Director of Sales

Location: Seaside, OR
Reports To: CEO
Department: Sales & Marketing
Employment Type: Full-Time | On-Site / Hybrid
The Opportunity

We're looking for a Director of Sales who can sell, coach, think, challenge, build, and close.

This is not a position where you sit above the sales team and review reports. You'll be a true player/coach. We expect you to know how to close a sale yourself, listen to how our team is selling, identify where opportunities are being lost, coach improvement, and then use the numbers to determine whether it worked.

Our sales program has been successful for more than a decade. The fundamentals are solid. The presentation, technology, training, and strategy are ready for a refresh.

Gitty up AI and hit record.

You'll work directly with the company owner to learn the existing program, understand why it works, question where it can be better, and help build the next generation of it.

We don't want someone who changes things simply to put their fingerprints on them.

We want someone who asks good questions, challenges assumptions, develops a point of view, and can make the case for a better approach.

Learn it. Question it. Improve it. Prove it.

Over time, the goal is straightforward: own the sales department.
What You'll Own

Sell & Close

You should genuinely enjoy selling.

Our guests range from people who know exactly what they want to families who need help finding the right home for their Oregon Coast vacation. You'll need to recognize the difference, adapt the conversation, overcome objections, create appropriate urgency, and confidently ask for the booking.

Great customer service matters here-but we're also in sales. We ask for the business.

You'll personally sell alongside the team and help demonstrate what great looks like.
Coach & Develop the Sales Team

We measure sales performance through a balanced operational scoreboard, including conversion, revenue, booking performance, follow-up, and other KPIs.

But numbers only tell you where to start looking.

When performance drops, your first instinct should be to get into the actual sales process. Listen to calls. Talk with the salesperson. Understand what's happening. Coach the behavior and then watch the numbers to determine whether it worked.

We believe in coaching first, setting clear expectations, measuring improvement, and holding people accountable.
Build the Next Version of Our Sales Program

Our sales handbook/program is more than 10 years old.

There's a lot worth keeping-and plenty of opportunity to modernize it.

You'll work 1:1 with the owner to refresh training, sales techniques, scripts, objection handling, follow-up, technology, AI tools, and performance measurement.

We're not looking for someone to throw away a proven system on Day 1.

Understand it first. Then bring ideas.

And when you bring a problem, bring your thinking and a recommendation with it.

Know the Numbers

You don't need to be our revenue manager, but numbers shouldn't scare you.

You'll work with the Owner and Tech Admin on pricing, booking trends, OTA performance, market data, and revenue strategy. Experience with tools such as KeyData and PriceLabs is a big plus.

There are plenty of conceptual puzzles in this business. If figuring out why something is happening sounds entertaining to you, you'll probably enjoy working with us.

Accuracy also matters.

CRM records, follow-up, KPIs, sales documentation, and reporting need to be right. If the underlying data is garbage, the fancy dashboard isn't going to save us.

Grow Our Returning Guest Business

We have something many companies would love to have: a strong base of loyal returning guests.

We want more of them booking directly with us.

You'll work with the Owner on campaigns, messaging, promotions, segmentation, and opportunities to turn previous guests into their next Oregon Coast vacation.

Try things. Measure them. Keep what works. Learn from what doesn't and move forward.

Marketing & New Opportunities

We're already killing it with the majors-Airbnb, VRBO, and the major vacation-rental channels.

From time to time, we'll pursue niche travel agencies, booking platforms, partnerships, and other opportunities. You'll participate in evaluating those opportunities and work with our technical team when we decide one makes sense.

Marketing experience is valuable here, too. Depending on your background, you may work with the Owner on social media, digital campaigns, guest acquisition, promotions, and brand reach.

We aren't expecting one person to be an expert in everything.

Bring your strengths. We'll build from there.
Who We're Looking For

You'll probably enjoy this role if you:
• Know how to sell-and aren't afraid to ask for the business
• Can coach someone else to become a better salesperson
• Naturally question why something is or isn't working
• Enjoy taking a problem apart and figuring out the variables
• Are comfortable challenging an idea, including the CEO's, when the facts point somewhere else
• Can make your case without making it personal
• Move quickly without getting sloppy
• Care whether the details and data are accurate
• Enjoy building better people, processes, and systems
• Can manage multiple priorities without losing follow-through
• Research what you don't know before asking someone else to solve it
• Own mistakes, learn from them, adjust, and keep moving
• Want increasing autonomy as you learn the business and earn it

We don't need someone who has every answer.

We need someone who knows how to find one.
Experience That Will Help

A strong background in sales is important. Experience leading or coaching salespeople is highly valuable.

Hospitality, vacation rentals, travel, real estate, or another consultative sales environment would give you a head start-but we're more interested in what you've actually accomplished than checking boxes on a résumé.

A bachelor's degree and 7+ years of sales experience are welcome, but they're not hard requirements.

Some additional experience that would be great to see:
• Revenue management
• KeyData or PriceLabs
• Airbnb, VRBO, and OTA strategy
• CRM management and KPI reporting
• Digital marketing
• Google Ads / AdWords
• Social media marketing
• Adobe Illustrator or Photoshop
• AI-assisted sales and marketing tools
• Sales training or professional sales certifications

Have three of those? Great.

Have none of them but you're an exceptional sales leader who can close, coach, think, and build? We still want to talk.
Where You'll Work

Ideally, you'll have a regular presence in our Seaside office.

There is real value in knowing the homes you're selling and working alongside the operational teams responsible for delivering the experience you've promised the guest.

If you live more than approximately 45 minutes from Seaside, we're open to discussing a hybrid arrangement. Remote team members should plan on a minimum of three days on-site each month to tour new inventory, work with the sales team, and meet with department leads.

Schedule: 9:30 AM-6:00 PM PST, five days per week, including weekends. Days off are negotiable.
What We Offer
• Competitive base salary + performance-based bonus
• Health reimbursement
• Vacation that increases with tenure
• Sick pay
• Professional development and continued education
• A direct working relationship with company ownership
• Real opportunity to shape-and eventually own-the direction of an established sales department
• A locally owned company with more than 30 years of history on the Oregon Coast
Run With The BEST

We're not looking for someone to simply maintain what already exists.

We're looking for someone who wants to understand why it works, figure out how to make it better, teach others to execute it, and then prove the improvement in the numbers.

If you can think, sell, coach, close, and build, we'd like to hear from you.