{"id":1017365,"url":"https://alion.io/job/observe-ai-senior-enterprise-account-executive-midwest-territory","title":"Senior Enterprise Account Executive (Midwest Territory)","company":{"id":2599,"name":"Observe.AI","domain":"observe.ai","url":"https://alion.io/company/observe-ai","size_band":"51-200","is_staffing_agency":false,"is_intermediary":false,"ats_vendor":"Greenhouse","truth_index":{"grade":"B","score":75,"open_postings":3,"ghost_share":0,"stale_share":1,"repost_share":0,"time_to_fill_p50_days":null,"computed_at":"2026-09-24T05:45:00Z"}},"role":"Sales","role_family":"Sales","seniority":"senior","employment_type":"full_time","work_mode":"hybrid","remote_scope":null,"hiring_geo_confidence":"structured","locations":[],"countries":[],"hiring_countries":[],"hiring_countries_total":0,"salary":{"min":270000,"max":300000,"currency":"USD","period":"year","gross":null,"usd_annual":300000},"salary_estimate":null,"experience_years_min":null,"visa_sponsorship":false,"relocation_package":false,"has_equity":true,"technologies":[{"name":"AI Agents","optional":false},{"name":"Salesforce","optional":true}],"status":"live","first_seen_at":"2026-02-18T19:18:11Z","employer_posted_date":"2026-09-11","last_verified_at":"2026-09-24T12:22:25Z","board_verified":true,"closed_at":null,"days_open":217,"trust":{"level":"stale","repost_count":0,"flags":["stale"],"days_open":217},"description":"(Primary locations for hiring will be in Chicago, Indianapolis, Detroit\n\nAbout Us\nObserve.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.\nEach 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.\nBuilt 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.\nWhy Join Us\nWe’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:\nRuns toward complexity\nOperates at startup speed\nOwns a business, not a book of accounts\nExcels in high-stakes technical sales cycles\nThis 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\nWhat You’ll Be Doing\n\nOwn Your Territory Like a CEO\nBuild and execute territory strategy across enterprise accounts.\nMaintain 4-5x pipeline coverage and deliver predictable outcomes.\nNavigate large matrixed organizations with technical and business stakeholders.\nLead Complex, Technical Enterprise Sales\nOwn multi-threaded sales cycles involving automation, architecture, workflows, security, and ROI.\nUse advanced sales methodologies (MEDDPICC, Command of the Message, Challenger, SPICED).\nDevelop champions and create urgency across C-suite, operations, and IT.\nOperate With Modern Sales Tools + GenAI\nLeverage a modern sales tech stack (Salesforce, Gong, Outreach, ZoomInfo, 6sense, Clari).\nUse GenAI tools + Observe.AI’s intelligence platform to:Accelerate research, account penetration, and personalization\nBuild repeatable outbound motions\nMultiply productivity beyond 1 + 1 = 2\nStrengthen MEDDPICC documentation and deal strategy\nEnhance storytelling, ROI models, and executive communications\n\nBuild & Scale the AI Agent Motion\nEstablish repeatable patterns and industry playbooks.\nProvide structured insights to Product, Engineering, CX, and Marketing.\nInfluence roadmap direction based on customer workflows and technical needs.\nOperational Excellence\nForecast accurately using Commit, Strong Upside, Upside, Pipeline.\nDrive account planning and expansion strategy.\nExecute land → expand → transform motions inside enterprise organizations.\nWhat You'll Bring To The Role \n\n7+ years in enterprise SaaS with complex, technical sales cycles.\nTrack record closing high six- and seven-figure enterprise deals in the last 3 years.\nDesigning and executing complex deal strategies and technical sales campaigns\nGathering, distilling, and processing complex market (industry, competitor, customer, prospect) intelligence\nWorking cross functionally with Engineering, Product Management, Marketing, and other relevant departments\nExperience selling AI/ML, automation, workflow, infrastructure, or security platforms a major plus.\nExpertise in executive selling, multi-threading, and influencing transformation.\nSkills & Attributes\nMastery in MEDDPICC or similar qualification frameworks.\nSkilled in using modern sales tech + GenAI for non-linear productivity.\nExecutive presence with ability to simplify technical value.\nBuilder mentality: scrappy, resourceful, resilient.\nHigh urgency + high accountability.\nWhy You’ll Love It Here \nCompetitive compensation including equity: Market-aligned base pay, performance incentives, and meaningful equity ownership\nExcellent medical, dental, and vision insurance options: Comprehensive medical, dental and vision benefits for employees and eligible dependents\nFlexible 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.\nAdditional Time to Recharge: 10 company holidays, an annual company-wide Winter Break, and paid parental leave to fully support life outside of work.\n 401(k) plan: Long-term financial planning support with tax-advantaged retirement savings\nQuarterly Lifestyle Spending Account: Flexible quarterly stipend to support wellness, learning and professional development, and personal growth\nMonthly Mobile + Internet Stipend: Support for remote and hybrid work connectivity needs\nPre-tax Commuter Benefits: Tax-efficient transit and commuting support for hybrid and in-office employees\nAutonomy and Agency: Play a meaningful role in scaling a category-defining GenAI platform transforming the future of customer experience.\nSalary Range\nThe 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.\nOur Commitment to Inclusion and Belonging\nObserve.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.\nWe 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.\nIf you are ambitious, make an impact wherever you go, and you're ready to shape the future of Observe.AI, we encourage you to apply. For more information, visit www.observe.ai. \n#LI- Remote","description_format":"text","description_chars":7166,"description_truncated":false,"requirements":{"experience_years_min":null,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":null,"security_clearance":false,"languages":[]},"benefits":["Equity","Hybrid work","Parental leave","Professional development","Vision insurance"],"hiring_locations":[{"name":"United States","iso":"US","kind":"country"}],"hiring_excludes":[],"relocation_offered":false,"industries":["Natural Language Processing","Conversational AI","Speech & Audio AI"],"lifecycle":[{"event":"open","at":"2026-09-18T00:22:39Z"}],"liveness":{"score":8,"band":"cold","label":"Long shot","p_open":1,"p_active":0.297,"p_room":0.28,"age_days":217,"expected_fill_days":42,"reasons":["conf:2","velocity","win:tail","crowd:"],"computed_at":"2026-09-24T05:45:00Z"},"pay":{"stated_usd_annual":300000,"is_top_pay":true},"html_url":"https://alion.io/job/observe-ai-senior-enterprise-account-executive-midwest-territory","json_url":"https://alion.io/job/observe-ai-senior-enterprise-account-executive-midwest-territory.json","meta":{"generated_at":"2026-09-24T12:33:56Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers"}}