Top Tech Jobs & Startup Jobs in Chicago, IL

Lead go-to-market strategy for Breeze Assistant, define positioning, messaging, launches, and monetization. Partner with Product, Pricing, Sales, and CS to build enablement, demo narratives, adoption programs, and AI use-case content. Gather customer insights and competitive intelligence to refine messaging and drive adoption.

Lead Ads product strategy and roadmap, integrate paid media with CRM, partner with AI teams for intelligent campaign features, navigate ad-platform APIs and privacy constraints, use data-driven decision-making, and drive cross-functional execution from concept through launch to connect ad spend to revenue.

Lead frontend technical direction for the Trellis design system: design and build a production component library, define accessibility and theming models, create tooling and migration pipelines (codemods, refactoring automation), leverage AI coding agents, mentor senior engineers, and partner with PM/UX to drive frontend architecture and adoption across product teams.

Lead design-system work for Trellis, owning tokens, components, or patterns. Partner with product, engineering, and content to define scalable, accessible, machine-readable system guidance, improve Figma-to-code alignment, drive governance, adoption, and documentation, and enable AI-assisted workflows across HubSpot.

Lead pricing strategy for HubSpot's AI-first platform. Architect monetization models, conduct pricing research, and engage cross-functional teams to drive key initiatives.

Lead and scale Infrastructure Engineering to enable cloud-native, reliable, and observable platforms. Define long-term technical strategy, build high-performing teams, drive SRE and developer productivity, expand global infrastructure, and incorporate AI to transform engineering workflows while partnering across executive and product leadership.

Design the end-to-end meeting execution experience for Sales and Customer Success reps, partnering with stakeholders to build agentic-first workflows, prototype solutions, run research with users, and deliver polished product experiences that improve call efficiency, conversation quality, and deal progression.

Lead architecture and implementation of Revenue Hub (CPQ, Billing, Payments). Design APIs, domain models, and platform contracts; build and ship distributed, event-driven systems; ensure financial correctness and safe AI-agent interactions; own large cross-team initiatives; mentor senior engineers and drive platform patterns, reliability, and extensibility.

Design, install, maintain, and scale internal employee servicing servers and third-party application infrastructure. Lead projects, automate operations (Ansible/AWX, Python), integrate SaaS APIs (GSuite, Okta), and implement monitoring and security best practices across Windows, macOS, Linux, and cloud platforms (AWS/GCP).

Manage Workday Compensation end-to-end: configure and run annual/off-cycle cycles, design and test compensation functionality, ensure data integrity, troubleshoot issues, produce documentation and training, and partner with Total Rewards, HR, Finance, and Payroll to translate compensation strategy into scalable Workday configuration.