Top Artificial Intelligence Sales Jobs in Chicago, IL

Leads a team of Client Partners responsible for account growth, client and agency relationships, revenue quotas, KPI-driven measurement strategies, and vertical growth plans. Coaches and develops direct reports, supports quota and account assignments, translates market trends into business opportunities, and drives the sales process from planning through close. The role requires senior-level digital media sales experience, people management, strong client-facing communication, and collaboration across functions.

Supports strategic data platform partnerships with Databricks, Snowflake, Dataiku, and similar technology providers. Responsibilities include partnership governance, partner-influenced pipeline management, reporting and dashboards, joint account coordination, issue resolution, process improvement, documentation, and partner marketing campaigns. The role requires cross-functional collaboration, CRM proficiency, strong communication, organization, and the ability to manage multiple priorities in a client-facing consulting environment.

Manages a defined territory and sells software platforms to existing insurance agency customers through outbound and inbound engagement. Responsibilities include prospecting, discovery, solution selling, product demonstrations, negotiation, closing, forecasting, territory planning, quarterly business reviews, CRM maintenance, and internal sales process management. The role requires achieving quota and territory growth targets while consulting customers on business needs and platform compatibility.

Own the full sales cycle for EliseAI’s emerging AI products, from prospecting and discovery through demonstrations, negotiations, closing, and expansion. Build relationships with senior stakeholders, secure strategic design partners, navigate complex multi-party evaluations, and help shape pricing, packaging, positioning, and go-to-market strategy. Partner with Product, Engineering, Strategy, and Deployment teams to translate customer feedback into product direction, develop repeatable sales playbooks, and attend conferences and customer meetings.

Provides technical support throughout the sales cycle by delivering product demonstrations, leading proof-of-concept evaluations, supporting cloud architecture discussions, completing RFIs and RFPs, and presenting to executives and at industry events. Partners with sales teams, channel partners, customers, product management, and services teams. Requires deep observability expertise, strong technical communication, troubleshooting, and knowledge of cloud, DevOps, containers, Kubernetes, automation, and modern web and programming technologies.

Leads GumGum’s Central region sales organization across Chicago, Detroit, and Ohio. Owns regional revenue, exceeds sales targets, manages and develops 4–8 sellers, recruits talent, executes account-based strategies, strengthens brand and agency relationships, expands client investment in media solutions, drives new business, and partners with leadership and Product on growth initiatives. Requires deep digital advertising and ad-tech expertise, strong coaching ability, executive presence, and analytical business judgment.

Full-cycle SMB Account Executive responsible for inbound and outbound prospecting, qualifying leads, running demos, and closing deals. Maintain pipeline hygiene in Salesforce, forecast accurately, collaborate with Sales and Marketing, surface market insights, and support events and campaigns to drive revenue and improve messaging.

Manage and transform global sales operations by optimizing processes, leading cross-functional programs, improving Salesforce workflows, overseeing governance, and driving adoption of scalable sales capabilities. The role partners with senior leadership, analyzes business opportunities, manages requirements and UAT, develops transformation roadmaps, and presents data-driven recommendations.

Manage strategic employer accounts for retention, renewal, and growth. Build relationships with customers, brokers, and consultants; provide healthcare benefits consulting; develop account plans; negotiate renewals; identify upsell opportunities; lead internal account teams; present value and performance insights; facilitate implementations and quarterly planning; and support sales presentations, training, and mentoring.

Own the full sales lifecycle for healthcare and institutional accounts: source and qualify opportunities, lead complex RFPs, run discovery and demos, negotiate and close deals, collaborate cross-functionally on underwriting and compliance, and manage pipeline and forecasting in Salesforce.