Top AI Sales Jobs in Chicago, IL

Lead technical sales for Deepgram’s Voice Agent platform, owning discovery, architecture, proofs of concept, technical evaluations, and customer production launches. Partner with account executives on enterprise deals, carry a growth quota, build demos and integrations, develop sales enablement, provide product feedback, and collaborate with telephony, contact center, and LLM partners. The role requires deep voice-agent expertise across telephony, orchestration, streaming pipelines, and speech and language models.

Leads Americas partner sales strategy, go-to-market planning, and execution for Cisco’s AI infrastructure and connectivity portfolio. Manages a channel specialist sales team, drives growth across hardware and software offerings, builds executive partner relationships, oversees pipeline and forecasting rigor, and leads business transformation while fostering an inclusive, high-performing sales culture.

Make outbound calls for B2B technology companies, engage gatekeepers and decision-makers, and book qualified meetings for customer sales teams. Use an AI-enabled platform for lead lists, dialing, call preparation, and coaching. Contractors choose their schedules and accounts, complete training and certification, follow approved scripts, and earn commission based on attended qualified meetings.

Lead go-to-market strategy and strategic sales for AI and Neocloud accounts. Build executive relationships with hyperscale cloud and data-center customers, manage complex negotiations and long-term agreements, develop ecosystem partnerships, maintain forecasts and pipeline visibility, and collaborate cross-functionally to deliver infrastructure solutions at scale.

Leads strategic enterprise engagements to identify AI and Microsoft 365 Copilot use cases, demonstrate technical solutions, quantify business value, and accelerate adoption. Delivers workshops, sales presentations, and proofs of concept; addresses technical challenges; guides sales teams through competitive deal cycles; collaborates with partners and internal teams; and shares customer feedback to influence product, marketing, and support strategies.

Leads Verizon’s AI Connect sales strategy and performance, focusing on Dark Fiber, high-capacity networking, and AI connectivity solutions. Builds relationships with hyperscalers, data centers, AI vendors, and enterprise technology companies; executes go-to-market strategy; drives profitable revenue growth; and develops high-performing sales teams. The role requires strategic solution selling, alliance management, executive engagement, and cross-functional leadership in a complex matrix environment.

Lead Quantiphi’s co-sell motion with frontier AI partners including OpenAI, Anthropic, and LangChain. Build partner-seller relationships, originate and qualify enterprise AI opportunities, coordinate multidisciplinary pursuit teams, manage account and pipeline reviews, and drive proposals and commercial closures. Translate customer AI adoption needs into implementation services engagements, support production deployments, and develop repeatable sales plays and expansion opportunities.

Leads strategic enterprise sales pursuits involving Dynamics 365, Copilot, and agentic AI. Shapes competitive positioning, business value, solution strategies, technical validation, and customer decision criteria. Coordinates account teams, engineering, product, marketing, partners, and field stakeholders to remove blockers and advance complex opportunities. Develops competitive intelligence, enables sellers through coaching and readiness programs, and translates AI and business application capabilities into measurable customer outcomes, revenue, adoption, and usage.

Leads strategic enterprise engagements to identify high-value AI and Microsoft 365 Copilot use cases, deliver technical demonstrations and proofs of concept, quantify business value, and accelerate customer adoption. Provides technical sales strategy, competitive positioning, executive guidance, and coaching to sales teams. Partners with Microsoft engineering, marketing, and external partners to resolve technical barriers, scale successful sales motions, and influence product direction through customer feedback.

Drive technical sales engagements with healthcare organizations by conducting discovery, mapping workflows, delivering product demonstrations, responding to RFPs and RFIs, and designing tailored solutions. Advise sales teams and customers on EHR integrations, patient access workflows, revenue cycle processes, APIs, HL7, FHIR, and webhooks. Collaborate with product, marketing, and stakeholders to improve offerings and support go-to-market initiatives.

Drive enterprise adoption of Databricks Genie by achieving consumption, bookings, and activation goals. Build executive-backed opportunities, develop repeatable field plays, enable account teams, and coordinate sales, solutions architecture, business units, and partners. Translate customer and market feedback into product and go-to-market recommendations while expanding production deployments. The role requires enterprise software sales or consulting experience in BI, analytics, data platforms, embedded analytics, or business-facing AI, along with complex buying-center navigation, value selling, land-and-expand execution, and partner strategy development.

Leads Microsoft’s AI Workforce sales business across state and local government, education, academic medical centers, and software customers. Owns strategy, revenue growth, pipeline, forecasting, competitive execution, and customer adoption. Develops sales leaders and specialist teams, builds executive relationships, orchestrates Microsoft and partner resources, and drives scaled adoption of Copilot, AI agents, and cloud platforms. Establishes operating rhythms, strengthens competitive positioning, and translates AI transformation opportunities into measurable customer and business outcomes.

Partners with account executives to lead technical sales strategy, customer discovery, product demonstrations, workshops, and proof-of-value evaluations. Translates customer goals into Datadog solutions, develops technical champions, manages evaluation timelines, provides product feedback, documents opportunity progress, and collaborates with Product, Support, and go-to-market teams to resolve technical blockers and drive adoption.

Leads complex enterprise ERP and AI business application sales opportunities across the Americas. Builds executive and partner relationships, uncovers Dynamics 365 and Copilot opportunities, gathers requirements, develops solution demonstrations, and guides customers from envisioning through production deployment. Partners with account teams, engineers, customer success teams, and Microsoft partners to establish business sponsors, user cohorts, value cases, and sustained consumption. Success is measured through customer usage, realized value, and consumption revenue.

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.

Lead strategic sales of AI Workforce solutions, including Microsoft Copilot, AI agents, Viva, Windows 365, and Azure Virtual Desktop. Develop customer strategies, identify opportunities, build pipeline, conduct consultative business and technical conversations, and orchestrate internal teams and partners to close complex deals. The role requires expertise in technology sales, AI, forecasting, demand generation, stakeholder engagement, competitive positioning, and cross-selling across enterprise and regulated customers.

The Director, AI Sales will grow Databricks’ enterprise AI business by driving strategic account adoption, production usage, bookings, and consumption. Responsibilities include developing AI sales plays, enabling field teams, securing executive and technical sponsorship, advancing complex opportunities, coordinating sales and partner stakeholders, and translating customer feedback into product and go-to-market recommendations.

Own technical sales engagements for AI-powered customer experience assurance solutions, from discovery through technical win. Lead CX and AI stack discovery, solution design, tailored demos, workshops, proofs of concept, and executive business cases. Partner with Sales, Product, and Implementation teams on RFPs and handoffs, while creating enablement materials and mentoring teammates on agentic AI and prompt engineering.

Own a portfolio of 5–8 frontier AI and enterprise accounts, developing executive relationships, identifying AI security evaluation use cases, and managing opportunities through negotiation, contracting, close, and expansion. The role requires complex enterprise sales expertise, technical curiosity, disciplined qualification, account planning, value development, and collaboration with sales engineering, product, security, and professional services teams. The successful candidate will create meaningful revenue, maintain forecast accuracy, and support customer adoption.

Leads strategic enterprise sales pursuits involving Dynamics 365, Copilot, and agentic AI. Partners with field, engineering, and go-to-market teams to qualify opportunities, develop value narratives, validate business cases, guide technical and business conversations, and shape solution positioning, sales guidance, and adoption strategies for major customers across government, retail, financial services, and healthcare.

Own technical presales pilots for Commure Ambient AI across healthcare practices and ambulatory EHRs. Scope workflows, build and debug browser, DOM, and API integrations, configure advanced AI features, coordinate templates, triage issues, maintain Salesforce status, support RFPs and security questionnaires, and deliver documented handoffs to implementation. Partner with account executives, engineering, template, and operations teams while improving pilot tooling and processes.

Drive revenue growth for Yahoo’s AI and technology advertising category. Develop go-to-market strategies, build relationships with C-level brand and agency leaders, secure major strategic partnerships, and promote Yahoo’s full-funnel advertising solutions. Collaborate with content, product, business development, and agency teams while monitoring category trends, competitive dynamics, emerging technologies, and campaign performance.

Owns quota-bearing sales growth for application managed services and hybrid cloud solutions. Partners with account executives, architects, delivery, product, and marketing teams to identify opportunities, shape solution strategies, lead discovery and executive engagements, develop proposals and business cases, and close complex technology sales. Advises clients on application modernization, cloud, DevOps, managed services, and intelligent automation while providing market insight, forecasting, mentoring, and cross-functional sales leadership.

Develop and execute enterprise sales and go-to-market strategy for emerging AI agent products. Build executive relationships, identify use cases, manage sales from discovery through closing, and partner with product and engineering on positioning, packaging, pricing, pilots, and product requirements. Establish repeatable processes for converting experimentation into production deployments while providing market feedback and shaping a new product category.

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.