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 mid-market segment. In this role, you will focus on helping organizations adopt and leverage our cutting-edge data, AI, and analytics platform to transform their business. You will own the entire sales cycle, from prospecting to closing, and work closely with technical and business stakeholders to deliver innovative, high-value solutions. This role is pivotal in driving revenue growth by identifying, targeting, and closing new business opportunities. The ideal candidate thrives on building relationships, navigating complex sales cycles, and delivering tailored solutions that address prospective clients' needs. Key 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.
Location: Remote but with a high preference to candidates located within the NYC & Chicago metro area(s) Experience 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. Education Bachelor’s degree in business, marketing, or a related field; MBA is a plus.
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 Attributes 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