Top Tech Jobs & Startup Jobs in Chicago, IL

Leads a unified solutions organization spanning presales solution engineering, professional services, and value engineering. Owns technical wins, demo standards, certification, value-based business cases, services scoping, delivery plans, sales partnership, pipeline operating rhythm, customer engagement, hiring, and feedback to product and GTM leadership. The role is accountable for improving win rates, deal sizes, and ARR while building a high-performing technical go-to-market function.

Own renewals, retention forecasting, executive QBRs, adoption tracking, risk mitigation, and upsell opportunities across approximately 30 enterprise B2B customers. Serve as the primary customer advocate, manage usage-based billing conversations, maintain Salesforce data, and partner cross-functionally to improve renewal processes and revenue operations.

Own global people operations and employee experience, including HRIS data management, onboarding, performance reviews, payroll, benefits, compliance, reporting, employment documentation, and EOR coordination. Partner with Finance, Legal, IT, Recruiting, Operations, and vendors to build scalable processes. Drive continuous improvement through analytics, AI, and automation while ensuring accurate employee data and effective employee support.

Leads North American enterprise sales, owning bookings, ARR, quota, and sales team performance. Recruits and ramps Account Executives, manages complex seven-figure deals, enforces MEDDPICC and Salesforce discipline, builds pipeline, runs forecasting and QBRs, coaches leaders and reps, and partners with marketing on product-market fit. The role requires executive customer engagement, complex platform selling through partners and systems integrators, and experience across retail, CPG, or adjacent industries.

Generates qualified pipeline through outbound prospecting across phone, email, social, and events. Identifies target accounts, conducts discovery, qualifies opportunities using MEDDPICC, maps stakeholders, and hands opportunities to Account Executives. Builds multi-threaded relationships, manages outbound cadences, maintains CRM and prospecting-tool data, uses AI to personalize outreach, monitors performance, and may mentor junior BDRs.

Own a named enterprise account patch across new-logo hunting, inbound conversion, renewals, upsell, and cross-sell. Build pipeline through AI-first outbound, manage complex Fortune 500 sales, multithread buying committees, apply MEDDPICC, develop business cases, and maintain accurate Salesforce forecasts. Partner with SDRs, renewal teams, solution advisors, and ecosystem partners while serving as the customer escalation point. Regular customer visits, executive engagement, deal reviews, and market feedback are required.