Senior Enterprise Account Executive, Midwest Territory

🕒 February 18

🌽 Illinois, Ohio, +2 more states – Remote

🌽 Illinois – Remote 🏈 Ohio – Remote 🚗 Michigan – Remote 🔔 Pennsylvania – Remote

💵 $270k - $300k / year

⏰ Full Time

🟠 Senior

🧑‍💼 Account Executive

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Observe.AI

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2017

🤖 Artificial Intelligence

🏢 Enterprise

☁️ SaaS

Artificial Intelligence • Enterprise • SaaS

Observe. AI is an enterprise-grade AI platform focused on conversation intelligence for contact centers. It provides a comprehensive suite of AI-powered solutions, including real-time agent assistance, voice AI for automating complex customer interactions, post-interaction quality assurance (QA), and business analytics. The company's platform empowers contact centers to evaluate customer interactions fully, support agents with real-time guidance, improve customer satisfaction, and boost operational efficiency, all while ensuring compliance. Observe. AI caters to various industries, such as banking, financial services, and healthcare insurance, enhancing sales performance, customer experience, and compliance monitoring.

📋 Description

• 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: • Establish repeatable patterns and industry playbooks. • Provide structured insights to Product, Engineering, CX, and Marketing.

🎯 Requirements

• 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 • Experience selling AI/ML, automation, workflow, infrastructure, or security platforms a major plus. • Expertise in executive selling, multi-threading, and influencing transformation.

🏖️ Benefits

• Competitive compensation including equity • Excellent medical, dental, and vision insurance options • Flexible time off • 10 Company holidays + Winter Break and up to 16-weeks of parental leave • 401K plan • Quarterly Lifestyle Spend • Monthly Mobile + Internet Stipend • Pre-tax Commuter Benefits