Top Tech Jobs & Startup Jobs in Chicago, IL

Manage an established portfolio of legacy clients, driving retention, growth, and expansion. Audit account health, conduct strategic check-ins and workshops, advise business owners on offers, funnels, sales, prospecting, closing, fulfillment, and AI adoption, identify upsell opportunities, resolve issues, coordinate cross-functionally, and document account activity.

Own a portfolio of active clients across onboarding, growth, scale, and at-risk stages. Diagnose blockers across offers, funnels, campaigns, sales, and fulfillment; manage expectations; resolve escalations; conduct workshops and calls; identify upsell opportunities; and maintain accurate account documentation. The role requires consulting business owners, understanding B2B lead generation and payment flows, handling difficult conversations, and operating autonomously in a fast-moving, AI-focused environment.

Own at-risk customer relationships involving dissatisfaction, disengagement, cancellations, refunds, and lost confidence. Investigate customer journeys, diagnose root causes, troubleshoot issues, lead de-escalation and recovery conversations, coordinate cross-functional resolution, and maintain customer ownership through completion. The role requires consultative communication, sound commercial judgment, accurate documentation, and the ability to identify recurring retention issues and recommend improvements.

Own the most sensitive client relationships, diagnose issues, protect revenue, develop retention strategies, and enhance operational processes.

Full-cycle B2B closer converting outbound cold-email leads into qualified opportunities. Run discovery, demos, negotiations, and close mid-to-high-ticket deals. Maintain CRM, manage proposals and pipeline reporting, partner with SDRs and leadership to optimize outbound performance and hit aggressive conversion and quota targets.

Lead and scale B2B and B2C communities of founders and operators: moderate channels, design engagement systems, run live sessions, track engagement metrics, surface insights to internal teams, and support member retention, growth, and upsell through active community programming.

Execute customer onboarding from paid sign-up through activation, early milestones, and renewal. Run kickoff calls, follow and improve playbooks, manage a small portfolio of accounts, spot and remediate churn signals, and ensure proactive communication between Sales and delivery.