Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Own product positioning and messaging for Projects, Wiki, Intake, and Plane AI across Cloud, self-hosted, and air-gapped editions. Lead cross-functional launches, produce web-ready copy and enablement, run research (customer interviews, lost-deal analysis, competitive research), maintain sales/launch assets, and ensure claims match docs and engineering before release.

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.

The Account Executive will manage full-cycle sales for enterprise software, converting existing product interest into enterprise deals, navigating complex procurement processes, and providing deal intelligence to the product team.

Own and build Node.js/TypeScript backend services that power integrations, importers, queues, and developer-facing OAuth surfaces. Design reliable queue/worker systems (retries, idempotency, backpressure), integrate third-party APIs, collaborate with Django engineers, and repair partial failures to ensure safe, auditable data migrations and integrations.

Own and improve Plane's automated test suite for web and desktop clients: design frameworks, cover hard-to-test scenarios (concurrency, offline/recovery, agent-driven nondeterminism), keep tests fast and reliable, run suites in CI, test cloud and self-hosted environments, and triage failures across teams and community PRs.