The posting
About Us
Observe.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 leading brands, Observe.AI delivers fast time-to-value, measurable ROI, and consistent, high-quality customer experiences across every channel.
Why Join Us
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 (CX, quality, workforce, and support leaders) and the technology and finance executives who own architecture, security, and budget.
- Explain how voice and chat AI agents and copilots work, in plain terms, to a skeptical CIO. Cover guardrails, data handling and residency, integration with CCaaS platforms (such as Genesys, NICE, Five9, and Amazon Connect), and how performance is measured.
- Run proof-based evaluations. Work with Solutions Engineers and forward-deployed engineers to scope use cases and win the technical and security evaluation, and keep the process honest from first call to signature.
- 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 (business, product, technical, security, and commercial) before it advances.
Build and scale the AI agent motion
- 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, and help turn happy customers into references.
Operate with discipline
- Keep CRM and deal records current. Our goal is for AI to maintain most of the record, so what you put in should be accurate and brief.
- Run account plans and expansion strategies, and take pricing through our deal desk and discount tiers.
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 (CCaaS, workforce, or quality management). Agentic AI experience is a strong plus.
- Credibility with technical buyers: you can discuss architecture, security, and integration without a rehearsed script, and you know when to bring in an engineer.
- A record of self-sourced pipeline in a greenfield or lightly covered territory.
Skills & Attributes
- Mastery of MEDDPICC or an equivalent framework, and the discipline to use it when it slows a deal down.
- 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.
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 coverage for employees and eligible dependents.
- Flexible paid time off: Our flexible PTO policy lets you take the time you need to recharge, keep your balance, and perform at your best.
- Additional time to recharge: 10 company holidays, an annual company-wide Winter Break, and paid parental leave to support life outside of work.
- 401(k) plan: Long-term financial planning support with tax-advantaged retirement savings.
- Quarterly Lifestyle Spending Account: A flexible quarterly stipend for wellness, learning and professional development, and personal growth.
- Monthly mobile and internet stipend: Support for remote and hybrid work connectivity.
- 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 that is transforming the future of customer experience.
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. 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 and historically marginalized or underrepresented groups are strongly encouraged to apply.
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. For more information, visit www.observe.ai.
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