Senior Enterprise Account Executive (Midwest Territory)

(Primary locations for hiring will be in Chicago, Indianapolis, Detroit, Philadelphia, Pittsburgh, and Cleveland)About UsObserve.AI 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, Observe.AI enables enterprises to automate customer interactions, augment agent performance, and deliver governed AI at scale. On a single platform, Observe.AI 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, Observe.AI delivers fast time-to-value, measurable ROI, and consistent, high-quality customer experiences across every channel.Why Join UsWe’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:Runs toward complexityOperates at startup speedOwns a business, not a book of accountsExcels in high-stakes technical sales cyclesThis 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 careerWhat you’ll be doing:Own Your Territory Like a CEOBuild 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.Lead Complex, Technical Enterprise SalesOwn 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.Operate With Modern Sales Tools + GenAILeverage 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 personalizationBuild repeatable outbound motionsMultiply productivity beyond 1 + 1 = 2Strengthen MEDDPICC documentation and deal strategyEnhance storytelling, ROI models, and executive communicationsBuild & Scale the AI Agent MotionEstablish repeatable patterns and industry playbooks.Provide structured insights to Product, Engineering, CX, and Marketing.Influence roadmap direction based on customer workflows and technical needs.Operational ExcellenceForecast accurately using Commit, Strong Upside, Upside, Pipeline.Drive account planning and expansion strategy.Execute land → expand → transform motions inside enterprise organizations.What you'll bring to the role 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 campaignsGathering, distilling, and processing complex market (industry, competitor, customer, prospect) intelligenceWorking cross functionally with Engineering, Product Management, Marketing, and other relevant departmentsExperience selling AI/ML, automation, workflow, infrastructure, or security platforms a major plus.Expertise in executive selling, multi-threading, and influencing transformation.Skills & AttributesMastery 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.Why You’ll Love It Here Competitive compensation including equity: Market-aligned base pay, performance incentives, and meaningful equity ownershipExcellent medical, dental, and vision insurance options: Comprehensive medical, dental and vision benefits for employees and eligible dependentsFlexible Paid Time Off: Our unlimited, flexible PTO policy empowers you to take the time you need 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 fully support life outside of work.401(k) plan: Long-term financial planning support with tax-advantaged retirement savingsQuarterly Lifestyle Spending Account: Flexible quarterly stipend to support wellness, learning and professional development, and personal growthMonthly Mobile + Internet Stipend: Support for remote and hybrid work connectivity needsPre-tax Commuter Benefits: Tax-efficient transit and commuting support for hybrid and in-offic