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Account Executive - Enterprise

AI Squared

Role overview

Qualifications

  • 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.
  • 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.

Responsibilities

  • 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.
  • Build deep relationships with C-suite and VP-level leaders including CIOs, CTOs, CDOs, and business unit heads.
  • Develop and manage a strong, high-value pipeline with clear deal strategy, close plans, and accurate forecasting.

Key facts

Hard skills

Enterprise Sales Solution Selling Employee Engagement Business Development Pipeline Planning Full-Cycle Sales Software As A Service (SaaS) Open Source Intelligence

Other skills

  • Negotiation
  • Communication
  • Strategic Thinking
  • Organizational Skills
  • Collaboration

About the company

AI Squared logo

AI Squared

Artificial Intelligence & Machine Learning Services

We help companies realize the full value of AI by empowering their teams to instantly make any application AI-intelligent. We value and believe in equitable access to AI where all people can adopt AI and have access to AI technology and insights regardless of their ethnicity, socio-economic status, educational or career level, work role, age, physical ability, or any other quality. The goal of our AI Squared technology is to level this playing field by providing AI integration technologies that would increase AI adoption and enable access to AI for anyone. This is our story. Dr. Benjamin Harvey was the Chief of Operations Data Science at NSA where he experienced challenges first-hand associated with the inability to adopt AI, provide equitable access to AI, and unlock the value of AI for intelligence analysts and the military warfighter. His inspiration came from his two brothers who were Army officers recently deployed to the Middle East (Kuwait, Iraq and Qatar) and SW Asia (Afghanistan and Pakistan) who both relied on intelligence to achieve mission. He began a journey and developed a solution to solve these inequities that simplifies and accelerates AI integration into applications ultimately protecting lives of Americans and military warfighters in similar situations as his brothers. Our vision is to build the world’s most powerful model integration framework and AI integration software which enables any application to become AI-powered. For the first time ever data scientists can describe their models using our model integration framework and our AI integration software will overlay intelligence from inference results directly into a pre-existing web application. We provide application developers with a software (e.g. SDK) and analysts with a no/low-code solution to customize the user experience

Company details

Company typeStartup
IndustryArtificial Intelligence & Machine Learning Services
Company size11 - 50

Links

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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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MR

Marcus Rivera

Chief Revenue Officer

m.rivera@company.com
linkedin.com/in/marcusrivera
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