Top Senior Level Artificial Intelligence Sales Jobs in Chicago, IL

Partner with sales to lead technical evaluations for enterprise prospects: run demos, proofs-of-concept, architecture and security reviews, and drive deployments. Advise stakeholders from data teams to C-level, inform product roadmap with prospect feedback, create demo content, and occasionally travel for on-site demos and events.

Drive new business and expansions in the Media & Entertainment vertical. Manage enterprise accounts, qualify opportunities, run demos, negotiate contracts, coordinate with Customer Success and cross-functional teams, and meet monthly/quarterly quotas while maintaining accurate CRM records and participating in industry events.

Lead and grow a US-based SDR team to generate and qualify SME-to-growth pipeline, hire and coach SDRs, implement handoff processes, enforce quality control, and align with AEs to meet pipeline and sales metrics.

As a Senior Solutions Consultant, you will drive complex SaaS deals, collaborate across teams, lead technical discovery, and mentor peers while focusing on customer success and integration solutions.

Lead and develop a team of eight Account Executives for the Commercial (Mid-Market) segment. Drive quota attainment, coaching, forecasting, pipeline accuracy in Salesforce, hiring and onboarding, cross-functional GTM execution, and streamline sales processes while occasionally acting as a player-coach in customer negotiations.

The role involves selling Qualtrics' platform to K-12 educational leaders, driving revenue growth through strategic relationships, prospecting, and consultative selling, while focusing on team collaboration and self-development.

The Enterprise Sales Director - Health will manage the sales cycle for AI-powered solutions in health insurance, cultivate relationships, and achieve sales targets.

Build and scale Motive’s strategic partner ecosystem by recruiting and onboarding partners, developing co-sell and referral frameworks, leading joint go-to-market initiatives, enabling partner and sales teams, managing strategic relationships, overseeing deal processes, and tracking partner performance, KPIs, deal registrations, and revenue attribution. Lead QBRs and collaborate cross-functionally with Sales, Legal, Marketing, Product, and Finance to drive indirect revenue.

Prospect for new compliance business within existing customers, drive whitespace acquisition and upgrades, and grow revenue through consultative solution selling. Position legal, ethics, safety, and OSHA compliance solutions to senior decision-makers. Build and manage pipeline, conduct outbound prospecting, develop tailored presentations, negotiate value-based deals, close opportunities, collaborate across sales and support teams, and report pipeline health, risks, and progress to management.

Partners with account executives to lead technical sales strategies, conduct customer discovery, deliver product demos and workshops, and guide enterprise technical evaluations from scoping through adoption. Translates business needs into Datadog solutions, develops customer champions, manages multiple opportunities, documents deal activity, provides product feedback, and collaborates with Product, Support, and go-to-market teams to resolve technical blockers.