Senior Enterprise Account Executive

Observe.AI

Senior Enterprise Account Executive leading enterprise sales initiatives for Observe.AI's AI Agents platform. Focused on complex, technical sales cycles across Midwest territory.

Posted 7/30/2026full-timeRemote • Illinois, Missouri, Ohio, Pennsylvania • 🇺🇸 United StatesSenior💰 $270,000 - $300,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in enterprise SaaS sales with a focus on complex, technical sales cycles, leveraging advanced sales methodologies and modern sales tools. Proven ability to build and execute territory strategies, influence C-suite stakeholders, and drive operational excellence in account planning and expansion.

Highest-signal resume keywords

Enterprise SaaS SalesComplex Deal StrategiesAdvanced Sales MethodologiesExecutive SellingAI/ML Sales Experience

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Complex Sales CyclesTechnical Sales CampaignsMarket Intelligence GatheringAccount PlanningForecasting

Soft Skills

Influencing TransformationCross-Functional CollaborationBuilding Champions

Tools & Technologies

SalesforceGongOutreachZoomInfo6senseClariObserve.AI

Industry Keywords

AutomationWorkflowsSecurity PlatformsROI ModelsC-Suite Engagement

About the role

Key responsibilities & impact

Own Your Territory Like a CEO
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.
Lead Complex, Technical Enterprise Sales
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.
Operate With Modern Sales Tools + GenAI
Leverage 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 personalization
Build repeatable outbound motions
Multiply productivity beyond 1 + 1 = 2
Strengthen MEDDPICC documentation and deal strategy
Enhance storytelling, ROI models, and executive communications
Build & Scale the AI Agent Motion
Establish 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 Excellence
Forecast accurately using Commit, Strong Upside, Upside, Pipeline.
Drive account planning and expansion strategy.
Execute land → expand → transform motions inside enterprise organizations.

Requirements

What you’ll need

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

Comp & perks

Competitive compensation including equity: Market-aligned base pay, performance incentives, and meaningful equity ownership
Excellent medical, dental, and vision insurance options: Comprehensive medical, dental and vision benefits for employees and eligible dependents
Flexible 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 savings
Quarterly Lifestyle Spending Account: Flexible quarterly stipend to support wellness, learning and professional development, and personal growth
Monthly Mobile + Internet Stipend: Support for remote and hybrid work connectivity needs
Pre-tax Commuter Benefits: Tax-efficient transit and commuting support for hybrid and in-office employees
Autonomy and Agency: Play a meaningful role in scaling a category-defining GenAI platform transforming the future of customer experience.