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Senior Director, Product - Head of Property Management

Bay Area, CA; Oakland, California, United States

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 & Scaling

  • Design products that drive operational efficiencies for the property management business
  • Create scalable solutions that can support Roofstock's growth ambitions
  • Develop tools and systems that enhance productivity and reduce manual processes
  • Ensure product compliance with legal, security, and privacy requirements
  • Establish and optimize product development processes to maximize team efficiency

Qualifications

Experience

  • 10+ years of product management experience with at least 5+ years in a leadership role
  • Proven track record of successfully launching and scaling technology products that drive business results
  • Experience in real estate, property management, proptech, or relevant SaaS platforms
  • Previous experience working with internal tools, B2B platforms, and consumer-facing products
  • History of leading cross-functional teams and working effectively with engineering, design, and business stakeholders
  • Background in developing product visions, roadmaps, and strategies that align with business objectives

Skills & Knowledge

  • Deep understanding of modern product development methodologies, including agile practices
  • Strong analytical skills with the ability to use data to inform product decisions
  • Excellent communication and presentation skills with the ability to articulate complex concepts clearly
  • Strategic thinker with the ability to translate business challenges into product opportunities
  • Collaborative leadership style with the ability to influence without direct authority
  • Familiarity with AI/ML concepts, large language models, and their application to operational use cases
  • Proven ability to deliver tech-enabled process automation or AI-powered features
  • Understanding of property management processes, challenges, and KPIs
  • Knowledge of SaaS business models and metrics
  • Experience with user research, UX design principles, and product analytics

Education

  • Bachelor's degree in Computer Science, Business, or equivalent experience
  • MBA or advanced degree preferred but not required

Nice-to-haves

  • Prior experience in a high-growth company, navigating scaling challenges.
  • Experience in real estate, internal tooling, and larger scale operational organizations

Location

Bay Area/Oakland, CA

This position is classified as HYBRID within the Greater Oakland Area with an expectation to be in-office on Tuesdays and Thursdays weekly. 

Travel Required

n/a

Compensation

$200,000 - $290,000 range on annual base salary. The compensation range may be adjusted based on experience and location.

Pay Transparency

Our compensation reflects several US geographic markets. The base pay for this position represents the expected salary for this position.  Ultimately, in determining your pay it will be based on several factors including location, job-related knowledge, skills, experience and other job related factors.  Roofstock is a total compensation company; the base salary is only a part of our total compensation package.

Competitive & Unique Benefits Package

  • Generous PTO Policy
  • 12 Paid Holidays
  • Volunteer Time Off
  • Paid Parental Leave
  • 401k Program
  • Wellness and home office/cell phone subsidies
  • Robust health, dental, vision insurance, and more

 

Must be authorized to work in the U.S. is a precondition of employment and we are unable to sponsor H1-B Visas at this time.

Any offer of employment is conditioned upon the successful completion of a background investigation.  

Commitment to Equal Employment Opportunity 

The company provides equal opportunity in all of our employment practices to all qualified employees and applicants without regard to race, color, religion, sex, gender, gender expression, gender identity, national origin, ancestry, citizenship, age, physical or mental disability, marital status, sexual orientation, military or veteran status, genetic information or any other category protected by federal, state and local laws. This policy applies to all aspects of the employment relationship, including recruitment, hiring, compensation, promotion, transfer, disciplinary action, layoff, return from layoff, training and social, and recreational programs. All such employment decisions will be made without unlawfully discriminating on any prohibited basis.

 

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