Top Tech Jobs & Startup Jobs in Chicago, IL

Act as strategic compensation advisor embedded with Sales leadership. Lead annual compensation planning, advise on offers, promotions, retention, and equity negotiations. Conduct market analyses, influence compensation strategy, ensure internal equity and budget alignment, coach managers, and evolve enterprise compensation structures and policies.

Lead end-to-end quantitative and mixed-method market research to uncover customer needs, market opportunities, and competitive dynamics. Design surveys and sampling, analyze data (including AI-assisted workflows), synthesize multi-source findings, partner with Product/Marketing/UX/Strategy, deliver executive recommendations, manage external vendors, and evolve AI-powered research methodologies.

Own and evolve the end-to-end buying, discovery, and upgrade experience for HubSpots freemium products. Define product-led monetization strategy for AI-era, build credit/usage-based monetization infrastructure, partner across product and GTM teams, and lead pricing and upgrade campaigns. Present results to senior leadership and drive cross-functional alignment to deliver personalized, contextual upgrade moments across UI and LLM interfaces.

Own full-cycle enterprise sales for HubSpots specialized offerings (Service Hub, Customer Agent, Revenue Hub). Self-source pipeline through aggressive outbound prospecting, run complex multi-stakeholder deals, lead discovery, demos, and solution design, translate technical value into business outcomes, collaborate with internal partners, and drive quota attainment and account expansion.

Lead, hire, train, coach, and manage a team of Growth Specialists/Account Executives for the Small Business segment. Drive performance through data-driven coaching, KPI management, forecasting via CRM, structured deal management, recruiting and retaining talent, and cross-functional collaboration to improve sales processes and outcomes.

Own the end-to-end roadmap for associations in HubSpot's data platform, driving relationship definitions, association behavior, limits, and record creation. Lead initiatives to generate associations from unstructured data, validate lookup properties, fix data dead-ends, engage customers, and align cross-functional teams to ensure backward-compatible, AI-ready relational data.

The Senior Product Marketer will lead pricing strategies, collaborate with cross-functional teams, build messaging frameworks, and enhance customer-facing experiences to better communicate HubSpot's evolving pricing models.

Lead a ~25-person threat operations organization to set strategy, detect and respond to security incidents, build threat intelligence and detection capabilities, ensure compliance, and partner with legal, compliance, and executive stakeholders to improve HubSpot's security posture.

Lead technical strategy and hands-on development of HubSpot's build, test, and deploy platform. Design scalable CI/CD, test orchestration, and AI-powered QA agents, drive architectural decisions, remove pipeline bottlenecks, and deliver cross-team initiatives that increase deployment velocity and reliability for thousands of engineers.

Lead design and delivery of AI-powered legal solutions: build and deploy AI agents and agentic workflows, own and optimize legal SaaS ecosystem, develop integrations and automations (Workato/iPaaS), translate attorney needs into technical solutions, drive AI adoption and enablement, shape roadmap, and measure technology impact for legal leadership.