Top Tech Jobs & Startup Jobs in Chicago, IL

Owns high-priority revenue growth initiatives across funnel performance, multi-product expansion, go-to-market channels, customer journey optimization, AI adoption, and agentic workflow automation. Partners with Product, Marketing, Sales, Customer Success, Support, Finance, Data, and GTM Engineering to improve conversion, retention, channel development, and operational efficiency. This senior individual contributor influences executive decisions and drives measurable outcomes without formal authority.

Drive enterprise sales of BILL’s accounts receivable and B2B payment solutions to supplier finance organizations. Responsibilities include outbound prospecting, pipeline generation, complex sales-cycle management, executive relationship building, account planning, CRM documentation, forecasting, data analysis, and quota achievement. The role requires engaging CFOs, treasurers, controllers, and accounts receivable leaders while coordinating internal stakeholders and supporting customer implementations.

Own the full sales cycle for acquiring new accounting and wealth management firms, from outbound prospecting through close. Sell BILL’s Spend and Expense products, conduct client demos, manage pipelines, maintain CRM and forecast accuracy, and meet quota and activity targets. Partner with Account Managers on co-selling and independently identify cross-sell opportunities. The role requires consultative selling, cold calling, discovery, negotiation, objection handling, and managing a high volume of opportunities.

Leads BILL’s revenue accounting and accounts receivable operations, including monthly, quarterly, and annual close activities, reconciliations, journal entries, reporting, and audit coordination. Owns ASC 606 compliance across multiple revenue streams and translates accounting policies into ERP and sub-ledger workflows. Drives automation, accounting system implementation, cross-functional product integration, SOX controls, and process scalability while hiring and developing accounting teams.

Own and improve BILL’s Adaptive Planning system, including models, workflows, and integrations with NetSuite and Workday HCM. Lead corporate FP&A activities such as planning, forecasting, variance analysis, executive reporting, and financial forecast consolidation. Partner with Accounting and business leaders, deliver strategic financial insights, perform ad hoc analysis, and apply AI and automation tools to improve FP&A efficiency.

Qualifies inbound and outbound leads, schedules demos and discovery calls, prospects creatively, manages opportunities across multiple outreach channels, and meets sales KPIs. The role requires high-volume prospecting, product learning, objection handling, relationship building, and collaboration with Account Executives and sales leadership.

Lead CX data intelligence initiatives using SQL, dashboards, analytical models, and AI/LLM techniques. Analyze customer journeys, operational metrics, churn risks, and retention indicators; develop insight agents and self-service reporting; define CX health metrics; and translate findings into strategic recommendations, process improvements, and experiments. Partner with operations, support, product, data, and engineering teams while maintaining data quality, governance, and documentation.

Build and scale agentic AI systems that automate customer experience workflows across Slack and Salesforce. Analyze transcripts, detect SLA risks and escalations, provide self-service operational insights, and develop AI memory architecture. Partner with data, QA, workforce management, and customer advocacy teams to ensure system accuracy, reliability, trustworthy outputs, and measurable operational impact. Productize internal tools and design human escalation patterns for scalable deployment.

Lead technical direction for high-impact machine learning initiatives, from research and experimentation through production deployment. Build and fine-tune LLMs, document understanding systems, model-serving infrastructure, evaluation frameworks, and data feedback loops. Establish standards for model quality, calibration, reproducibility, and responsible deployment while mentoring ML engineers and influencing organizational roadmaps. The role requires hands-on software and ML engineering expertise, production-scale model development, and strong statistical judgment.