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AI SqauredAS

Account Executive - Enterprise

AI Squared is a pioneering organization that is dedicated to revolutionizing the synergy between data and artificial intelligence (AI).

AI Sqaured

Employee count: 51-200

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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

About the job

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Posted on

Job type

Full Time

Experience level

Education

Bachelor degree

Experience

10 years minimum

Location requirements

Open to candidates from all countries.

Hiring timezones

Worldwide

About AI Sqaured

Learn more about AI Sqaured and their company culture.

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AI Squared is a pioneering organization that is dedicated to revolutionizing the synergy between data and artificial intelligence (AI). Our mission focuses on the seamless integration of AI insights into critical business applications, enhancing workflows across various sectors. Founded in 2021, we are committed to fostering widespread AI adoption by providing solutions that empower businesses to leverage data effectively.

At AI Squared, we understand the importance of making intelligent insights accessible to all. Our data and AI integration platform simplifies the process of enriching business applications with machine learning capabilities. By optimizing workflows and facilitating collaboration between data scientists and business users, we ensure that organizations can utilize AI-derived insights to drive significant outcomes and enhance decision-making capabilities. With a vision towards future innovations, AI Squared continues to lead the charge in embedding AI into the operational fabric of everyday business, unlocking new potentials for growth and efficiency.

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