Top Tech Jobs & Startup Jobs in Chicago, IL

Owns marketing strategy and execution for a high-growth startup or technology portfolio company. The role is intended for senior marketing leaders, ranging from Chief Marketing Officer to Head of Marketing, with responsibility for driving growth and leading the company’s marketing function.

Leads data architecture and engineering modernization across business domains. Designs and implements complex pipelines, integrations, data models, and orchestration using Snowflake, AWS, and Airflow. Establishes data quality, governance, security, testing, observability, CI/CD, and reliability practices. Provides architectural guidance, evaluates technical solutions, leads cross-team initiatives, mentors engineers, and improves platform performance and cost efficiency.

Lead Pearl’s global legal strategy as General Counsel, advising the CEO, executive team, and Board on AI, product, privacy, consumer protection, governance, transactions, litigation, employment, and regulatory matters. Build and manage a lean, high-performing Legal team while supporting responsible product innovation, international operations, compliance, and strategic growth. Drive AI adoption across Legal and provide practical, business-focused counsel in a complex technology and e-commerce environment.

Develops and executes B2B sales and marketing strategies for fleet leasing, management, maintenance, fuel, outsourcing, software, and consulting solutions. Identifies prospects, generates leads, manages client relationships, presents and negotiates proposals, closes long-term contracts, and supports customer onboarding. Conducts market and competitive analysis, collaborates with internal teams, and manages a sales pipeline across a California territory.

Owns new business and expansion across the Pacific Northwest and Mountain Range States. Builds territory and account plans, generates pipeline, manages complex enterprise security software deals, co-sells with cloud and data partners, forecasts accurately, and develops customer references. The role sells to SOC leaders, detection engineers, CISOs, and data platform leaders, requiring expertise in SIEM costs, security data lakes, detection engineering, and AI-powered SOC operations.

Drive new business and strategic account expansion for intellectual property services and technology solutions. Manage the full consultative B2B sales cycle, from prospecting and discovery through proposals, negotiation, and contract execution. Build relationships with corporate IP departments, legal teams, law firms, and innovation-focused organizations. Develop territory and account plans, maintain sales forecasts in CRM systems, support cross-selling and upselling, attend industry events, and collaborate with delivery and customer success teams to ensure retention and growth.

Leads product marketing strategy and execution for Calendly products, including AI capabilities. Responsibilities include customer and market analysis, product positioning and messaging, go-to-market planning, launch execution, cross-functional coordination, executive communication, campaign measurement, and adoption improvement. The role also requires using AI tools and building reusable AI workflows to improve product marketing efficiency and quality.

Own enterprise sales for Wisconsin and surrounding territories, including prospecting cybersecurity organizations, managing complex sales cycles, delivering product demonstrations, developing strategic customer relationships, and meeting quarterly targets. The role also partners with Product, Marketing, and leadership to refine go-to-market strategy, sales methodology, and messaging for an early-stage cybersecurity company.

Design, develop, and maintain automated test frameworks and scripts for React and Node.js applications using TypeScript and Selenium. Perform manual, regression, performance, database, and data validation testing; manage defects; integrate tests into CI/CD pipelines; and collaborate with Agile teams to troubleshoot complex issues and ensure software quality. Requires a bachelor’s degree, at least five years of experience, and an active or obtainable TSA clearance.

Reviews prevailing wage and apprenticeship compliance reports, researches Inflation Reduction Act and Davis-Bacon requirements, advises clients, answers regulatory questions, and improves compliance processes, templates, tools, and resources. The role manages multiple client engagements, serves as a primary client contact, collaborates with product and engineering teams, and translates complex labor regulations into practical recommendations.