Sales Director

Loop is a domain-specific AI company specialized in logistics and the physical economy. By leveraging verticalized AI, Loop transforms operational and financial signals within logistics data into structured insights that drive automation, financial transparency, and supply chain optimization at scale. Their solutions support enterprise shippers in modernizing back-office operations and uncovering hidden value within complex logistics networks.

Our investors include J.P. Morgan, Index Ventures, Founders Fund, 8VC, Flexport, and 50 industry-leading angel investors. Our team brings subject matter expertise from companies like Uber, Google, Flexport, Meta, Samsara, Intuit, Rakuten, and long-standing industry leaders like C.H. Robinson.

Loop is looking for a strategic and results-oriented Sales Director to lead and scale a high-performing enterprise sales team. Reporting directly to the CRO, this individual will oversee a team of Account Executives and play a critical role in driving pipeline generation, enterprise deal execution, forecasting accuracy, and overall revenue growth. 

This is a highly cross-functional leadership role requiring close partnership with Marketing, Solutions Engineers, Customer Success and Revenue Operations. The ideal candidate brings a strong track record of managing enterprise sales teams, closing complex platform-based deals, and developing scalable sales processes in fast-paced technology environments. 

• →Lead and develop a team of Account Executives across enterprise sales motions
• →Own team performance against revenue targets, including quota attainment and pipeline health
• →Establish and maintain strong forecasting discipline and deal inspection processes
• →Guide Account Executives through complex, multi-threaded enterprise deals and procurement cycles
• →Build and refine pipeline generation strategies in partnership with Marketing and Revenue Operations
• →Partner closely with Customer Success and Implementation teams to ensure smooth customer handoffs and long-term value realization
• →Collaborate with cross-functional stakeholders to improve win rates, deal velocity, and overall sales efficiency
• →Analyze deal and market data to identify trends, risks, and opportunities for growth
• →Help recruit, onboard, and scale a high-performing enterprise sales team
• →Contribute to the development of scalable sales processes and operating rhythms as the organization grows

• 5+ years of experience in sales leadership roles within enterprise SaaS or complex technical sales environments
• Experience managing teams of quota-carrying Account Executives
• Proven success driving enterprise revenue growth and consistently meeting or exceeding team targets
• Track record of closing and coaching through large, complex deals 
• Strong understanding of enterprise sales cycles, including procurement, legal, and RFP processes
• Experience building pipeline generation processes and improving conversion across the funnel
• Comfort working cross-functionally with Product, Marketing, Customer Success, and Operations teams
• Strong analytical mindset with experience in forecasting, reporting, and performance management
• Clear communicator with strong leadership presence and ability to coach at multiple levels
• Experience in logistics, supply chain, or AI-driven platforms is a plus
• Hybrid role with preference for candidates based in Chicago, San Francisco, or New York City