Top Tech Jobs & Startup Jobs in Chicago, IL

Drive outbound prospecting and qualify leads to build pipeline alongside Account Executives. Conduct outreach via email, phone, and social, log activity in Salesforce, refine messaging, become product expert, collaborate with Marketing and Ops, and travel occasionally for onboarding and events.

Build and deploy production-grade agentic workflows for enterprise customers using Webflow APIs, CMS, AI capabilities, and external integrations. Design safeguards, observability, rollback paths, and permission boundaries; support live web properties at scale; collaborate with sales and engineering on complex deployments; and convert customer implementation learnings into reusable architecture blueprints and platform improvements.

Leads global sales compensation design, administration, analytics, payouts, and non-standard deal strategy. Partners with Sales, Finance, RevOps, Legal, and Total Rewards to align incentive programs with business goals. Oversees compensation metrics, quota and capacity modeling, reporting, policies, enablement, and executive insights. Manages and develops a team responsible for sales compensation and deal strategy, including analysis of custom deal structures.

Own and close complex SaaS deals ($50k+ ACV) for mid-market accounts (300–2,500 employees). Build outbound pipeline, run full sales cycle, perform consultative discovery, negotiate multi-year contracts, collaborate with cross-functional teams, and travel (~25%) for onboarding and events.

Leads Webflow’s Revenue Marketing organization and owns marketing-sourced and influenced pipeline, iARR, forecasting, channel ROI, and full-funnel performance. Builds demand creation and capture programs, ABM initiatives, partner-led growth, lifecycle and expansion marketing, and web conversion optimization. Partners with Sales, Partnerships, Product, Customer Success, and RevOps to develop integrated revenue plays, feedback loops, customer proof, and AI-enabled marketing operations. Reports to the Chief Marketing Officer and leads a multidisciplinary team.

Designs and operates batch, streaming, and real-time data platforms and pipelines using Spark, Kafka, Iceberg, Airflow, and cloud infrastructure. Owns data lake evolution, data quality, observability, reliability, governance, event instrumentation, schema management, and privacy controls for PII, retention, deletion, and residency. Leads complex initiatives end-to-end, troubleshoots production issues, mentors engineers, and develops AI agent harnesses that enforce data engineering standards and quality gates.

Execute and optimize full-funnel paid social campaigns across LinkedIn and Meta, including regional, brand, partner, and account-based programs. Build audiences, manage bids and budgets, run experiments, maintain campaign QA and UTM discipline, and report performance against CRM-sourced pipeline metrics using Salesforce and Tableau. The role requires independent execution, multi-region campaign management, and strong optimization judgment focused on pipeline outcomes.

Lead multi-year vision, strategy, and roadmap for Webflow's agent surfaces and AI platform. Align cross-functional teams, set quality standards and guardrails for non-deterministic agent experiences, serve both developers and creators, prototype and ship product improvements (including contributing code), and mentor PMs while measuring and iterating on outcomes.

Leads the engineering team building Webflow’s code-native platform, including high-fidelity visual-to-code workflows and coding-agent integration. Sets technical and product direction, shapes architecture, owns developer experience, sequences platform and customer-facing work, and partners across product, design, and engineering. This player-coach role includes architecture reviews, prototyping, hands-on contributions, hiring, coaching, and developing a high-performing technical culture.

Lead the technical vision and architecture for backend systems supporting experimentation, personalization, analytics, and conversion optimization. Design and operate high-throughput distributed systems and APIs, build data infrastructure, and productionize AI/ML capabilities. Drive complex multi-team initiatives, influence engineering strategy, establish technical standards and operational excellence, and mentor senior engineers. Partner with product, data science, ML, and engineering teams to translate business needs into scalable solutions.