Director of Sales-Remote-Hybrid-Onsite

Director of Sales

Location: Seaside, OR

Reports To: CEO

Department: Sales & Marketing

Employment Type: Full-Time | On-Site / Hybrid

Seaside Vacation Homes is a second-generation, family-owned vacation rental company that has been serving the Oregon Coast since 1993. We manage more than 100 vacation homes and have built our business around something pretty simple: take great care of our guests, take great care of our homes, and keep getting better at what we do.

We have a strong brand, an established sales program, a loyal returning-guest base, and a team that knows this market.

Now we're ready to level up our sales game.

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 will 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.

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 will 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 will 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 will work with the Owner and Tech Admin on pricing, booking trends, OTA performance, market data, and revenue strategy. Experience with tools such as Key Data and Price Labs 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 will 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 will 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…