Regional Vice President of Enterprise Sales, Observe.AI

• 8–10+ years of B2B SaaS sales experience, including 3+ years in leadership managing mid-market or SMB teams
• Strong track record of net-new logo acquisition via outbound prospecting—personally and as a team leader
• Experience as a player-coach, balancing individual contributor responsibilities with team leadership
• Comfort building from scratch—people, processes, sales motions, and culture—in a high-growth or startup environment
• Familiarity with sales methodologies like MEDDIC, CCS, or Challenger, and tools like Salesforce, Outreach/Salesloft, Clari, Gong
• Strong storytelling and discovery skills; able to earn trust with technical and business stakeholders alike

Desirable

• We are hiring a Regional Vice President, Enterprise Sales to build and lead our outbound-led sales motion
• The RVP, Enterprise Sales will be at the forefront of driving new logo growth and engaging C-level executives across industries
• This is a hunter-first, player-coach role ideal for a high-energy leader who thrives in whitespace, has a track record of outbound pipeline generation, and is ready to build and lead a high-performing team
• You’ll be accountable for owning pipeline generation, closing new logos, and building the people, processes, and playbook to scale outbound-led revenue growth in the enterprise segment
• If you thrive in high-growth environments and are passionate about translating GenAI innovation into measurable customer outcomes, and shaping the future of customer experience - this role is for you
• Hunter Mentality & Outbound Strategy:
• Own and execute an outbound-first GTM motion targeting mid-market and enterprise accounts (typically <500 agents)
• Build and refine ICPs, persona-based messaging, outbound cadences, and prospecting strategies to drive predictable top-of-funnel activity
• Collaborate with marketing and SDR teams to align on high-converting campaigns
• Player-Coach Sales Leadership:
• Lead from the front as a quota-carrying seller, personally prospecting, engaging, and closing deals
• Hire, train, and coach a team of Mid-Market AEs, setting the tone for a metrics-driven, outbound culture
• Instill discipline around outbound KPIs—activities, pipeline coverage, conversion rates—while celebrating grit and curiosity
• Build & Scale the Function:
• Design the team structure, territories, compensation, hiring plan, and onboarding for an outbound-led mid-market motion
• Establish CRM best practices, forecasting cadences, pipeline review rituals, and enablement workflows
• Partner with RevOps, Product Marketing, and Enablement to iterate quickly based on data and feedback
• AI/GenAI Fluency:
• Understand and position the value of GenAI-powered solutions in contact center, CX, and revenue acceleration workflows
• Translate technical capabilities into business outcomes tailored for mid-market buyers across ops, support, and IT
• Stay ahead of GenAI trends, competitors, and evolving use cases in the customer engagement space