Top Tech Jobs & Startup Jobs in Chicago, IL

Lead product strategy and execution for a defined A/E ERP domain within an AI-accelerated cross-functional pod. Own problem framing, requirements, prototyping, roadmap prioritization, launch execution, customer adoption, and post-launch iteration. Apply customer and market insight, analytics, data-model knowledge, AI-assisted development, and responsible AI practices to build differentiated product capabilities and improve customer outcomes.

Own the product strategy and roadmap for SEO and AI visibility across thousands of real estate websites. Lead technical SEO foundations, structured data, performance, experimentation, migrations, measurement, and AI citation visibility. Partner with engineering and product teams to establish scalable defaults, safeguards, acceptance criteria, and reporting that improve organic discovery, client conversions, and platform-wide search quality.

Drives sales operations for North American distributor and retail partners by managing SKU-level forecasting, inventory planning, purchase orders, trade spend, dashboards, shipment and POS reporting, and business reviews. Partners with sales, supply chain, demand planning, and distributor replenishment teams to improve performance, reconcile trade spend, and deliver customer and leadership presentations.

Conduct high-volume outbound calls to identify, engage, and qualify education-sector prospects. Research decision-makers, map accounts, overcome objections, and generate qualified opportunities for Account Executives. Maintain accurate CRM records, track activity metrics, learn the company’s products and market, and collaborate in training and sales initiatives.

Enterprise Sales Executive responsible for selling complex SaaS solutions to large organizations, managing full enterprise sales cycles, presenting to executive stakeholders, building strategic account plans, developing territories, creating new business opportunities, and exceeding revenue targets. The role requires experience with six-figure deals, enterprise customers, executive presentations, cross-functional collaboration, and strategic relationship management.

Assess product and application architectures, develop threat models, identify security risks, and guide engineering teams on remediation. Promote security culture through training, mentoring, vulnerability management, and internal security initiatives. Build security tooling, automation, patterns, and workflows that embed secure-by-design practices across engineering. Partner with product managers, designers, and engineers to secure complex, large-scale cloud systems.

Owns revenue operations strategy and GTM planning, including forecasting, annual planning, business reviews, incentive design, analytics, KPI dashboards, and performance insights. Partners with Finance, Product, and Operations to improve sales productivity, align headcount with revenue goals, and execute multi-quarter strategic workstreams. The role translates complex data into leadership recommendations and manages cross-functional projects in a fast-paced environment.

Own end-to-end BSA/AML investigations for cannabis banking clients, including alert monitoring, risk assessments, marijuana-related SAR filings, transaction-monitoring rule calibration, CRB onboarding, license verification, beneficial ownership analysis, account reviews, and support for audits and regulatory examinations. The role requires expertise in FinCEN guidance, state cannabis regulations, BaaS compliance models, AML platforms, and cannabis banking typologies.

Drive full-cycle enterprise sales for flexible labor solutions across hospitality, catering, food service, venue, and event organizations. Prospect and close strategic accounts, manage complex multi-stakeholder buying processes, build accurate pipelines, develop account plans, communicate labor ROI, and collaborate on proposals and proofs of concept. Represent WorkWhile at industry events and executive meetings while exceeding quota and expanding strategic customer relationships.

Create and manage digital-first video content across web, social, and CTV. Responsibilities include concept development, storyboarding, filming, editing, motion graphics, animation, agency direction, and end-to-end project ownership. The role translates complex ideas into engaging visual stories, manages multiple productions, improves workflows with AI-enabled tools, and maintains brand and design quality across campaigns and platforms.