Founding Account Executive — B2B Sales

About Coast to Cabin Partners
Coast to Cabin Partners is building a nationwide services platform for short-term rental owners, operators, and professional property managers.
We provide Revenue Management + Listing Optimization, 24/7 STR Operations, Bookkeeping, and bundled solutions designed to give short-term rental businesses professional infrastructure without the traditional percentage-based management model.
We are now hiring a Founding Account Executive to help build our sales organization from the ground up.
The Opportunity
This is not an SDR or appointment-setting position.
We are looking for a proven B2B salesperson who can take qualified opportunities and own the sales process from initial discovery through signed agreement and payment.
Coast to Cabin is building multiple customer-acquisition channels across paid search, outbound, organic social, community outreach, partnerships, and referrals.
Your primary responsibility will be converting those opportunities into customers, properties, and recurring revenue.
You'll work directly with the founder during the initial stage of the company and have the opportunity to help shape our sales process as we scale.
For the right person, this role has a potential path toward leading the Coast to Cabin sales organization.
What You'll Own
• Conduct discovery calls with qualified prospects
• Understand each prospect's portfolio, operations, technology, challenges, and business objectives
• Identify and recommend the appropriate Coast to Cabin services
• Clearly communicate our value proposition, pricing, and differentiation
• Run presentations and sales conversations with owners, operators, and property-management companies
• Handle objections and navigate complex buying decisions
• Prepare and present proposals
• Own follow-up until every qualified opportunity reaches a clear outcome
• Negotiate within established pricing and deal parameters
• Drive prospects through agreement and payment
• Maintain an accurate CRM pipeline with clear next actions
• Track objections, competitors, loss reasons, and customer feedback
• Work with marketing and leadership to continuously improve conversion
• Provide a clean Closed Won handoff to our implementation/client-success team
• Help develop a repeatable Coast to Cabin sales playbook
The Sales Funnel You'll Own
Qualified Lead
→ Discovery
→ Needs Analysis
→ Solution
→ Proposal
→ Objection Handling
→ Follow-Up
→ Negotiation
→ Agreement + Payment
→ Closed Won
Who We're Looking For
We care more about demonstrated sales performance than impressive titles.
Strong candidates will have:
• Proven full-cycle B2B sales experience
• A track record of meeting or exceeding quota
• Experience personally owning opportunities from discovery through close
• Experience selling SaaS, recurring services, or another recurring-revenue offering
• Experience with meaningful B2B deal sizes, ideally $5K–$100K+ in annual contract value
• Strong consultative discovery skills
• Excellent objection handling, negotiation, and follow-up discipline
• Experience managing a pipeline in a modern CRM
• Strong written and verbal communication
• Confidence speaking with founders, business owners, and executives
• Ability to quickly learn a somewhat technical service offering
• Comfort operating in an entrepreneurial, fast-growing environment
Experience selling into PropTech, hospitality technology, property management, vacation rentals, real estate technology, revenue management, financial technology, outsourced business services, or vertical SaaS is particularly relevant.
Direct short-term rental experience is helpful but not required.
What This Role Is NOT
This is not a role for someone whose responsibility ends when a meeting is booked.
We are not looking for an appointment setter, lead-list builder, SDR who has never personally closed business, or consultant who only wants to design sales strategy.
We want someone who takes ownership of opportunities and drives them through the entire funnel.
Growth Opportunity
We intend to build a meaningful sales organization as Coast to Cabin grows.
The potential progression for an exceptional performer is:
Founding Account Executive
→ Senior / Lead Account Executive
→ Head of Sales
→ Broader Sales Leadership
Leadership is not guaranteed based on tenure. It will be earned through sales performance, leadership ability, and contribution to building a repeatable sales organization.
We are looking for someone who can close first and potentially lead later.
Compensation
Competitive base compensation + uncapped performance-based commission.
We want exceptional salespeople to have meaningful upside for creating meaningful revenue.
Final compensation will depend on experience and demonstrated performance.
How to Apply
Along with your application, please provide specific information about your sales background, including:
• Products/services you've personally sold
• Typical ACV or deal size
• Quota and quota attainment
• Approximate number of new customers personally closed
• Largest B2B deal personally closed
• Typical sales cycle
• Inbound vs. outbound opportunity mix
• CRM experience
• Experience selling recurring services or SaaS
Please also be prepared to walk us through a real opportunity you personally took from discovery through Closed Won.
Company: Coast to Cabin Partners
Website: coasttocabinpartners.com

Work arrangement
No