Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and manage complex commercial, construction, and government-related litigation in state and federal courts. Develop strategy, draft dispositive motions, take/defend depositions, support trial preparation (second-chair and potential first-chair), advise sophisticated clients, mentor junior attorneys, and contribute to business development and firm leadership with a clear path to partnership.

Manage a portfolio of high-value real-money gaming players, building relationships and delivering personalized communications, rewards, and experiences. Drive retention, reactivation, engagement, and player lifetime value through data-informed initiatives. Resolve VIP requests and escalations professionally, collaborate with Product and Marketing, provide player insights, and ensure responsible gaming and regulatory compliance. The role is fully remote, primarily aligned with US time zones, with occasional weekend availability required.

The Staff Accountant manages domestic and international accounting activities, including accounts payable, bank and general ledger reconciliations, fixed assets, depreciation, taxes, payroll postings, corporate card expenses, accruals, and prepaids. The role supports month-end and year-end close, flux analysis, financial reporting, dashboards, and external audits. It requires accurate, independent execution, collaboration with leadership and vendors, and proficiency in advanced Excel and Microsoft Office tools.

Lead end-to-end implementations of Pinewood.AI for North American dealership accounting teams, including discovery, configuration, workflow validation, training, go-live, and hypercare. Coach users on dealership financial processes, localize training materials, support change adoption, manage multi-site rollouts, and collaborate with product and delivery teams. The role requires extensive travel across the United States and Canada and involves mentoring colleagues and improving implementation methodologies.

Own Salesforce client solutions from discovery through go-live. Lead requirements discovery, recommend scalable solutions, configure declarative Salesforce features, and support data migration, integrations, testing, UAT, training, and deployment. Manage priorities across multiple SOW-based engagements while balancing scope, budget, timelines, maintainability, and business value. Advise senior stakeholders, identify risks, and collaborate with developers and architects on complex solutions.

Own the end-to-end strategy, roadmap, requirements, delivery, launch, and measurement of AI-powered security operations products. Partner closely with engineering, sales, customer success, and enterprise security customers to prioritize work, build trust through transparency and control, and define how autonomous agents transform SOC workflows.

Serves as a client-facing technical advisor during enterprise payment sales cycles. Designs payment solutions, leads technical discovery, delivers demonstrations, supports RFPs and RFIs, prepares integration documentation, manages proof-of-concepts, and guides clients through sandbox testing and integration planning. Partners with sales, product, engineering, legal, compliance, customer success, and integration teams while translating customer needs into technical requirements and product feedback.

This position trains transitioning service members in talent acquisition through hands-on experience in candidate sourcing, engagement, and ATS management, alongside job posting and compliance tasks.

Leads sales strategy and execution, owning new business bookings, ARR growth, enterprise renewals, retention, expansion, forecasting, deal execution, quota attainment, pipeline coverage, conversion rates, and sales productivity. The role requires building a repeatable sales motion, coaching and enabling teams, negotiating with senior stakeholders, developing strategic relationships, and using data-driven insights to improve performance.

Leads overall brand and marketing strategy across digital, PR, events, and traditional channels. Manages and develops the marketing team, partners with Sales and Product Development, oversees content and social media, and directs SEO/SEM, email, display, affiliate, and marketplace campaigns. Uses market research, analytics, KPI reporting, testing, and competitive analysis to optimize performance. Manages marketing budgets, vendors, resources, and return on investment while supporting product launches and brand growth.