Senior Enterprise Account Executive (Midwest Territory)

How to use this kit

Ground every answer in facts on this page and the original listing. We never invent Glassdoor-style reviews or salaries that are not in our data.

Interview prep

• Walk a full enterprise deal: discovery → pilot → close
• Explain Observe.AI value for agent assist and contact-center outcomes
• Territory plan for Midwest remote coverage
• Handle objections on AI accuracy, security, and change management

Fit summary

Strong fit if you close complex B2B SaaS/AI deals, manage long cycles, and can sell outcomes to CX and ops leaders remotely across the Midwest.

Day in the role

As a Senior Enterprise Account Executive for the Midwest, you run complex sales cycles for Observe.AI’s contact-center AI with multi-stakeholder buyers (ops, IT, CX, finance). Days mix discovery, demos of real-time agent assist value, ROI/business cases, procurement, and forecast hygiene across a remote Midwest territory.

Skills to emphasize

Prioritize enterprise discovery, multi-threading, MEDDIC/similar qualification, and storytelling around AI ROI for contact centers. No certification resources were provided for this listing.

FAQ from this listing

Is this role remote?

Yes—the listing is Remote-US with Midwest territory focus.

What does Observe.AI sell?

Contact-center AI, including real-time agent assist, for enterprise customers.

What experience helps most?

Enterprise AE track record in SaaS or AI, multi-stakeholder selling, and consistent pipeline discipline.

Occupation tasks (O*NET)

Public-domain labor data — prepare examples for 2–3 of these.

• Plan and prepare advertising and promotional material to increase sales of products or services, working with customers, company officials, sales departments, and advertising agencies.
• Inspect layouts and advertising copy, and edit scripts, audio, video, and other promotional material for adherence to specifications.
• Confer with department heads or staff to discuss topics such as contracts, selection of advertising media, or product to be advertised.
• Coordinate with the media to disseminate advertising.
• Coordinate activities of departments, such as sales, graphic arts, media, finance, and research.
• Plan and execute advertising policies and strategies for organizations.
• Direct, motivate, and monitor the mobilization of a campaign team to advance campaign goals.
• Prepare budgets and submit estimates for program costs as part of campaign plan development.

O*NET source

Company facts (cached)

Website: observeai.com

Public cache only — not an employee review.

Role overview (listing rewrite)

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…

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Questions to ask them

• What does success look like in the first 90 days for this role?
• How is the team structured, and who would I work with most?
• What tools and systems does this role use daily?
• Is the work primarily based in Remote-US, hybrid, or fully remote?