Top Artificial Intelligence Sales Jobs in Chicago, IL

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.

Lead and coach Strategic Enterprise Account Executives across North America to exceed revenue targets. Define regional GTM strategy, use data and AI to prioritize opportunities, deliver accurate forecasts, engage as executive sponsor on key accounts, and collaborate cross-functionally to drive customer value and team development.

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.

10-week sales internship supporting Field Sales and Account Management. Learn NYL GBS products, use Salesforce/BenefitFlow/Tableau and generative AI, collaborate cross-functionally, participate in mentorship and a capstone project, and present recommendations to stakeholders.

Manage and grow a portfolio of Mid-Market advisor, asset management, and institutional clients. Serve as primary contact, drive retention and expansion, own full sales cycle, deliver revenue and retention targets, conduct client meetings and demos, partner with cross-functional teams to drive adoption and forecasting.

Own incentive compensation planning and payouts, quota setting, CEO Circle administration, sales analytics, and BI reporting for commercial field teams. Build allocation models, dashboards, and executive-ready insights using CRM, warehouse, and finance data. Partner with Finance, HR, Legal, and commercial leadership to ensure accurate, compliant compensation cycles, improve field performance, automate processes, resolve disputes, and mentor junior analysts.

Owns sales compensation policy strategy, crediting frameworks, exception governance, audits, and field enablement. The role manages compensation policies across draws, transfers, promotions, terminations, clawbacks, renewals, overlays, splits, and non-standard deals. It partners with sales and cross-functional leaders, documents decisions, improves governance controls, and translates recurring exceptions into policy and plan changes.

Drive new business across the North Central territory by building strategic territory plans, prospecting enterprise accounts, engaging executive stakeholders, managing complex sales cycles (discovery, POC, negotiation, close), and selling Nexthink software, services, and support to exceed bookings and create expansion opportunities.

Manage a portfolio of enterprise travel customers, build relationships with decision-makers, increase product adoption, identify expansion opportunities, and drive retention and revenue growth. Provide data-driven business reviews and presentations, resolve account issues, coordinate product integrations, and collaborate with AmTrav and Perk teams. The role requires strong communication, prioritization, analytical, and client relationship skills in a fast-paced SaaS environment.

Lead strategy and execution for a tiered partner program: identify, qualify, and onboard partners; manage Tier 1/2 executive relationships; structure alliance deals; drive co-marketing and enablement; build partner performance dashboards; partner with sales, product, marketing, and legal; mentor junior team members and scale partner operations to drive joint revenue.