Sr. Sales Representative (SaaS)

Job Description

Job Category: Sales
Job Type: Full Time
Job Location: Chicago
Job Location Type: Remote

Imagine combining your SaaS sales expertise with the fast-moving world of logistics and supply chain. If you love hunting for opportunities, running killer demos, and sealing enterprise-level deals—this one’s for you.

 

We’re looking for a Senior SaaS Sales Representative who’s excited to:

  • SaaS Sales (Cloud-based / Subscription Model): Proven experience selling software delivered via online subscription, not traditional on-premise solutions.
  • Freight/Logistics Knowledge: Beneficial to understand freight movement in the U.S., but SaaS sales expertise is more critical.
  • Bilingual Ability: English is required; Spanish is highly valuable for international growth.
  • Own the full sales cycle (from cold outreach → demo → close)
  •  Build relationships with freight + logistics leaders
  • Deliver sharp, tailored product demos that wow prospects
  • Keep deals on track in HubSpot CRM
  • Share insights that help shape the product roadmap

 

What makes you a match?

  • 6+ years in SaaS sales (must-have)
  • Comfortable with long sales cycles + complex deals
  • Outbound pro (prospecting, cold calls, LinkedIn outreach—bring it on!)
  • Logistics/freight know-how = a bonus 🚛
  • Tech-savvy with tools like HubSpot, Jira, Excel
  • Startup hustle: proactive, hands-on, team-first

 

Why join?

Because here, you’re not just selling software—you’re shaping how an entire industry handles claims 🌎. You’ll work with a collaborative, international team, where your voice matters and your wins fuel company growth.

If you’re a go-getter who thrives on closing deals and wants to make an impact—hit that apply button. Let’s win together.

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