Enterprise Account Executive

The role

You will build and own an enterprise territory selling a technically complex AI platform to contact center owners and executives. You will lead complex sales cycles, source your own pipeline, and land new logos while expanding existing accounts.

What you will do

• Build and run a territory plan for enterprise accounts
• Source pipeline through multi-threaded outreach to operations leaders and executives
• Run outbound campaigns
• Navigate large, matrixed organizations with technical and business stakeholders
• Sell to contact center operations and technology/finance executives
• Explain voice and chat AI agents and copilots
• Run proof-based evaluations
• Build ROI cases for CFO sign-off
• Run deals on MEDDPICC
• Mentor Enterprise AEs on technical selling and executive engagement

Required qualifications

• 8 or more years in enterprise SaaS with complex, technical sales cycles
• A record of closing six- and seven-figure net-new deals, with ACVs of $250K or more, in the last three years
• Experience selling AI/ML, automation, workflow, infrastructure, security, or contact center technology (CCaaS, workforce, or quality management)
• Credibility with technical buyers
• A record of self-sourced pipeline in a greenfield or lightly covered territory
• Mastery of MEDDPICC or an equivalent framework
• Comfort with usage-based and committed-spend pricing models
• Executive presence

Nice to have

• Agentic AI experience

Benefits

• Market-aligned base pay
• Performance incentives
• Meaningful equity ownership
• Medical, dental, and vision insurance options
• Flexible paid time off
• 10 company holidays
• Annual company-wide Winter Break
• Paid parental leave
• 401(k) plan
• Quarterly Lifestyle Spending Account
• Monthly mobile and internet stipend
• Pre-tax commuter benefits

About the company

Observe.AI is the enterprise-grade Customer Experience AI platform that unifies conversations, intelligence, and action to turn contact centers into performance engines.