Oversee

Head of Sales - AgentSee

United StatesRemoteFull timeSales

Salary not posted. The employer did not include pay in this listing. Ask for the range in your first conversation; it is a fair question.

Posted 2 days ago · listed on Workable

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Should you apply?

Company website ↗

Open: 2 days; Fresh. First-week applicants get read first.
Open roles at this company: 2; A few open seats. Your application will get a real look.
Salary: Not posted; No range in the posting. Ask early. It is a fair question and it saves everyone time.

Days open comes from the posting date. Fill time and reposting rate come from this company's recent public postings.

The job, broken down

You'd be the first Head of Sales for AgentSee, Oversee's AI productivity tool for travel management companies. You start as the primary salesperson closing early deals, then build out the sales org as the business scales.

What you'd actually do

Personally run discovery calls, demos, pilots, negotiations, and closes for early enterprise customers
Define and refine ICP, positioning, messaging, pricing, and packaging as you learn from deals
Translate AgentSee's AI/automation capabilities into business value for senior enterprise buyers
Feed customer and market insights into Product, Engineering, Marketing, and Customer Success
Build a repeatable sales methodology and GTM playbook
Eventually hire, train, and lead a sales team while staying hands-on selling

Must-haves

8+ years of B2B technology sales experience with a track record of personally closing complex enterprise deals
Experience building a GTM motion from scratch, taking a product from first customers to repeatable sales
Experience selling AI, SaaS, automation, workflow, or data solutions to enterprise buyers
Ability to translate complex/technical AI capabilities into measurable business value
Experience building and leading sales teams while remaining willing to personally sell
Comfort operating with an evolving ICP, product, messaging, and playbook

Nice to have

Familiarity with MEDDPICC, Force Management, or similar enterprise sales methodologies
Travel technology or TMC (Travel Management Company) industry experience

Read before you apply

0-to-1 role means no existing playbook, established ICP, or proven pricing; expect ambiguity and higher risk
You're the sole salesperson initially, so quota and pipeline depend entirely on your own individual output with no team support
No compensation, quota, or OTE details included in the posting

Written from the posting text only. Check the full description below before you decide.

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Steps to get this job

1In your outreach, mirror the phrase '0-to-1' and reference building a GTM motion from scratch, since that's the core framing of this role
2Lead with a specific story of closing a complex enterprise deal for an AI, SaaS, or automation product, ideally one where you also shaped ICP and pricing
3If you have TMC or travel tech experience, put it in your first two sentences since it's explicitly called out as a plus
4Reach out directly to the CRO mentioned in the posting since the role reports to and works closely with them, and name-check AgentSee's specific use case (automating traveler emails, bookings) in your pitch

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About the role

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.

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