Principal Product Manager, Pro

At Evolve, we’re on a mission to make vacation rental easy for everyone. Our high-performing, customer-obsessed team runs on curiosity, communication, and accountability—working together to create exceptional experiences for our owners and guests. Whether solving big challenges, delivering outstanding results, or celebrating wins, we approach every day with purpose and passion. If you’re ready to join a mission-driven company where every teammate has the opportunity to thrive, Evolve might just be the place for you.

Why this role

Evolve’s Pro offering serves short-term rental operators and HOAs managing larger portfolios of properties. These customers often think like businesses: they need to evaluate whether Evolve can support their operation, bring a portfolio onto the platform, manage teams and properties, and deliver a reliable experience to their own customers.

Today, Pro spans a broad and evolving product surface. Operators and HOAs have distinct needs, and solving each one with a separate, custom solution will not scale. We need a dedicated product leader to set the direction for Pro and build a flexible platform that can support different customer needs without fragmenting the experience.

As Principal Product Manager, you’ll own the Pro roadmap end to end. You’ll connect acquisition, onboarding, day-to-day operations, and retention into a coherent product strategy, partnering closely with Commercial, Design, Engineering, and other teams to turn complex customer needs into scalable product capabilities.

What you’ll do

• Define and own the product vision, strategy, and roadmap for Pro, balancing customer needs, business opportunity, and platform investment.

• Build a deep understanding of portfolio operators and HOAs: how they assess providers, bring properties and teams onto a platform, manage their operations, and decide whether to stay.

• Improve the end-to-end experience—from evaluating and adopting Pro through onboarding, ongoing portfolio management, and renewal or expansion.

• Identify shared needs across customer types and shape modular, configurable product capabilities that avoid one-off development for each use case.

• Make clear product choices across a large, ambiguous surface area, sequencing work and explaining tradeoffs to senior stakeholders and delivery teams.

• Partner with Commercial strategy to understand target customers, define what we offer, and lead the product roadmap to support how Pro is positioned and sold.

• Work with Engineering and Design to turn complex workflows into useful, dependable experiences. Prioritize usability and operational efficiency for customers managing many properties and users.

• Establish success measures for Pro, use customer research and product data to understand performance, and adjust the roadmap as evidence changes.

• Lead cross-functional work through discovery, definition, delivery, launch, and iteration, aligning partners across teams with different priorities.

• Represent the voice of Pro customers in product decisions and help the organization build a shared understanding of their needs.

What makes you a great fit

• Minimum 10 years of product management experience, driven 0-1 product buildouts, including ownership of strategy and delivery for complex products or product areas.

• You have a business and commercial mindset. You grasp how product capabilities fuel client acquisition, top-line performance, user retention, and streamlined operations, enabling you to assess strategic opportunities through commercial and user perspectives.

• Experience building for B2B or B2B2C customers, particularly products involving customer acquisition, onboarding, user or account management, retention, or expansion.

• A track record of bringing structure to ambiguous problems and turning a broad product opportunity into a focused, outcome-driven roadmap.

• Strong customer discovery skills: you can learn how customers work, identify the needs shared across segments, and distinguish those from requirements that call for configuration or a different approach.

• Experience partnering with Commercial, Sales, or go-to-market teams to connect product strategy with customer acquisition and business growth.

• The judgment to balance customer-specific needs with scalable platform capabilities, and to make progress when requirements or ownership are unclear.

• Comfort working closely with Engineering on technical tradeoffs, system constraints, and sequencing.

• A practical approach to product experience: you know when a workflow needs refinement and when clarity, reliability, and efficiency matter most.

• Strong communication skills and the ability to align senior stakeholders and cross-functional teams around decisions and outcomes.

• An AI builder mindset with a pragmatic approach to leveraging AI tools, LLMs, and agents. You can rapidly prototype solutions, validate hypotheses, and address core customer needs. You move beyond standard development workflows to test ideas quickly, collaborating closely with Engineering to transition proven concepts into scalable production features.

• Experience in enterprise SaaS, property technology, vacation rentals, or software for managing portfolios of properties, locations, accounts, or users is a plus.

Compensation

For this role, our base salary is $170K to $205K. The role is also eligible for a variable annual bonus based on company and individual performance.