Business Development

Attract and Keep the Right Property Owners

Build a reputation that grows your inventory, builds trust and strengthens long-term relationships.

Struggling to Find and Keep Quality Owners?

Your business can’t scale without the right inventory, and inventory starts with trust. Many vacation rental managers find it challenging to attract new homeowners or to keep them happy once they’ve signed. Without clear messaging and a strong retention strategy, even your best properties can be at risk.

A Strategy Built on Trust and Alignment

Annie & Co. partners with your team to create an intentional plan for owner acquisition and retention. We help you define and communicate your unique value, build credibility, and establish a repeatable system to grow and protect your owner portfolio.

Our Signature STRive Method

Owner relationships aren’t won with a single pitch. We apply our STRive Method to ensure you’re consistently positioned as the management partner of choice.

Discover

We assess your current approach to owner communication, onboarding, and retention, including team alignment and brand perception.

Analyze

You receive a detailed breakdown of what’s working, where owners may feel disconnected, and where your messaging or experience is falling short.

Architect

Alongside your team develop a full acquisition and retention plan customized to your brand, team strengths, and market positioning.

Activate

We support messaging development, team training, referral program setup, and targeted outreach strategies.

Optimize

We identify retention benchmarks and build in regular review points to ensure your strategy continues to meet evolving owner expectations.

What’s Included

Identify your unique value proposition and message
Owner onboarding and ongoing communication strategy
Team training on value-based communication
Referral and partnership program setup
Strategic outreach and campaign planning

This Is Ideal For

Vacation rental managers with inconsistent or stagnant owner growth
Teams struggling to communicate their value clearly
Operators losing properties due to poor retention or lack of engagement
Companies entering new markets or expanding their portfolio

Ways to Work Together

Strategy only
Strategy with execution support
Monthly retainer for ongoing optimization and consulting

"Annie Holcombe does it all. Full stop. And, for reasons I can’t quite explain, she does it flawlessly and with astonishing ease. Whether she’s co-hosting the most influential podcast in the industry, connecting the dots between key players, leading business development for a major OTA, or applying her deep expertise in channel management, Annie’s Swiss Army knife-like versatility is unmatched. Her ability to collaborate, communicate, and (we assume) caffeinate makes her a true powerhouse—and honestly, the rest of us are just trying to keep up. If the vacation rental industry had a mayor, Annie would already be in office… probably running unopposed."

Alex Alioto Head of Growth, Whimstay

Get in Touch with Us

Have questions or need assistance? We are here to help you navigate your rental property challenges. Reach out to schedule a consultation today!