Head of AI Sales
ChatGPT Jobs, Orlando, FL, United States
Head of AI Sales
Location
Chicago, IL (Hybrid - 3 days/week in-office)
Remote (New York, Miami, Austin, or Boston)
Salary Range $200,000 – $300,000, plus eligibility for performance‑based bonus.
Job Description Groupon is seeking a Head of AI Sales to build and manage a two‑layer AI sales system. This role will revolutionize how Groupon sells by creating AI agents that operate autonomously in parallel with the human sales team and agents that augment human reps. The goal is to achieve a 10x sales organization by leveraging proprietary data and behavioral sales data.
Responsibilities
Build and own the agent architecture for various sales motions (prospecting, outreach, qualification, reactivation, inbound triage).
Run and iterate the AI fleet on live data, owning in‑production performance and defining signal logic, trigger conditions, and prompt architecture.
Own both autonomous AI agent motions (Layer 1) and human augmentation (Layer 2), including the handoff between them.
Coordinate with internal stakeholders to align the AI architecture with business needs.
Own the vendor stack, evaluating and deploying AI tools.
Qualifications
Top‑tier academic background or equivalent in AI/technology, or proven experience from companies like OpenAI, Palantir, or a serious AI startup.
7+ years of experience at the intersection of AI and commercial/sales (enterprise AI SaaS, GenAI, or AI solutions) with a builder track record.
Shipped multi‑agent sales automation in production (sequencing, routing, CRM automation, AI dialers, call analysis, reactivation).
Full‑stack fluency at Level 8+ agentic maturity, including orchestrator + specialist agent architecture, parallel sessions, autonomous loops, LLM APIs, and relevant frameworks/tools.
Experience deploying AI SDR platforms and a clear build‑vs‑buy framework.
Commercial judgment across sales motions and a focus on measurable ROI.
About You
Builder‑first mentality.
AI‑native, designing agents that own full workflows autonomously.
Ability to move quickly, test in production, and iterate on live data.
Commercially sharp with a focus on GP growth.
Benefits
Medical, dental, vision, EAP, 401(k) match, ESPP, life and disability insurance, FSAs, flexible PTO, and more.
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Chicago, IL (Hybrid - 3 days/week in-office)
Remote (New York, Miami, Austin, or Boston)
Salary Range $200,000 – $300,000, plus eligibility for performance‑based bonus.
Job Description Groupon is seeking a Head of AI Sales to build and manage a two‑layer AI sales system. This role will revolutionize how Groupon sells by creating AI agents that operate autonomously in parallel with the human sales team and agents that augment human reps. The goal is to achieve a 10x sales organization by leveraging proprietary data and behavioral sales data.
Responsibilities
Build and own the agent architecture for various sales motions (prospecting, outreach, qualification, reactivation, inbound triage).
Run and iterate the AI fleet on live data, owning in‑production performance and defining signal logic, trigger conditions, and prompt architecture.
Own both autonomous AI agent motions (Layer 1) and human augmentation (Layer 2), including the handoff between them.
Coordinate with internal stakeholders to align the AI architecture with business needs.
Own the vendor stack, evaluating and deploying AI tools.
Qualifications
Top‑tier academic background or equivalent in AI/technology, or proven experience from companies like OpenAI, Palantir, or a serious AI startup.
7+ years of experience at the intersection of AI and commercial/sales (enterprise AI SaaS, GenAI, or AI solutions) with a builder track record.
Shipped multi‑agent sales automation in production (sequencing, routing, CRM automation, AI dialers, call analysis, reactivation).
Full‑stack fluency at Level 8+ agentic maturity, including orchestrator + specialist agent architecture, parallel sessions, autonomous loops, LLM APIs, and relevant frameworks/tools.
Experience deploying AI SDR platforms and a clear build‑vs‑buy framework.
Commercial judgment across sales motions and a focus on measurable ROI.
About You
Builder‑first mentality.
AI‑native, designing agents that own full workflows autonomously.
Ability to move quickly, test in production, and iterate on live data.
Commercially sharp with a focus on GP growth.
Benefits
Medical, dental, vision, EAP, 401(k) match, ESPP, life and disability insurance, FSAs, flexible PTO, and more.
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