Senior Director, Product - Head of Property Management

What we do and why we do it

As the leading end-to-end investment platform for single-family rental homes (SFR), our mission is to make real estate investing radically accessible, cost effective, and simple. We successfully merge our passion for helping investors build wealth through real estate with cutting edge technology that transforms the way they do it.

How it’s going (and growing)

With a talented team of 600+ Roofsters, our collaborative, can-do culture is what fuels our growth. In 2022, we closed on our Series E, raising $240 million, and have offices in California, Texas, and New York as well as many remote opportunities. Our growth includes recent acquisitions of Stessa (financial and asset management software), RentPrep (tenant screening and placement service for landlords), and Mynd (property management platform for both Retail and Institutional investors). In 2025, Roofstock took an ownership stake in Casago (short-term rental management services), expanding our platform to support both long-term and short-term rental investment services.

About the Role

As the Sr Director, Product for Roofstock's Property Management division, you will drive the vision and execution for all products related to our property management business line. This includes internal tooling, external portals for investors, residents, and vendors that power our property management operations.

This is a strategic leadership role where you will be responsible for developing and executing the product roadmap that enables our property management business to scale efficiently, drive operational excellence, and strengthen core value propositions that fuel growth. You'll collaborate closely with cross-functional teams including engineering, design, operations, and business stakeholders to build innovative solutions that transform how residential property management functions.

The ideal candidate is a visionary product leader with experience in proptech, SaaS platforms, or related fields, who can translate complex business requirements into elegant product solutions. You should be equally comfortable discussing technical architecture with engineers as you are presenting ROI metrics to executives.

Key Responsibilities

Strategic Leadership & Vision

• Develop and communicate the product vision, strategy, and roadmap for the property management business line, aligning with Roofstock's overall company objectives
• Identify and prioritize opportunities to drive operational efficiency, enhance user experience, and create competitive differentiation through product innovation
• Translate business objectives into product requirements that deliver measurable outcomes for all stakeholders
• Identify opportunities to apply AI and automation to reduce cost, improve quality, and enhance customer and operator experiences
• Champion a data- and AI-driven product approach, ensuring scalable solutions through advanced technologies
• Stay ahead of industry trends and evolving technologies to ensure Roofstock remains at the forefront of proptech innovation

Product Development & Execution

• Lead the end-to-end product development process from ideation to launch for all property management products
• Create, maintain, and effectively communicate the product roadmap to all stakeholders
• Define and track key performance metrics to measure product success and drive continuous improvement
• Prioritize product features based on business impact, technical feasibility, and resource constraints
• Partner with engineering teams to ensure successful implementation of product features
• Collaborate with data science and AI teams to build and integrate AI capabilities into property management workflows
• Oversee user testing and gather feedback to inform product iterations

Cross-Functional Leadership

• Lead and mentor a team of product managers who oversee specific aspects of the property management product portfolio
• Collaborate with engineering, design, and data science teams to deliver innovative, data-driven solutions
• Work closely with operations teams to deeply understand user needs and pain points
• Partner with marketing and sales to develop go-to-market strategies for new product features
• Serve as the connective tissue between product and operations, ensuring technology enables execution at scale
• Engage with customers and users (investors, residents, vendors) to gain insights that inform product decisions
• Present product plans, progress, and performance to executive leadership and other stakeholders

Operational Excellence