AI Vendor Integrations Associate Director in Chicago, Illinois at Sidley Austin LLP

We are seeking a technical AI Vendor Integrations Associate Director to lead the Firm's relationships with AI and technology vendors and serve as the hands-on technical lead for integrating solutions across our AI ecosystem. This role extends well beyond managing deployments of tools like Claude or GPT. The ideal candidate will evaluate, integrate, and operationalize a broad portfolio of AI platforms, legal technology solutions, and enterprise systems, connecting APIs, data flows, and integrations to transform vendor capabilities into practical, scalable solutions for the Firm.

Sitting at the intersection of product management and solutions engineering, this individual will serve as the primary technical liaison for vendors. They will translate the Firm's business and technical requirements into integration strategies, oversee implementation, and hold vendors accountable for delivering secure, reliable, and high-performing solutions.

Duties and Responsibilities:

• Serve as the primary liaison between the firm and its AI/technology vendors, owning day-to-day relationships, escalations, roadmap discussions, and contract/SLA follow-through.

• Design, build, and maintain integrations between vendor platforms and firm systems including APIs, SDKs, webhooks, SSO/identity, and emerging standards such as Model Context Protocol (MCP) across multiple AI providers (e.g., Anthropic, OpenAI, Google, Microsoft) and legal/enterprise tools.

• Run structured evaluations and proofs of concept for new AI tools and models; benchmark capabilities, cost, and fit against firm use cases and make build/buy/integrate recommendations.

• Partner with information security, risk, and general counsel teams to shepherd vendors through security review, data protection, and compliance requirements appropriate to a legal environment.

• Translate stakeholder needs into technical requirements, integration specs, and prioritized backlogs; manage delivery timelines across vendors and internal IT.

• Monitor integration health, usage, and performance; establish observability and escalation paths so issues are caught and resolved before they impact users.

• Track the AI vendor landscape and advise leadership on emerging platforms, model releases, and consolidation opportunities across the stack.

Education and/or Experience:

Required:

• A minimum of 10 years in technical product management, solutions engineering, integration engineering, or a similar hybrid technical/product role.

• Hands-on experience building and maintaining API-based integrations (REST, OAuth, webhooks, SSO/SAML/SCIM); able to read code, work in a terminal, and prototype independently.

• Working fluency across multiple LLM providers and platforms not limited to a single vendor including model capabilities, pricing/token economics, and deployment options (API, cloud marketplaces, private hosting).

• Demonstrated success managing external vendor relationships, including negotiations, escalations, and joint delivery.

• Strong communication skills; able to translate between engineers, vendors, and non-technical senior stakeholders.

Preferred:

• Experience in legal technology or another regulated professional-services environment (financial services, healthcare, consulting).

• Familiarity with legal AI tools (e.g., Harvey, CoCounsel, Relativity aiR) and document management systems (e.g., iManage, NetDocuments).

• Experience with enterprise identity, data governance, and security review processes.

• Background in agentic AI patterns, RAG architectures, or MCP-based tool integration.

Other Skills and Abilities:

The following will also be required of the successful candidate:

• Strong organizational skills

• Strong attention to detail

• Good judgment

• Strong interpersonal communication skills

• Strong analytical and problem-solving skills

• Able to work harmoniously and effectively with others

• Able to preserve confidentiality and exercise discretion

• Able to work under pressure

• Able to manage multiple projects with competing deadlines and priorities

#LI-OE1

#LI-Hybrid

Applicants must be authorized to work in the United States without the need for employer sponsorship, now or in the future.

The target salary range for this role is:

Salaries vary by location and are based on numerous factors, including, but not limited to, the relevant market, skills, experience, and education of the selected candidate. Our compensation package also includes bonus eligibility and a comprehensive benefits program. Benefits information can be found at Sidley.com/Benefits.

To perform this job successfully, an individual must be able to perform the Duties and Responsibilities above satisfactorily and meet the requirements. The requirements listed above are representative of the minimum knowledge, skill, and/or ability required. Reasonable accommodations will be made to enable individuals with disabilities to perform the essential functions of the job. If you need such an accommodation, please email sidleytalentacquisition@sidley.com (current employees should contact Human Resources).

Sidley Austin LLP is an Equal Opportunity Employer.

Sidley is an elite global law firm with a known reputation of deploying innovative strategies to achieve powerful results.