Top Tech Jobs & Startup Jobs in Chicago, IL

Process multistate U.S. and multiprovince Canadian payrolls, including timecards, deductions, adjustments, reconciliations, year-end reporting, and final pay. Support benefits, leave payments, retirement contributions, audits, compliance notices, and employee inquiries. Maintain accurate records, resolve discrepancies, coordinate with Finance and benefits providers, and escalate complex tax or compliance issues. The role requires strong Excel skills, payroll expertise, confidentiality, and Pacific Time availability.

Build and grow Upsun’s systems integrator and digital agency business across North America. This quota-carrying role owns prospecting, pipeline development, discovery, pilots, negotiations, forecasting, and full-cycle sales. The manager will convert pilots into recurring partner practices, collaborate with Agency, Solutions Engineering, Product, and Marketing teams, provide partner feedback, and represent Upsun at partner visits, roadshows, and regional events.

Leads regional grocery sales across the Western United States, developing sales strategies, forecasts, trade plans, promotions, and retail execution programs. Manages broker, distributor, and retailer relationships; negotiates commercial agreements; monitors revenue, profitability, fill-rate, and other performance metrics; and identifies growth opportunities. Requires extensive CPG food sales experience, strong analytical and communication skills, and travel of up to 40%.

Leads growth and traffic acquisition across BOLD’s brands, owning job distribution, paid acquisition, SEO, attribution, bidding, traffic quality, and growth technology roadmaps. Partners with marketing, engineering, data science, and executive stakeholders to define acquisition strategies, run large-scale experiments, improve conversion and retention, and manage KPIs including traffic, CAC:LTV, ROAS, and user growth. Coaches product managers and drives cross-functional alignment.

Own the platform’s performance, security, reliability, and operational foundations. Design scalable distributed systems, secure execution and software supply chains, improve CI performance, manage observability and alerting, automate compliance evidence and cost monitoring, respond to incidents, patch vulnerabilities, and convert recurring findings into guardrails, checks, conventions, and agent workflows. Collaborate across engineering, product, security, and finance while operating production systems and evaluating AI-driven engineering risks.

Lead AI/ML initiatives for Air Force condition-based maintenance, from predictive model development through production deployment. Architect data pipelines, develop machine learning, deep learning, NLP, and generative AI solutions, and build knowledge graph capabilities. Provide technical leadership, integrate models into applications and workflows, and monitor data quality, model performance, drift, and bias. Collaborate with engineering, cloud, software, and product teams while supporting defense aviation logistics and sustainment missions.

The Director of People Partnership serves as an HR business partner across the ASPCA, advising leaders and employees on employee relations, performance management, organizational effectiveness, workforce planning, change management, conflict resolution, and career development. The role conducts investigations, supports restructures and compensation processes, coaches managers, facilitates training, and collaborates with Legal, Talent Acquisition, Learning and Development, and other People Team functions. This remote role supports multiple time zones, includes quarterly weekend on-call shifts, and requires up to 20% travel.

Manages financial analysts and leads financial modeling, budgeting, forecasting, reporting, close activities, cost analysis, and large-data analysis. Presents financial findings and recommendations to senior leadership, maintains accurate financial databases, monitors competitive conditions, and partners cross-functionally to support organizational financial goals.

Leads the Client Accounting division as a business unit, owning P&L, staffing, KPIs, profitability, client relationships, and service quality. Oversees inventory and cost accounting, GAAP reporting, ERP implementations, and proactive advisory for startup clients. Manages, coaches, and hires team members; handles performance, capacity, and client escalations. Drives business development, cross-functional collaboration, technology adoption, and AI-enabled efficiency.

Coordinate Crewfare’s brand and marketing activities across social media, content creation, B2B campaigns, partner marketing, creator collaborations, and live-event activations. Manage content calendars, produce short-form video and written content, support launches and co-marketing campaigns, oversee the ambassador program, track campaign performance, and travel to festivals, sporting events, and conferences.