Senior Manager, Vacation Rental Business Development

Vail Resorts•Keystone, FL

3d•Onsite

About The Position

The Senior Manager, Vacation Rental Business Development is accountable for driving net inventory growth and owner retention across assigned market(s) through full-cycle owner acquisition and senior-level relationship management. The role builds and converts a high-quality pipeline, establishes long-term owner partnerships, and ensures owner strategies translate into improved unit performance, guest experience, and overall portfolio value. Operating in either a single-region or multi-market configuration, this role partners closely with market and corporate teams to deliver inventory growth, retention, and market share objectives.

Requirements

2–4+ years of experience in business development, account management, client services, real estate, or vacation rental management.
Demonstrated success owning a pipeline, building relationships, and closing agreements.
Proficiency with Microsoft Office; comfort with CRM tools and analytics/reporting platforms.
Relationship-first growth mindset; credible, senior owner-facing presence.
Persuasive communicator (written, phone, and in-person) with strong follow-through and persistence.
Highly organized; able to manage a high volume of owner/partner interactions and competing priorities.
Data-literate and metrics-driven; able to interpret performance, market, and competitor insights and translate them into action plans.
Comfortable using CRM and reporting tools (e.g., Salesforce and BI dashboards) to manage pipeline and performance.

Nice To Haves

Experience in vacation rentals/short-term rental economics is strongly preferred.

Responsibilities

Own the end-to-end business development lifecycle, from pipeline generation through signed management agreement, delivering against inventory growth targets.
Build and convert a high-quality pipeline aligned to market growth priorities.
Conduct discovery conversations to understand owner goals; present the VRM value proposition; handle objections; and close new owner agreements.
Execute targeted outreach and relationship-based prospecting to source high-value properties aligned to market priorities.
Maintain disciplined pipeline tracking and improve conversion across all stages.
Own ongoing owner relationships and retention outcomes across assigned portfolio, maintaining ownership beyond initial signed agreement to drive engagement and long-term retention.
Serve as the primary relationship leader for vacation rental owners, leading key touchpoints (1:1s, town halls, owner events).
Proactively identify at-risk owners early and lead retention and win-back strategies.
Partner with Operations, Revenue Optimization, Marketing, and other key stakeholders to ensure owner expectations translate into consistent execution.
Manage audit process of units, aligned with GX scores and revenue to determine renovation or unit improvement opportunities and develop a unit enhancement program to support needed improvements with the intent to drive ADR and occupancy by unit.
Leverage market and performance data to inform owner strategy and market positioning.
Monitor local competitive dynamics (fees, splits, service offerings, tech-enabled capabilities) and translate insights into actionable owner and market strategies.
Use market and performance data to set goals with owners/partners, develop action plans, and secure adoption of recommended tactics.
Maintain a metrics-driven operating rhythm across pipeline, conversion, retention, and market share.
Identify cross-market trends and scale best practices that improve performance across the portfolio.
Partner with corporate and market teams to improve owner and guest outcomes and enable scalable execution.
Act as a liaison between market execution and corporate initiatives/functions (systems, tools, marketing, finance).
Define best practices, identify points of friction, and partner with Corporate teams to improve scalability and consistency in owner and guest experience related to vacation rental management, driving alignment on solutions.
Coordinate with accounting/owner billing partners as needed to resolve owner issues and improve trust through transparency and accuracy.
Pilot improvements in-market, capture learnings, and drive adoption across VRM markets through clear toolkits and communication.

Benefits

Free passes for employees
Employee discounted lift tickets for friends and family
Free ski lessons
40% retail discounts
401(k) Retirement Plan
Employee Assistance Program
Excellent training and professional development
Referral Program
Health Insurance
Medical Insurance
Dental Insurance
Vision Insurance plans (for eligible seasonal employees after working 500 hours)
Free ski passes for dependents
Critical Illness and Accident plans
Wellness benefits