Top Tech Jobs & Startup Jobs in Chicago, IL

Own the end-to-end product strategy, roadmap, monetization, analytics, and experimentation for a consumer VPN business. Grow subscription revenue through pricing, paywalls, trials, retention, and billing improvements while launching a free ad-supported tier. Manage hybrid monetization, app-store compliance, acquisition economics, P&L performance, and cross-functional delivery across engineering, design, data, monetization, legal, and user acquisition.

Owns enterprise business development for major automotive OEMs and industry partners, creating and closing complex strategic opportunities. Builds executive relationships, develops account strategies, leads discovery and negotiations, shapes deal structures, maintains pipeline forecasts, and expands initial wins into long-term accounts. Partners cross-functionally on business cases and implementation handoffs while reporting enterprise pipeline strategy to the CMO. Requires substantial travel and independent execution.

Develops, tests, deploys, and supports attended and unattended UiPath RPA automations. Works with stakeholders to analyze processes, gather requirements, identify automation opportunities, and translate needs into technical solutions. Builds database and API integrations using SQL and programming languages, applies web technologies for browser automation, and maintains documentation. Troubleshoots automations, supports Agile and Waterfall development, participates in testing and project planning, and provides operational status updates.

Generate qualified sales pipeline through inbound and outbound lead follow-up across a defined territory. Research target accounts, engage prospects through phone, email, social media, and partners, identify business pain points, communicate Zimperium’s mobile security value proposition, and schedule high-quality meetings for sales representatives. Collaborate with sales and support teams to plan, execute, and measure targeted activities.

Independent contractor role responsible for introducing Clocktower’s Strategy, Research & Advisory offering to hedge funds, allocators, banks, and corporates. Duties include leveraging senior financial-market relationships, arranging warm introductions, joining initial meetings, providing local market insight, and bringing relevant contacts to regional events. Compensation is commission-based with no salary or guaranteed minimum. The role is remote, flexible, and conducted under a consulting agreement.

Coordinates website projects from kickoff through delivery, managing timelines, client communication, cross-functional collaboration, quality reviews, documentation, feedback, and revisions. The role uses Asana and established workflows to keep multiple builds on schedule, identify risks, and support continuous process improvement while developing toward independent project ownership.

Leads enterprise leadership and organizational development initiatives across a healthcare system. Responsibilities include assessing workforce needs, designing and evaluating learning programs, facilitating leadership training, coaching leaders and teams, consulting with executives, managing complex initiatives, and measuring organizational outcomes. The role requires strong facilitation, instructional design, communication, relationship-building, change leadership, and program management skills in a complex matrixed environment.

Enhances sales effectiveness by managing sales content libraries, developing playbooks and training, supporting product launches, creating competitive materials, and improving pricing and margin execution. Partners with product management, marketing, and field teams to translate technical information into sales resources. Maintains CRM and enablement technology proficiency, gathers field feedback, and tracks content, training, and productivity metrics.

Own the full sales cycle for new enterprise brand accounts, from prospecting and qualification through demos, negotiation, and close. Build strategic pipelines, sell consultatively to senior marketing and partnership stakeholders, develop data-driven proposals, manage complex multi-stakeholder deals, forecast accurately in CRM, and collaborate cross-functionally through onboarding. The role focuses on closing mid-five- to seven-figure SaaS contracts within the sponsorship intelligence market.

Lead and coach a team of underwriters for a Real Estate Umbrella program, ensure underwriting integrity and profitability, monitor portfolio performance, enforce compliance, partner with sales and program managers, use data analytics to drive pricing and growth, implement process improvements, and underwrite risks as needed.