Principal Product Manager- Activation

Accountabilities:

In this role, you will lead product strategy and execution for the activation journey, ensuring that homeowners can move efficiently from signing an agreement to launching a fully operational vacation rental listing. You will work closely with cross-functional teams to eliminate friction, improve conversion, and deliver measurable business outcomes. Your responsibilities will include:

• Owning the product roadmap from signed agreement through to a live, bookable property listing, with accountability for activation rates, time to launch, and 180-day retained activations.

• Identifying and prioritizing the main barriers to onboarding completion, including property setup, photography scheduling, permits and compliance, pricing configuration, and multi-property onboarding.

• Developing and executing a product strategy that translates customer needs, operational challenges, and business objectives into prioritized initiatives.

• Designing and launching product improvements that reduce manual onboarding tasks through self-service experiences, automated scheduling, reminders, and streamlined workflows.

• Managing the full experimentation lifecycle, from formulating hypotheses and defining scope to evaluating results and deciding whether to scale, refine, or discontinue initiatives.

• Partnering with analytics teams to establish and maintain product instrumentation, ensuring every stage of the journey from signup to activation can be measured and analyzed by cohort.

• Collaborating with Onboarding and Operations teams to redesign underlying processes, eliminate operational bottlenecks, and deliver scalable solutions rather than increasing manual workloads.

• Working with Lifecycle Marketing to improve onboarding communications, engagement, and completion rates throughout the owner journey.

• Coordinating with the Funnel Conversion Product Manager to ensure a seamless transition from signup into the activation experience.

• Conducting research and direct conversations with individual property owners and multi-property portfolio owners to understand their needs, challenges, and expectations.

• Translating customer feedback, behavioral data, and experimental findings into clear product requirements and actionable decisions.

• Using AI-powered tools to accelerate product discovery, research synthesis, specification development, and analytical workflows.

• Continuously monitoring activation and retention performance, identifying improvement opportunities, and iterating on product solutions to achieve sustainable growth.

Requirements:

The ideal candidate combines extensive product management experience with a strong track record of improving onboarding, activation, and early customer retention. You should be highly analytical, comfortable working closely with engineers and operational teams, and capable of taking products from discovery through launch and continuous improvement. The following qualifications and skills are expected:

• At least 8 years of product management experience, including significant ownership of onboarding, activation, or time-to-value initiatives.

• Experience working in a two-sided marketplace or an operations-intensive business, ideally focused on the supply side, sellers, or service providers.

• Demonstrated success improving activation, conversion, or early retention metrics, supported by measurable results from product experiments.

• Proven experience partnering with operations or field teams to automate manual processes and develop scalable operational workflows.

• Strong SQL skills and hands-on experience with product analytics platforms such as Amplitude, including independently building funnels, analyzing cohorts, and interpreting behavioral data.

• Ability to translate customer insights and quantitative analysis into clear product strategies, requirements, and prioritized roadmaps.

• Technical fluency to collaborate effectively with engineers at the specification level and guide products from discovery through launch and iteration.

• A strong experimentation mindset, with the ability to develop hypotheses, evaluate outcomes, and make evidence-based product decisions.

• A proactive, hands-on approach to leveraging AI tools such as Claude or Cursor in daily work, including product specification writing, research synthesis, and data analysis.

• Excellent communication and collaboration skills, with the ability to align product, marketing, onboarding, and operations stakeholders around shared goals.

• Strong organizational skills and the ability to manage multiple initiatives while remaining focused on measurable business outcomes.

The following experience would be an advantage:

• Experience with compliance-intensive or regulated onboarding processes, including permits, licensing, or credentialing.

• Familiarity with vacation rentals, real estate, hospitality, or property management.

• Experience serving both individual customers and multi-property owners, portfolio operators, or business customers.

Benefits:

The company offers a competitive compensation package and a comprehensive range of benefits designed to support employees' financial security, health, family needs, and professional growth. Benefits include:

• Annual base salary of $190,000–$210,000 USD, depending on relevant experience.

• Eligibility for an annual variable bonus based on company and individual performance.

• Equity participation in the company.

• A 401(k) retirement plan with a 4% employer match that vests immediately.

• Comprehensive medical, dental, and vision insurance.

• 100% employer-paid dental and vision coverage for individual plans, along with a low-cost medical plan option.

• Paid parental leave of 16–18 weeks for birthing parents and 10 weeks for non-birthing parents.

• Infertility coverage and additional family support benefits.

• Ten complimentary mental health visits and access to wellness resources.

• Pet insurance.

• Generous paid time off, sick leave, holidays, and a personal holiday.

• Recharge time off (RTO) for eligible full-time exempt employees.

• An annual travel credit after one year of employment, plus discounts on stays at vacation properties.

• Structured onboarding, learning resources, and professional development opportunities.

• Employee Resource Groups that foster connection, inclusion, and community.

• Remote work opportunities across eligible U.S. locations, subject to geographic and position-specific restrictions.