Top Tech Jobs & Startup Jobs in Chicago, IL

Perform transactional accounting, journal entries, bank and balance sheet reconciliations, fixed asset and accounts payable support, accruals, financial statements, and indirect tax filings. The role supports monthly close, tax compliance, and client reporting under US GAAP while maintaining accurate financial records and improving accounting processes through technology and AI tools.

Leads the strategy, compliance, audits, reporting, controls, and technology transformation of indirect tax operations across U.S. states, Canada, and global jurisdictions. Builds and mentors a tax team, oversees sales/use tax, VAT/GST, parking and excise filings, manages disputes and risk, and implements tax engines, ERP integrations, AI analytics, dashboards, and automated compliance processes.

Lead data science for Growth Marketing by developing attribution, lifetime value, acquisition cost, retention, and predictive models. Design and analyze experiments, including A/B tests, geo-tests, holdouts, and incrementality studies. Partner with Growth, Finance, Product, analytics, and engineering teams to optimize marketing spend, establish data pipelines, and create executive dashboards. Translate complex analyses into strategies that improve user acquisition, retention, and profitability.

Manage full-cycle, high-volume recruiting for field operations roles across multiple geographic markets. Source candidates through job boards, community partnerships, trade schools, hiring events, and referrals; screen applicants; coordinate interviews; maintain ATS pipelines; extend offers; support background checks and onboarding; and monitor recruiting metrics. Partner with field operations managers and People Operations to address hiring needs, reduce time to fill, and support facility launches.

Owns retention, financial performance, reporting, escalations, and growth for a portfolio of strategic B2B partners. Serves as the primary relationship owner and internal advocate, coordinating product, data, operations, and finance teams to deliver partner value. Builds executive trust, leads business reviews, champions product adoption, identifies expansion opportunities, and ensures commitments are completed. The role requires strong financial acumen, data storytelling, communication, ownership, and approximately 5–10% travel.

Leads retail growth and commercial strategy, owning revenue expansion, national account wins, partnerships, B2B marketing, deal structures, product-market fit, and vertical offerings. Builds retail industry relationships, coordinates sales, product, marketing, operations, and data teams, establishes growth reporting, and represents the company through trade press, conferences, and industry thought leadership.

Lead Metropolis’s hospitality growth strategy, owning segment revenue and expanding its location base through national account sales, partnerships, vertical marketing, and commercial innovation. Develop hospitality-specific value propositions, deal structures, product roadmaps, and marketing initiatives while collaborating with sales, operations, product, marketing, and data teams. Commercialize the Recognition Platform, establish performance dashboards, build industry partnerships, and drive thought leadership across the hospitality sector.

Supports corporate risk management through loss modeling, metrics reconciliation, insurance documentation review, KPI reporting, risk data analysis, and recommendations. Assists with policy renewals, loss-control materials, and compliance communications while gaining exposure to insurance and surety markets, brokers, actuaries, claims administrators, and underwriters. The internship is a 12-week hybrid role requiring at least four days per week in the downtown Chicago office.

Own the full sales lifecycle for healthcare and institutional accounts: source and qualify opportunities, lead complex RFPs, run discovery and demos, negotiate and close deals, collaborate cross-functionally on underwriting and compliance, and manage pipeline and forecasting in Salesforce.

Analyze deal structure, build and stress-test underwriting and proforma financial models, quantify client value, automate workflows, and partner with sales and operations to drive pricing, margin, and GTM decisions supporting revenue growth.