Senior Enterprise Account Executive (Midwest Territory) at Observe.AI

This role is designed for a high-performing, "builder-mentality" sales professional with at least 7 years of experience in technical enterprise SaaS. You should

Work type: remote

Location: Remote-US

Salary: $270,000 – $300,000/yr

Type: Full-time

Summary

This role is designed for a high-performing, "builder-mentality" sales professional with at least 7 years of experience in technical enterprise SaaS. You should have a proven track record of closing six and seven-figure deals within complex, multi-threaded environments. The team is looking for someone who doesn't just manage a territory but "owns it like a CEO," utilizing modern AI sales tools and methodologies like MEDDPICC to drive high-stakes outcomes. The compensation is a significant highlight, with an OTE ranging from **$270,000–$300,000**, plus equity and specialized perks like a "Lifestyle Spend" and a winter break. While the role is remote-friendly, they are specifically targeting candidates residing in major Midwest hubs (Chicago, Indianapolis, Detroit, etc.) to lead the charge in a high-growth AI category. **You might be a good fit if you:** * Have successfully closed $500k+ enterprise deals in the last 3 years. * Are a master of sales rigor (MEDDPICC) and technical discovery. * Thrive in a fast-paced startup environment where you help shape the product roadmap. * Live in or near Chicago, Indianapolis, Detroit, Philadelphia, Pittsburgh, or Cleveland.

Job Description

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

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

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.

• 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.

• 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

• Experience selling AI/ML, automation, workflow, infrastructure, or security platforms a major plus.

• Expertise in executive selling, multi-threading, and influencing transformation.

• 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.

• 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

• Autonomy and Agency: Play a meaningful role in scaling a category-defining GenAI platform transforming the future of customer experience.

The OTE (On Target Earnings) compensation range targeted for this full-time position is $270,000-$300,000 Rangeper annum. Compensation may vary outside of this range depending on a number of factors, including a candidate’s qualifications, skills, competencies and experience. Base pay is one part of the Total Package that is provided to compensate and recognize employees for their work, and this role may be eligible for additional discretionary bonuses/incentives and equity (in the form of options). This salary range is an estimate, and the actual salary may vary based on the Company’s compensation practices.

Our Commitment to Inclusion and Belonging

Observe.AI is an Equal Employment Opportunity employer that proudly pursues and hires a diverse workforce. Observe AI does not make hiring or employment decisions on the basis of race, color, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender identity, sexual orientation, disability, age, military or veteran status, or any other basis protected by applicable local, state, or federal laws or prohibited by Company policy. Observe.AI also strives for a healthy and safe workplace and strictly prohibits harassment of any kind.We welcome all people. We celebrate diversity of all kinds and are committed to creating an inclusive culture built on a foundation of respect for all individuals. We seek to hire, develop, and retain talented people from all backgrounds. Individuals from non-traditional backgrounds, historically marginalized or underrepresented groups are strongly encouraged to apply.If you are ambitious, make an impact wherever you go, and you're ready to shape the future of Observe.AI, we encourage you to apply. For more information, visit[](http://www.observe.ai)www.observe.ai.#LI- Remote

View this job on nocollar jobs