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Oversee is seeking a Head of Sales to lead the go-to-market strategy and sales execution for AgentSee, an AI-powered productivity platform designed for Travel Management Companies (TMCs). This is a 0-to-1 opportunity where you will be the primary salesperson initially, working directly with the Chief Revenue Officer to identify product-market fit, refine the ideal customer profile and positioning, close early strategic enterprise customers, and build a repeatable GTM motion.
In this role, you will own the complete sales strategy for AgentSee, including defining and refining the ICP, positioning, messaging, pricing, and sales process. You'll personally lead discovery, demos, pilots, negotiations, and closes with enterprise prospects. A key responsibility is translating complex agentic AI and automation technology into clear business value for senior enterprise buyers. You'll leverage customer conversations and market data to identify where AgentSee has the strongest product-market fit and inform product development priorities.
You'll build a repeatable sales methodology and operating cadence, establishing a GTM playbook that scales. As the business grows, you'll hire, develop, and lead the AgentSee sales organization while remaining hands-on and personally selling. You'll work closely with Product, Engineering, Marketing, and Customer Success, bringing customer and market insights directly into strategy and product decisions.
The ideal candidate has 8+ years of B2B technology sales experience with a proven track record of personally owning and closing complex enterprise deals. You should have demonstrated success building a GTM motion from the ground up, taking new products or businesses from early customers toward repeatable sales motions. Experience selling AI, SaaS, automation, workflow, or data solutions to enterprise customers is essential. You're commercially sharp, analytically minded, and comfortable operating in ambiguity as the ICP, product, messaging, and playbook evolve. Experience with MEDDPICC or Force Management methodologies, as well as travel technology or TMC background, is a plus. Above all, you're a builder at heart, genuinely curious about AI and technology, and excited by the opportunity to turn an emerging product into a meaningful business.
