Aspire Software

Head of Sales

Aspire Software

full-time

Posted on:

Location Type: Remote

Location: United States

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Job Level

Lead

About the role

  • Own and lead all sales activities, including new customer acquisition, renewals, and expansion (upsell and cross-sell) initiatives
  • Design and implement standardized sales processes, including CRM discipline, pipeline management, forecasting, and qualification frameworks
  • Execute pricing normalization strategies across new and renewing customers
  • Drive adoption and revenue growth of payroll processing and HRMS modules within the existing customer base
  • Develop and execute account-based sales strategies tailored to broadband and telecommunications contractors
  • Leverage AI-native sales and marketing tools to improve lead qualification, pipeline velocity, forecasting accuracy, and customer targeting
  • Partner with marketing to apply AI-driven insights to account prioritization, messaging, and campaign performance
  • Continuously evaluate and implement modern sales technologies to increase efficiency, consistency, and scalability across the go-to-market function
  • Build repeatable sales playbooks and reduce dependency on founder-led demos and deal closings
  • Establish and grow strategic channel partnerships (e.g., GIS providers, industry consultants, and utility ecosystem partners)
  • Collaborate closely with product, operations, and leadership to align sales execution with broader business objectives

Requirements

  • 5+ years of sales leadership experience in vertical SaaS, workforce management, field service, or similar B2B software environments
  • Proven track record of scaling ARR from approximately $5M to $20M+
  • Experience selling complex B2B software to operational and business buyers
  • Strong understanding of pricing strategy, renewals, and expansion revenue models
  • Experience using modern, AI-enabled sales and marketing tools to drive pipeline management, forecasting, and performance insights
  • Comfort operating in founder-led and post-acquisition environments
  • Hands-on mindset with the ability to lead demos, close deals, and build processes concurrently
  • Experience in telecommunications, broadband, utilities, or field service industries (preferred)
  • Familiarity with contractor-based labor models and operational workflows (preferred)
  • Prior experience building or scaling sales teams and GTM infrastructure in high-growth SaaS organizations (preferred)
Applicant Tracking System Keywords

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

Hard Skills & Tools
sales leadershipaccount-based sales strategiespipeline managementforecastingpricing strategyrenewalsexpansion revenue modelsB2B software salessales process designsales playbooks
Soft Skills
collaborationstrategic thinkingleadershipcommunicationhands-on mindsetcustomer targetingadaptabilityproblem-solvingprocess buildingrelationship management