Head of Sales - AgentSee

Oversee · Remote · US

Base: Not disclosed
OTE: Not disclosed
Posted: 1mo ago

Still open · checked 2h agoon Oversee's careers page

Apply on Oversee →

The job

What you'd do: Sell AgentSee, an agentic AI platform for Travel Management Companies, to enterprise buyers. Build the GTM from scratch by personally closing early strategic deals, then hire and lead the sales team.
Who you'd sell to: Still reading the posting. Check back within the hour.
Where deals come from: Not stated in the posting.

The Braun Read

Proceed with caution

A few things here deserve a hard look before you spend time on it.

Pay: No pay listed at all.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle.
Time on market: Open 55 days. Ask why it's been hard to fill.
Company hiring: 3 sales roles open, hiring at a steady pace.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
2.
What are the base and the OTE for this role?
No point investing hours before you know the number.
3.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
4.
Where does pipeline come from: inbound, SDRs, or me?
Tells you how much of your week is prospecting versus selling.
5.
How long is ramp, and what's the quota during it?
Full quota on day one means you start behind.
6.
Why is this role open? Did someone leave, or is it new?
New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

1.
Can I see the full comp plan in writing, including clawbacks and accelerators?
What's in writing is what gets paid. Read it before you sign.
2.
Can I see the actual comp distribution for the team last year, not just the OTE?
The spread shows what most reps really take home. OTE is just the target.
3.
I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?
Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

Got an offer from Oversee? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh

Full posting

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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