Top Tech Jobs & Startup Jobs in Chicago, IL

Owns GTM finance for Sales and Marketing, including CRO OpEx budgeting, variance analysis, forecasting, revenue modeling, and headcount planning. The role analyzes CAC, LTV, payback, pipeline, and territory ROI; leads monthly and quarterly forecast operations; prepares executive and board financial packages; and improves scalable reporting processes. It partners closely with CRO and VP-level stakeholders to guide investment and revenue decisions.

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.

Own and improve revenue and sales operations workflows, including Salesforce administration, CRM data governance, reporting, dashboards, KPI analysis, and process execution. Analyze operational data to support decisions, prepare executive presentations, and identify scalable process improvements. Partner cross-functionally with Sales, Marketing, Strategy, Data, Pricing, Finance, and BizTech to maintain effective go-to-market operations.

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.

Supports BILL’s risk organization through strategic portfolio planning, program and vendor management, process automation, AI tooling, dashboard development, governance documentation, and cross-functional coordination. The role analyzes project and risk data, tracks performance and ROI, develops control strategy recommendations, and communicates insights to stakeholders across risk, strategy, product, and engineering.

Build and support scalable payment systems using Java, Spring Boot, AWS, microservices, APIs, messaging, and event-driven architectures. Integrate third-party payment providers, troubleshoot production issues, automate deployment and infrastructure management, and contribute to reliable, secure, scalable payment platforms. Collaborate with product and business teams to develop payment capabilities and leverage generative AI and LLMs to improve software engineering workflows.

Drive enterprise sales of BILL’s accounts receivable and B2B payment solutions to supplier finance organizations. Generate and manage pipelines, lead complex multi-stakeholder sales cycles, build strategic account plans, analyze customer data, engage executive decision-makers, maintain CRM forecasting requirements, and achieve assigned quotas. The role involves outbound prospecting, relationship management, solution selling, and collaboration with internal stakeholders. Up to 25% travel may be required.

Owns go-to-market strategy for BILL’s partner integrations, APIs, developer ecosystem, and embedded-finance offerings. Responsibilities include audience research, product positioning, competitive analysis, roadmap influence, launches, developer marketing, pricing and packaging input, sales enablement, win/loss analysis, and partner-channel collaboration. The role drives commercial outcomes across developer, technical buyer, finance buyer, and partner audiences.

Own two strategic embedded-finance partnerships with a major ERP and U.S. commercial bank. Drive partner-platform adoption, transaction volume, customer activation, joint revenue, product roadmaps, executive relationships, negotiations, financial models, and cross-functional execution. The role requires influencing Product, Engineering, Finance, Legal, and senior leadership while navigating platform migration and contract priorities.