[Hiring] Enterprise Account Executive @Observe.AI

Role Description

You will build and own an enterprise territory, selling a technically complex AI platform to contact center owners and to the CIO, CTO, finance and, at times, CEO sponsors who fund the change. We sell to companies with 1,000 to 10,000 employees and roughly 300 to 2,000 contact center agents. In these companies, the buying group is small enough to reach the executive who decides, and you are expected to reach them.

This is a high-ownership role with a high bar. You will land the platform through the intelligence that shows where automation pays off, then expand into AI agents. You will also help set the playbook that the next hires follow.

What Success Looks Like

• Land 5 or more new logos per year at a target ACV of $250K or more.
• Win one or two expansions or upsells inside your existing account base each year.
• Hold 4 to 5x pipeline coverage, with a meaningful share self-sourced in your own territory.
• Forecast within 10% of actual, using Commit, Strong Upside, Upside, and Pipeline.

What you'll be doing:

• Own your territory like a CEO.
• Build and run a territory plan for enterprise accounts that fit our profile, and say no to accounts that do not.
• Source your own pipeline through multi-threaded outreach to operations leaders and executives.
• Personally run outbound campaigns, with AI doing the heavy lifting on research and personalization.
• Navigate large, matrixed organizations with technical and business stakeholders.
• Lead complex, technical sales cycles.
• Sell to two buying centers: contact center operations and the technology and finance executives.
• Explain how voice and chat AI agents and copilots work, in plain terms, to a skeptical CIO.
• Run proof-based evaluations with Solutions Engineers and forward-deployed engineers.
• Build ROI cases that a CFO will sign off on, tied to cost per contact, containment, quality, and agent productivity.
• Run deals on MEDDPICC, and hold every deal to our Five Wins gates before it advances.
• Turn what works in your deals into repeatable plays, and share what you learn with Product, Engineering, CX, and Marketing.
• Mentor Enterprise AEs on technical selling and executive engagement.
• Show up in person for executive roundtables and customer events.
• Keep CRM and deal records current.
• Run account plans and expansion strategies.

How We Work

Observe.AI is an AI-native company, and we expect you to be too. You will build your own AI workflows for account research, outbound, deal strategy, and forecasting, and pick up new tools as they appear. You do not need a specific stack. You need curiosity and a record of changing how you work when something better arrives.

We move at startup speed, debate openly, and expect people to hold a position and change it when the evidence changes. We want people who welcome deal inspection and coaching, ask for help early, and partner closely with Sales Development, Solutions Engineering, and forward-deployed engineering. Everyone follows the process, leaders included.

What you'll bring to the role

• 8 or more years in enterprise SaaS with complex, technical sales cycles.
• A record of closing six- and seven-figure net-new deals, with ACVs of $250K or more, in the last three years.
• Experience selling AI/ML, automation, workflow, infrastructure, security, or contact center technology.
• Credibility with technical buyers: you can discuss architecture, security, and integration without a rehearsed script.
• A record of self-sourced pipeline in a greenfield or lightly covered territory.

Skills & Attributes

• Mastery of MEDDPICC or an equivalent framework.
• Comfort with usage-based and committed-spend pricing models.
• Executive presence, and the ability to simplify technical value for a CIO and an operations leader alike.
• A builder's mindset: scrappy, resourceful, and resilient, with high urgency and high accountability.

Benefits

• Competitive compensation including equity.
• Excellent medical, dental, and vision insurance options.
• Flexible paid time off.
• Additional time to recharge: 10 company holidays, an annual company-wide Winter Break, and paid parental leave.
• 401(k) plan for long-term financial planning support.
• Quarterly Lifestyle Spending Account for wellness and personal growth.
• Monthly mobile and internet stipend.
• Pre-tax commuter benefits.
• Autonomy and agency in scaling a category-defining GenAI platform.

Salary Range

The on-target earnings (OTE) for this role are $270,000-$300,000 with a target 50/50 split between base and variable, plus equity in the form of options. Compensation varies based on qualifications, skills, location and experience.

Our Commitment to Inclusion and Belonging

Observe.AI is an Equal Employment Opportunity employer that proudly pursues and hires a diverse workforce. We celebrate diversity of all kinds and are committed to creating an inclusive culture built on a foundation of respect for all individuals.

If you are ambitious, make an impact wherever you go, and are ready to shape the future of Observe.AI, we encourage you to apply.