Top Tech Jobs & Startup Jobs in Chicago, IL

Own the operational health, observability, reliability, and failover of AI model providers and endpoints. Build SLO monitoring, canaries, quality regression detection, automated provider-operations tooling, and load-testing systems. Lead incident response, communicate with external providers, produce reliability scorecards, and drive postmortems and corrective actions. Support capacity planning and launch readiness for high-volume LLM inference traffic.

Conduct outbound prospecting into enterprise accounts, research AI initiatives, engage technical and business stakeholders, qualify opportunities, and generate pipeline for Enterprise Account Executives. Responsibilities include cold calls, personalized email, LinkedIn outreach, discovery conversations, CRM maintenance, opportunity nurturing, and improving messaging and account-selection strategies. The role requires strong communication, organization, enterprise prospecting experience, and curiosity about AI infrastructure and LLM technologies.

Build and ship Ori developer tools across CLI, Slack, desktop, and cloud surfaces. Develop multi-model agent runtimes with model switching, provider fallbacks, tool integrations, sandboxing, secrets management, session handling, and version-controlled agent state. Own the full product experience, including installation, authentication, reliability, observability, and evaluations. Collaborate with product, design, and platform teams while feeding platform requirements into OpenRouter APIs and SDKs.

Own enterprise product marketing from messaging and positioning through launches, sales enablement, competitive analysis, strategic deal support, customer advocacy, and campaign collaboration. Partner with Product, Engineering, Sales, Solutions Engineering, Customer Success, Demand Generation, and Field Marketing to support enterprise growth, improve seller effectiveness, gather customer feedback, and influence product packaging and roadmap decisions.

Own the Connect product roadmap for a platform enabling partners to offer multi-model AI inference. Define strategy, partner onboarding, APIs, controls, billing, observability, and reusable multi-tenant abstractions. Work directly with design partners, engineering, design, partnerships, finance, and go-to-market teams to launch and scale the product from early integrations through general availability.

Own and operate OpenRouter’s compliance and GRC program, including Drata administration, SafeBase management, audit readiness, evidence collection, personnel compliance, access reviews, penetration tests, risk assessments, and incident-response exercises. Partner with Engineering, HR, Legal, Customer Support, and Finance to implement controls across SOC 2, HIPAA, PCI DSS, GDPR, CCPA, BIPA, and the EU AI Act, while translating emerging AI regulations into practical controls.

Lead and grow the Provider Ecosystem engineering team while remaining hands-on in code reviews, incidents, and development. Own provider adapters, endpoint lifecycle, routing, integrations, multimodal expansion, benchmarks, and inference quality. Partner directly with model labs and inference providers to launch offerings rapidly, use telemetry and evaluations to guide traffic decisions, and collaborate with GTM, business development, and legal on partner onboarding.

Own the technical side of enterprise sales by leading discovery, solution design, architecture discussions, proofs of concept, integrations, security reviews, and technical enablement. Translate customer infrastructure and LLM requirements into OpenRouter solutions, support deal strategy, troubleshoot implementations, and provide customer feedback to Product and Engineering.

Develop and manage strategic enterprise accounts for OpenRouter’s AI routing and infrastructure platform. Own complex, multi-stakeholder sales cycles from prospecting through activation, build executive relationships, create account strategies, lead demos and negotiations, and close large enterprise deals. Contribute to go-to-market strategy, monitor AI and competitive trends, maintain accurate CRM forecasting, and attend conferences and client meetings with up to 30% travel.

Own and grow OpenRouter’s developer community across Discord, Twitter/X, Reddit, and other channels. Lead moderation, contributor recognition, community programs, events, automations, and sentiment tracking. Build scalable playbooks and systems, recruit and support moderators, synthesize feedback for product and engineering, and represent OpenRouter publicly. The role is primarily digital with regular in-person event involvement and requires hands-on experience building with LLMs and their APIs.