About Us

Observe.AI is transforming customer service with AI agents that speak, think, and act like your best human agents—helping enterprises automate routine customer calls and workflows, support agents in real time, and uncover powerful insights from every interaction.

With Observe.AI, businesses boost automation, deliver faster, more consistent 24/7 service and build stronger customer loyalty.

Trusted by brands like Accolade, Prudential, Concentrix, Cox Automotive, and Included Health, Observe.AI is redefining how businesses connect with customers—driving better experiences and lasting relationships at every touchpoint.

The Opportunity

This is a rare chance to build and lead the Strategic Accounts business for one of the fastest-growing innovators in the AI-powered customer experience space. We are seeking a dynamic and proven sales leader to architect and scale our Strategic Accounts business from the ground up. The RVP, Strategic Accounts will be at the forefront of driving new logo growth in greenfield markets, engaging C-level executives at some of the world’s largest and most innovative enterprises. You will design and lead a high-performing enterprise sales organization, build repeatable sales processes, and personally lead high-value, complex sales cycles. This is both a strategic leadership and hands-on execution role, ideal for a player-coach who thrives in high-growth environments, can translate GenAI innovation into measurable customer outcomes, and is passionate about shaping the future of customer experience. This role reports directly to the VP, Strategic Accounts.

What you’ll be doing

Hunter Mentality & New Logo Growth

• Identify and open doors into greenfield strategic accounts—from Global 5000 to digitally transforming enterprises. 500+ agents
• Lead with value, tailoring solutions to strategic customer pain points and use cases across the contact center and customer experience landscape.
• Build trusted advisor relationships with C-level executives, influencing enterprise innovation strategies through AI/GenAI-powered capabilities.

Build from Scratch

• Architect the global Strategic Accounts org from the ground up—define structure, headcount, roles, territories, KPIs, and compensation.
• Recruit, onboard, and mentor a high-performing team of Strategic Account Executives, supported by Solutions Engineers and SDRs.
• Stand up sales processes and infrastructure to enable rapid, repeatable scaling (CRM workflows, enablement, playbooks, forecasting, etc.).

Enterprise Sales Execution

• Own the full-cycle sales process for strategic accounts—from prospecting to C-level engagement, solution selling, and complex negotiations.
• Partner with Product, Marketing, and Customer Success to influence roadmap and ensure alignment with enterprise customer needs.
• Consistently meet or exceed new ARR targets, pipeline coverage goals, and win rates.

Player-Coach Execution

• Personally lead high-value, complex enterprise sales cycles—owning prospecting, stakeholder engagement, solution design, and negotiation.
• Operate as a true player-coach: setting the pace, modeling best-in-class sales behaviors, and actively closing business while building the team.
• Drive predictable pipeline generation and pipeline hygiene through consistent coaching and inspection.

GenAI Fluency & Value Selling

• Be a credible executive voice in AI/GenAI, particularly in contact center and CX innovation.
• Translate complex AI capabilities into business outcomes and customer value stories.
• Guide strategic clients through their AI transformation journeys and innovation roadmaps.

What you bring to the role

• 12+ years of enterprise SaaS sales experience, with 5+ years in a senior leadership role focused on Strategic or Global Accounts.
• Proven hunter with a track record of landing new logos, especially in whitespace markets or new geographies.
• Experience building and scaling a new function or region from scratch—team, process, and GTM.
• Strong understanding of contact center, CX, or AI-powered technologies; able to lead technical discussions with CxOs and IT leaders.
• Familiar with enterprise sales motions such as MEDDIC, Challenger, or Customer Centric Sales.
• Comfortable with ambiguity, high-growth, and iterative experimentation—startup/scale-up experience a plus.
• Strategic, data-driven, and resilient with a relentless drive to win.

Preferred Background

• Deep familiarity with GenAI, NLP, LLMs, or ML applications in enterprise use cases.
• Global or multi-regional sales leadership experience (North America, EMEA, or APAC).
• Background in building high-performing sales teams at companies in post-Series B to pre-IPO stages.
• Bachelor's or Master’s degree in Business, Engineering, or a related technical discipline.

What you can expect

• Competitive compensation including equity
• Excellent medical, dental, and vision insurance options
• Flexible time off
• 10 Company holidays + Winter Break and up to 16-weeks of parental leave
• 401K plan
• Quarterly Lifestyle Spend
• Monthly Mobile + Internet Stipend
• Pre-tax Commuter Benefits

Salary Range

The OTE (On Target Earnings) compensation range targeted for this full-time position is $420,000 OTE (On Target Earnings) 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.