AISquared · 7 hours ago
Account Executive - Mid Market
United States
Full-time
Remote
Senior Level, Lead/Staff
10+ years expaisquared is seeking a dynamic and results-driven Strategic Account Executive to focus on acquiring new customers and expanding their market presence in the mid-market segment. The role involves managing the entire sales cycle and collaborating with stakeholders to deliver innovative solutions that drive revenue growth.
Artificial Intelligence (AI)Data Collection and LabelingInformation ServicesInformation TechnologyMachine Learning
Responsibilities
Proactively identify and pursue prospects and new business opportunities to secure new logos, expanding the company’s customer base
Use a consultative approach to understand prospective clients’ business challenges and articulate the value of our platform in solving their data and AI needs
Build relationships with senior decision-makers, including CIOs, CTOs, and data and business leaders, to establish trust and influence decision-making
Build and manage a robust sales pipeline, ensuring consistent achievement of sales targets and KPIs
Utilize various tools and strategies (e.g., cold outreach, networking, events) to engage potential customers and qualify leads
Understand prospective clients' unique challenges and objectives, delivering tailored solutions that demonstrate clear value and ROI
Manage the entire sales process, including prospecting, discovery, solution presentation, negotiation, and contract closing
Stay informed about industry trends, competitors, and market conditions to identify opportunities and position the company’s offerings effectively
Partner with marketing, product, and other internal teams to create compelling go-to-market strategies and ensure smooth onboarding for new clients
Maintain accurate records of prospect interactions, sales activities, and progress in CRM systems (e.g., Salesforce, HubSpot)
Consistently achieve or exceed sales quotas and report on progress, pipeline, and forecast accuracy
Qualification
Required
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
Preferred
MBA is a plus
Candidates located within the NYC & Chicago metro area(s) are preferred
Company
AISquared
AISquared helps large organizations bring AI to where work happens.
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
$19.8MKey Investors
Ansa CapitalNew Enterprise Associates
2024-04-17Series A· $13.8M
2022-06-27Seed· $6M
Leadership Team
Darren Kimura
President and Chief Executive Officer
Recent News
Business News: Pasadena Star-News
2025-09-19
Company data provided by crunchbase