[Remote] Senior Enterprise Account Executive - Pacific NorthWest

Note: The job is a remote job and is open to candidates in USA. Observe.AI is hiring a Senior Enterprise Account Executive to drive enterprise sales of its AI Agents platform for customer experience. The role owns territory strategy and complex technical sales cycles, builds repeatable AI Agent sales motions, and manages forecasting, account planning, and expansion.

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
• Use advanced sales methodologies (MEDDPICC, Command of the Message, Challenger, SPICED)
• Develop champions and create urgency across C-suite, operations, and IT
• Leverage a modern sales tech stack (Salesforce, Gong, Outreach, ZoomInfo, 6sense, Clari)
• Use GenAI tools + Observe.AI’s intelligence platform to:
• Accelerate research, account penetration, and personalization
• Build repeatable outbound motions
• Multiply productivity beyond 1 + 1 = 2
• Strengthen MEDDPICC documentation and deal strategy
• Enhance storytelling, ROI models, and executive communications
• Establish repeatable patterns and industry playbooks
• Provide structured insights to Product, Engineering, CX, and Marketing
• Influence roadmap direction based on customer workflows and technical needs
• Forecast accurately using Commit, Strong Upside, Upside, Pipeline
• Drive account planning and expansion strategy
• Execute land → expand → transform motions inside enterprise organizations

Skills

• 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 (industry, competitor, customer, prospect) intelligence
• Working cross functionally with Engineering, Product Management, Marketing, and other relevant departments
• Expertise in executive selling, multi-threading, and influencing transformation
• Mastery in MEDDPICC or similar qualification frameworks
• Skilled in using modern sales tech + GenAI for non-linear productivity
• Executive presence with ability to simplify technical value
• Builder mentality: scrappy, resourceful, resilient
• High urgency + high accountability
• Experience selling AI/ML, automation, workflow, infrastructure, or security platforms a major plus

Benefits

• Equity ownership, in the form of options
• Performance incentives
• Comprehensive medical, dental and vision benefits for employees and eligible dependents
• Unlimited, flexible PTO
• 10 company holidays
• Annual company-wide Winter Break
• Paid parental leave
• 401(k) plan
• Quarterly Lifestyle Spending Account: flexible quarterly stipend to support wellness, learning and professional development, and personal growth
• Monthly Mobile + Internet Stipend to support remote and hybrid work connectivity needs
• Pre-tax Commuter Benefits for hybrid and in-office employees
• Autonomy and agency to play a meaningful role in scaling a category-defining GenAI platform transforming the future of customer experience

Company Overview