Kirby Winfield

Kirby Winfield

I run Dwellable, the #1 vacation rental app.

Seattle, Washington, United States
Accredited investor
Member since February 05, 2009
  • About
Investor interests
Type of investor Angel
Typical investment size $50,000 - $100k
Typical investments in a year 1
Categories of interest
Locations of interest
Credentials Accredited Investor
Investments made Marchex,, Primus Biovision, SharperAgent, Rare Crowds, Dwellable, Rare Crowds, Marchex,, Primus Biovision, SharperAgent
Board seats SharperAgent, AdXpose
1996 Middlebury College , BA , English

I am a(n):


If you're an entrepreneur or corporate innovator, why?

I want to take great ideas and scale them into meaningful businesses.

My favorite startups:


What's most frustrating and rewarding about entrepreneurship/innovation?

Frustrating: Triage
Rewarding: Growth

What's the No. 1 mistake entrepreneurs/innovators make?

Lack of focus.

What are the top three lessons you've learned as an entrepreneur?

Nothing beats an amazing team. Follow your customers. Partner up with strategics.

Full bio

Kirby Winfield is a veteran digital media executive, investor and advisor. Kirby is currently Chief Executive Officer at leading vacation rental search engine Dwellable. Kirby was most recently the Senior Vice President, Corporate Development, for comScore (SCOR). Prior to comScore, Kirby served as President and Chief Executive Officer of AdXpose, which created the "viewable ad impression" metric and was acquired by comScore in August 2011. Before AdXpose, he operated Ascend Solutions, a consultancy to startups and venture capital firms. Additionally, Kirby was on the founding team and served as General Manager of publishing and content for Marchex (MCHX), and prior to that, was responsible for all corporate, brand, and product marketing at Go2Net (GNET). Kirby was also a Board Director of SharperAgent, LLC, which was acquired by Market Leader (LEDR) in 2011, and invests in and advises a number of online media startups. 

Kirby speaks regularly at industry events, and was recently a recipient of the Puget Sound Business Journal’s “40 Under 40” award. He is a Board Member at Special Olympics of Washington, and is an active supporter of the Global Down Syndrome Foundation.