Product Manager, Business Systems

Del Mar Vacations, Inc; Orleans (MA); On-site; USD 120,000 - 150,000; Full time

Benefits offered by this job

2 weeks vacation

1 week sick time

Health insurance (partially subsidized

HSA (health savings account)

401k with up to 4% match

Yearly bonus program

Job summary

Del Mar Vacations, Inc. is seeking a Product Manager to elevate how our team uses our platform. You will own discovery through rollout and measure outcomes by improvements in workflows, data quality, and user experience for guests and homeowners.

The role requires guiding cross-functional teams, owning the platform health, and driving integration projects with engineering and vendors. Remote-friendly, onsite Cape Cod work is expected.

Qualifications

• 3–5 years in Product Management, Product Ops, or Business Systems PM ownership.
• Portfolio of real outcomes, not just completed projects.
• Deep, practical HubSpot experience; governance and cleanup.
• Hands-on API/webhook integration experience.
• Strong process analysis to spot issues in workflows.
• Proven ability to drive cross-functional teams to outcomes without formal authority.
• Excellent written and verbal communication; explain complex integrations.
• Data-driven decision making; honesty about what's working.
• Remote work success with async communication and reliable follow-through.
• Experience in property management, hospitality, field service, or seasonal businesses is a plus.

Responsibilities

• Own end-to-end improvement of how teams use the platform; ensure workflows are reliable and measurable.
• Shadow teams to translate observations into clear requirements and user stories.
• Decompose work into buildable tickets; manage backlog grooming.
• Audit platform health and prioritize by business impact.
• Balance hygiene with new capabilities and maintain operating rhythm.
• Design and QA integrations and data flows; monitor for breakages.
• Coordinate with engineering and vendors to drive delivery to completion.
• Follow up after launch to ensure changes stick.

Skills

Product management

Data-driven decisions

Cross-functional leadership

Process analysis

Communication

Remote collaboration

Tools

HubSpot

API / Webhooks

Job description

We're a growing, operationally strong company looking to level up how we use our systems — and we need a Product Manager to lead that charge. Our platform is functional and active across the business; we’re now at the stage where we want to go from good to great: cleaner data, more consistent workflows, and smarter use of the tools we have.

This is a current-state product role as much as a forward-looking one. The biggest opportunities in front of us aren't about adding features — they're about sharpening how our teams use the systems we have, so information flows cleanly, decisions happen faster, and our guests and homeowners feel the difference.

You’ll own the full cycle: discovery - spec - build - QA - rollout - adoption - measured impact. All of it - including the follow-through.

We want someone who leads with questions before jumping to solutions, who can sit with a team for a day and come back with a clear picture of what’s broken and why, and who measures their own success by outcomes - not output. This role isn’t measured in decks delivered or roadmaps built - it’s measured in workflows that work better. If that’s how you keep score too, keep reading.

Core Responsibilities

This role owns the end-to-end improvement of how Del Mar teams use our platform — ensuring workflows are reliable, data stays clean, and outcomes are measurable.

Product Discovery & Specs

• Shadow teams across Ops, Marketing, Owner Revenue, Guest Revenue, and Guest Experience to understand how work actually happens
• Turn observations into requirements that engineers don’t have to interpret, and user stories that reflect user reality
• Decompose work into well-sized, buildable tickets; own backlog grooming and refinement
• Ask \"why\" until you’ve hit the real problem - not the stated one

Platform Roadmap Ownership

• Conduct an ongoing audit of platform health: where the biggest opportunities are, what they’re worth, and how to sequence them
• Own the business systems roadmap and prioritize by business impact - knowing when to say no is just as important as knowing what to build
• Balance platform hygiene with new capabilities without letting either slip
• Maintain a clear operating rhythm: weekly loop, monthly roadmap review, quarterly planning alignment
• Continuously scan for AI opportunities across the platform - prompt/API-based workflows, intelligent routing, automated quality checks - and bring the best ones into the roadmap

Data Quality & System Integrity

• Own HubSpot data hygiene: properties, lifecycle stages, governance, and standards
• Define system rules that make accuracy the path of least resistance - validation, required fields, routing, defaults
• Create visibility into where things break and fix root causes, not just symptoms

Delivery & Cross-Functional Accountability

• Rally stakeholders around clear ownership, realistic timelines, and prioritized work
• Coordinate with engineering and vendors; drive delivery all the way to done
• Follow up after launch - changes need to stick, not just ship

Integrations & Orchestration

• Design, document, and QA integrations and data flows
• Manage API/webhook-based connections and vendor roadmaps
• Monitor system changes proactively - preventing breakages, not just reacting to them

Qualifications

• 3- 5 years in Product Management, Product Ops, or Business Systems PM ownership
• A portfolio of real outcomes, not just completed projects
• Deep, practical HubSpot experience - you’ve owned it, governed it, and cleaned it up
• Hands-on integration experience: you’ve built and managed API/webhook-based workflows
• Strong process analysis skills - you can walk a workflow and spot what’s broken before anyone tells you
• Proven ability to drive cross-functional teams to outcomes without formal authority - you lead through clarity and influence
• Excellent written and verbal communicator - you can explain a complex system integration to a field ops manager and a technical spec to an engineer, and neither conversation feels off
• You use data to make decisions and tell the truth about what’s working, including when that truth is inconvenient
• Demonstrated remote work success - you have real habits: how you run standups, how you communicate async, how you make sure nothing falls through the cracks
• Experience in property management, hospitality, field service, or seasonal businesses is a plus

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.

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

Salary Range

$120,000-$150,000+ base (depending on experience) & generous performance bonus

Schedule

Full-time | Onsite on Cape Cod