Founding Account Executive, AI-Native

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🕒 April 8

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Aspire Software

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

☁️ SaaS

🏢 Enterprise

🤝 B2B

SaaS • Enterprise • B2B

Aspire Software is a company that focuses on acquiring and nurturing businesses with a strong foundation in outstanding products and passionate teams. As part of the Valsef Group, Aspire Software offers resources, knowledge, and a suite of best practices to enhance and expand operations for continuous improvement and sustainable growth. The company emphasizes decentralization to unlock innovation and adaptability within its acquired entities. Aspire Software is dedicated to serving its customers through long-term technology partnerships, leveraging capital and expertise in various verticals to grow both the businesses and individuals involved.

📋 Description

• Own the Full Sales Cycle • Run end-to-end deal execution: prospecting, discovery, demo, proposal, negotiation, and close • Build pipeline through targeted outbound, events, partnerships, and personal network leverage • Navigate complex buying committees (IT, procurement, finance) in enterprise and public-sector organizations • Land net-new logos across higher ed, healthcare, and adjacent verticals • Sell with AI as Your Unfair Advantage • Use AI tools, agents, and automation to drive outbound volume that would normally require a full SDR team • Build AI-powered workflows for prospecting, personalization, call prep, and follow-up sequencing • Leverage AI to analyze customer conversations, extract buying signals, and surface patterns that sharpen your approach • Treat your GTM stack like a product—always experimenting, always iterating • Help Build the Playbook • Refine ICP, positioning, and talk tracks based on what actually converts in-market • Capture buyer feedback and partner with product/engineering to shape the roadmap • Document what works so the next hires can ramp faster—you’re laying the foundation for a team • What Success Looks Like • First 30 days: Deep product fluency, target account list built, outbound motion live and producing conversations • 60–90 days: Qualified pipeline with measurable conversion, early wins in motion, AI workflows accelerating velocity • 6–12 months: Consistent closed-won revenue, multiple reference customers, and a clear case for expanding the sales team

🎯 Requirements

• 4–10+ years in B2B SaaS sales with full-cycle closing experience • Proven ability to create pipeline and close deals—you manufacture demand, not just manage inbound • Experience selling into complex organizations with multiple stakeholders and procurement processes • Active, demonstrated use of AI tools in your sales workflow—not aspirational, real • Builder mindset: high ownership, structured execution, comfort in ambiguity • Experience in higher ed, public sector, healthcare, or other regulated environments • Familiarity with ITSM, ITAM, SAM, or procurement/vendor management concepts • Experience launching a new product or building a GTM motion from scratch • Partner or channel experience (associations, consultants, resellers)