Director of Datasets

About the Role

As Side continues to expand its Datasets business, we are seeking an experienced Director of Datasets to define and lead the next stage of our growth across AI training data, speech technology, multimodal datasets and emerging data collection services. Reporting to the Senior Director of Audio & Datasets, this role will provide the strategic, commercial and operational leadership for Side’s global Datasets line of business.

The successful candidate will oversee the continued expansion of our market-leading speech and voice dataset services, while helping establish new capabilities across image, video, transcription, annotation, multimodal and crowdsourced data collection.

This is a highly strategic position combining: solution design, commercial leadership, operational excellence, client partnership, and industry expertise.

The Director of Datasets will work closely with Sales, Solutions, Production and Legal teams to define scalable service offerings, pricing models, delivery methodologies and long-term business strategy.

The ideal candidate will bring significant experience delivering large-scale dataset collection programmes, along with deep knowledge of industry processes, commercial models and emerging trends across AI data generation and machine learning.

Key Responsibilities

• Strategic Leadership: Define and execute the long-term strategy for Side’s Datasets business. Identify opportunities to expand beyond speech datasets into new collection services, including image, video, multimodal, transcription, annotation and other AI training data. Evaluate emerging technologies, methodologies and market trends to ensure Side remains competitive. Help shape investment priorities, capability development and future service offerings. Support diversification of the client portfolio across technology, AI and adjacent industries.
• Solution Architecture and Delivery: Lead solution design for complex client requirements across bespoke dataset collection projects. Develop scalable methodologies for global data collection programmes involving professional talent, crowdsourced contributors, partner studios and distributed workforces. Identify the most appropriate collection platforms, tooling, technologies, payment methods and workflows for each engagement. Collaborate with Production, Legal and other business units to ensure practical and commercially viable delivery models. Define best practices for quality assurance, validation, metadata, rights management and delivery standards.
• Commercial and Pricing Expertise: Act as the subject matter expert for dataset pricing, costing and commercial strategy. Develop pricing frameworks covering a wide range of dataset collection methodologies and licensing models. Support Sales and Solutions teams during client discovery sessions, proposal development and contract negotiations. Evaluate project scope, assumptions, commercial risks and resource requirements. Advise leadership on market pricing, competitive positioning and new commercial opportunities.
• Client Partnership: Serve as a trusted adviser during client discussions involving AI training data and dataset collection. Translate complex technical requirements into practical, scalable delivery solutions. Build trusted relationships with AI companies, technology organisations, publishers and enterprise clients. Demonstrate Side’s expertise and capabilities throughout the sales process. Support key client engagements from initial consultation through to successful delivery.
• Operational Leadership: Lead and develop the global Datasets team. Provide coaching, mentoring, performance management and career development. Establish KPIs and operational objectives aligned with business growth. Develop scalable internal processes that support efficient delivery across multiple collection types and global regions. Foster collaboration across Audio, QA, Player Support and other business units.