Legal Counsel – Employment, AI, Platform Work & Workforce Privacy (Freelance)

Company Intro

At Toloka AI we create data that powers leading GenAI models and innovations. We work with frontier labs, big tech, renowned AI startups, enterprises and non-profit research organizations worldwide. We use a combination of Experts + Crowd + Tech Platform to teach AI models to reason and evaluate their efficacy and safety. We have experts in more than 50 different domains—from doctors and lawyers to physicists and engineers—and boast one of the most diverse global crowds, representing over 100 countries and speaking 40+ languages. We are a well-funded startup with an enviable portfolio of clients including Anthropic, Amazon, Microsoft, poolside, Recraft, and Shopify.

Recently, we secured strategic investment led by Bezos Expeditions with participation from Mikhail Parakhin, CTO of Shopify and board advisor to leading GenAI companies, who now serves as our Chairman of the Board. Our remote-first team is globally distributed around the world: USA, UK, the Netherlands, Israel, Czech Republic, Serbia, and more. We are headquartered in Amsterdam.

Role Description

We are looking for a Legal Counsel with strong EU labour / employment law experience and deep familiarity with worker classification and platform / contractor models. You will be the primary in-house owner for misclassification risk, employment‑related policies, and people‑facing legal frameworks in Europe, including EU regulations that apply to Toloka and you will help shape how we manage platform experts and contractors, including DAC7‑relevant aspects. You will work cross‑functionally with HR, Finance, Delivery, and Product, helping teams reach their business goals while clearly explaining and managing legal and regulatory risk. This role is a good fit for someone who is comfortable balancing pragmatism and flexibility with a clear view of legal boundaries. US labour / contractor‑model experience is a strong plus, but not required, especially where it touches platform models and misclassification.

What you’ll do

• Act as primary in‑house counsel for EU labour and employment questions, working closely with People/HR and Operations across key European jurisdictions.

• Design, update, and maintain practical frameworks to manage worker classification and misclassification risk in the EU (employees vs contractors vs platform experts) and, where relevant, in the US, including documentation, playbooks, and escalation paths.

• Partner with Finance/Tax and Operations on platform‑related tax and reporting workflows, including DAC7‑relevant processes for experts and contractors (for example, data capture, reporting logic, and related disclosures in terms).

• Support and refine global and local people policies.

• Advise on hiring, onboarding, transitions, and exits in the EU, including employment agreements, contractor agreements, local addenda, and separation arrangements, coordinating with local counsel where needed.

• Partner with Product and Operations on platform and expert terms, ensuring alignment with EU labour law, misclassification risk, worker‑protection rules, and relevant platform‑worker regulations.

• Advise on the use of AI and data in HR and workforce management, including:

• Use of AI tools for performance monitoring or quality review of employees, contractors, and experts.

• Transparency, fairness, and information obligations toward workforce populations.

• Intersection with emerging rules such as the EU AI Act in HR / employment contexts.

• Provide clear, practical guidance on workforce‑facing communications, including reviewing and shaping the language used with employees, contractors, and platform experts in policies, notifications, performance and conduct letters, product UX, and lifecycle communications, so that messaging is accurate, fair, and aligned with legal and regulatory requirements.

• Advise on privacy and data protection as they relate to employees, contractors, and experts, in close collaboration with Privacy/Security, including:

• DPIAs and risk assessments for monitoring and evaluation tools.

• Notices and information rights for workforce groups.

• Retention and access controls for HR and expert‑related data.

• Draft, review, and negotiate people‑centred commercial and operational contracts, such as:

• Contractor, consultancy, and services agreements.

• Outsourcing / BPO or expert‑services arrangements.

• MSAs and SOWs where staffing, resourcing, or expert services are key.

• Support the General Counsel in managing contentious or high‑risk employment matters (investigations, claims, regulator queries), working with external counsel and translating their advice into scalable internal practices.

• Act as a pragmatic business partner: present options and mitigations, explain trade‑offs, and help stakeholders choose paths that balance legal risk, operational constraints, and growth objectives.

What we’re looking for

• Qualified lawyer in an EU jurisdiction, with approximately 7–10+ years of post‑qualification experience, including substantial EU labour / employment law experience.

• Strong track record advising on:

• Worker classification / misclassification in Europe (employees, contractors, platform workers, gig models).

• Cross‑border or multi‑jurisdiction EU employment setups.

• People policies, investigations, disciplinary and grievance processes.

• Experience working with or for platform, gig, marketplace, staffing, or services businesses that rely heavily on contractors or flexible workforces.

• Prior in‑house experience at a tech, SaaS platform, or AI company.

• Experience with or strong exposure to workforce‑related privacy and data protection, including employee and contractor data, monitoring tools, and HR systems (for example, DPIAs, transparency and access rights, retention, and security expectations).

• Comfort drafting and negotiating commercial contracts with a people / workforce component, such as:

• Contractor, consultancy, and services agreements.

• Outsourcing / BPO or expert‑services arrangements.

• Customer MSAs and SOWs where human services and staffing‑like models are central.

• Ability to spot and manage intersections between employment law, privacy, tax / reporting, and AI, especially where monitoring, evaluation, or automated decision‑making tools are used for workers or experts (including DAC7‑relevant scenarios).

• Strong stakeholder and communication skills: able to work closely with HR, Delivery, Finance, and Product, and to balance legal risk with operational reality, giving clear, business‑oriented recommendations rather than abstract legal theory.

Nice to have

• Dutch speaker.

• US labour / employment or contractor‑model experience, particularly around misclassification and platform or gig‑economy issues.

• Experience with European platform‑worker reforms and related regulatory developments.

• Deeper familiarity with data protection and AI regulation as they apply to HR and workforce management (for example, complex DPIAs, information duties about automated decision‑making, AI governance in HR settings).