Aspire Software

We never stop building. A vertical acquisition software company that owns, operates and manages a diverse portfolio.

Head of Sales

SalesSalesFull TimeRemoteTeam 1,001-5,000H1B No SponsorCompany SiteLinkedIn

Location

United States

Posted

39 days ago

Salary

Not specified

5 yrs expEnglish

Job Description

• 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

Job 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)

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