Remote Enterprise AI Sales Executive

Observe.AI; United States; Remote; USD 270,000 - 300,000; Full time

Benefits offered by this job

Competitive compensation including in‑

equity

Excellent medical, dental, and vision

Flexible paid time off

10 company holidays

Winter Break

Paid parental leave

401(k)

Lifestyle Spending Account

Monthly stipend for mobile/internet

Pre-tax commuter benefits

Autonomy and agency

Job summary

Observe.AI is hiring an enterprise sales leader to own a US territory, selling a technically complex AI platform to contact centers and senior sponsors. You will lead complex, multi-stakeholder deals, build ROI cases for CIOs, and drive self-sourced pipeline.

Expect high ownership, executive exposure, and a path to scalable plays across a growing AI-native platform. The role emphasizes MEDDPICC discipline, evangelizing AI/CCaaS integration, and coaching other enterprises on successful

Qualifications

• 8+ years in enterprise SaaS with complex, technical sales cycles.
• Record of closing six- and seven-figure net-new deals (ACV $250K+) in the last 3 years.
• Experience selling AI/ML, automation, workflow, infrastructure, security, or CCaaS.
• Credibility with technical buyers; ability to discuss architecture and security without a script.
• Self-sourced pipeline in a greenfield or lightly covered territory.

Responsibilities

• Sell to two buying centers: CX/operations and technology/finance executives.
• Explain how AI agents and copilots work to CIOs in plain terms, including data residency and integrations.
• Run proof-based evaluations with Solutions Engineers and forward-deployed engineers.
• Build ROI cases CFOs will sign off on, tied to cost per contact and agent productivity.
• Operate using MEDDPICC and enforce gates before progress.

Skills

Enterprise SaaS sales

Technical stakeholder engagement

MEDDPICC framework

Executive engagement

Self-sourced pipeline

Job description

Observe.AI is hiring an enterprise sales leader to own a US territory, selling a technically complex AI platform to contact centers and senior sponsors. You will lead complex, multi-stakeholder deals, build ROI cases for CIOs, and drive self-sourced pipeline.

Expect high ownership, executive exposure, and a path to scalable plays across a growing AI-native platform. The role emphasizes MEDDPICC discipline, evangelizing AI/CCaaS integration, and coaching other enterprises on successful