Head of Sales - AgentSee

Blumberg Capital Company; United States; On-site; USD 180,000 - 260,000; Full time

Job summary

Oversee seeks its first Head of Sales for AgentSee to craft the GTM and drive early enterprise wins, directly with the CRO, and lay the foundations for a scalable sales machine.

You will define ICP, pricing, and messaging while partnering with Product, Engineering, Marketing, and Customer Success to translate Artificial Intelligence into measurable business value for senior executives.

Qualifications

• 8+ years of B2B technology sales experience.
• Proven track record of owning and closing complex enterprise deals.
• Experience building a GTM motion from ground up.
• Experience selling AI, SaaS, automation, data or similar tech to enterprises.

Responsibilities

• Own and build the GTM and sales strategy for AgentSee.
• Lead and close early strategic enterprise opportunities from discovery to close.
• Define ICP, messaging, pricing, packaging, and sales process.
• Translate AI and complex tech into business value for senior buyers.
• Identify where product-market fit is strongest and what to build to win.
• Build a repeatable sales methodology and cadence.
• As the business scales, hire and lead the AgentSee sales organization.

Skills

B2B sales

Enterprise deals

GTM strategy

AI knowledge

Leadership

Pricing strategy

Job description

At Oversee, we are reimagining how corporate travel is managed.

Our advanced technology and machine learning eliminate outdated, manual processes that hold companies back - driving cost savings, improving efficiency, and enabling smarter decision-making.

We combine travel analytics with actionable insights, giving global enterprises the tools to gain visibility into their travel spend while continuously optimizing their programs.

We are the global leader for air and hotel reshopping solutions and also provide “AgentSee”, an AI-powered productivity tool designed to help Travel Management Companies (TMCs) work smarter and faster. AgentSee automates manual tasks like processing traveler emails, booking flights, and managing travel arrangements; enabling TMCs to reduce costs and improve service quality.

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.