Account Executive

About Us

olive is building the AI-native commerce stack for the hotel industry. We aspire to be the next great travel brand, and we're attacking an unsolved problem: how to deliver personalization at scale.

Hotels were once pioneers of technology, introducing innovations like computerized reservation systems and loyalty programs. A failure to adapt, plus the rise of OTAs, has left the industry behind. With so much exciting progress happening in AI, we fear a similar fate awaits hotels if they don't take charge of their own distribution.

We’ve partnered with the world’s leading hotel brands and operators to redefine what the modern hotel experience can be. Our first product reimagines the booking journey with a beautiful UI/UX enhanced by AI-driven personalization, one that meaningfully increases conversion and direct revenue while reflecting the same care and craft our partners bring to their properties every day.

We pride ourselves on building cutting-edge software for a sorely underserved industry that continues to be failed by its technology partners.

About the Role

You'll own the full sales cycle: prospecting, discovery, demo, and close for independent hotels and small portfolios. Your buyers are GMs, owner-operators, head of revenue, marketing, distribuition or sales. You'll report directly to the Head of Sales.

The sales playbook is built. We're in execution mode. You'll inherit a clear Ideal Customer Profile, qualification gates, and stage-by-stage rationale, plus the operational SOPs that sit underneath. What you won't inherit is a 10-year-old motion that can't be questioned. You'll have real input into how we refine it as we scale. You'll keep HubSpot clean and current so we have real visibility into pipeline health and forecast accuracy.

You'll own pipeline generation end-to-end, supported by inbound flow as it comes in.

Deal Profile

• Accounts: SMB, Independent hotels and small portfolios, named accounts assigned by size and fit
• Deal Size: Mid-five to six-figure ACV
• Cycle: 30 to 90 days, velocity-driven
• Motion: Discovery, demo, occasional pilot, close
• Demos: Self-conducted. You'll be self-sufficient on product, with product team support as needed for edge cases

Role Details

• Reports to: Head of Sales
• Location: California, or US West Coast
• Travel: 25 to 30%, primarily industry events (HITEC, Commercial Strategy Conference) and client meetings as needed
• Ramp: Structured ramp period, details discussed during hiring

Tech Stack

We invest in a modern software stack so our AEs can focus on selling, not admin. HubSpot CRM, Claude for AI-powered productivity, and the tools you need to run a high-velocity motion.

What We're Looking For

Required:

• Direct hospitality industry experience. You've worked in hospitality tech, sold into hotels, run a hotel commercial function, worked at an OTA, or otherwise lived inside this space. This is non-negotiable: we need someone who knows the buyer because they've been them or sold to them.
• Hunter mindset. You build your own pipeline and you're not waiting to be fed.
• Self-sufficient. You can run discovery, demo, and negotiation end-to-end.
• Bias toward velocity. You keep deals moving and don't let them stall.
• Commercially literate. You can talk ADR, RevPAR, conversion, and direct vs OTA economics with revenue managers and owners without faking it.
• Polished written and verbal communication. You're presentable to a GM at a luxury property and credible in a boardroom."

Two candidate paths we welcome:

1. The SaaS AE with hospitality DNA, with 2+ years of full-cycle B2B SaaS sales with a proven attainment record, plus direct hospitality industry experience.
2. The hospitality pro ready to break into SaaS. You know the buyer cold because you've been one, or you've sold to them in a non-SaaS context. You have the commercial instincts and hunter DNA to thrive in a velocity sales role. We'll teach you the SaaS motion.

What matters most is that you bring the industry expertise and the hunter mindset. We can build the SaaS muscle.

Compensation & Perks

• Competitive base + variable + meaningful equity (final equity package being finalized)
• Direct access to founders and a real seat at the table
• A front-row seat to an industry being remade in real time
• Already live in the US, Mexico, and Canada with more markets coming
• Beautiful office on Main Street in Santa Monica (remote possible for exceptional candidates)
• Comprehensive health coverage and catered, healthy meals on-site

The Best Work of Your Career

We model ourselves on a sports team, not a family. Every player knows their position, but when the game is on the line, everyone does what needs to be done. There’s no “that’s not my job” on a team that’s building from scratch.

The honest truth about olive: the playbook is built, but the commercial motion is being shared. There is no one to tell you what to do next. If that sentence makes you anxious, olive is probably not the right place for you. If it makes you lean forward, welcome. We’ve found that the people who thrive here share a few things:

*** They own it.** Not just their work, the outcome. They don’t hand problems off; they solve them. They aren’t waiting for permission; they move and course-correct.

*** They care about hospitality.** Not as a vertical, but as a craft. The best hoteliers pour their hearts into their properties. We pour ours into our product. That standard of care runs through everything we do: how we build, how we sell, how we show up for our partners.

*** They’re energized by the obstacle.** Displacing entrenched incumbents is hard. There will be moments that test you. The people who belong at olive find those moments clarifying, not discouraging.

*** They bring their whole self. We’re a cast of characters. You’ll be spending a real chapter of your career with us, so your weird should align with our weird.

What You Get In Return

Real ownership: of your work, your equity, and the direction of this company. A front-row seat to an industry being remade in real time. Colleagues who will push you to do the best work of your career.

And the chance to look back someday and say: I was there when hotels took back control.

Our EEO Statement

• olive is an equal opportunity employer committed to cultivating a work environment that supports, inspires, and respects all individuals. Our hiring practices are merit-based and we do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity/expression, marital status, age, disability, medical condition, genetic information, national origin, ancestry, military or veteran status, or other protected characteristic.