Senior Enterprise Account Executive (Midwest Territory)

Senior Enterprise Account Executive (Midwest Territory)Remote-USObserve.AI is the AI Agents platform for customer experience, designed to help organizations deliver faster, smarter, and more efficient customer service at scale. The platform enables businesses to deploy specialized AI Agents that autonomously execute work across the full CX lifecycle—from handling customer conversations to supporting frontline teams and optimizing operations.Each AI Agent is purpose-built for a specific role, equipped to understand context, make decisions, take action, and continuously improve outcomes. This allows organizations to increase resolution speed, elevate service quality, and reduce operational costs while empowering your frontline team to focus on higher-value work.Built on a CX-native foundation, Observe.AI helps leading brands like DoorDash, Affordable Care, Signify Health, and Verida improve customer satisfaction, boost agent productivity, and deliver consistent, scalable performance across every customer interaction.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: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 DoingOwn 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 Role7+ 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 HereCompetitive 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 employeesAutonomy and Agency: Play a meaningful role in scaling a category-defining GenAI platform transforming the future of customer experience.Salary RangeThe OTE (On Target Earnings) compensation range targeted for this full-time position is $270,000-$300,000 Range per annum. Compensation may vary outside of this range depending on a number of factors, including a candidate's qualifications, skills, competencies and experience. Base pay is one part of the Total Package that is provided to compensate and recognize employees for their work, and this role may be eligible for additional discretionary bonuses/incentives and equity (in the form of options). This salary range is an estimate, and the actual salary may vary based on the Company's compensation practices.Our Commitment to Inclusion and BelongingObserve.AI is an Equal Employment Opportunity employer that proudly pursues and hires a diverse workforce. Observe AI does not make hiring or employment decisions on the basis of race, color, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender identity, sexual orientation, disability, age, military or veteran status, or any other basis protected by applicable local, state, or federal laws or prohibited by Company policy. Observe.AI also strives for a healthy and safe workplace and strictly prohibits harassment of any kind.We welcome all people. We celebrate diversity of all kinds and are committed to creating an inclusive culture built on a foundation of respect for all individuals. We seek to hire, develop, and retain talented people from all backgrounds. Individuals from non-traditional backgrounds, historically marginalized or underrepresented groups are strongly encouraged to apply.