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 enterprise-grade Customer Experience AI platform that unifies conversations, intelligence, and action to turn contact centers into performance engines. Built to optimize the full lifecycle of human and AI agents, Observe.AI enables enterprises to automate customer interactions, augment agent performance, and deliver governed AI at scale.

On a single platform, Observe.AI combines Voice and Chat AI Agents, real-time AI Copilots, and Conversation Intelligence with 100% interaction coverage for quality, compliance, and performance management. Trusted by brands like DoorDash, Affordable Care, Signify Health, and Verida, Observe.AI delivers fast time-to-value, measurable ROI, and consistent, high-quality customer experiences across every channel.

Companies like DoorDash, Affordable Care, Signify Health, and Verida use Observe.AI to transform customer experiences every day by accelerating service speed, increasing operational efficiency, and strengthening customer loyalty across every channel.

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.