Mid-Market Account Executive , Rose Rocket

• Executive presence and the poise to navigate complex organizations with grace and levity
• A genuine curiosity about modern tools and methodologies, and a drive to stay ahead of them
• A real desire to understand how our customers' businesses actually run
• 3+ years of software sales success, including a track record of closing mid-market deals at $25K+
• Resilience and adaptability, with comfort operating in a fast-changing environment
• Deep expertise in consultative, value-based selling, including building ROI models and executive-level business cases

Desirable

• As a Mid-Market Account Executive, you'll be central to Rose Rocket's growth, owning the full sales cycle for our most complex and high-value opportunities, accounts ranging from $25,000 to $150,000 in annual contract value
• You'll navigate multi-stakeholder buying processes, build relationships at the executive level, and position Rose Rocket as a strategic platform investment rather than a point solution
• It's a role built for a consultative seller, someone comfortable managing longer, structured sales cycles and focused on delivering real return on investment for customers
• Sell the first AI-native operating system built for the transportation industry, and operate as an AI-native seller yourself by using modern AI tools and workflows to unlock greater ROI for customers and sharpen your own performance
• Consistently meet and exceed quota while providing exceptional value to customers, maintaining rigorous pipeline hygiene, accurate forecasting, and detailed CRM documentation
• Build and manage a robust pipeline of mid-market prospects across the trucking, logistics, and freight brokerage space, with a focus on accounts in the $25K–$150K ACV range
• 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 account plans with clearly defined stakeholder maps, champion strategies, and mutual success timelines
• Construct and present compelling ROI models and business cases that justify investment at the executive level
• Partner closely with solutions engineering, marketing, and our FDS implementation team before close to deliver a seamless, high-caliber buying experience, and after close to ensure a smooth handoff and maintain relationships with key stakeholders through onboarding
• Manage your book of business, with a focus on renewals, expansion, and long-term account growth
• Surface market intelligence, customer feedback, and industry trends, including competitive dynamics and regulatory developments, to inform product strategy, competitive positioning, and go-to-market approach