Observe.AI

Helping teams drive revenue, enhance CX and improve agent performance

Senior Enterprise Account Executive, Midwest Territory

Account ExecutiveSalesFull TimeRemoteTeam 51-200Since 2017H1B SponsorCompany SiteLinkedIn

Location

Illinois + 3 moreAll locations: Illinois, Ohio, Michigan, Pennsylvania

Posted

25 days ago

Salary

$270K - $300K / year

7 yrs expEnglish

Job Description

• Build 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. • Own 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. • Leverage a modern sales tech stack (Salesforce, Gong, Outreach, ZoomInfo, 6sense, Clari). • Use GenAI tools + Observe.AI’s intelligence platform to: • Establish repeatable patterns and industry playbooks. • Provide structured insights to Product, Engineering, CX, and Marketing.

Job Requirements

  • 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 campaigns
  • Gathering, distilling, and processing complex market (industry, competitor, customer, prospect) intelligence
  • Working cross functionally with Engineering, Product Management, Marketing, and other relevant departments
  • Experience selling AI/ML, automation, workflow, infrastructure, or security platforms a major plus.
  • Expertise in executive selling, multi-threading, and influencing transformation.

Benefits

  • Competitive compensation including equity
  • Excellent medical, dental, and vision insurance options
  • Flexible time off
  • 10 Company holidays + Winter Break and up to 16-weeks of parental leave
  • 401K plan
  • Quarterly Lifestyle Spend
  • Monthly Mobile + Internet Stipend
  • Pre-tax Commuter Benefits

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