Manager, Pilot Team

Digital Divide Data (DDD Kenya) is seeking an experienced and results-driven Manager, Pilot Team to lead the end-to-end delivery of AI/ML data operations programs. This is a senior operational role at the intersection of client partnership, program delivery, and continuous improvement — ideal for professionals who thrive in fast-paced, KPI-driven technical environments where precision and accountability matter.

In this role, you will manage annotation workflows, oversee cross-functional delivery teams, and serve as a key liaison between clients and internal operations. You will translate complex client requirements into executable workflows, maintain rigorous quality standards, and drive performance insights that strengthen outcomes across Computer Vision, NLP, AV/ADAS, and related AI data programs.

• Support client discovery sessions to understand dataset needs, ML objectives, and workflow rules; translate these into annotation guidelines, taxonomies, and quality frameworks.
• Provide clients with regular delivery updates, performance insights, and actionable workflow recommendations.
• Support solution scoping, demos, proposal inputs, and clarifications during the pre-delivery phase.
• Oversee daily execution of AI/ML, Computer Vision, AV/ADAS, and related data annotation workflows against agreed KPIs and SLAs.
• Manage team onboarding, calibration sessions, guideline updates, workflow transitions, and production readiness checks.
• Partner with Delivery Leads to ensure staffing levels, training completion, tool readiness, and operational consistency across programs.
• Build and maintain dashboards and reports tracking accuracy, productivity, error trends, latency, and overall program health.
• Conduct root-cause analysis for quality issues and implement corrective actions in collaboration with QA and Training teams.
• Present clear, data-backed performance updates to clients and internal stakeholders.
• Coordinate with QA, Training, Technical Operations, Business Development, and client-facing teams to support pilot setup and workflow testing.
• Recommend and support automation opportunities including pre-labeling, AI-assisted annotation, QC automation, and improved audit methodologies.
• Promote consistent ways of working, strong calibration practices, and a culture of continuous improvement across all programs.

• Must hold a Bachelor's degree in Computer Science, Information Systems, Engineering, Data/AI, Business Operations, or a closely related field.
• Must demonstrate at least 5 years of hands-on experience in AI/ML operations, data annotation management, technical program delivery, or BPO operational environments.
• Must be able to manage and execute annotation workflows across 2D/3D Computer Vision, NLP, LiDAR/RADAR datasets, and AV/ADAS data pipelines.
• Must have proven ability to deliver against KPIs and SLAs in a client-facing technical delivery setting.
• Must demonstrate experience leading teams, managing escalations, and implementing quality and productivity improvements.
• Must be able to build performance dashboards, conduct root-cause analyses, and translate data insights into operational decisions.
• Must communicate effectively with both technical teams and non-technical client stakeholders, presenting complex information clearly.
• Should be familiar with annotation tools, ontology management, schema changes, and guideline development for AI training datasets.

The salary for this role is not explicitly stated. Based on the seniority level, technical specialization, and Kenyan market benchmarks for AI/ML operations management, the estimated monthly compensation range is KES 250,000 – KES 400,000. DDD Kenya is a global social enterprise known for providing competitive remuneration and meaningful work opportunities. Final compensation will be commensurate with experience and qualifications.

Ideal candidates are seasoned AI/ML operations professionals or technical program managers with deep experience in data annotation delivery, client relationship management, and team leadership. You are analytical, process-oriented, and comfortable operating across multiple workstreams simultaneously. You understand the nuances of Computer Vision, NLP, and autonomous vehicle data workflows, and you can both manage people and drive strategic improvements.

Do not apply if you have fewer than 5 years of relevant operational experience, have no exposure to AI/ML data pipelines or annotation environments, or if you are uncomfortable working in a high-accountability, KPI-driven delivery setting with direct client interaction.

• Prepare an updated CV clearly highlighting your experience in AI/ML operations, program delivery, and team leadership.
• Write a concise cover letter explaining your specific experience with annotation workflows, client-facing delivery, and any AI data tools you have worked with.
• Submit your application through the DDD Kenya careers portal or the job board where this listing was found.
• Only shortlisted candidates will be contacted. If you do not hear back within 3 weeks of applying, consider your application unsuccessful for this cycle.