Senior Enterprise Account Executive (Midwest Territory)

(Primary locations for hiring will be in Chicago, Indianapolis, Detroit

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 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.

Skills & Attributes

• 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.

Why You’ll Love It Here  

• 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.

Salary Range

The OTE (On Target Earnings) compensation range targeted for this full-time position is $270,000-$300,000 Range per 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 www.observe.ai. 

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