Senior Enterprise Account Executive (Midwest Territory)

<p><strong>(Primary locations for hiring will be in Chicago, Indianapolis, Detroit, Philadelphia, Pittsburgh, and Cleveland)<br></strong></p> <p><strong>About Us</strong></p> <p class="p1"><a href="https://www.observe.ai/"><span class="s1">Observe.AI</span></a> is the enterprise-grade Customer Experience AI platform that unifies conversations, intelligence, and action to turn contact centers into performance engines. Built to optimize the full lifecycle of human and AI agents, <a href="https://www.observe.ai/"><span class="s1">Observe.AI</span></a> enables enterprises to automate customer interactions, augment agent performance, and deliver governed AI at scale.</p> <p class="p1">On a single platform, <a href="https://www.observe.ai/"><span class="s1">Observe.AI</span></a> combines Voice and Chat AI Agents, real-time AI Copilots, and Conversation Intelligence with 100% interaction coverage for quality, compliance, and performance management. Trusted by brands like DoorDash, Affordable Care, Signify Health, and Verida, <a href="https://www.observe.ai/"><span class="s1">Observe.AI</span> </a>delivers fast time-to-value, measurable ROI, and consistent, high-quality customer experiences across every channel.</p> <p>Companies like DoorDash, Affordable Care, Signify Health, and Verida use <a href="http://observe.ai/">Observe.AI</a> to transform customer experiences every day by accelerating service speed, increasing operational efficiency, and strengthening customer loyalty across every channel.</p> <p><strong>Why Join Us</strong></p> <p>We’re looking for a Senior Enterprise Account Executive (Midwest Territory)—a rare combination of builder, operator, and elite enterprise seller. The ideal candidate is someone who:</p> <ul> <li>Runs toward complexity</li> <li>Operates at startup speed</li> <li>Owns a business, not a book of accounts</li> <li>Excels in high-stakes technical sales cycles</li> </ul> <p>This is not a 9–5 job. This is an opportunity to build a category and influence the direction of enterprise AI adoption. Agentic AI experience is a plus but not required. What matters most is depth in complex enterprise selling, mastery of sales rigor, and a builder’s mindset. If you’re a builder, operator, and elite seller ready to redefine enterprise AI, this is the place to do the best work of your career</p> <p><strong>What you’ll be doing:<br></strong></p> <p>Own Your Territory Like a CEO</p> <ul> <li>Build and execute territory strategy across enterprise accounts.</li> <li>Maintain 4–5x pipeline coverage and deliver predictable outcomes.</li> <li>Navigate large matrixed organizations with technical and business stakeholders.</li> </ul> <p>Lead Complex, Technical Enterprise Sales</p> <ul> <li>Own multi-threaded sales cycles involving automation, architecture, workflows, security, and ROI.</li> <li>Use advanced sales methodologies (MEDDPICC, Command of the Message, Challenger, SPICED).</li> <li>Develop champions and create urgency across C-suite, operations, and IT.</li> </ul> <p>Operate With Modern Sales Tools + GenAI</p> <ul> <li>Leverage a modern sales tech stack (Salesforce, Gong, Outreach, ZoomInfo, 6sense, Clari).</li> <li>Use GenAI tools + Observe.AI’s intelligence platform to: <ul> <li>Accelerate research, account penetration, and personalization</li> <li>Build repeatable outbound motions</li> <li>Multiply productivity beyond 1 + 1 = 2</li> <li>Strengthen MEDDPICC documentation and deal strategy</li> <li>Enhance storytelling, ROI models, and executive communications</li> </ul> </li> </ul> <p>Build Scale the AI Agent Motion</p> <ul> <li>Establish repeatable patterns and industry playbooks.</li> <li>Provide structured insights to Product, Engineering, CX, and Marketing.</li> <li>Influence roadmap direction based on customer workflows and technical needs.</li> </ul> <p>Operational Excellence</p> <ul> <li>Forecast accurately using Commit, Strong Upside, Upside, Pipeline.</li> <li>Drive account planning and expansion strategy.</l ... (truncated, view full listing at source)