Leadership
The team leading Awayday
Awayday brings together top-tier vacation rental companies under one national platform. The executives below set direction across the portfolio, while each local brand keeps running its own market.
Executive team
Who sets the direction
- Office of the CEO
Jakob Dwyer
Chief Executive Officer
- Finance
David Reed
Chief Financial Officer
- Revenue
Ryan Olin
Chief Revenue Officer
- Revenue
Eric Schueller
Executive Vice President, Revenue
- Revenue & Marketing
Danny Bradford
Executive Vice President, Revenue & Marketing
- Sales Operations
Dan Yankley
Executive Vice President, Sales Operations
- Technology
Tom Chess
Executive Vice President, Technology
- People
Aimee Shaw
Director of Human Resources
Looking for the right person on this list? Send a note through our contact form and we'll route it to the correct team.
How this team is set up
Awayday is deliberately not a single brand with regional offices. It is 60+ established local management companies, most of them running their markets for decades, that kept their names and their teams when they joined. That shapes what a corporate executive here actually does: set standards, build the shared tools, and then get out of the way of the people who know their beach, lake or mountain town better than anyone at headquarters could.
So the functions above (revenue, operations, marketing, technology, finance and people) exist to serve the local brands, not to override them. Revenue management sets pricing strategy across 15,000+ homes while the local team keeps the final call on their own inventory. Technology builds one booking, housekeeping and maintenance backbone so a brand isn't paying for its own software stack. Marketing drives demand nationally so a local team doesn't have to buy its own traffic.
What that means in practice
- Decisions stay close to the home. The person who inspects your property, meets your guests and handles a Saturday-night maintenance call lives in your market.
- Standards are shared. When one brand finds a better way to clean, price or communicate, it becomes a practice across the collection rather than a local secret.
- One accountable operating platform. Revenue management, marketing, distribution, finance, HR and technology run centrally, so an acquired brand plugs into infrastructure it would take years to build. See our footprint for where the collection operates today.
- Founders stay involved. Owners of brands that join often continue leading their market, which is why we look for fit before scale on the partner side.
How we lead
Leading as one across a family of local brands
01
Local Expertise, National Excellence
Our local brands have been in operation for an average of 23 years and are pillars of excellence in their local communities.
02
An entrepreneurial spirit
The entrepreneurial spirit infuses all areas of our company. We're constantly improving and evolving to establish best practices and share them across our family of companies.
03
Invested in our people
Our commitment to investing in our team paves the way for the exceptional service our owners and guests have come to expect, across a team of more than 1,200 professionals.