilitate decision-making across the leadership team

Operating Model & Governance

• Establish operating rhythms (planning cycles, leadership cadence, KPI tracking)
• Build simple, scalable processes and governance structures
• Improve visibility, accountability, and execution discipline

Cross-Functional Initiatives

• Lead high-impact projects across teams
• Step into gaps and drive delivery where needed
• Coordinate initiatives spanning product, growth, and operations

Prioritisation & Focus

• Help define and maintain company priorities
• Ensure focus on highest-impact work
• Reduce fragmentation across teams

Data & Decision Support

• Build reporting and performance visibility across the business
• Support leadership with structured analysis and insights
• Improve speed and quality of decision-making

Organisational Scaling

• Support hiring priorities and team structure evolution
• Contribute to organisational design as the company grows
• Reinforce a high-performance, ownership-driven culture

Required Experience

• 5+ years in strategy, operations, consulting, or Chief of Staff roles
• Must have experience in a startup, scale-up, or small high-growth environment
• Experience working closely with founders or executive teams
• Proven ability to drive cross-functional execution
• Experience operating in ambiguous, fast-paced environments
• Strong stakeholder management and influencing skills

Qualifications

• Degree in Business or a related field

 

Nice to Have / Strongly Preferred

• Experience in AI, SaaS, or technology-led businesses
• Exposure to healthcare or regulated environments
• Experience in fundraising, partnerships, or international expansion

 

Ideal Candidate Traits

• Builder mindset — thrives in ambiguity
• Highly structured, with strong execution focus
• Hands-on operator with high ownership
• Strong communicator across technical and business teams
• Comfortable working in a small, fast-growing team

Why This Role Matters

As Pinotage scales, complexity increases rapidly.

This role ensures:

• The directors and decision makers are effectively leveraged
• The leadership team remains aligned
• The business executes with speed and focus

 

Why Join Pinotage Health?

Work directly with the CEO, CTO, and Chief Product Officer to help scale an AI-driven healthcare platform and play a central role in building the operating system of a high-growth company.