Freelance Senior DevSecOps Engineer

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, Serbia, and more. We are headquartered in Amsterdam.

About the Position

Toloka is growing rapidly, adding new platforms and infrastructure across multiple cloud environments. We are hiring a senior, hands-on security engineer to own infrastructure security and vulnerability management: Kubernetes and service-mesh security, cloud hardening, and vulnerability remediation.

This is a senior, self-directed role. It requires the ability to define scope and drive execution independently, with ownership of core security tooling and processes from day one.

What you'll actually do

• Own vulnerability management. Operate and maintain the vulnerability-management platform. Ensure container images are scanned and patched on a defined cadence. Maintain supply-chain scanning tooling and its severity-classification configuration. Define and enforce remediation SLAs.
• Own cloud security across multiple providers. AWS, GCP, and Azure hardening, logging, and service-account governance.
• Own Kubernetes and service-mesh security. Operate the service mesh and maintain the policy-as-code rollout so that policy is enforced automatically.
• Audit and secure infrastructure in newly added environments. Review build pipelines and infrastructure in newer parts of the business as they come online, and remediate findings.
• Contribute to security architecture and design review. Review new integrations and internal systems, including AI agents running in production, for security risk.
• Support workforce and endpoint security. Contribute to VDI and browser-isolation initiatives as the program matures.
• Use agentic tooling in your workflow. Use coding agents for first-pass review of infrastructure-as-code, container configuration, and cloud policy, verifying findings against source configuration before acting on them.

Key Priorities for the First 6 Months

The first six months focus on establishing full ownership of infrastructure and vulnerability management.

• Weeks 1–2 - Onboard to the cloud environment, Kubernetes architecture, and existing security tooling.
• Month 1 - Establish ownership of the vulnerability-management process; findings triaged and remediated on a defined cadence.
• Month 2 - Complete configuration of supply-chain scanning tooling; implement automated image scanning and patching; deploy initial policy-as-code rules.
• Month 3 - Complete policy-as-code rollout in at least one environment; begin infrastructure audits in newly added environments.
• Month 4 - Close outstanding cloud logging and service-account gaps; establish and enforce a documented multi-cloud hardening baseline.
• Months 5–6 - Full ownership of infrastructure and cloud security as a domain; independently deliver security-architecture design reviews.

Core Tech Stack

Kubernetes and service mesh, policy-as-code tooling (Kyverno/OPA), Terraform, AWS/GCP/Azure, vulnerability-management and supply-chain scanning platforms, container tooling, CI/CD, and Git. Detections and access rules are managed as code through pull requests. Familiarity with coding/agentic tools for infrastructure review is expected.

What We Evaluate

• Production experience hardening cloud infrastructure - IAM, logging, service accounts, network security, on at least one major cloud provider (multi-cloud experience is a plus).
• Kubernetes and container security - service mesh (Cilium, Istio, or similar) and policy-as-code (Kyverno, OPA, or similar).
• Vulnerability-management experience - SCA/SAST tooling and SLA-driven remediation practice.
• Fluency with coding agents - experience using agentic tools for infrastructure-as-code review or investigation work, and verifying their output.
• Ability to work independently at a senior level - defining scope and priorities without detailed direction.
• Clear written and verbal communication - able to run design reviews and communicate risk to engineers and leadership.

Nice to Have, None Required

Experience securing multi-tenant or multi-identity-domain environments; supply-chain security tooling (SBOM, Socket, JFrog, or similar); secure-SDLC or AppSec experience; Terraform/IaC at scale; relevant certifications (e.g. AWS/GCP/Azure security specialties, CKS).

What We Can Offer

• Contract (B2B) collaboration, with a path into a project team if things go well;
• Flexible, fully remote schedule (40 hours per week);
• Work at the leading edge of AI development, alongside a dedicated and dynamic team of experts;
• Projects with customers that are AI industry leaders and well-known household names;
• Friendly community.

[Important Notice] Scam Alert Regarding Fake Job Postings

It has come to our attention that an individual or group is fraudulently impersonating Toloka to post fake jobs and solicit personal information from applicants.Please be aware:

• Official Communication: Our recruiting team will only contact you from an official "" email address. We will NEVER use Gmail, Yahoo, Tolokainc, toloka.inc, or other personal or seemingly business email accounts.
• Our Process: We will never ask for your bank account details, credit card number, or any fees as part of the application or interview process.
• Official Listings: All legitimate job openings are posted on our official careers page: