Enterprise Account Executive (North America - Remote Only)

Hospitable; Oregon (WI); Remote; USD 101,000 - 128,000; Full time

Benefits offered by this job

Healthcare (EPO/PPO/HSA)

401(k)

Commissions & PSUs

Equity via HOST token

Performance PSUs

35 days off per year

Mental health support

Employee recognition rewards

Job summary

Hospitable is a remote-only, fully distributed company that hires by time zone, not country. The role focuses on Enterprise B2B SaaS sales across North American time zones, with a strong emphasis on building pipelines, leading product demos, and guiding complex deals from first contact to close.

You will collaborate with Product, Marketing, and Customer Success to deliver an exceptional buying experience while targeting strategic accounts and refining outbound messaging.

Qualifications

• 3-5 years of hands-on experience in Enterprise B2B SaaS sales.
• Proven track record of managing complex sales cycles with multiple stakeholders.
• Native or bilingual proficiency in English, both written and spoken.

Responsibilities

• Partner with Enterprise prospects to understand their business, challenges, and growth goals via Google Meet, email, live chat, and phone.
• Manage complex sales opportunities from first conversation through negotiation and close.
• Prospect into strategic accounts and build your own pipeline alongside inbound opportunities.
• Lead tailored product demonstrations and executive-level presentations for multiple stakeholders.
• Be a trusted advisor and product expert for software that is constantly evolving.
• Manage your pipeline and forecast accurately in HubSpot.
• Collaborate with Product, Marketing, Customer Success, and Onboarding to deliver an exceptional buying experience.

Skills

Enterprise SaaS sales

English fluency

HubSpot

Intercom

Airbnb experience

Tools

HubSpot

Intercom

Job description

tldr; We build software for Airbnbs to rent themselves, with a state-of-the-art product and user experience.

We are bold, like risks, and take on big challenges together. We believe in the value of team diversity and seek candidates from a wide range of backgrounds in their work, life, culture, and experiences. We have crafted an Applicant Handbook, which we highly recommend you check out, where you can find out more about the company, culture, how we recruit, what we do, and how we do it: https://hsptb.com/hndbk

Our customers love the product, provide valuable feedback, and trust us to rapidly help with their problems. Feel free to check out one of ourpublic Town Hallsfor yourself: https://hsptb.com/twnhll

Hospitable.comis a remote-only and fullydistributed company. We hire based on timezones, not countries.

What will you be working on?

• Partnering with Enterprise prospects to understand their business, challenges, and growth goals through Google Meet, email, live chat, and phone.
• Managing complex sales opportunities from first conversation through negotiation and close.
• Prospecting into strategic accounts and building your own pipeline alongside inbound opportunities.
• Leading tailored product demonstrations and executive-level presentations for multiple stakeholders.
• Becoming a trusted advisor and product expert for software that is constantly evolving.
• Managing your pipeline and forecast accurately in HubSpot.
• Collaborating with Product, Marketing, Customer Success, and Onboarding to deliver an exceptional buying experience.
• Creating and testing new outbound messaging, sequences, and sales plays to improve conversion.
• Smashing through quarterly revenue targets while maintaining a consultative, customer-first approach.
• Knowing that Allison’s favorite fruit is Papaya.
• Understanding the operational challenges of professional short-term rental managers and bringing that feedback back to the team.
• Working closely with our onboarding team to ensure a smooth transition from signed contract to successful launch.
• Have an idea that could improve the way we sell? Bring it. We’ll help make it happen.

Providing feedback on our sales process so we continue getting better as we grow.

What does the schedule look like?

For this position, we are mostly aiming for the North American time zones (PT/ET). This role will be reporting Monday through Friday.

Caring about the impact your work has on your team, your customers, and the company.

• 3-5 years of hands-on experience in Enterprise B2B SaaS sales.
• A proven track record of managing complex sales cycles with multiple stakeholders.
• Attention to detail and a constant drive to improve your craft.

• Very special kudos if you’re an Airbnb host or have experience working with short-term rental businesses.

If you’re hesitant to apply because you don’t meet every qualification, we’d still love to hear from you if:

• You have experience selling complex, solution-based software.
• You know how to navigate long sales cycles and multiple decision makers.
• You have experience prospecting and creating your own pipeline through outbound.
• You’re not afraid to challenge the status quo and suggest better ways of doing things.
• You actively seek feedback and use it to improve.
• A script? You’d rather understand the customer than memorize one.
• You enjoy turning skeptical buyers into long-term customers.
• You thrive in a flat organization where ownership and initiative matter more than hierarchy.
• You have native or bilingual proficiency in English, both written and spoken.
• Experience with HubSpot, Intercom, Airbnb, short-term rentals, vacation rentals, or startups is a plus.

The company itself is also a product, one that we iterate on. We're always improving and creating an environment where we all love to work.

• A supportive, radically transparent, and caring team environment, where you are trusted, not managed—and a culture that is focused on results and output.
• The total budget for this role is within USD$101,000.00 - $127,600.00 depending on the cost of living in your location. We can hire talent internationally as contractors—or employees if you are based in the United States, the European Union, or Australia, taking into account payroll taxes to determine your gross compensation. For US employees, the compensation could be between USD$93,097.15 to $117,615.80.
• On top of the base compensation, there is a quarterly commission structure of 100% of the new business MRR brought in for any given quarter provided that you meet the quarterly target of closed deals—with the possibility of earning USD$80,000.00 of commission per year.
• We also offer options into the company equity through our $HOST token (RSU's), with a grant value of up to $23,200.00, to share in the long-term upside value of the company.
• Separately, this role is eligible for up to an additional USD $316,452.00 per year in Performance Share Units (PSUs). These PSUs do not vest over time and are granted only upon the achievement of clearly defined business performance targets. The size and payout of this award are directly tied to measurable outcomes and are intended to strongly align compensation with company impact.
• 35 days off per year, encouraged (including self-serve public holidays) and parental leave.
• For US employees: healthcare (including EPO, PPO and HSA), 401(k).
• Complimentary mental health and emotional support with therapists on call through Slack by Spill.
• Earn virtual coins through our peer recognition platform and redeem them through gift cards, donations, or monetary rewards.