Top Tech Jobs & Startup Jobs in Chicago, IL

Leads USPS strategy, compliance, promotions, reporting, and operational improvement for direct mail programs. Serves as the company’s USPS liaison and postal subject matter expert, analyzes regulations and performance data, coordinates cross-functional execution, manages vendor and industry relationships, influences postal policy, identifies cost-saving opportunities, implements new postal services and technologies, and trains internal teams. The role requires deep USPS expertise, knowledge of mail classification and optimization, and experience in direct mail, logistics, or manufacturing environments.

Owns revenue operations strategy and GTM planning, including forecasting, annual planning, business reviews, incentive design, analytics, KPI dashboards, and performance insights. Partners with Finance, Product, and Operations to improve sales productivity, align headcount with revenue goals, and execute multi-quarter strategic workstreams. The role translates complex data into leadership recommendations and manages cross-functional projects in a fast-paced environment.

Own three to five concurrent cross-functional programs spanning Finance, Product, Engineering, Legal, Operations, and Go-to-Market. Diagnose and redesign workflows, perform data-driven analysis, coordinate dependencies, communicate recommendations to leadership, and transition completed initiatives to permanent owners. Support FP&A, Deal Desk, business operations analytics, QBRs, and leadership offsites.

Manages accounts receivable and revenue recognition under GAAP and ASC 606, including billing, collections, reconciliations, journal entries, monthly close, and reporting. Resolves billing discrepancies across Salesforce, billing systems, and NetSuite; maintains internal controls; supports audits; communicates with customers; and drives billing-to-cash process improvements and automation.

Drive new business in Mid-Market and Enterprise accounts for a direct-mail SaaS platform. Own full sales cycle, build pipeline with outbound outreach, engage executive stakeholders, lead RFP/RFI responses, collaborate with Solutions/Product/Marketing, deliver technical discovery and demos with Solutions Engineers, negotiate enterprise contracts, and run territory strategy within a POD structure to drive adoption, expansion, and renewal.