Top Tech Jobs & Startup Jobs in Chicago, IL

Own post-sale relationships for a portfolio of B2B SaaS accounts from onboarding through renewal and expansion. Develop tailored adoption plans, monitor usage and support patterns, identify renewal risks, and lead customer conversations. Partner with sales on handoffs and collaborate with support and product to resolve issues. Support technically sophisticated customers running self-hosted or open-source Plane deployments, including those in regulated and enterprise environments.

Own technical architecture for enterprise and regulated-industry Plane deployments, including self-hosted and air-gapped environments. Lead customer discovery, security reviews, migration planning, technical sales support, deployment documentation, and requirements feedback to engineering. The role requires translating infrastructure, identity, compliance, and security requirements into practical deployment decisions and serving as the technical voice for major customer deals.

Own collaborative editing across React clients and Node services, including offline storage, queued mutations, realtime WebSocket synchronization, conflict resolution, and data persistence. Build agent-enabled editing experiences, investigate data-loss issues across environments, and collaborate with designers, backend engineers, and open-source contributors. The role requires production TypeScript experience across React and Node, rich-text editor frameworks, offline applications, WebSockets, and advanced Postgres skills.

Own end-to-end custom integrations for strategic customers, from technical discovery through production deployment. Build Python-based integrations against unfamiliar APIs and infrastructure, collaborate directly with customer engineers and stakeholders, diagnose issues remotely, and distinguish one-off requests from broader product gaps. The role requires independently delivering production code, communicating with both technical and executive audiences, and supporting deployments in cloud, self-hosted, regulated, and air-gapped environments.

Build and operate production AI agent features for Plane, including agent workflows, MCP servers, retrieval systems, customer-facing interfaces, evaluation harnesses, tracing, permissions, and audit models. The role requires shipping reliable LLM-backed features to real users, managing tool calling and failure recovery, measuring quality and performance, and partnering with engineering and product teams to deliver production surfaces.

Own end-to-end product design for core workflow surfaces (issues, cycles, views). Ship high-fidelity specs, balance design system consistency, run usability tests, collaborate with PMs and engineers across locations, and defend design decisions in public forums and engineering discussions.

Build Plane's outbound engine end-to-end: source and enrich prospect lists, create AI-powered personalization and multichannel sequences, maintain email deliverability and sender reputation, integrate data with CRM and sequencing tools, instrument metrics from reply to pipeline, and automate signal-based trigger plays for technical buyers.

Build and own backend surfaces for Plane: APIs, data models, migrations, real-time sync (CDC/event streams), caching, and query performance. Instrument, monitor, and debug production incidents; collaborate with product and frontend teams across locations.

Build and maintain Plane's local-first browser client surfaces: large, virtualized workspaces, collaborative editor, offline/caching layers, and shared design-system components. Work cross-functionally with designers and backend engineers, extend sync and conflict-resolution behavior, optimize rendering performance, and triage cross-browser and self-hosted issues.

Lead frontend architecture and technical strategy for a collaborative work platform. Build scalable React/TypeScript applications, design systems, real-time collaboration (sync, offline, serialization), optimize performance and observability, mentor engineers, and collaborate with Product, Design, and Backend teams to deliver high-quality, maintainable user experiences.