Senior Enterprise Account Executive (Midwest Territory)

(Primary locations for hiring will be in Chicago, Indianapolis, Detroit, Philadelphia, Pittsburgh, and Cleveland)

About Us

Observe.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.

Why Join Us

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 complexity
• Operates at startup speed
• Owns a business, not a book of accounts
• Excels in high-stakes technical sales cycles

This 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

What You’ll Be Doing

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.

What You'll Bring To The Role 

• 7+ years in enterprise SaaS with complex, technical sales cycles.
• Track record clo