[Remote] Account Executive - Mid Market

Note: The job is a remote job and is open to candidates in USA. AISquared is seeking a Strategic Account Executive to acquire new mid-market customers and expand its market presence. The role owns the full sales cycle, develops customer relationships, and sells the company’s data, AI, and analytics platform.

Responsibilities

• New Business Development: Proactively identify and pursue prospects and new business opportunities to secure new logos, expanding the company’s customer base
• Solution Selling: Use a consultative approach to understand prospective clients’ business challenges and articulate the value of our platform in solving their data and AI needs
• Executive Engagement: Build relationships with senior decision-makers, including CIOs, CTOs, and data and business leaders, to establish trust and influence decision-making
• Pipeline Management: Build and manage a robust sales pipeline, ensuring consistent achievement of sales targets and KPIs
• Prospecting & Outreach: Utilize various tools and strategies (e.g., cold outreach, networking, events) to engage potential customers and qualify leads
• Consultative Selling: Understand prospective clients' unique challenges and objectives, delivering tailored solutions that demonstrate clear value and ROI
• Sales Cycle Management: Manage the entire sales process, including prospecting, discovery, solution presentation, negotiation, and contract closing
• Market Intelligence: Stay informed about industry trends, competitors, and market conditions to identify opportunities and position the company’s offerings effectively
• Collaboration: Partner with marketing, product, and other internal teams to create compelling go-to-market strategies and ensure smooth onboarding for new clients
• CRM Mastery: Maintain accurate records of prospect interactions, sales activities, and progress in CRM systems (e.g., Salesforce, HubSpot)
• Metrics & Reporting: Consistently achieve or exceed sales quotas and report on progress, pipeline, and forecast accuracy

Skills

• 10+ years in sales or business development, with a proven track record of acquiring new clients, preferably selling SaaS, data, AI, or analytics solutions into the mid-market
• Bachelor's degree in business, marketing, or a related field
• Strong prospecting and lead generation expertise, including cold calling, outbound email, LinkedIn/social selling, and event-based networking
• Experience managing high-velocity mid-market sales cycles from first touch to signed contract
• Ability to effectively qualify opportunities using structured methodologies (e.g., MEDDICC, BANT, or similar)
• Excellent communication and storytelling skills, with the ability to present to both technical and non-technical audiences
• Strong negotiation and objection-handling abilities
• Comfort running product demos and solution presentations independently
• Experience selling consultative, value-based solutions with clear ROI articulation
• Familiarity with SaaS business models, subscription-based pricing, and expansion/upsell strategies
• Strong working knowledge of CRM systems, pipeline management, forecasting, and reporting
• Ability to manage multiple deals in parallel while maintaining accuracy and speed
• Highly motivated, target-driven professional who takes full ownership of outcomes
• Results-oriented with a healthy competitive edge and a bias for action
• Self-starter who thrives in autonomy and doesn't need to be micromanaged
• Resilient and persistent — handles rejection without losing momentum or confidence
• Organized, detail-oriented, and disciplined in follow-through
• Curious, coachable, and always looking to improve performance
• Adaptable and flexible in evolving, high-growth environments
• Strong sense of accountability, professionalism, and integrity
• Collaborative team player who also knows how to run their own book of business
• Comfortable with ambiguity and able to make smart decisions with limited information
• MBA is a plus

Benefits

• Remote work; high preference for candidates located within the NYC and Chicago metro areas

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