Top Tech Jobs & Startup Jobs in Chicago, IL

Lead enterprise expansion across strategic accounts: develop account plans, self-generate pipeline, multi-thread stakeholders, run cross-sell plays, manage a BDR/AI SDR rhythm, and help codify enterprise expansion playbooks.

Build zero-to-one products from prototype through production, working through ambiguity and partnering closely with product, design, and customers. Develop scalable systems, run experiments and technical spikes, influence product direction, and uphold reliability, performance, engineering standards, and customer experience. Mentor engineers and contribute to architecture, coding practices, and cross-functional collaboration.

Own the full enterprise SaaS sales cycle, including self-sourced pipeline generation, discovery, product demonstrations, forecasting, negotiation, and close. Develop strategic account plans, manage complex multi-stakeholder deals, and engage executive buyers such as CFOs and CROs. Collaborate with solutions engineering, product, marketing, customer success, and BDR teams while contributing to sales playbooks and go-to-market strategy.

Serve as the finance partner to Sales, Marketing, and Customer Success leadership. Own GTM planning, forecasting, capacity and ARR modeling, commissions analysis, variance reporting, SaaS metrics, unit economics, ROI modeling, and financial process automation. Translate complex analyses into executive recommendations, improve planning systems, and support compensation plan design and GTM investment decisions.

Lead engineering for CaptivateIQ’s Incentive Compensation Operations platform. Hire, develop, and manage software engineers; partner cross-functionally on product vision, roadmaps, and strategy; oversee delivery, reliability, performance, security, and operational excellence; guide architecture and technical decisions; and transform compensation operations into an AI-native experience using intelligent agents to reduce manual work.

Lead and scale a Project Management function for enterprise SaaS implementations: build delivery governance, risk-visibility systems, milestone gates, and a PM/coordinator organization. Own delivery operating rhythm and reporting, improve enterprise delivery accountability, hire and develop PM staff, and design scalable, multi-tier delivery models to support both high-touch and high-volume engagements.

Lead end-to-end delivery and architecture of complex enterprise incentive compensation implementations. Design scalable, high-performance compensation models, act as senior technical escalation, advise cross-functional stakeholders, influence product roadmap, and uplift Professional Services standards and reusable modeling frameworks.