Remote Vacation Rental Property Management Jobs (NOW HIRING)

Are you ready to Level Up! Join our growing team as a Director of Product.
At Track, we combine deep hospitality expertise with forward-thinking technology and a customer-obsessed mindset to help property managers win. Track is proud to be named an Inc. 5000 Fastest Growing Company in America and a People’s Choice Award winner, reflecting our commitment to innovation, service, and customer success.
Track is an end-to-end SaaS and Service Operating Platform for Short Term Rental. For over 21 years, we have helped hospitality professionals achieve digital transformation and operational excellence. Our single-vendor ecosystem includes 70+ integration partners and a growing list of native features.
This role is perfect for someone who is:
-A self-starter with tremendous initiative and a strong work ethic
-An excellent communicator and collaborator across functional teams
-Eager to make a high impact at a product-driven company
-Adaptable, quick to embrace change, and a fast learner
-Skilled in creative and critical thinking
-Detail-oriented, even in a fast-paced environment
-Passionate about technology and innovation, particularly the future of applied AI in our sector.
About Track
For over 21 years, Tracks has provided integrated software and marketing solutions for the hospitality industry, anchored by our flagship Track Property Management System and other products under the Track banner.
Our single-vendor ecosystem equips growing vacation rental companies with all the enterprise-class tools they need to scale. With ongoing investments in platform development, 70+ integration partners, and a growing suite of native features, Track, built on a customer-obsessed mindset, empowers hospitality professionals to achieve digital transformation and operational excellence. Our development includes a focus on leveraging AI-driven tools to enhance pricing, distribution, and guest communication.

Our Core Values reflect the behaviors that shape the tone of how we work with each other, our partners, and our customers:
-Serve Others: Nurturing growth to help others succeed
-Grit: Taking ownership and never giving up on what matters most
-Create the Future: Innovating to disrupt the status quo
Why Join Us?
-Be part of a fast-moving, dynamic team focused on growth and success.
-Work alongside a talented, collaborative, and supportive team.
-Work for a portfolio company offering a one-vendor solution for SaaS technology, marketing, and distribution.
-Help reshape the hospitality industry through technology and service innovation.
Perks and Benefits:
-Full medical, dental, and vision coverage
-Flexible Paid Time Off
-Unlimited access to professional training and development
-Health Savings Account with up to a $2,000 annual match
-Up to $900 in annual Wellness Rewards
-Flexible work environment
-Free life insurance and long-term disability coverage
-Flexible Spending Accounts
-Retirement plan with employer match
-$150 quarterly gift for personal use
-Competitive wages
-Work with an amazing team!
Summary and Responsibilities:
The Director of Product leads the Core Product team, overseeing the vision, strategy, and execution of the Core product suite. This suite is at the heart of our Short Term Rental Property Management System. Beyond traditional product leadership, this role will help shape Track's evolution into an AI-enabled platform - identifying opportunities where intelligence, automation, and agentic workflows create meaningful customer value and internal opportunities for benefit.
The Director partners with Engineering, Customer Success, Sales, Marketing, and Executive Leadership to drive innovation and customer value, while influencing the Non-Core Product team to ensure portfolio alignment. The Director is accountable for KPIs — product adoption, NPS, retention, and delivery predictability. The role will report directly to the Senior VP of Product, and will have several direct reports.
We are looking for an AI-forward candidate that brings experience leveraging AI tooling to make customer-facing products and internal processes better.
Product Strategy amp; Vision
- Develop and maintain a clear roadmap for the Core product line aligned with the company’s mission, market opportunities, and customer needs.
- Translate product strategy into actionable objectives with measurable outcomes tied to KPIs such as product adoption, NPS, churn, and delivery predictability.
- Leverage data, customer insights, and competitive analysis to drive prioritization and decision-making.
- Ensure alignment of Core product priorities with the broader product portfolio strategy while partnering with and influencing the Non-Core Product team.
- Drive Track's evolution from a system of record toward a system of intelligence by identifying opportunities for AI-powered workflows, automation, and decision support.
AI amp; Product Innovation
- Identify opportunities where AI can simplify complex workflows, eliminate repetitive work, and improve customer decision-making.
- Partner with Engineering and AI teams to bring intelligent capabilities into the Core Platform using LLMs, automation, predictive insights, and agentic experiences.
- Ensure AI initiatives solve meaningful customer problems and deliver measurable business outcomes rather than simply adding new technology.
- Establish a culture of experimentation using customer feedback, analytics, and rapid iteration to validate AI-driven product investments.
- Champion responsible AI practices, ensuring customer trust, transparency, and data privacy remain foundational principles.
Leadership amp; Team Development
- Lead, coach, and develop the Core Product team of 3-5 Product Managers, fostering a culture of collaboration, ownership, and customer focus.
- Partner with the SVP of Product on organizational planning, capacity needs, and resource allocation.
- Ensure cross-functional alignment and effective communication of priorities.
Product Execution
- Improve and drive the end-to-end product lifecycle from discovery to launch, including requirements, user stories, and acceptance criteria.
- Collaborate closely with Engineering and Design to ensure timely, high-quality delivery.
- Remove barriers, make trade-off decisions, and ensure the Core team stays focused on the highest-value work.
- Leading product evolution through growth, technical modernization, and market shifts.
- Improving product processes as the company scales.
Cross-Functional Collaboration
- Partner with Customer Success, Professional Services, Support, and Revenue teams to understand customer pain points and ensure successful adoption.
- Work with Marketing and Sales to support go-to-market planning, messaging, and enablement.
- Communicate updates, progress, and risks to the SVP of Product and senior leadership.
Customer and Market Focus
- Act as a champion of customer needs and internal stakeholder feedback.
- Conduct market research and maintain awareness of industry trends and competitive landscape.
- Continuously seek opportunities to enhance product usability, performance, and customer outcomes.
- Become a subject matter expert on the Core product, understanding its complexities and interdependencies within the broader portfolio.
- Drive improvements in key company outcomes - Pipeline, Close rates, Retention rates,Product adoption.
Minimum Qualifications:
- 8+ years of product management experience, including leadership of complex B2B SaaS products.
- Proven success leading and developing Product Managers.
- Strong background in vertical B2B SaaS; experience with accounting-centric or operationally complex systems strongly preferred.
- Experience working in a PE-backed or high-growth environment.
- Comfortable operating at both strategic and execution levels.
- Strong data/product analytics fluency, discovery practices, and roadmap tooling. Ability to communicate with and influence executives.
Diversity and Inclusion:
We celebrate diversity of thought, culture, and background and are committed to creating an inclusive environment. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, disability, or veteran status or any other protected status under applicable federal, state, or local law. We comply with all applicable laws governing nondiscrimination in every location where we operate and encourage individuals from all backgrounds to apply.

Compensation:
The expected starting base salary range for this role is $170,000–$190,000, plus eligibility for a 20% annual incentive tied to company performance. Final compensation will be determined based on factors such as relevant skills, experience, education, and geographic location.