Data Annotation Lead

Robin AI is on a mission to revolutionize the legal industry by simplifying contracts and making law accessible to everyone. We utilize cutting-edge machine learning and contract software, enhancing traditional legal services and bringing together experts in engineering, AI, and law. Robin AI has recently raised $26m in Series B funding and has seen an impressive 5x revenue growth in the last 12 months.

We’re looking for passionate, resourceful and collaborative people to join Robin. If you’re motivated about leveraging technology to make essential business services more accessible, come join us!

About this role:

Robin AI is seeking a detail-oriented Data Annotation Lead to oversee the annotation process of our training data for machine learning models in the legal domain. You will create taxonomies for new contract types, and manage and quality control annotation projects and teams working with a range of legal documents. As part of the Legal Engineering team, you will be at the forefront of the development at Robin AI, shaping our company-wide approach to data collection and data annotation. You will collaborate closely with legal engineers and machine learning specialists to develop new AI models that power our platform. You will also partner with our Implementation team to ensure the successful delivery of new product offerings to clients, providing key insights into model training data needs.

What you’ll do:

  • Develop and document annotation guidelines and taxonomies for legal datasets including contracts, case law, and other legal documents.
  • Recruit, train, and manage data annotation teams with a focus on accuracy, consistency and productivity.
  • Continuously monitor annotation quality through statistical analysis and auditing.
  • Work closely with machine learning engineers to iteratively improve guidelines and datasets.
  • Research and implement new annotation tools and approaches, specifically through leveraging the capabilities of Large Language Models.


  • 4+ years experience working on data annotation, data labelling, discovery or due diligence projects, and experience managing reviewers as part of these projects.
  • Deep understanding of legal documents like contracts and case law.
  • Experience developing annotation guidelines and quality assurance protocols.
  • Ability to recruit, train, and manage skilled annotation team members.
  • Data science skills such as statistical analysis and sampling for quality control.
  • Technically savvy with annotation tools and workflows.
  • Proven leadership and project management abilities.
  • Ability to work cross-functionally with engineering, product, and implementation teams.
  • Excellent communication, presentation, and documentation skills.
  • Sharp attention to detail and process orientation.
  • Bachelor’s degree in a relevant field like linguistics, data science, law or paralegal studies.

Compensation at Robin AI:

  • Salary: £75,000 – £100,000
  • Generous Equity package: When you help build Robin AI, everyone deserves to be an owner.
  • Please Note: If your salary expectations look a little different to that outlined, we’d still be keen to hear from you if this is a role that excites you and one that you think you could really excel in.

Benefits at Robin AI:

At Robin AI, we put humanity first— we believe a great product is inextricably linked to a great internal community.

We’re a quickly growing, cross-functional team that values supporting each other’s development. As part of the team, you can expect:

  • 25 days PTO, excluding bank holidays, cultural leave, and birthday leave
  • Unlimited, trust-based sick leave
  • Enhanced gender-neutral parental leave
  • Technology to enable you to work seamlessly from the office or home
  • Focus on continual learning and development
  • Free healthy breakfast on Tuesdays, cinnamon rolls on Thursdays, and a fridge of beverages ordered to request!

Robin’s flexible work model aims to meet the needs of our diverse employee community by making work more flexible, connected, and inclusive. Depending on the role and needs of the team, Robin employees have the flexibility to work from home 2/3 days per week.

Robin is deliberate about the culture we are building and are committed to creating an inclusive environment that attracts the best talent from diverse backgrounds. Whether it’s helping curate the Robin Spotify playlist, discussing gender equality in tech, or taking a meditation break with our holistic health plan, we want you to find your space within the Robin community.

From our offices in Liverpool Street, London you’ll have access to all of the WeWork amenities including co-working space, bike lockers, pool tables, table tennis, free barista-made coffee and free beer in the evenings.

Diversity, equity and Inclusion at Robin AI:

We want to break diversity, inclusion and equality barriers within the tech industry. In building our team, we welcome the unique contributions that you can bring, and welcome applications regardless of ethnicity, religion, sexual orientation, gender identity and expression, disability, education, opinions, nation of origin, languages spoken, age, pregnancy and maternity, or veteran’s status. To request reasonable accommodation, we encourage you to communicate any reasonable accommodations you may need to your recruiter as you move forward.

💰£75,000 - £100,000/Yearly

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