Top Tech Jobs & Startup Jobs in Chicago, IL

Lead growth strategy and execution for a business line: own growth targets and KPIs, coordinate cross-functional teams to drive acquisition, conversion, and revenue, run data-driven experiments, launch and scale initiatives, and improve systems through automation and AI.

Lead companywide recruiting and help build the organization’s people infrastructure. Responsibilities include sourcing candidates, developing compensation and retention programs, managing payroll and benefits, overseeing performance evaluations, creating onboarding and training processes, and advising leadership on employment-law compliance. The role supports a distributed team and works closely with executive and legal teams.

Manage and optimize accounting processes, controls, and financial reporting. Oversee affiliate payments, audits, UI, deferred revenue, month-end close, tax compliance, registered agents, AP, credit card reconciliation, lender reporting, and lead ad-hoc projects while collaborating with accounting staff and external stakeholders.

Designs prompts, context-management strategies, subagent architectures, routing systems, and agentic workflows for conversational LLMs. Builds prototypes using APIs, RAG, fine-tuning, and multimodal prompting; reviews agent conversations and feedback to improve performance. Documents processes, trains colleagues, and becomes the internal expert on the dialogue platform and prompting practices.

Own the full B2B SaaS sales cycle, from prospecting and qualification through discovery, demos, trials, negotiation, and close. Build qualified pipelines across the U.S. and Europe, develop customer relationships, test and improve sales messaging and processes, address objections, document the sales motion, and share customer feedback with product and leadership teams.

Build and maintain scalable financial data infrastructure, including ingestion, validation, normalization, and integrations. Develop systems that calculate portfolio performance metrics efficiently across high-volume datasets, improve reliability and observability, and support distributed processing. Create internal tools, dashboards, reusable schemas, asset data feeds, and self-service analytics capabilities. Collaborate cross-functionally to expand market-data coverage, support B2B integrations, and strengthen operational resilience.

Serve as the outsourced CFO for a portfolio of startups and SMBs. Lead financial strategy, cash flow management, FP&A, budgeting, forecasting, modeling, KPI tracking, fundraising, debt and equity financing, board presentations, reporting, compliance, internal controls, and profitability improvements. Build trusted CEO and founder relationships while overseeing financial operations and delivering actionable insights.

Generate demand and build sales pipeline for account executives by identifying and cold-calling high-potential businesses. Manage client relationships, optimize sales processes, track performance metrics, communicate product value, gather customer feedback, and build corporate partnerships. The role requires ambition, strong reasoning, teamwork, reliability, transparency, and proficient English.

Own end-to-end analytics across marketing, revenue, product, and partnerships. Build reliable data models and semantic layers in a lakehouse, maintain dashboards and monitoring, investigate anomalies, conduct experimentation, and translate complex analyses into recommendations for senior stakeholders. The role requires advanced SQL, Python, data modeling, stakeholder communication, autonomy, and mentoring, with responsibility for improving data quality and building analytical standards in a high-growth startup.

Close qualified sales opportunities with eCommerce founders and decision-makers. Conduct discovery calls, identify business challenges, sell CRO redesigns and A/B testing services, manage proposals through close, follow up consistently, maintain an accurate pipeline, and improve conversion rates. The role requires strong B2B sales skills, eCommerce and DTC knowledge, and ownership of sales targets and results.