Director of Sales (Player-Coach) at Aspire Software

We are looking for a Director of Sales (Player-Coach) to build and lead our North America revenue engine for Rentworks+, a next-generation platform for rental operators.

Requirements

• 5+ years of B2B SaaS sales experience with a strong record of closing new business.
• Demonstrated ability to generate a pipeline through outbound (not reliant on inbound-only environments).
• Experience building or materially improving a sales motion (process, messaging, cadence, forecasting).
• Strong deal leadership: disciplined qualification, multi-stakeholder selling, and negotiation.
• Player-coach mindset: you can lead and coach, while personally carrying and delivering on a quota.
• Experience selling into car rental, fleet management, mobility, automotive, or transportation industries is a strong plus
• Experience in vertical market software and/or operationally complex environments.
• Experience selling multi-product suites, add-ons, or platform + modules.
• Strong familiarity with modern sales tooling and RevOps best practices (CRM, sequencing, analytics, forecasting)

Benefits

• Competitive base salary with uncapped commission and high OTE potential
• Build the GTM engine for a next-generation platform at the start of its growth curve.
• High ownership and direct partnership with a collaborative, driven and entrepreneurial management team
• Opportunity to shape commercialization and product strategy for both the platform and a suite of new AI products.