About Del Mar Vacations

Del Mar Vacations is a Veteran-owned and operated, full-service vacation property management company with over 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.

Product Manager, Business Systems — Del Mar Vacations

Salary Range: $120,000–$150,000+ base (depending on experience) + generous performance bonus

Who we are

Del Mar Vacations is a veteran-owned, full-service vacation rental company with 400 homes across Cape Cod. We create lifelong memories through 5-star guest and homeowner experiences by putting hospitality and service at the center of everything we do. Our team is high-energy, curious, and hands-on — we live by R.R.R.E.E.E. (Readiness. Responsiveness. Resolution. Empathy. Efficiency. Enthusiasm.) and values like “Be Reliable” and “The Obstacle is the Opportunity.”

Important note on Location:

This role requires being onsite on Cape Cod frequently to observe real workflows, build trust, and drive adoption across teams. The expectation: 3 days/week onsite in our Cape Cod office. Candidates based off-Cape are encouraged to apply only if you’re truly willing to commute.

Problem statement

We need a senior Product Manager who executes the CTFO + CEO’s platform vision by optimizing how people actually use our systems — so data is clean, workflows are reliable, and outcomes happen.

This is a current-state product role as much as a future roadmap role. Our biggest platform problems aren’t “lack of features” — they’re data quality, inconsistent user behavior, unclear requirements, and process drift that create rework, escalations, and wasted time. You’ll take messy operational reality and turn it into simple, reliable workflows, integrations, and AI automations. 

You’ll drive accountability end-to-end: definition → build → QA → rollout → adoption → measured impact.
We are NOT hiring a theorist, and we are NOT looking to replatform. We want an operator-PM who makes the systems work and proves it with outcomes.

The role — quick pitch

Own the end-to-end improvement of how Del Mar teams use our platform—so data is clean, workflows are reliable, and outcomes actually happen. You’ll observe real user behavior across departments, turn friction into clear specs and prioritized work, and drive new tech / products from definition → build → QA → rollout → adoption.

You’ll be hands-on in HubSpot and across our system stack (Guesty, Zuper, Zapier, custom guest and owner portals, pricing/marketing tools). Your north star is simple: less wasted effort, fewer escalations, better decisions, better service for our customers, and smarter work for our team members.

Where you fit

You’ll report to our Chief Technology & Finance Officer, Colin, and work closely with the CEO and functional directors. You’ll own product delivery for the business systems that run the company — and you’ll be the person teams call when systems need to actually work (not just look pretty in a diagram).

How you’ll run the job (your weekly operating loop)

Every week, you will repeat this loop like a professional menace to chaos (we think…)

• Observe users 
• Fix workflow + data 
• Ship improvements 
• Drive adoption 
• Measure outcomes 

Core responsibilities

User work optimization

• Shadow teams across Ops, Marketing, Owner Revenue, Guest Revenue, + Guest Experience
• Map processes, workflows, find friction, reduce variance, and eliminate rework
• Fix forms and data capture so information is accurate by default, not by heroics
• Improve enablement and adherence so systems and data  stay healthy over time

Platform roadmap ownership

• Own the business systems roadmap and prioritize initiatives by business impact
• Balance platform hygiene with new capabilities (no “AI on top of a dumpster fire”)
• Maintain a ruthless focus on reducing wasted effort and improving service outcomes

Data quality & system integrity

• Own HubSpot data hygiene: properties, lifecycle stages, governance, and standards
• Define system rules that prevent garbage-in (validation, required fields, routing, defaults)
• Create visibility into where data quality breaks and fix root causes

Delivery, specs, and cross-functional accountability

• Turn messy requests into clear requirements, user stories, and acceptance criteria
• Rally stakeholders around prioritized work, clear ownership, and timelines
• Coordinate with engineering and vendors; drive delivery to done.

Integrations & orchestration

• Design, document, and QA integrations and data flows
• Manage API/webhook-based connections and vendor roadmaps
• Monitor system changes and proactively prevent breakages

Product delivery & QA

• Lead pilots, run QA across multiple personas, manage rollout, and own rollback/change control
• Ensure changes actually stick (not “launched and forgotten”)

Success measurement & reporting

• Build dashboards and reporting that reflect real operational outcomes
• Own accountability for improvements in:
• • Cycle time
  • Adoption
  • Error rates / rework
  • Escalations 
  • NPS / owner satisfaction 

Required qualifications

• 4+ years in Product Management, Product Ops, or Business Systems PM ownership 
• Deep, practical HubSpot experience 
• Hands-on integration experience 
• Strong process analysis and documentation
• Proven ability to drive cross-functional teams to outcomes without formal authority
• Excellent communicator who can translate tech ↔ non-tech cleanly
• Comfortable using dashboards/data to tell the truth and drive decisions

Nice-to-haves

• Experience in property management, hospitality, field service, or seasonal businesses
• Familiarity with pricing/marketing intelligence tools and dynamic pricing concepts
• Exposure to AI automation and prompt/API-based workflows

30 / 60 / 90 day expectations

30 days — platform reality check + low hanging fruit

• Build relationships across teams through onsite observation and shadowing
• Map the current workflows and data flows across the platform
• Deliver a platform health + data quality audit (what’s breaking, why, and what it costs us)
• Ship 3–5 high-impact quick fixes that reduce rework and improve data quality immediately
• Align on success metrics and baseline current performance (adoption, errors, escalations, cycle time)

60 days — systematic improvements

• Implement data governance + workflow standards that prevent drift
• Launch a cadence of small releases with consistent QA + adoption follow-through
• Improve at least one core workflow end-to-end (definition → build → rollout → adoption → measured impact)
• Begin supporting AI initiatives only after foundational data/workflow hygiene is in motion (no “AI on top of messy inputs”)

90 days — scale + one meaningful AI deliverable

• Demonstrate measurable improvement in at least 2–3 of: data quality, adoption, error rate, cycle time, escalations
• Bring at least one AI-enabled workflow into testing + QA that supports owner revenue
• Establish a durable operating rhythm for platform improvement: weekly loop + monthly roadmap review + quarterly planning alignment