Aspire Software · 3 days ago
Director of Sales (Player-Coach)
United States
Full-time
Remote
Lead/Staff, Director/Executive
5+ years expAspire Software, an operating group of Valsoft Corporation, focuses on acquiring and growing vertical market software companies. They are seeking a Director of Sales (Player-Coach) to build and lead their North America revenue engine by driving new business growth and implementing a robust sales strategy.
Information TechnologySoftware
Responsibilities
Own the full sales cycle: prospecting → discovery → demos → proposals → negotiation → close
Build and maintain a target account strategy by segment and customer cohort
Develop and iterate on talk tracks, competitive positioning, and objection handling
Share customer insights and inputs with internal stakeholders to develop a clear commercial plan to bring the platform and AI products to market
Lead outbound strategy and execution; coach BDRs to consistently generate a qualified pipeline
Create repeatable playbooks (segments, sequences, cadences, qualification, demo structure)
Establish pipeline creation targets and inspection routines that translate activity into predictable results
Run weekly operating rhythms: pipeline inspection, deal reviews, and forecast calls
Define sales stages and exit criteria; maintain a clean CRM and reporting that leadership can trust
Track and improve conversion metrics (lead → meeting → SQL → win), cycle times, and win/loss learnings
Provide actionable inputs on pricing/packaging and commercialization over time
Establish tight handoffs with Customer Success to ensure a consistent customer experience and closed-loop feedback
Share structured market feedback with Product (buyer needs, blockers, competitive themes)
Coordinate internal resources to move deals forward and support successful launches
Qualification
Required
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
Preferred
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)
Company
Aspire Software
Aspire Software is a vertical acquisition software company that owns, operates and manages a portfolio of companies in various industries. It is a sub-organization of Valsoft.
1001-5000 employees
Funding
Current Stage
Late StageLeadership Team
Dennis Hall
Chief Technology Officer
Gustavo Vargas
Operating Partner
Company data provided by crunchbase