Product Manager- Business Systems

Del Mar Vacations•Orleans, MA

1d•$120,000 - $150,000•Onsite

About The Position

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. 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.

Requirements

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

Nice To Haves

Experience in property management, hospitality, field service, or seasonal businesses is a plus

Responsibilities

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