Top Tech Jobs & Startup Jobs in Chicago, IL

Own end-to-end development of consumer lending products: define roadmap, balance growth, risk, and compliance, partner with underwriting and external lenders, use analytics and AI to measure impact, iterate, and scale products cross-functionally.

Manage a book of personal-lines business including renewals, remarketing, invoicing, endorsements, and claims assistance. Serve as primary client contact, collaborate with underwriters and sales, monitor reports, delegate to account associates, and mentor team members to ensure service, accuracy, and performance standards.

Lead end-to-end engineering for complex outside plant (OSP) fiber and copper builds, overseeing design, permitting, field validation, construction readiness, QA/QC, budgeting, and closeout. Mentor junior engineers, coordinate with utilities/agencies, produce sealed plans and splicing/loss documentation, manage permits/ROW and pole attachments, and drive continuous improvements and reporting.

Paid, one-time remote voice recording study contributing English speech data for AI research. Participants complete a guided session from a compatible device, follow instructions, and receive $25 on successful completion.

Design, build, and maintain scalable backend services and integrations. Debug production issues, lead architecture and technical decisions, mentor engineers, ensure API backward compatibility, implement auto-scaling, and architect real-time data syncing for large volumes.

Manage and administer global sales commission programs, ensuring accurate commission calculations, reporting, accruals, and payouts. Maintain compensation systems and data, analyze results, support forecasting, accounting, audits, and month-end close. Partner with Sales, Finance, HR, and Operations to resolve issues, provide guidance, and drive process automation and improvements.

Lead and build Fleetio's product marketing and GTM commercialization function. Create repeatable launch frameworks, positioning, messaging, pricing, sales plays, and enablement. Align Product, Sales, Marketing, Customer Success, and Partners; hire and grow a commercialization team; establish operating rhythms, templates, and metrics to drive adoption, pipeline, and revenue.

Manage end-to-end settlement payment operations including creating and distributing payments per court orders, performing compliance reviews and audits, processing replacements/wires/deposits, preparing tax forms, investigating payment discrepancies with vendors and banks, and safeguarding confidential financial data.

Manage a Mid-Market portfolio (~120 small business accounts, $40-100k ARR), drive renewals and retention, log activities in Salesforce, prepare business reviews, handle contracts/invoicing/quotes, identify upsell opportunities, lead trainings, resolve escalations, and collaborate with internal teams to improve customer adoption and satisfaction.

Lead federal business development for health, readiness, and workforce support: build and manage pipeline, qualify opportunities, support capture and proposals, mentor BD staff, develop account strategies, and present strategic insights to leadership to drive revenue growth.