Top AI Sales Jobs in Chicago, IL

Lead and scale the Enterprise AI & Digital Natives sales segment in the NYC region. Own revenue targets, recruit and mentor a field sales team, advise CTOs and engineering leaders on Cloudflare solutions (Workers AI, R2, network security), drive new logo acquisition and account expansion, partner with Product/Customer Success/Solutions Engineering for go-to-market execution, and personally help close complex, high-value enterprise deals.

The AI Sales Director will drive sales for Wasabi's hot cloud storage solutions to AI/ML-focused clients, leveraging marketing resources and existing relationships.

The AI Sales Director will drive sales for Wasabi's hot cloud storage solutions focused on AI/ML customers, prospecting, engaging with clients, and providing consultative advice.

Lead execution of industrial cloud and AI sales strategy, drive pipeline progression and forecasting, enable sellers with pitches/demos, align cross-functional teams, manage key accounts, and partner with marketing and product to deliver customer value.

Lead high-volume outbound prospecting, run discovery calls, qualify and manage high-ticket opportunities through the full sales cycle, book and conduct meetings, handle objections, collaborate with founders/sales leadership, and consistently meet outreach, meeting, and revenue KPIs.

Lead consultative, value-driven enterprise sales to plan, orchestrate, and deliver AI Workforce solutions (Copilot, Windows 365, Viva, Agents). Build stakeholder strategies, drive pipeline, cross-sell/up-sell, and partner with internal teams to scale AI adoption and measurable business outcomes.

The AI Sales Executive drives new business growth and expands client relationships by selling AI-driven solutions for engineering and manufacturing sectors, managing the full sales cycle with a consultative approach.

The Network for AI Sales Specialist leads Data Center and Routing network sales, collaborates with Account Managers, drives pipeline development, and builds client relationships to negotiate and close deals.

The Pre-Sales Data and AI Architect will design and operationalize enterprise data architectures, collaborating with teams to ensure effective integration of Salesforce D360 into complex ecosystems while driving customer success through innovative data solutions.

Quota-carrying sales executive responsible for sourcing, developing, and closing technology consulting engagements focused on AI. Manage full sales cycle from prospecting to proposal and contract negotiation, build and maintain pipeline, collaborate on go-to-market strategies, engage executive-level buyers, and participate in marketing events. Hybrid role with travel (~20-25%).

Sell AI-driven solutions to mid-market businesses: prospect, qualify, consult with decision-makers, manage the full sales cycle, close deals, build long-term client relationships, and identify upsell opportunities with support from leadership and technical teams.

The role involves selling AI-driven logistics solutions, engaging with senior leaders, and driving revenue growth through understanding logistics operations and AI applications.

Commission-only outside sales role selling a quantitative AI trading platform to active retail and professional traders. Prospect at events, run live demos, host educational meetups, pursue B2B outreach to prop shops and small funds, and manage a sales pipeline to grow recurring subscriber revenue.

Lead customer engagements to qualify and close cloud and AI opportunities on Azure. Drive sales strategy, pipeline hygiene, partner co-sell, and AI-driven forecasting. Collaborate across account teams, enable customer adoption and consumption, and act as trusted advisor to accelerate AI and cloud transformations.

Sell advanced visualization, AI, and cardiopulmonary imaging solutions across the Midwest territory. Build strategic sales plans, grow accounts, deliver clinical/technical presentations, support purchasing decisions, forecast sales, maintain CRM records, and collaborate with cross-functional teams to drive adoption and ensure compliance with company policies and quality standards. Travel ~50%.

Drive pre-sales for NICE Customer Service Automation by designing technical solutions, delivering demos, evaluating customer infrastructures, responding to RFIs/RFPs, and partnering with sales, product, and engineering to apply conversational AI, analytics, and digital engagement to CX problems.

Drive the expansion of software development and AI services by managing client relationships, building sales pipelines, and negotiating contracts.