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Salary
≈ $41k – $103k per year (Estimated)
Location
Remote (LATAM, United States, CT hours)
Seniority
Staff
Employment
Contractor

Confirmed on the employer's own hiring board on Oct 27, 2026. First seen by Alion on Aug 21, 2026. Upwork scores B on the Alion truth index.

Overview
Company
Impact
Profile match
Upwork is an American freelance marketplace formed in 2015 from the merger of Elance and oDesk, and it connects businesses with independent professionals in software development, design, writing, marketing and increasingly artificial intelligence work. Its revenue comes from taking a percentage of what clients pay freelancers, which means it has spent years balancing take rate against the incentive for established pairs to leave the platform and transact directly. Headquartered in San Francisco and listed on Nasdaq, it has been positioning itself around higher-value professional work rather than competing at the commodity end of the market.

We are seeking a hands-on AI Platform Technical Lead to serve as the technical owner for a general-purpose, AI-enabled enterprise collaboration ecosystem. This role will design, build, integrate, operate, and improve production AI agents, reusable skills, workflows, search capabilities, and enterprise AI platform integrations.

The ideal candidate combines deep applied AI engineering experience with practical enterprise platform and systems-administration knowledge. This is a hands-on individual contributor leadership role with no direct reports. You will lead through technical expertise and influence by establishing standards, mentoring other contributors, reviewing technical solutions, and serving as a senior escalation point.

Enterprise experience strongly preferred.

Key Responsibilities

* Design, build, test, deploy, and maintain production-quality AI agents, skills, prompts, tools, workflows, assistants, and automations.

* Build AI solutions using Model Context Protocol (MCP), function calling, APIs, agent frameworks, and integration technologies.

* Translate business requirements into technical designs, prototypes, and stable production-ready AI capabilities.

* Build secure integrations across collaboration, productivity, search, AI assistant, and enterprise systems.

* Develop APIs, data connectors, webhooks, search integrations, retrieval-augmented generation solutions, and semantic-search capabilities.

* Ensure AI systems preserve source-system permissions, access controls, data-security requirements, and governance policies.

* Design and evaluate grounding, citation, memory, retrieval, and context-management approaches for AI applications.

* Test and evaluate AI solutions for quality, reliability, safety, performance, grounding, and production readiness.

* Administer and optimize enterprise AI platforms, including access, configuration, integrations, monitoring, and lifecycle management.

* Troubleshoot complex AI platform, integration, connector, identity, search, and data-retrieval issues.

* Establish reusable technical standards and patterns for AI agents, integrations, configurations, testing, deployment, and security.

* Lead technical solution reviews and provide technical guidance and mentoring to other administrators and engineers.

* Serve as a senior technical escalation point for complex AI platform and integration issues.

* Evaluate emerging AI capabilities and provide technical recommendations to platform leadership.

Must-Have Skills

* Demonstrated experience building and maintaining production-quality AI agents, skills, assistants, workflows, or integrations.

* Strong understanding of AI application concepts including agents and agentic workflows, skills and tools, function calling, Model Context Protocol, prompt and context design, retrieval-augmented generation, enterprise search, and data connectors.

* Strong understanding of grounding, citations, memory, context management, model and agent evaluation, AI safety, and access controls.

* Proven ability to move AI solutions from proof of concept to stable, supportable production services.

* Experience integrating systems through APIs, SDKs, webhooks, identity services, or automation platforms.

* Working knowledge of enterprise security, privacy, compliance, and data-governance principles.

* Significant hands-on experience administering or engineering enterprise SaaS, collaboration, productivity, search, automation, or AI platforms.

* Practical experience with several enterprise collaboration and AI platforms such as Slack, Google Workspace, Gemini for Workspace, Glean, Claude, ChatGPT, or comparable enterprise AI products.

* Strong systems-administration knowledge including identity and access management, role-based permissions, configuration management, logging, monitoring, incident response, and change management.

* Strong troubleshooting, technical writing, architecture documentation, and stakeholder-communication skills.

* Ability to lead technically through expertise and influence without direct people-management authority.

Nice-to-Have Skills

* Experience with single sign-on, SCIM provisioning, OAuth, service accounts, delegated authorization, and enterprise identity providers.

* Familiarity with cloud platforms, infrastructure as code, source control, CI/CD, secrets management, and observability.

* Software development experience with Python, TypeScript, JavaScript, or similar languages.

* Experience creating MCP servers or integrating MCP-compatible clients and tools.

* Experience operating an enterprise AI platform or supporting an internal AI enablement program.

* Familiarity with responsible-AI practices, AI security frameworks, and model or agent evaluation methodologies.

Required Tools & Platforms

* Practical experience with several of the following or comparable enterprise products: Slack, Google Workspace, Gemini for Workspace, Glean, Claude, and ChatGPT.

* Hands-on experience with AI integration patterns involving MCP, function calling, APIs, SDKs, webhooks, enterprise search, data connectors, and identity services.

Location, Time & Engagement

* Remote contract engagement.

* Candidates must be located in the United States or LATAM, excluding Mexico.

* Central Time working-hour overlap is preferred.

* Full-time allocation of approximately 40 hours per week.

* Expected engagement through March 31, 2027.

* This is an individual contributor technical leadership role with no direct reports.

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