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Enterprise Account Executive-SaaS

CS Recruiting
Chicago, IL Full Time
POSTED ON 3/27/2025
AVAILABLE BEFORE 4/25/2025
Enterprise Account Executive - SaaS

Our client is seeking an experienced and highly motivated Enterprise Account Executive to join their sales team. As a key member of the team, you will play a critical role in defining and executing sales outreach and go-to-market strategy, focusing on new business development with enterprise-level shippers. This is a hands-on, full-cycle sales role that requires strong relationship-building skills, strategic selling mindset, and the ability to navigate complex sales cycles.

Job Type: Full-time/Work from home

Responsibilities

  • Identify and engage enterprise-level shippers through outbound outreach and inbound lead follow-ups.
  • Own and manage the full sales cycle, from initial outreach to contract negotiation and closing deals.
  • Help define and refine our client’s sales process, including outreach strategies, messaging, and qualification criteria.
  • Work closely with the product team to tailor and support sales demos for potential customers.
  • Stay informed on freight industry trends, attend networking events, and identify opportunities for strategic partnerships.
  • Collaborate with marketing, product, and customer success teams to refine messaging, relay customer feedback, and enhance the overall buyer experience.
  • Work with leadership to define key sales metrics, focusing on pipeline growth, meetings booked, and revenue generation.
  • Guide prospects through pricing discussions and procurement processes to close high-value enterprise deals.

Experience:

  • Minimum of 10 years of experience in enterprise-level software sales or freight brokerage/tech sales targeting enterprise shippers.
  • Proven track record of selling to Director and VP-level decision-makers in large enterprise shipping organizations.
  • Experience managing long, complex B2B sales cycles.
  • Proficiency in CRM software and a strong preference for familiarity with Transportation Management Systems (TMS).
  • Exceptional executive-level communication skills and ability to present complex solutions effectively.
  • Experience in a startup or high-growth environment.
  • Established industry network with enterprise shippers, accelerating deal flow.
  • Expertise in freight brokerage, logistics, or supply chain tech beyond sales experience.
  • Track record of exceeding revenue targets in high-velocity sales environments.
  • Strong consultative selling approach—educating shippers on the value of transparency in broker margins and operations.
  • Strong problem-solving and adaptability skills in a fast-paced, evolving sales environment.

This position offers a competitive base salary.

Related to: SaaS, Software as a Service, Technology, Software Solutions, Technology Solutions, Data Solutions, Analytics, lead generation, networking, cold calling, revenue growth, negotiate rates, customer service, RFP, RFQ, business development, enterprise, CRM, prospect, client development, client relationships, Independent Contributor, Team Player, Individual Contributor, IC

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Salary : $100,000 - $150,000

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