Head of Sales

🔥 1 minute ago

🇺🇸 United States – Remote

⏰ Full Time

🔴 Lead

🤑 Sales

👻 Ghost score 12%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Oversee (formerly FairFly)

WebsiteLinkedInAll Job Openings

11 - 50 employees

✈️ Travel

📦 Logistics

🤖 Artificial Intelligence

Travel • Logistics • Artificial Intelligence

Oversee is a company that specializes in travel spend optimization, providing comprehensive solutions for travel management companies, travel agencies, and online travel agencies. Its platform utilizes AI-driven tools to optimize travel policies, assure air and hotel prices, and transform fare and rate fluctuations into client savings. Oversee partners with businesses to ensure compliance, maximize travel budgets, and unlock growth opportunities without compromising service quality. Their technology aids in real-time sourcing optimization and contract auditing, ensuring significant discount savings and error reduction. The company is committed to elevating travel programs with data-driven insights and actionable supplier performance metrics, enhancing traveler experiences while maintaining cost-effectiveness.

📋 Description

• Own and build the GTM and sales strategy for AgentSee • Personally lead and close early strategic enterprise opportunities, from discovery and demos through pilots, negotiation, and close • Define and continuously refine the ICP, positioning, messaging, pricing, packaging, and sales process • Translate agentic AI and complex technology into clear business value for senior enterprise buyers • Use customer conversations and market data to identify where AgentSee has the strongest product-market fit and what needs to be built to win • Build a repeatable sales methodology, operating cadence, and GTM playbook • As the business scales, hire, develop, and lead the AgentSee sales organization • Work directly with the CRO and collaborate with Product, Engineering, Marketing, and Customer Success • Bring customer and market insights directly into product and GTM strategy

🎯 Requirements

• 8+ years of B2B technology sales experience, with a strong track record of personally owning and closing complex enterprise deals • Proven experience building a GTM motion from the ground up, taking a new product or business from early customers toward a repeatable sales motion • Experience selling AI, SaaS, automation, workflow, data, or similarly technical solutions to enterprise customers • Strong understanding of AI and ability to translate complex technology into measurable business value • Experience building and leading sales teams, with the willingness to remain hands-on and personally sell as AgentSee scales • Commercially sharp, analytical, and comfortable operating when the ICP, product, messaging, and playbook are still evolving • MEDDPICC, Force Management, or similar enterprise sales methodologies are a plus • Travel technology or TMC experience is a plus