Head of AI Sales

TL;DR

Head of AI Sales: Building and running a production-grade fleet of AI agents for sales with an accent on autonomous operation, human augmentation, and data-driven optimization. Focus on designing the agent architecture, iterating on live data, and coordinating with stakeholders to drive pipeline velocity and GP growth.

Location: US-based - Chicago (hybrid, 3 days a week in-office) or remote New York, Miami, Austin, or Boston

Salary: $200,000 – $300,000, plus eligibility to participate in a performance-based bonus program.

Company

hirify.global is a marketplace where customers discover new experiences and services everyday and local businesses thrive.

What you will do

• Build and own the agent architecture for lead scraping, ICP-scoring, BD outbound sequencing, IB triage and routing, MD reactivation, and multi-touch National/Enterprise engagement.
• Run and iterate the fleet on live data, defining signal logic, trigger conditions, prompt architecture, and account prioritization intelligence.
• Own both layers of the AI sales system: autonomous motions and human augmentation, designing the handoff between them.
• Coordinate with internal stakeholders across Sales, Commercial, and LOB leadership on what the fleet should solve next.
• Own the vendor stack, evaluating, deploying, and exiting vendors based on a clear build-vs-buy framework.

Requirements

• Top-tier academic background or equivalent formation in a high-calibre AI or technology environment.
• 7+ years at the intersection of AI and commercial/sales, with a builder track record.
• Experience shipping multi-agent sales automation in production, including sequencing, routing, CRM automation, AI dialers, call analysis, or reactivation.
• Full-stack fluency at Level 8+ agentic maturity, including LLM APIs, LangChain/Dust/CrewAI, Clay/Apollo/ZoomInfo, Python, and Salesforce Opportunity-level flows.
• Experience deploying AI SDR platforms and a clear build-vs-buy framework.
• Commercial judgment across sales motions, knowing what an agent can own end-to-end vs. where a human must take over.

Culture & Benefits

• Committed to building smarter, faster, and more innovative ways of working with AI.
• Encourage candidates to leverage AI tools during the hiring process.
• Medical, dental, vision, EAP, 401(k) match, ESPP, life and disability insurance, FSAs, flexible PTO, and more.