[Remote] Account Executive - Enterprise at AI Sqaured

Remote

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Not SpecifiedCompensation

Senior (5 to 8 years)Experience Level

Full TimeJob Type

UnknownVisa

Technology, AI, Data Analytics, Enterprise SoftwareIndustries

Requirements

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
Location: Remote with a high preference for candidates within the NYC & Chicago metro area(s)
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
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 aware

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

Skills

Key technologies and capabilities for this role

Enterprise SalesSolution SellingAccount-Based SellingPipeline ManagementSales ForecastingExecutive EngagementC-Suite NetworkingComplex Sales CyclesStrategic ProspectingDeal NegotiationRevenue GrowthConsultative Selling

Questions & Answers

Common questions about this position

Is this position remote or does it require office work?

The role is remote with a high preference for candidates within the NYC & Chicago metro areas.

What experience is required for this Account Executive role?

Candidates need 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.

What key skills are needed for success in this position?

Required skills include proven ability to prospect, develop, and close enterprise-level opportunities, experience managing full-cycle multi-stakeholder enterprise sales motions, and strong command of structured sales methodologies like MEDDICC or Challenger.

What is the salary or compensation for this role?

This information is not specified in the job description.

What makes a strong candidate for this Account Executive position?

A strong candidate has 10+ years closing 6-7+ figure enterprise deals in SaaS/AI/data platforms, excels in full-cycle complex sales with C-suite engagement, and uses structured methodologies like MEDDICC or Challenger; a Bachelor’s degree is required and MBA is a plus.

AI Sqaured

Integrates AI models into business applications

About AI Sqaured

Squared.ai focuses on predictive and generative artificial intelligence to enhance business productivity. The company helps businesses integrate AI and machine learning models into their operations, making AI-generated insights more accessible. By bridging the gap between data science and business teams, Squared.ai enables faster launches of AI projects and optimizes machine learning models for real-time integration with business applications. Their services include designing user-friendly experiences and ensuring model performance through real-time monitoring and auto-tuning. This approach allows businesses to gain insights quickly without lengthy development cycles. The goal of Squared.ai is to democratize AI, making it easier for organizations to adopt and leverage AI-driven decision-making.

Washington, District of ColumbiaHeadquarters

2021Year Founded

$19.3MTotal Funding

SERIES_ACompany Stage

Data & Analytics, AI & Machine LearningIndustries

51-200Employees

Risks

Emerging competition from Nvidia's mini supercomputer offering significant AI computing power.

Integration challenges from Multiwoven acquisition may disrupt operations.

Rapid expansion post-funding could lead to overextension and resource strain.

Differentiation

AI Squared bridges data science and business teams for faster AI project launches.

The platform democratizes AI-enhanced decision-making for businesses.

Real-time performance monitoring ensures optimal AI model performance in business applications.

Upsides

Acquisition of Multiwoven enhances data integration capabilities for seamless AI model integration.

Partnership with UNIFI Music expands AI integration services into the music industry.

$13.8M Series A funding boosts AI integration capabilities and platform features.

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