AI Squared
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.
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.
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