Sales Executive

Salesfolks; United States; Remote; USD 120,000 - 150,000; Full time

Job summary

Confidential — Vacation Rental SaaS Company is seeking a Founding Sales Executive to build the first sales motion in a remote U.S. setting.

You’ll own the early pipeline from prospecting to close, shape messaging, and work directly with leadership to craft a scalable customer‑acquisition engine. The role targets 3–10 property operators in initial US markets like Florida and the Carolinas, with expansion as we validate channels, segments, and playbooks.

Qualifications

• Demonstrated history of generating measurable sales results.
• Experience creating pipeline and driving new business.
• Comfort with outbound prospecting and cold outreach.
• Experience selling software/tech requiring consultative discovery.
• Strong technology fluency and quick learning of new software.
• Ability to demonstrate a product and explain tech in business terms.

Responsibilities

• Own sales process from prospecting to signed customer.
• Build pipeline through outbound channels and partnerships.
• Conduct discovery to map customer pain and fit.
• Demonstrate platform and connect to outcomes.
• Maintain pipeline visibility and disciplined follow-up.
• Help document early sales playbook and scalable patterns.

Skills

Outbound prospecting

Software sales

Consultative selling

Product demonstrations

Pipeline development

Relationship building

Tools

CRM software

Job description

Confidential — Vacation Rental SaaS Company

Remote — United States

Help Build the Sales Engine for the Next Generation of Vacation Rental Operators

Our client is an emerging SaaS company building a powerful, easy-to-use software platform for vacation-rental owners and property managers who are turning a handful of properties into a real business.

The platform helps operators manage critical aspects of their vacation-rental business from one place, including property and reservation management, calendars, guest communications, channel integrations, payments and payouts, and other operational workflows.

The company is now looking for a Founding Sales Executive to help take the business to its next stage of growth.

This is not a conventional sales position where you inherit a mature territory, established playbook, large inbound funnel, and years of historical data.

You will help build those things.

You will work directly with the company’s leadership team to acquire customers, learn from the market, refine the sales approach, and help develop a repeatable customer‑acquisition engine that can scale.

The Opportunity

The initial target customer is the growing vacation‑rental operator, often an Airbnb host or property owner managing approximately 3–10 properties and transitioning from a side business into a more sophisticated operation.

Initial sales efforts are focused on major U.S. vacation‑rental markets, including Florida and the Carolinas, with the opportunity to expand nationally as the company identifies the channels, geographies, customer segments, and messages that produce the strongest results.

You will be one of the people helping figure that out.

This role is ideal for someone who likes selling but also wants to build something.

What You’ll Do

You will own much of the sales process from initial prospect identification through signed customer, including:

• Identify and engage vacation‑rental owners and property managers who fit the company’s ideal customer profile.
• Build pipeline through outbound prospecting, including phone, email, social outreach, referrals, partnerships, and other channels.
• Conduct discovery conversations to understand how prospective customers currently manage their properties and where operational pain exists.
• Demonstrate the platform and connect its capabilities to meaningful customer outcomes.
• Follow opportunities consistently from initial conversation through decision and close.
• Develop relationships with prospects rather than relying exclusively on transactional sales tactics.
• Work directly with company leadership to refine positioning, messaging, targeting, and sales strategy.
• Capture recurring objections, customer requests, competitive intelligence, and market feedback.
• Help identify which customer segments, geographic markets, messages, and acquisition channels offer the greatest potential to scale.
• Maintain disciplined sales activity, pipeline visibility, and follow-up.
• Help document the early sales playbook as successful patterns emerge.

Over time, the role has the potential to grow alongside the company’s sales organization.

What We’re Looking For

We care more about what you have actually accomplished than whether your résumé follows a predetermined formula.

The strongest candidates will likely bring:

• A demonstrated history of generating measurable sales results.
• Experience creating pipeline rather than relying exclusively on company-generated leads.
• Comfort with outbound prospecting and cold outreach.
• Experience selling software, technology, or another solution requiring consultative discovery.
• Strong technology fluency and the ability to learn new software quickly.
• Confidence demonstrating a product and communicating technical capabilities in simple business terms.
• Excellent follow‑up and personal organization.
• High personal accountability and a results‑oriented mindset.
• Curiosity about customers and a willingness to experiment with different approaches.
• Comfort working directly with company leadership in an evolving early‑stage environment.
• The ability to operate without every process, script, or answer already being established.

Experience in vacation rentals, short‑term rentals, property management, PropTech, hospitality technology, or SMB SaaS is attractive, but it is not required if you bring the right sales track record and entrepreneurial mindset.

Who This Role Is Probably Not For

This may not be the right opportunity if you:

• Need a large inbound lead engine to generate your pipeline.
• Prefer account management to new‑business development.
• Want to manage a sales team rather than personally sell.
• Require a highly prescribed sales process before you can execute.
• Are uncomfortable prospecting or initiating conversations.
• Prefer a mature organization where the ICP, messaging, compensation model, processes, and sales playbook have already been completely defined.

The company is looking for someone who sees this stage of the business as an opportunity rather than a limitation.

What Success Looks Like

Early success will be measured not simply by activity, but by the creation of a functioning sales motion.

During the first several months, we expect the Founding Sales Executive to:

• Build a consistent pipeline of qualified vacation‑rental operators.
• Generate meaningful discovery conversations and product demonstrations.
• Begin converting qualified prospects into paying customers.
• Help identify the messages and customer segments producing the strongest response.
• Establish disciplined prospecting, follow‑up, pipeline management, and sales reporting.
• Develop repeatable patterns that can eventually be taught to additional sales hires.

An important longer‑term performance objective is the ability to consistently generate meaningful net‑new monthly recurring revenue, with the opportunity to substantially increase that level as the sales model matures.

Compensation & Upside

The company intends to create a compensation structure that strongly aligns successful selling with significant financial upside.

The package may include:

• Expected OTE of $120,000–$150,000
• Performance bonuses and accelerators
• Potential long‑term equity participation

The philosophy is straightforward:

Exceptional performance should create exceptional upside.

Why This Opportunity?

The vacation‑rental industry includes thousands of entrepreneurs who have grown from owning one property into managing several—and suddenly find themselves running a real operating business.

That transition creates an opportunity for better software, better automation, and a simpler way to manage the increasingly complicated world of bookings, channels, guest communication, properties, and payments.

The company is still early enough that the person joining today will have the opportunity to influence considerably more than a sales number.

You can help shape:

Who we sell to.

How we reach them.

What we say.

How we sell.

And ultimately, how the company builds its sales organization into a category leader.

For the right person, that is the opportunity.