Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and establish Five9s AQM Prompt Engineering practice: define methodology and standards, build reusable prompt libraries, mentor a small team, lead complex customer engagements, validate prompts with sampling and precision/recall analysis, collaborate with product and pre-sales, and deliver training and enablement for prompt-driven QM deployments.

Design, author, and iteratively optimize LLM evaluation prompts for Five9 AQM; define evaluation scope and pass/fail criteria with customers; select and analyze call samples; measure precision/recall; maintain a versioned prompt library; collaborate with QA and implementation teams; debug prompt failures; develop standards, templates, and support pre-sales demonstrations.

Design and produce digital and print marketing assets (web, social, presentations, events), collaborate with cross-functional teams, manage multiple projects to deadline, ensure brand consistency, prepare print-ready files, and stay current on design trends and tools.

Implement and support DNS and Kubernetes architecture in a private cloud environment, ensuring scalability, resilience, and performance optimization through IaC tools, while collaborating with teams and managing incidents.

The Mid-Market Account Director manages customer relationships, develops sales strategies, upsells products, and drives revenue within existing accounts, while ensuring customer satisfaction.

The Enterprise Solution Consultant will drive solution discovery, collaborate with sales, deliver demonstrations, and provide subject matter expertise on AI Agents solutions.

Lead the strategy and execution for Five9's Workforce Engagement portfolio, focusing on AI-driven Quality and Workforce Management solutions, while aligning with company objectives and market opportunities.

Lead end-to-end administration and governance of global sales commission programs, manage a small team, own the ICM system and ETL integrations, ensure SOX-compliant processes, validate calculations and payouts, resolve disputes, and partner cross-functionally with Sales Operations, Finance, Payroll, HR, and Audit to maintain accurate, timely commission payments.

The Associate Solution Consultant at Five9 supports the sales team by demonstrating cloud contact center solutions, creating proofs of concept, and communicating customer needs and product feedback to various teams.

The Manager, Sales Commissions oversees the administration of sales commission programs, ensuring accurate payments and managing a team. They lead commission processes, maintain ICM tools, design commission models, and collaborate with Finance and Sales Operations.