Head of Sales

Head of Sales - AgentSee

Oversee · United States (Remote) · Full-time · Posted 2026-09-07

Workplace: remote

Department: Sales

Description

Oversee is a travel technology company building AI-powered products that are changing how the travel industry operates.

Our newest product, AgentSee, is an agentic AI platform built for Travel Management Companies (TMCs), automating complex travel workflows and helping agents work faster and more efficiently.

We’re now at an exciting stage of bringing AgentSee to market and scaling the business globally. 

If you are looking for a dynamic, fast-paced, and positive environment  and want to help solve a $17B global problem - Oversee is the place to build, grow, and make an impact.

We’re growing fast, with exponential YoY revenue growth and partnerships with some of the world’s largest Fortune 500 companies.

Why join us?

We’re looking for our first Head of Sales dedicated to AgentSee.

This is a true 0-to-1 opportunity. Initially, you’ll be the primary salesperson for the business, working directly with our CRO to identify where AgentSee wins, refine our ICP and positioning, close our first wave of strategic customers, and turn those learnings into a repeatable GTM motion.

As the business scales, you’ll build the sales organization around it.

You’ll have significant influence not only over how we sell, but also over what we build. You’ll work closely with Product, Engineering, Marketing, and Customer Success, bringing customer and market insights directly into our product and GTM strategy.

Come shape the future of business travel with us!

What you’ll do:

• 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 our 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 we have the strongest product-market fit and what we need to build to win;
• Build a repeatable sales methodology, operating cadence, and GTM playbook;
• As the business scales, hire, develop, and lead the AgentSee sales organization;

About you:

• 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 also a plus.

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.

We are proud to be an equal opportunity workplace.

We provide employment opportunities without regard to race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or veteran status.

Apply

Apply at Oversee

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