Enterprise AI Sales Leader for Complex Deals

Observe.AI; Seattle (WA); On-site; USD 270,000 - 300,000; Full time

Benefits offered by this job

Competitive base pay with equity

Medical, dental, vision insurance

Flexible paid time off

Company holidays and parental leave

401(k) plan

Lifestyle Spending Account

Monthly mobile & internet stipend

Pre-tax commuter benefits

Autonomy and agency

Job summary

Observe.AI is seeking a Senior Enterprise Account Executive to drive a Midwest territory and expand our enterprise AI adoption. You will own multi-threaded, complex sales cycles, engage C-suite stakeholders, and build a scalable go-to-market motion across large enterprise accounts.

Ideal candidates have 7+ years in enterprise SaaS, a proven track record closing six- to seven-figure deals, and深 familiarity with MEDDPICC and modern sales tools.

Qualifications

• 7+ years in enterprise SaaS with complex, technical sales cycles.
• Track record closing six- and seven-figure enterprise deals in the last 3 years.
• Experience selling AI/ML, automation, workflow, infrastructure, or security platforms is a major plus.
• Cross-functional experience with Engineering, Product, Marketing, and other teams.
• Expertise in executive selling, multi-threading, and transforming enterprise sales.

Responsibilities

• 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.
• Develop champions and create urgency across C-suite, operations, and IT.
• Leverage MEDDPICC and modern sales tools to drive deals.

Skills

Complex enterprise SaaS sales

Executive selling

Multi-threading deals

Deal strategy & campaigns

Tools

Salesforce

Gong

Outreach

ZoomInfo

6sense

Clari

Job description

Observe.AI is seeking a Senior Enterprise Account Executive to drive a Midwest territory and expand our enterprise AI adoption. You will own multi-threaded, complex sales cycles, engage C-suite stakeholders, and build a scalable go-to-market motion across large enterprise accounts.

Ideal candidates have 7+ years in enterprise SaaS, a proven track record closing six- to seven-figure deals, and深 familiarity with MEDDPICC and modern sales tools.