Top Tech Jobs & Startup Jobs in Chicago, IL

Process accurate, compliant payroll for multiple clients across varying frequencies and multiple states. Responsibilities include validating and balancing payroll, managing off-cycle payments, supporting tax filings and year-end activities, resolving discrepancies, maintaining payroll configurations, improving processes, documenting procedures, managing client relationships, and meeting billable utilization targets.

Drive net-new business and revenue growth by prospecting, managing territories, leading technical discovery conversations, and closing enterprise SaaS/PaaS deals. Own the full sales cycle, quota, forecasting, and pipeline management while engaging technical and executive stakeholders. Collaborate with sales development, sales engineering, professional services, and customer success teams to deliver an effective buyer journey.

Own significant product areas from customer problem discovery through solution definition, prototyping, shipping, measurement, and iteration. Build AI-powered prototypes and production products using tools such as Claude and Cursor, engage directly with customers and commercial stakeholders, lead small squads, influence product direction, and contribute to an AI-native product engineering culture.

Define clinical reasoning, safety boundaries, evaluation scenarios, datasets, rubrics, and acceptance thresholds for AI-enabled chronic disease products. Analyze failures and edge cases, support clinical validation and outcomes research, interpret clinical and EHR data, and collaborate with Product, Engineering, AI/ML, Data, informatics teams, and clinical stakeholders on integrations and workflows.

Own full-cycle enterprise sales and new business development across the US and Canada. Close complex SaaS deals with hedge funds and asset managers, engage senior investment executives, build institutional relationships, represent Arcana at industry events, and provide market feedback to Product and Leadership. The role requires strong enterprise selling experience, institutional investment workflow knowledge, a proven record of high-value deal closures, and an established industry network.

Lead Reprise’s marketing function and redesign its B2B go-to-market approach with an AI-first strategy. Own pipeline generation, demand generation, ABM, content, events, partnerships, analyst relations, social media, marketing tooling, budget, and external partners. Set and achieve monthly pipeline targets, establish category leadership in demo automation, optimize program spending, and combine strategic leadership with hands-on execution.

Own end-to-end B2B SaaS sales cycles in global markets, selling to technical buyers and senior managers. Generate pipeline through outbound prospecting, lead discovery and qualification, manage forecasts in CRM tools, and lead POVs or POCs. The role requires consultative selling, autonomy, strong deal progression, and collaboration across flexible US and Israeli time zones in a fast-paced startup environment.

Lead developer relations as the company’s first DevRel hire. Create technical content, demos, examples, and projects; speak at conferences, meetups, and podcasts; build relationships with engineering teams and technical communities; gather product feedback; establish the company as a leading voice in AI-driven engineering; and grow its social following.

Lead client engagements on benefits strategy, plan design, open enrollment, and administration. Stabilize operations, manage carriers/brokers, execute transitions and platform migrations, ensure compliance, advise on cost optimization and multi-state/global expansion, and expand client relationships.

Own the organization’s end-to-end YouTube strategy, including channel architecture, content cadence, audience growth, editorial direction, packaging, analytics, experimentation, and monetization. The role partners with production, creative, marketing, social, and partnerships teams; develops growth playbooks and performance reporting; identifies revenue opportunities; tracks platform and creator trends; and coaches teams on YouTube best practices.