Top AI Sales Jobs in Chicago, IL

Lead enterprise sales for Braze AI Decision Studio by developing new and existing senior customer relationships, guiding AI solution evaluations, quantifying business impact, and supporting proofs of value. Partner with sales, pre- and post-sales, implementation, product, and marketing teams. Train colleagues on reinforcement learning in marketing, communicate customer needs, and represent Braze AI at executive meetings, events, conferences, and trade shows.

Leads enterprise sales for Microsoft Azure cloud and AI platforms. Develops customer-specific sales strategies, qualifies and closes complex opportunities, manages pipelines and forecasts, coordinates partners and internal teams, and advises stakeholders on AI-driven cloud transformation. Uses market intelligence, consumption data, and predictive analytics to drive adoption, expansion, renewals, and customer value. Requires strong consultative selling, enterprise relationship management, and knowledge of Azure infrastructure, data, and AI application platforms.

Own and grow the U.S. corporate sales pipeline for AI-driven software development training. Responsibilities include engaging decision-makers, identifying business needs, tailoring training solutions, selling multi-day programs and ongoing enablement, developing long-term client relationships, and contributing to pricing, packaging, and go-to-market strategy. This is a remote, commission-based, consultative B2B sales role with potential for a future base salary.

Leads AI and experience orchestration sales initiatives by advising executives, supporting account teams, shaping deal strategy, creating territory plans, and driving pipeline growth. Conducts customer workshops, develops AI use cases and proof-of-concept opportunities, supports proposals and pricing, and coordinates cross-functional execution across marketing, product, customer success, and professional services. Acts as an AI subject matter expert and enables broader sales teams.

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.

Drives sales excellence for Microsoft’s Cloud and AI Platform across the Americas. Responsibilities include pipeline health management, sales execution governance, sales transformation, sales methodology adoption, partner insights, planning workstreams, and four-quarter business outcome management. The role advises senior segment and sales leaders, uses data to improve revenue and consumption growth, and influences cross-functional decisions in complex, ambiguous environments.

Leads enterprise Azure sales strategy, pre-sales engagements, forecasting, territory planning, and strategic account growth. Advises customers on cloud, data, analytics, AI, applications, and infrastructure transformations; develops business cases, technical strategies, proofs of concept, and deployment roadmaps. Coordinates Microsoft teams, partners, and solution engineers to close deals, drive Azure consumption, generate pipeline, and deliver customer value. Mentors colleagues, shares industry insights, supports partner strategies, and acts as a trusted technical advisor and customer advocate.

Leads sales excellence for Microsoft’s Americas AI Business Solutions organization. Drives pipeline health, predictable revenue and consumption growth, sales methodology adoption, governance, partner insights, sales transformation, and planning across business segments. Partners with senior sales, finance, and operations leaders to improve execution, manage change, and deliver rolling business outcomes. This strategic individual contributor role requires strong stakeholder influence, data-driven decision-making, and expertise in sales operations or related disciplines.

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.

Partner with Account Executives on technical discovery, solution positioning, demonstrations, RFPs, and proofs of concept. Design and configure AI-native CPQ solutions, including product catalogs, configuration rules, pricing logic, and CRM or ERP integrations. Explain AI behavior and quoting workflows to technical and non-technical audiences. Collaborate with Product, Engineering, Demo, and Forward-Deployed teams while building expertise in applied AI, CPQ, and quote-to-cash technologies.

Own global enterprise sales strategy, pipeline, forecasting, and revenue execution for Hammerspace’s NVIDIA AI Data Platform. Develop and close complex AI infrastructure and data-platform opportunities with large enterprises, coordinating account executives, NVIDIA, OEMs, cloud providers, systems integrators, and partners. Lead executive discovery, business-case development, proof-of-value initiatives, negotiations, and production adoption while positioning solutions for generative AI, RAG, enterprise search, and AI infrastructure use cases.

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.

Leads enterprise sales strategy and revenue growth for AI-powered eDiscovery, legal technology, compliance, analytics, and data intelligence solutions. Builds pipelines, manages complex consultative sales cycles, develops executive client relationships, expands strategic accounts, and positions responsible AI adoption. Partners with product, operations, legal, security, marketing, and executive teams on solution development, pricing, contracts, implementation, and market expansion across corporations, law firms, government, and regulated industries.

Owns sales strategy, revenue growth, pipeline, and enterprise account expansion for AI infrastructure, platforms, TokenOps, and strategic AI solutions across the Americas. Builds C-level relationships, leads multimillion-dollar Fortune 500 AI transformation deals, develops hyperscaler and technology partnerships, positions portfolio startups, and drives joint go-to-market initiatives. Requires deep enterprise technology sales experience, AI and cloud expertise, executive presence, and the ability to create strategic opportunities in a fast-paced environment.

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.

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.

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

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.

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.

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.