Director of Sales-Remote-Hybrid-Onsite

Seaside Vacation Homes • Remote, OR

4d • Hybrid

About The Position

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 taking great care of our guests, our homes, and continuously improving. We have a strong brand, an established sales program, a loyal returning-guest base, and a team that knows this market. We are looking for a Director of Sales who can sell, coach, think, challenge, build, and close. This is a player/coach role where you will be expected to close sales yourself, listen to the team, identify opportunities, coach improvement, and use data to measure success. The sales program is solid but ready for a refresh in presentation, technology, training, and strategy. You will work directly with the company owner to learn the existing program, understand its successes, identify areas for improvement, and help build the next generation of the sales program. The goal is to eventually own the sales department.

Requirements

• Know how to sell and ask for the business.
• Ability to coach others to become better salespeople.
• Natural inclination to question why things are or aren't working.
• Enjoy taking problems apart and figuring out the variables.
• Comfortable challenging ideas, including leadership's, when facts support it.
• Ability to make a case without making it personal.
• Ability to move quickly without becoming sloppy.
• Care about the accuracy of details and data.
• Enjoy building better people, processes, and systems.
• Ability to manage multiple priorities without losing follow-through.
• Research unknown information before asking others for solutions.
• Own mistakes, learn from them, adjust, and keep moving forward.
• Desire for increasing autonomy based on learning and earning trust.
• Strong background in sales.
• Experience leading or coaching salespeople is highly valuable.
• Bachelor's degree and 7+ years of sales experience are welcome but not hard requirements.

Nice To Haves

• Hospitality, vacation rentals, travel, real estate, or another consultative sales environment experience.
• Revenue management experience.
• Experience with KeyData or PriceLabs.
• Experience with Airbnb, VRBO, and OTA strategy.
• CRM management and KPI reporting experience.
• Digital marketing experience.
• Google Ads / AdWords experience.
• Social media marketing experience.
• Adobe Illustrator or Photoshop experience.
• Experience with AI-assisted sales and marketing tools.
• Sales training or professional sales certifications.

Responsibilities

• Sell and close sales, adapting to guest needs and overcoming objections.
• Personally sell alongside the team to demonstrate best practices.
• Coach and develop the sales team by analyzing performance metrics and observing the sales process.
• Implement coaching strategies, set clear expectations, measure improvement, and hold team members accountable.
• Refresh and modernize the sales handbook/program, including training, sales techniques, scripts, objection handling, follow-up, technology, AI tools, and performance measurement.
• Collaborate with the Owner and Tech Admin on pricing, booking trends, OTA performance, market data, and revenue strategy.
• Ensure accuracy in CRM records, follow-up, KPIs, sales documentation, and reporting.
• Grow returning guest business through campaigns, messaging, promotions, and segmentation.
• Evaluate and participate in pursuing niche travel agencies, booking platforms, partnerships, and other opportunities.
• Potentially work with the Owner on social media, digital campaigns, guest acquisition, promotions, and brand reach.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Director