Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and own Syllo's QA strategy, build scalable automated testing frameworks integrated into CI/CD, and drive quality across Engineering, Product, and Customer Success. Champion QA processes, measure and improve release standards, reproduce and validate complex customer issues, and leverage AI/LLM tools to modernize test generation, failure analysis, and automation to increase release confidence and reduce manual testing.

Lead end-to-end onboarding for strategic, complex customers—transforming and migrating investment data, advising on data structure, resolving escalations, improving processes and tools, mentoring team members, and building reusable AI-supported onboarding workflows.

Assess and document current and target-state Martech architecture, identify consolidation and integration opportunities, define unified data/process flows and integration patterns, produce architecture artifacts and implementation guidance, and work with stakeholders to plan and govern consolidation for an AI-ready future state.

Lead enterprise Compliance Testing and Monitoring for consumer lending, designing risk‑based test plans, automated testing solutions, and monitoring frameworks; oversee execution, issue tracking, remediation, regulatory readiness, and executive/Board reporting while managing a team of compliance professionals.

Manage ongoing relationships with established mental health providers to retain and grow their practices. Conduct proactive outreach, run availability reviews, enable feature adoption, log interactions in HubSpot, escalate issues cross-functionally, and meet measurable activity and retention goals.

Manage and administer the Business Development tech stack (Salesforce, ZoomInfo, Power BI, Kalibrate), ensure data integrity and lead routing, handle vendor contracts and renewals, produce executive pipeline and market intelligence reports, support BD managers with research and meeting materials, and execute marketing campaigns to build employer-sponsored solutions awareness.

Drive new, add-on, and product expansion sales within assigned East territory. Own account strategy, maintain executive relationships, manage pipeline and forecasts, collaborate with pre-sales and support teams, present product demos, and meet quarterly and annual quota while traveling frequently to customer sites.

Support day-to-day AP/AR, billing, cash application, reconciliations, and transaction processing. Prepare and review vendor bills and customer invoices, assist month-end close, research discrepancies, respond to stakeholders, and support process improvements and reporting to ensure accurate financial records and audit readiness.

Convert qualified prospects into high-ticket VIP clients via 45-minute Zoom consultations. Manage a high-volume pipeline in HubSpot, meet sales KPIs, handle enrollment and payments, perform follow-up, maintain accurate CRM records, and collaborate with Sales and Customer Success teams in a fully remote, high-performance environment.

Own and grow a US Government account portfolio by responding to pricing requests, preparing quotations, managing OTG contract administration, tracking opportunities, supporting bookings/documentation, updating pricing guidelines, and coordinating with internal teams to increase volume and revenue.