Senior Enterprise AI Sales Leader (Midwest)

Observe.AI; Portland (OR); Hybride; USD 270 000 - 300 000; Plein temps

Avantages offerts par ce poste

Equity

Medical, dental, vision insurance

401(k) with company match

Flexible PTO

Remote/hybrid-friendly

Annual performance bonuses

Résumé du poste

Observe.AI is seeking a Senior Enterprise Account Executive for the Midwest territory to lead complex, technical enterprise sales of AI-enabled CX platforms. You will own multi-threaded cycles, engage C-suite stakeholders, and drive MEDDPICC-based deals with strategic value and ROI emphasis.

You will leverage a modern sales tech stack and GenAI tools to accelerate account penetration, build repeatable outbound motions, and influence product roadmap through customer feedback.

Qualifications

• 7+ years in enterprise SaaS with complex, technical sales cycles.
• Track record closing high six- and seven-figure enterprise deals in the last 3 years.
• Designing and executing complex deal strategies and technical sales campaigns.
• Gathering, distilling, and processing complex market intelligence.
• Working cross functionally with Engineering, Product Management, Marketing, and other departments.
• Experience selling AI/ML, automation, or security platforms a major plus.

Responsabilités

• Build and execute territory strategy across enterprise accounts.
• Maintain 4–5x pipeline coverage and deliver predictable outcomes.
• Navigate large matrixed organizations with technical and business stakeholders.
• Own multi-threaded sales cycles involving automation, architecture, workflows, security, and ROI.
• Use MEDDPICC, Challenger, SPICED methodologies.
• Develop champions and create urgency across C-suite, operations, and IT.

Connaissances

Enterprise SaaS

Complex sales cycles

Executive selling

Multi-threading

MEDDPICC

GenAI / AI sales tools

Outils

Salesforce

Gong

Outreach

ZoomInfo

6sense

Clari

Description du poste

Observe.AI is seeking a Senior Enterprise Account Executive for the Midwest territory to lead complex, technical enterprise sales of AI-enabled CX platforms. You will own multi-threaded cycles, engage C-suite stakeholders, and drive MEDDPICC-based deals with strategic value and ROI emphasis.

You will leverage a modern sales tech stack and GenAI tools to accelerate account penetration, build repeatable outbound motions, and influence product roadmap through customer feedback.