Rose Rocket 🚀 is a market leader in Transportation Management Software. We’re a startup going after the $700+ billion dollar trucking industry, leading the shift to SaaS while revolutionizing the way trucking companies sell, service, and innovate. We are a “more human, less corporate” culture that is built around doing work that matters, winning as a team, and celebrating success. We’d love to hear from you if you want to build this with us.

We understand that joining a team is one of the most important decisions you make ❤️, and adding a team member is one of the most important decisions we’ll make. Through our process, we want you to get to know us and understand how you approach problems, learn, and what motivates you.

As a Mid-Market Account Executive, you will be a critical driver of Rose Rocket’s growth by owning the full sales cycle for our most complex and high-value opportunities, targeting accounts in the $25,000–$100,000 ACV range. You’ll navigate multi-stakeholder buying processes, build executive-level relationships, and position Rose Rocket as a strategic platform investment, not just a point solution. This role requires a consultative seller with a track record of managing longer, more structured sales cycles and delivering measurable business outcomes for customers.

What You’ll Do

- Build and manage a robust pipeline of mid-market prospects across the trucking, logistics, and freight brokerage space, with a focus on accounts with $25K–$100K annual contract value.

- Lead sophisticated, multi-threaded discovery across economic buyers, technical evaluators, and operational stakeholders to build comprehensive business cases.

- Deliver tailored, outcomes-oriented product demonstrations and proof-of-concept engagements that map directly to each customer’s operational priorities.

- Navigate complex procurement cycles including RFP responses, security reviews, legal negotiations, and multi-year contract structures.

- Develop and execute acco...