Senior Enterprise Account Executive (Midwest Territory)

Observe.AI is hiring a remote Senior Enterprise Account Executive (Midwest Territory) to lead high-stakes, technically complex sales across enterprise accounts. If you think like a founder and sell like a category creator, this remote-US role is your stage to shape how large organizations adopt agentic AI.

About the Role

This is a remote-US position with hiring focused on the Midwest and Northeast corridor — Chicago, Indianapolis, Detroit, Philadelphia, Pittsburgh, and Cleveland. As a Senior Enterprise Account Executive at Observe.AI, you'll own your territory like a business, not a list of accounts. Expect long, multi-threaded cycles spanning automation, architecture, security, and ROI. Prior agentic AI experience is welcome but optional; what counts is depth in complex enterprise selling, disciplined sales rigor, and a builder's instinct.

Key Responsibilities

• Craft and run a territory strategy across enterprise accounts while sustaining 4–5x pipeline coverage and predictable results.
• Drive multi-stakeholder, technical sales motions across C-suite, operations, and IT, building champions and momentum.
• Apply leading methodologies such as MEDDPICC, Command of the Message, Challenger, and SPICED.
• Operate a modern stack — Salesforce, Gong, Outreach, ZoomInfo, 6sense, Clari — and use GenAI plus Observe.AI's platform to scale research, outreach, deal strategy, and executive storytelling.
• Establish repeatable playbooks, feed insights to Product, Engineering, CX, and Marketing, and influence the roadmap.
• Forecast with accuracy and execute land, expand, and transform motions inside large organizations.

Qualifications

• 7+ years in enterprise SaaS with complex, technical sales cycles.
• Proven record of closing high six- and seven-figure deals within the past three years.
• Experience designing technical sales campaigns and distilling market, competitor, and customer intelligence.
• Strong cross-functional collaboration with Engineering, Product, and Marketing.
• Selling AI/ML, automation, workflow, infrastructure, or security platforms is a strong plus.
• Mastery of MEDDPICC or similar frameworks, executive presence, multi-threading, and a scrappy, accountable, high-urgency mindset.

About Observe.AI

Observe.AI is the AI Agents platform for customer experience, helping organizations deliver faster, smarter service at scale. Purpose-built AI Agents understand context, make decisions, take action, and improve continuously across the full CX lifecycle. Trusted by brands including DoorDash, Affordable Care, Signify Health, and Verida, the platform lifts customer satisfaction, agent productivity, and consistent performance.

How to Apply

To apply, complete your application directly on this page, or you'll be redirected to the employer's application platform to finish submitting there.