AI Squared
divh2Account Executive - Enterprise/h2pWe are seeking a dynamic and results-driven Strategic Account Executive to focus on acquiring new customers and expanding our market presence in the enterprise segment. In this role, you will help large, complex organizations adopt and scale our cutting-edge data, AI, and analytics platform to drive transformation at scale. You will own the entire sales cycle, from strategic prospecting to contract execution and work closely with senior technical and business stakeholders to deliver high-impact, tailored solutions. This role is pivotal in driving revenue growth through the pursuit, development, and closure of high-value enterprise opportunities. The ideal candidate thrives in highly complex sales environments, is trusted at the executive level, and knows how to move big deals forward./ph3Key Responsibilities/h3ulliEnterprise New Business Development: Identify, qualify, and pursue large-scale enterprise opportunities to secure new logos and major expansion deals./liliSolution Selling: Use a consultative, value-based approach to diagnose enterprise challenges and align our platform to business and technical objectives./liliExecutive Engagement: Build deep relationships with C-suite and VP-level leaders including CIOs, CTOs, CDOs, and business unit heads./liliStrategic Pipeline Management: Develop and manage a strong, high-value pipeline with clear deal strategy, close plans, and accurate forecasting./liliTargeted Prospecting: Execute strategic outreach including account-based selling, executive-level networking, and event-based engagement./liliComplex Sales Cycle Management: Lead all phases of multi-stakeholder, multi-month enterprise sales cycles including discovery, demos, proposals, business cases, negotiations, and closure./liliMarket
Account Intelligence: Monitor industry trends, account priorities, budgets, and competitive activity to identify and shape opportunities./liliCross-Functional Leadership: Partner with marketing, product, customer success, and leadership to support enterprise deal strategy and post-sale success./liliCRM Discipline: Maintain detailed and accurate activity, pipeline, and account information in CRM systems (Salesforce/HubSpot or equivalent)./liliRevenue Performance: Consistently meet or exceed enterprise quota targets and key performance indicators./li/ulpLocation: Remote with a high preference for candidates within the NYC
Chicago metro area(s)./ppExperience: 10+ years of enterprise sales experience with a strong record of closing large, complex deals (67+ figure ACVs), preferably selling SaaS, data, AI, or analytics platforms./ppEducation: Bachelors degree in business, marketing, or a related field; MBA is a plus./ppSkills:/pulliProven ability to prospect, develop, and close enterprise level opportunities/liliExperience managing full cycle, multi stakeholder enterprise sales motions/liliStrong command of structured sales methodologies (MEDDICC, Challenger, Spin, etc.)/liliExecutive level communication, presentation, and influence skills/liliProven ability to navigate complex buying groups and long procurement cycles/liliExpertise in building business cases and articulating ROI at scale/liliComfortable delivering executive-level demos and strategy sessions/liliStrong negotiation and closing abilities, including contract and pricing strategy/liliDeep familiarity with SaaS models, multi-year contracts, and expansion planning/liliAdvanced CRM, pipeline management, and forecasting capabilities/liliAbility to manage a small number of high-impact accounts with precision and discipline/li/ulpAttributes:/pulliConfident, strategic, and credible with senior executives/liliResults-obsessed with a strong sense of urgency and ownership/liliHighly resilient and comfortable operating in ambiguity and long sales cycles/liliStrategic thinker with the ability to execute at a tactical level/liliOrganized, disciplined, and detail-oriented with strong follow-through/liliCurious, commercially sharp, and continuously improving/liliComfortable being the quarterback for large, cross-functional deal teams/liliPolished, professional, and trusted both internally and externally/liliCollaborative but fully capable of running complex deals independently/liliComposed under pressure and able to keep momentum through setbacks/li/ul/div
Account Intelligence: Monitor industry trends, account priorities, budgets, and competitive activity to identify and shape opportunities./liliCross-Functional Leadership: Partner with marketing, product, customer success, and leadership to support enterprise deal strategy and post-sale success./liliCRM Discipline: Maintain detailed and accurate activity, pipeline, and account information in CRM systems (Salesforce/HubSpot or equivalent)./liliRevenue Performance: Consistently meet or exceed enterprise quota targets and key performance indicators./li/ulpLocation: Remote with a high preference for candidates within the NYC
Chicago metro area(s)./ppExperience: 10+ years of enterprise sales experience with a strong record of closing large, complex deals (67+ figure ACVs), preferably selling SaaS, data, AI, or analytics platforms./ppEducation: Bachelors degree in business, marketing, or a related field; MBA is a plus./ppSkills:/pulliProven ability to prospect, develop, and close enterprise level opportunities/liliExperience managing full cycle, multi stakeholder enterprise sales motions/liliStrong command of structured sales methodologies (MEDDICC, Challenger, Spin, etc.)/liliExecutive level communication, presentation, and influence skills/liliProven ability to navigate complex buying groups and long procurement cycles/liliExpertise in building business cases and articulating ROI at scale/liliComfortable delivering executive-level demos and strategy sessions/liliStrong negotiation and closing abilities, including contract and pricing strategy/liliDeep familiarity with SaaS models, multi-year contracts, and expansion planning/liliAdvanced CRM, pipeline management, and forecasting capabilities/liliAbility to manage a small number of high-impact accounts with precision and discipline/li/ulpAttributes:/pulliConfident, strategic, and credible with senior executives/liliResults-obsessed with a strong sense of urgency and ownership/liliHighly resilient and comfortable operating in ambiguity and long sales cycles/liliStrategic thinker with the ability to execute at a tactical level/liliOrganized, disciplined, and detail-oriented with strong follow-through/liliCurious, commercially sharp, and continuously improving/liliComfortable being the quarterback for large, cross-functional deal teams/liliPolished, professional, and trusted both internally and externally/liliCollaborative but fully capable of running complex deals independently/liliComposed under pressure and able to keep momentum through setbacks/li/ul/div