Account Executive, Leisure Travel

Oversee · Remote · US

Base: Not disclosed
OTE: $180K–$240K
Quota attainment: Not disclosed
Posted: 1mo ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 1h agoon Oversee's careers page

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The job

Who you'd sell to: Still reading the posting. Check back within the hour.
Where deals come from: A mix. Some leads come to you, some you find yourself.

The Braun Read

Worth a look

Solid on the basics. Use the first call to fill in the gaps.

Pay: OTE is listed. Ask what the base is.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle.
Pipeline: A mix of self-sourced pipeline and inbound or SDR help.
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.

Red lights

None spotted.

Green lights

Publishes OTE. It tells you the on-target earnings up front. Most postings don't.
SDR or inbound support. You won't be building all of your own pipeline from zero.

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 percentage of reps on the team have been here more than 18 months?
Tenure shows whether people stay long enough to get paid.
3.
Has the comp plan changed in the last 12 to 18 months? What changed?
A plan that changes every year means the goalposts keep moving.
4.
Who sits with reps and reviews calls each week?
Coaching is often what's behind a good or bad attainment number.
5.
What's the base, and how is the rest paid out?
OTE without a base doesn't tell you what you can count on.
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 →

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Full posting

Oversee is a travel technology company building products that use AI, automation and deep industry expertise to solve complex challenges across the travel ecosystem. After years of building technology used by some of the world’s largest travel organizations, we’re entering a new stage of growth and expanding into the leisure travel market. This is an opportunity to join us early in that journey, help bring a new solution to market, and play a key role in building our presence in a new and significant segment of the travel industry. 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? This is not a traditional territory-based AE role. You’ll help build an entirely new market for Oversee, selling our air and hotel reshopping technology across the leisure travel ecosystem, including OTAs, leisure travel agencies, tour operators, vacation providers, and other high-volume travel businesses. You’ll own deals end-to-end while helping us determine where we win, who we should target, how we position the product, and what the leisure GTM motion should look like. We’re looking for someone who already knows this market. You understand the players, decision-makers, technology landscape, and economics of leisure travel and can bring that knowledge and network to Oversee from day one. Come shape the future of business travel with us! What you'll do: - Own the full sales cycle for Oversee’s leisure travel business, from prospecting through close; - Build relationships with senior executives and decision-makers across OTAs, leisure agencies, tour operators, vacation providers, and other travel businesses; - Build and maintain a strong pipeline of qualified leisure travel opportunities; - Help define and continuously refine our leisure ICP, positioning, messaging, value proposition, and sales motion; - Identify the segments, accounts, and use cases where Oversee has the strongest product-market fit; - Lead complex enterprise sales processes across commercial, technology, operations, product, finance, and executive stakeholders; - Partner closely with Product and Engineering to bring market intelligence back into our product and GTM strategy; - Turn early customers and market learnings into a repeatable sales motion for the leisure vertical. About you: - 5+ years of B2B technology sales experience, with a strong track record of owning and closing complex enterprise deals - Significant experience selling technology into the leisure travel industry - Strong relationships and experience across OTAs, leisure travel agencies, tour operators, vacation providers, or other leisure travel businesses - Deep understanding of the leisure travel ecosystem, including its key players, decision-makers, business models, technology landscape, and buying processes - Proven ability to prospect and create opportunities from scratch rather than relying primarily on inbound leads - Experience navigating complex, multi-stakeholder enterprise sales cycles and working with technical stakeholders - Strong commercial instincts and the ability to build compelling ROI and business cases for customers - Independent, entrepreneurial, and comfortable building a market without an established playbook Experience being an early or first AE at a startup or scale-up is a strong plus. You’re a hunter and a market builder. You know the leisure travel industry, have relationships within it, and are excited by the opportunity to help Oversee build an entirely new business from the ground up. Compensation & Benefits At Oversee, we believe great work deserves great rewards. This role comes with a competitive On-Target Earnings (OTE) of $180,000–$240,000 per year, which includes base salary plus performance-based incentives. Benefits are an important part of Oversee’s Total Rewards package, and this role is eligible for comprehensive coverage including medical, dental, vision, a 401(k) plan, paid time off, and more. 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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