[Remote] Senior Enterprise Account Executive (Midwest Territory)

Note: The job is a remote job and is open to candidates in USA. Observe.AI is the AI Agents platform for customer experience, designed to help organizations deliver faster, smarter, and more efficient customer service at scale. They are seeking a Senior Enterprise Account Executive for the Midwest Territory, who will be responsible for building and executing territory strategy across enterprise accounts and leading complex, technical enterprise sales cycles.ResponsibilitiesBuild and execute territory strategy across enterprise accountsMaintain 4–5x pipeline coverage and deliver predictable outcomesNavigate large matrixed organizations with technical and business stakeholdersOwn multi-threaded sales cycles involving automation, architecture, workflows, security, and ROIUse advanced sales methodologies (MEDDPICC, Command of the Message, Challenger, SPICED)Develop champions and create urgency across C-suite, operations, and ITLeverage 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 communicationsEstablish repeatable patterns and industry playbooksProvide structured insights to Product, Engineering, CX, and MarketingInfluence roadmap direction based on customer workflows and technical needsForecast accurately using Commit, Strong Upside, Upside, PipelineDrive account planning and expansion strategyExecute land → expand → transform motions inside enterprise organizationsSkills7+ years in enterprise SaaS with complex, technical sales cyclesTrack record closing high six- and seven-figure enterprise deals in the last 3 yearsDesigning 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 departmentsExpertise in executive selling, multi-threading, and influencing transformationExperience selling AI/ML, automation, workflow, infrastructure, or security platforms a major plusMastery in MEDDPICC or similar qualification frameworksSkilled in using modern sales tech + GenAI for non-linear productivityExecutive presence with ability to simplify technical valueBuilder mentality: scrappy, resourceful, resilientHigh urgency + high accountabilityBenefitsCompetitive 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-office employeesCompany OverviewObserve.AI builds AI Agents for Customer Service It was founded in 2017, and is headquartered in Redwood City, California, USA, with a workforce of 201-500 employees. Its website is https://observe.ai.