[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.
Responsibilities
- 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:
- 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
- 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
- Forecast accurately using Commit, Strong Upside, Upside, Pipeline
- Drive account planning and expansion strategy
- Execute land → expand → transform motions inside enterprise organizations
Skills
- 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
- Expertise in executive selling, multi-threading, and influencing transformation
- Experience selling AI/ML, automation, workflow, infrastructure, or security platforms a major plus
- Mastery 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
Benefits
- 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
Company Overview