Aspire Software

Director of Sales – Player-Coach

Aspire Software

full-time

Posted on:

Location Type: Remote

Location: United States

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Job Level

Lead

Tech Stack

SQL

About the role

  • 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.

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.

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
B2B salessales cycle managementpipeline generationsales forecastingnegotiationCRM managementconversion metrics trackingobjection handlingcompetitive positioningsales process improvement
Soft skills
leadershipcoachingcommunicationstrategic thinkingcollaborationcustomer insight sharingdeal leadershipdisciplineadaptabilityproblem-solving