Top Tech Jobs & Startup Jobs in Chicago, IL

Analyze product, user, transactional, and repayment data to develop risk and underwriting models, reduce losses and fraud, monitor model performance, and guide product and growth strategy. Build Looker dashboards and LookML models, conduct segmentation and experimentation, measure CAC and LTV, and communicate actionable insights to product, engineering, marketing, finance, and leadership.

Own Rain’s revenue operations infrastructure across Sales, Marketing, Partnerships, and Customer Success. Design and administer GTM compensation plans, maintain revenue dashboards and analyses, manage HubSpot architecture and integrations, support GTM systems, automate workflows with AI tools, and optimize cross-functional sales processes. The role requires strong analytical, systems administration, compensation, and process improvement skills in a fast-growing fintech environment.

Own and optimize Rain’s revenue and go-to-market systems, including HubSpot CRM. Design scalable processes, automate workflows, improve data quality, align cross-functional teams on KPIs and handoffs, and deliver insights that support revenue strategy. The role also drives systems adoption through documentation and training, evaluates productivity tools, and partners with senior leadership to improve funnel efficiency and operational excellence.

Corporate Counsel will advise on employment law, employment and commercial litigation, procurement contracts, whistleblower investigations, and company policies. The attorney will research applicable laws, assess legal risks, develop settlement options, review service-provider agreements, support People and Procurement teams, and prepare written legal analyses. The role reports to the General Counsel and offers advancement opportunities within the Legal Department.

Own Rain’s financial model, budgeting, cash forecasting, runway analysis, debt facility monitoring, and strategic finance initiatives. Partner with leadership, accounting, investors, and department heads on capital allocation, reporting, fundraising, and business decisions. Build complex financial scenarios, analyze new products and partnerships, improve planning automation with Drivetrain, and translate financial insights into recommendations for executives and board members.

Develop and manage the enterprise sales pipeline for Rain’s financial technology solutions. Qualify prospects, collaborate with sales development representatives, maintain market and competitor expertise, engage C-level executives, present product and business value propositions, manage account relationships, support ordering, and close enterprise opportunities. The role requires selling HCM and Earned Wage Access solutions while contributing throughout the sales lifecycle.

Generate outbound pipeline through high-volume prospecting (calls, email, social), research and personalize outreach, qualify leads, schedule meetings for AEs, maintain CRM hygiene, hit KPIs, iterate messaging, and collaborate cross-functionally while participating in coaching.