Senior Enterprise Account Executive

This is a fully remote position, open to applicants in Illinois, +3 more states.

📋 Description

• Take ownership of your territory as if you were the CEO.

• Develop and implement a territory strategy for enterprise accounts.

• Maintain a pipeline coverage of 4–5x and ensure predictable results.

• Navigate complex matrixed organizations with both technical and business stakeholders.

• Lead intricate and technical enterprise sales processes.

• Manage multi-threaded sales cycles that encompass automation, architecture, workflows, security, and ROI.

• Employ advanced sales methodologies such as MEDDPICC, Command of the Message, Challenger, and SPICED.

• Cultivate champions and instill a sense of urgency among C-suite executives, operations, and IT teams.

• Operate with cutting-edge sales tools and GenAI technologies.

• Utilize a modern sales tech stack, including Salesforce, Gong, Outreach, ZoomInfo, 6sense, and Clari.

• Implement GenAI tools and Observe.AI’s intelligence platform to:

• Expedite research, account penetration, and personalization efforts.

• Create repeatable outbound sales motions.

• Enhance productivity beyond simple addition.

• Strengthen MEDDPICC documentation and deal strategies.

• Improve storytelling, ROI models, and executive communications.

• Build and scale the AI Agent Motion.

• Develop repeatable patterns and industry-specific playbooks.

• Deliver structured insights to Product, Engineering, Customer Experience, and Marketing.

• Influence the direction of the roadmap based on customer workflows and technical requirements.

• Achieve operational excellence.

• Provide accurate forecasts using Commit, Strong Upside, Upside, and Pipeline metrics.

• Drive account planning and expansion strategies.

• Execute land → expand → transform strategies within enterprise organizations.

⛳️ Requirements

• A minimum of 7 years in enterprise SaaS with complex, technical sales cycles.

• Proven track record of closing high six- and seven-figure enterprise deals within the last 3 years.

• Experience in designing and executing sophisticated deal strategies and technical sales campaigns.

• Ability to gather, distill, and analyze complex market intelligence (industry, competitor, customer, prospect).

• Proven skills in cross-functional collaboration with Engineering, Product Management, Marketing, and other relevant departments.

• Experience in selling AI/ML, automation, workflow, infrastructure, or security platforms is a significant advantage.

• Expertise in executive selling, multi-threading, and driving transformation.

🏝️ Benefits

• Competitive compensation package including equity: Market-aligned base salary, performance incentives, and significant equity ownership.

• Comprehensive medical, dental, and vision insurance options: Inclusive benefits for employees and eligible dependents.

• Flexible Paid Time Off: Our unlimited, flexible PTO policy allows you to take the necessary time to recharge, maintain balance, and perform at your best.

• Additional Time to Recharge: 10 company holidays, an annual company-wide Winter Break, and paid parental leave to support life outside of work.

• 401(k) plan: Assistance with long-term financial planning through tax-advantaged retirement savings.

• Quarterly Lifestyle Spending Account: Flexible quarterly stipend to promote wellness, learning, professional development, and personal growth.

• Monthly Mobile + Internet Stipend: Support for remote and hybrid work connectivity needs.

• Pre-tax Commuter Benefits: Tax-efficient support for transit and commuting for hybrid and in-office employees.

• Autonomy and Agency: Contribute meaningfully to the scaling of a category-defining GenAI platform that is shaping the future of customer experience.