Account Executive - Enterprise
Remote · location unlistedFull-timePosted 10mo agoStill listed 1w ago
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Job overview
AI Squared is hiring an Account Executive - Enterprise. AI Squared is seeking a Strategic Account Executive to acquire new customers and expand market presence in the enterprise segment. This role involves helping large organizations adopt their data, AI, and analytics platform to drive transformation. The executive will own the entire sales cycle, from prospecting to contract execution, working closely with senior technical and business stakeholders to deliver tailored solutions and drive revenue growth.
Key focus areas include Identify, qualify, and pursue large-scale enterprise opportunities to secure new logos and major expansion deals, Use a consultative, value-based approach to diagnose enterprise challenges and align our platform to business and technical objectives, and Build deep relationships with C-suite and VP-level leaders including CIOs, CTOs, CDOs, and business unit heads.
Successful candidates bring 10+ Years Enterprise Sales Experience and Bachelor's Degree In Business/Marketing. Important skills include Enterprise New Business Development, Solution Selling, Executive Engagement, Strategic Pipeline Management, Targeted Prospecting, and Complex Sales Cycle Management. Preferred (not required): Confident, Credible With Senior Executives, Results-Obsessed, and Strong Sense Of Urgency.
Skills & qualifications
Skills
Qualifications
Full job description
Position Overview
We 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.
Key Responsibilities
Enterprise New Business Development: Identify, qualify, and pursue large-scale enterprise opportunities to secure new logos and major expansion deals.
Solution Selling: Use a consultative, value-based approach to diagnose enterprise challenges and align our platform to business and technical objectives.
Executive Engagement: Build deep relationships with C-suite and VP-level leaders including CIOs, CTOs, CDOs, and business unit heads.
Strategic Pipeline Management: Develop and manage a strong, high-value pipeline with clear deal strategy, close plans, and accurate forecasting.
Targeted Prospecting: Execute strategic outreach including account-based selling, executive-level networking, and event-based engagement.
Complex Sales Cycle Management: Lead all phases of multi-stakeholder, multi-month enterprise sales cycles including discovery, demos, proposals, business cases, negotiations, and closure.
Market & Account Intelligence: Monitor industry trends, account priorities, budgets, and competitive activity to identify and shape opportunities.
Cross-Functional Leadership: Partner with marketing, product, customer success, and leadership to support enterprise deal strategy and post-sale success.
CRM Discipline: Maintain detailed and accurate activity, pipeline, and account information in CRM systems (Salesforce/HubSpot or equivalent).
Revenue Performance: Consistently meet or exceed enterprise quota targets and key performance indicators.
Qualifications
Location: Remote with a high preference for candidates within the NYC & Chicago metro area(s).
Experience 10+ years of enterprise sales experience with a strong record of closing large, complex deals (6–7+ figure ACVs), preferably selling SaaS, data, AI, or analytics platforms.
Education Bachelor’s degree in business, marketing, or a related field; MBA is a plus.
Skills
Proven ability to prospect, develop, and close enterprise level opportunities
Experience managing full cycle, multi stakeholder enterprise sales motions
Strong command of structured sales methodologies (MEDDICC, Challenger, Spin, etc.)
Executive level communication, presentation, and influence skills
Proven ability to navigate complex buying groups and long procurement cycles
Expertise in building business cases and articulating ROI at scale
Comfortable delivering executive-level demos and strategy sessions
Strong negotiation and closing abilities, including contract and pricing strategy
Deep familiarity with SaaS models, multi-year contracts, and expansion planning
Advanced CRM, pipeline management, and forecasting capabilities
Ability to manage a small number of high-impact accounts with precision and discipline
Attributes
Confident, strategic, and credible with senior executives
Results-obsessed with a strong sense of urgency and ownership
Highly resilient and comfortable operating in ambiguity and long sales cycles
Strategic thinker with the ability to execute at a tactical level
Organized, disciplined, and detail-oriented with strong follow-through
Curious, commercially sharp, and continuously improving
Comfortable being the quarterback for large, cross-functional deal teams
Polished, professional, and trusted both internally and externally
Collaborative but fully capable of running complex deals independently
Composed under pressure and able to keep momentum through setbacks
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