Workforce Management Analyst Remote Jobs in Naples, FL

About The Role

We\'re looking for a Senior Product Manager to join our Accounting Pod — the team responsible for one of the most critical and differentiated parts of the Rentvine platform. Trust accounting is at the heart of what we do, and this role sits at the intersection of product strategy and hands-on execution.

You\'ll own the roadmap for our accounting surface while also rolling up your sleeves to drive delivery. You\'ll partner closely with engineering, design, and customer success to build features that make complex financial workflows feel effortless — and you\'ll help infuse AI and automation into areas where it can meaningfully reduce manual work for our customers.

*Rentvine is unable to provide employment sponsorship now or in the future for this position.

What You\'ll Own

Trust Accounting Workflows

• Own the product vision and roadmap for Rentvine\'s trust accounting engine — the ledger, reconciliation flows, month-end close, and compliance guardrails that property managers depend on daily.
• Drive improvements to the monthly accounting workflow, reducing approval friction and surfacing anomalies earlier while preserving human oversight on high-value transactions.
• Deeply understand property management accounting regulations and proactively shape features that keep Rentvine ahead of compliance requirements.

AP/AR & Owner Disbursements

• Own the end-to-end experience for accounts payable and receivable, including vendor payments, owner distributions, and tenant billing.
• Identify friction in the disbursement workflow and deliver features that improve speed, accuracy, and transparency for property managers and their owners.
• Work closely with customers to understand real-world pain points around payment timing, exceptions handling, and reporting.

AI & Automation in Accounting

• Partner with Rentvine\'s AI Pod to identify high-value automation opportunities within accounting — from intelligent transaction categorization to anomaly detection to assisted reconciliation.
• Define where AI creates genuine leverage (reducing tedious manual work, catching errors) vs. where human judgment must remain in the loop.
• Help shape the product thinking around an accounting-focused agent workforce, with a bias toward augmenting — not replacing — the property manager\'s expertise.

Day-to-Day Responsibilities

• Translate customer research, support data, and market signals into a prioritized, shippable roadmap in collaboration with engineering and design.
• Write clear, well-scoped product specs and acceptance criteria using Rentvine\'s planning frameworks (Shippable Feature Slices).
• Lead sprint ceremonies and maintain pod momentum — unblocking teams, making tradeoff calls, and communicating progress to leadership.
• Build deep relationships with power users and key accounts in the accounting domain; you\'ll be in customer conversations regularly.
• Track feature adoption and impact metrics post-launch; use data to inform iteration priorities.
• Represent the Accounting Pod in cross-pod planning cadences and help elevate the broader product organization.

Qualifications

• 5+ years of product management experience, with at least 2 years in PropTech, property management software, or a closely adjacent domain.
• Strong command of property management accounting fundamentals — trust accounting, owner disbursements, ledger management, or similar.
• Demonstrated ability to own both strategy (roadmap, vision) and execution (delivery, scoping, unblocking) — a genuine player-coach.
• Experience working on or alongside AI/ML product initiatives; comfort defining where automation belongs and where it doesn\'t.
• Excellent communication skills — you can write a crisp spec, run a customer discovery call, and present a roadmap to executives with equal confidence.
• Strong analytical instincts; comfortable pulling data, running adoption analyses, and translating numbers into product decisions.
• Experience with modern product tooling: Linear (or similar), customer research platforms, and analytics tools.
• Candidates MUST currently reside in the United States of America to be considered - East Coast preferred

Even Better If You Have

• Direct experience with Rentvine, AppFolio, Buildium, or another property management platform.
• Background in fintech, accounting software, or payments.
• Exposure to agentic AI product development — understanding of how agent-based workflows change the PM\'s job.
• Familiarity with API ecosystems, partner programs, or platform product thinking.

Rentvine is unable to provide employment sponsorship now or in the future for any position.

#LI-Remote