Top Tech Jobs & Startup Jobs in Chicago, IL

Provide high-volume inbound phone, chat, and email support to retail brokerage customers. Assist with complex options and futures order execution, explain trading platform functionality, analyze customer positions, discuss strategy advantages and disadvantages, and identify timely solutions for self-directed investors. The role requires strong knowledge of brokerage services, options, futures, margin accounts, Regulation T, and portfolio margin, along with FINRA securities licenses and in-office availability.

Own the infrastructure and DevOps product roadmap, including AWS cloud infrastructure, CI/CD, and infrastructure-as-code. Partner with engineering, security, compliance, and leadership to prioritize platform improvements, evaluate tooling and vendors, improve deployment workflows, and measure reliability, incident frequency, recovery time, cost, and engineering velocity. The role requires strong technical depth, product management experience, and comfort operating in a regulated fintech environment.

Owner of trading operations and regulatory compliance between trading platforms and NFA/CFTC obligations. Monitor platforms, triage incidents, draft regulatory reports, manage capital charge oversight, payment rails, reconciliations, and operational runbooks. Support audits, margin compliance, MT4-to-MT5 migration, process improvements, and reporting to leadership.

Provide weekend and overnight customer support via phone, chat, and email for account management, funding/withdrawals, trade inquiries, and risk monitoring. Document interactions in Salesforce, triage urgent issues, escalate to licensed staff or teams, complete sponsored FINRA licensing, and contribute to shift handoffs and process improvements.

Own design for complex trading features across web, desktop, and mobile. Lead discovery, user research, and A/B experiments. Collaborate with PMs and engineers, drive product direction, mentor designers, and connect design work to business metrics like conversion, retention, and engagement.

Lead and scale tastytrade's fraud investigations function: hire and manage analysts, define fraud taxonomy and controls, set KPIs and budget, select tooling/vendors, drive investigations to resolution, build detection/monitoring, coordinate with compliance/product/technology, and report program performance to senior leadership.