Top Tech Jobs & Startup Jobs in Chicago, IL

Serves as a client-facing technical advisor during enterprise payment sales cycles. Designs payment solutions, leads technical discovery, delivers demonstrations, supports RFPs and RFIs, prepares integration documentation, manages proof-of-concepts, and guides clients through sandbox testing and integration planning. Partners with sales, product, engineering, legal, compliance, customer success, and integration teams while translating customer needs into technical requirements and product feedback.

Manage accounting, financial reporting, cash management, accounts payable and receivable, budgeting, forecasting, audits, tax engagements, vendor contracts, and financial controls for a holding company and subsidiaries. Oversee third-party fund administration, prepare financial statements and analyses, manage related-party transactions, support new business initiatives, and improve operational processes. The role requires strong QuickBooks, Excel, GAAP, communication, and deadline-management skills, with private fund accounting experience preferred.

Own outbound and inbound prospecting for mid-market B2B software opportunities. Research target accounts, identify decision-makers, conduct personalized multi-channel outreach, qualify AI-related needs, book qualified meetings, and maintain accurate pipeline data. The role also contributes to building a scalable outbound playbook by analyzing messaging, personas, industries, and prospecting approaches.

This position trains transitioning service members in talent acquisition through hands-on experience in candidate sourcing, engagement, and ATS management, alongside job posting and compliance tasks.

Analyze small-business loan applications, including bank statements, financial statements, tax returns, and supporting documents. Assess cash flow, repayment ability, credit risk, business credibility, and potential red flags; make approval or decline recommendations under company policies. Perform peer quality reviews, maintain compliant documentation, meet decision SLAs, communicate with brokers and merchants, and escalate complex cases. Use Excel, financial analysis tools, and AI-supported workflows responsibly while applying independent judgment.

Manages daily social publishing across Instagram, TikTok, YouTube, and Facebook; captures and edits short-form event video; engages dancers, studios, and parents; prepares weekly performance reports; identifies trends; and coordinates user-generated and creator content, including rights and approvals. The role requires strong brand-voice writing, social fluency, organization, trend awareness, and willingness to travel to events and work occasional peak-season weekends.

Own credit portfolio performance analysis, credit policy, underwriting strategy, risk frameworks, and portfolio growth initiatives across lending products. Partner with Data Science, Product, Engineering, Operations, leadership, and external lending partners to develop predictive models, automated decisioning, analytical tools, dashboards, and reporting. Present strategic recommendations on portfolio risk, borrower behavior, credit expansion, and company-wide risk strategy.

Owns SEO and AI-search visibility strategy for 6–12 B2B client accounts, including technical SEO, content planning, performance analysis, AEO/GEO measurement, and client recommendations. Leads analyst output, coaches team members, maintains account roadmaps, partners with project and account managers, and contributes to hiring and performance decisions. The role is fully remote and supports B2B SaaS and technology clients.

Conducts manual and automated software testing across requirements, user workflows, edge cases, regressions, APIs, and data validation. Creates test cases, investigates and documents defects using SQL, logs, browser tools, and source code, and contributes Playwright automation within CI/CD pipelines. Collaborates with engineers and product teams, supports accessibility and security-conscious testing, follows HIPAA data-handling practices, and uses Claude Code responsibly to improve test design and investigation.

Own the agency’s creative output across visual identity, campaign and web design, brand strategy, copywriting, video, and motion. Lead creative direction in client engagements, strategy sessions, and new business pitches while setting quality standards and shaping the agency’s market presence. This senior individual contributor role offers autonomy, remote flexibility, and a path toward building and leading a creative team.