Top Tech Jobs & Startup Jobs in Chicago, IL

Lead managers and ~40 specialists in Group Fulfillment to deliver timely, accurate benefits for customers. Set operational objectives, capacity planning, SLAs, policies, and cross-functional alignment. Build and execute an AI-driven automation roadmap, coach AI fluency, run performance calibration and development, and drive organizational change to improve accuracy, timeliness, and team capability.

As a Payroll Advocate, you will manage customer inquiries, enhance user experiences, provide expert support, and drive customer success in payroll services.

Early-career sales or onboarding role handling high-volume inbound calls, chats, and emails plus some outbound outreach. Advise small businesses on product selection, guide onboarding for successful adoption, use consultative selling, maintain Salesforce/CRM records, and meet performance goals.

The role involves developing insights and solutions to enhance productivity for sales teams, driving AI strategies, optimizing processes, and providing operational support while collaborating across teams.

The Expansion Account Manager will manage customer relationships, drive account retention, identify growth opportunities, and leverage data for proactive outreach to enhance customer success and satisfaction.

Lead Gusto's social and influencer marketing strategy, oversee team expansion, and drive brand engagement through innovative campaigns and AI integration.

Lead pricing and monetization strategy across Gusto's product portfolio. Partner with product, finance, marketing, sales, data science, and engineering to design, launch, and monitor pricing, build AI-powered pricing pilots and MVPs, and drive cross-functional go-to-market execution with executive visibility.

Lead design of complex, cross-team AI-enabled service journeys—mapping systems and handoffs, building AI-assisted service design workflows, enabling practitioners, and improving operational sustainability and measurement.

Founding leader to build Gusto's PEO sales org 0->1 while acting as a player-coach. Design sales motion and Salesforce pipeline, hire and onboard sales talent, develop channel strategy, convert existing payroll customers, plan around PEO selling season, collaborate cross-functionally, use data and AI to drive decisions, and ensure team expertise in PEO compliance and employment regulations.

The Expansion Account Executive will drive revenue by engaging customers through outreach, managing consultative sales calls, and optimizing sales strategies using AI. Key duties include tracking opportunities in Salesforce, collaborating with teams, and meeting monthly ARR quotas.