Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the end-to-end self-serve growth funnel—acquisition through conversion—owning strategy, roadmap, experiments, and metrics. Improve activation, retention, sharing, and free-to-paid conversion while partnering across Product, Engineering, Design, Data, Marketing, and Sales and applying AI-native approaches.

Lead post-sale strategy for ~15 high-value enterprise accounts, drive outcome-focused engagement cadences, conduct use-case discovery, analyze usage and adoption data to identify risk and expansion, partner with Sales and cross-functional teams to deliver enablement and measurable business impact, and manage stakeholders to secure renewals and organic growth.

As a Senior Financial Analyst, you will provide insights through financial modeling, analysis, and reporting to support business strategies and planning in a SaaS environment.

Lead and mentor a team of Account Executives in a SaaS sales environment, focusing on new logo acquisition and account expansion.

Lead end-to-end Customer Insights product: define the canonical usage data layer, build customer-facing analytics and audit surfaces, and deliver AI-native insights. Partner with engineering, data, design, Sales, and Customer Success to drive renewal and expansion narratives, ensure enterprise readiness (permissions, compliance), and translate ambiguous business questions into clear product experiences and APIs.

The Lead Product Designer will define AI-native features and design systems for human-agent collaboration, focusing on interaction models, workflows, and user experiences. Responsibilities include prototyping, mentoring, and contributing to product strategy and design systems.