Director of Homeowner Revenue at Del Mar Vacations – Orleans, Massachusetts

About Del Mar Vacations

Del Mar Vacations is a Veteran-owned and operated, full-service vacation property management company with 400 homes across Cape Cod. Our mission is to create lifelong memories through 5-star guest and homeowner experiences—and we do that by putting hospitality and service at the heart of everything we do.

We’re a team of passionate, smart, and engaged people who solve problems creatively and serve with care. Our ideal teammates thrive in a high-energy, tight-knit environment, are intellectually curious, optimistic, and ready to pivot when things change.

We live and work by our mantra:
R.R.R.E.E.E. – Readiness. Responsiveness. Resolution. Empathy. Efficiency. Enthusiasm. It’s how we show up, how we fix things, and how we treat people.

Our values make this more than just a job:

• Be Reliable. Reliable. Reliable.
• Think like a Guest. Think like a Homeowner. Think like a Team Member.
• The Obstacle is the Opportunity.
• Make it Happen.
• Be Anti-Fragile.

If that resonates with you, keep reading.

The Director of Homeowner Revenue is a dynamic business leader responsible for curating and executing a 5-star Client Experience strategy to Homeowners. With a clear focus on lead generation and retention for Homeowners, this individual will champion the client journey for continued success, while pioneering and grooming the efforts to get there.

The Director of Homeowner Revenue owns the full homeowner lifecycle and the performance outcomes tied to it. For each of the following functions, it is as is related to the Homeowner Prospect/Client: Acquisition (lead generation, sales operation, contract pricing, conversion, signups), Onboarding (Owner Admin, Home Readiness, Listing Build) Client Loyalty & Experience (owner retention, home value added services, client engagement and communication).

This role is responsible for all teams that are owner-related, including: Owner Marketing & Leads, Owner Sales & Pricing, Owner & Home Onboarding, and Ongoing Client Management.

Lead teams responsible for the below processes, playbooks and outcomes. Implement technology (AI, automations, workflows and existing platform tools) to reduce friction, simplify processes (especially the owner experience), and eliminate workload.

• Own homeowner retention & lifecycle health: Oversee homeowner relationships end-to-end, from initial inquiry through onboarding, property management, and ongoing retention- driving year-over-year loyalty, homeowner satisfaction, and reduced preventable escalations.
• Drive owner lead generation performance: Improve lead volume and quality, speed-to-contact, channel performance, and overall pipeline health.
• Increase conversion & owner signups: Optimize the homeowner lead funnel in partnership with Sales & Marketing to improve lead quality. Improve conversion rates and reduce cycle time from Inquiry to Listing Live by revising and simplifying processes while still achieving targets of 70-100 new homes per year ($2MM-$3MM new contribution margin)
• Ensure Client Manager service excellence: Maintain exceptional, proactive service delivery that builds homeowner trust and satisfaction and directly supports retention.
• Provide cross-functional leadership & accountability: Lead the Client Manager and Marketing & Sales teams with clear performance expectations, coaching, and a culture of excellence - ensuring teams stay aligned to company objectives and execute consistently.
• Lead AI initiatives: Improve performance across the entire homeowner lifecycle - owner acquisition, onboarding, client management/retention, and KPI reporting.

• Bachelor’s degree or equivalent experience required, MBA preferred
• Proven leadership of multiple teams in a client-facing, high-expectation service environment
• Demonstrated ability to lead Marketing, Sales, and Client teams and drive measurable results across the full lifecycle: lead generation → conversion → onboarding → retention
• Strong client relations and executive communication skills
• Analytical and operational rigor to include roles and experience in service operations, comfortable owning KPIs, dashboards/scorecards, and performance rhythms
• Experience leading inbound and relationship-driven marketing strategies
• Track record of using AI to solve real business problems and scale team performance
• A collaborative leadership style with the ability to bring multiple departments into one operating system

Why Join the Del Mar Vacations Team

Del Mar Vacations is a Veteran-owned and operated, full-service vacation rental company on Cape Cod. We specialize in providing 5-star experiences to our guests, homeowners and each other. As a hospitality and service first culture, our team and their talents are the key to our success.

Working at Del Mar means you will be surrounded by passionate, smart, and engaged people who are focused on superior problem solving and outstanding customer service. Our ideal candidates enjoy working in a small, tight-knit, high energy and supportive team, are intellectually curious, comfortable with ambiguity, have a positive outlook, and are able to pivot quickly as things change.

Benefits

• 2 weeks of vacation time
• 1 week of sick time
• Partially subsidized health insurance
• HSA (health savings account)
• 401k with up to 4% match
• Professional development opportunities
• Yearly bonus program (and other rewards and recognition both big and small)

Salary Range: $90,000-$110,000 with generous bonus

Schedule: Monday-Friday, Tuesday-Saturday in our peak season

Del Mar Vacation, Inc is an equal opportunity employer. All employment will be decided solely on the basis of your qualifications and merit and according to hiring needs. We are committed to creating a collaborative team and do not to discriminate based off race, color, religion, creed, gender, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender identity or expression, national origin, ancestry, age, disability, genetic information, marital status, amnesty, status as a covered veteran, military service, or any other class protected by applicable federal, state, and local laws.