Top Tech Jobs & Startup Jobs in Chicago, IL

Develop and execute enterprise sales and go-to-market strategy for emerging AI agent products. Build executive relationships, identify use cases, manage sales from discovery through closing, and partner with product and engineering on positioning, packaging, pricing, pilots, and product requirements. Establish repeatable processes for converting experimentation into production deployments while providing market feedback and shaping a new product category.

Provides hands-on technical leadership across the full stack, designing customer-facing experiences, APIs, services, data flows, and cloud systems. Leads complex cross-functional initiatives, shapes platform architecture, improves engineering standards, performance, reliability, observability, and security, and mentors engineers. Partners with Product, Design, Data Science, and SRE while driving responsible AI adoption and scalable solutions in a distributed global environment.

Drives revenue growth across a Southwest territory by acquiring and managing commercial insurance agency partners, brokers, MGAs, and MGUs. Builds relationships, develops distribution strategies, meets premium and production goals, conducts prospecting and negotiations, tracks KPIs, analyzes markets and competitors, and represents the company at industry events. Manages and coaches a high-performing business development team while improving partner onboarding and engagement processes.

Develop new institutional business and grow existing accounts by prospecting law schools and higher education institutions, conducting discovery meetings and presentations, managing sales pipelines, preparing proposals, supporting contracts and renewals, and partnering with internal teams. The role focuses on consultative sales of education, technology, SaaS, and professional services solutions, with responsibility for revenue generation, customer retention, and maintaining accurate CRM forecasts.

Manage end-to-end customer implementations, including scoping needs, configuring solutions, coordinating stakeholders, troubleshooting issues, and driving adoption. Partner with Sales, Customer Success, Product, and Engineering while managing multiple timelines and improving implementation processes. The role requires implementation or onboarding experience, customer-facing stakeholder management, project management skills, and familiarity with Jira, HubSpot, Salesforce, and similar systems.

Drive new-logo acquisition across an assigned territory by managing the full sales cycle, including prospecting, qualification, relationship building, negotiation, and closing. Build partnerships with senior decision-makers and ecosystem partners, maintain high sales activity, manage complex multi-stakeholder opportunities, and achieve revenue targets autonomously. The role focuses on selling Workday-related professional services and requires regional travel for events and customer meetings.

Volunteer UI/UX Designer to help build a design system and design internal applications. Work remotely 4–6 hours/week with a global nonprofit, collaborating with a senior UI/UX manager to improve front-end design practices and digital assets.

Marketing Manager responsible for B2B and B2B2C demand generation, brand and consumer marketing, client-specific collateral, campaign execution, market research, and performance optimization. The role partners cross-functionally with growth, account management, creative, product, and digital teams to drive awareness, enrollment, engagement, pipeline growth, and client success.

Own WorkHero’s growth marketing function, including strategy, budget, acquisition channels, conversion, lifecycle marketing, content, attribution, reporting, automations, and experimentation. Build a repeatable engine for acquiring HVAC contractors, improve funnel performance, manage freelance specialists, develop customer-informed messaging, and connect marketing activity to qualified pipeline, acquisition cost, and customer quality.

Manage Durango Boots sales across Washington and Oregon by meeting sales targets, soliciting orders, expanding retail distribution, building customer relationships, using structured sales processes, solving problems, and supporting marketing plans. The role requires extensive territory travel, retailer presentations, independent work, CRM and administrative tasks, and occasional physical labor, including lifting up to 50 pounds.