Alicia Diamond




I’m Alicia Diamond and I’m so happy you’re here. I’m looking forward to getting to you know you and talking about all things Chief of Staff. In the meantime, here is a bit more about me and my background.

I’ve worked exclusively for entrepreneurs since graduating college. I gravitated away from the traditional career path for my major (Economics) and found a very happy home working with a team of entrepreneurs with a big idea: expand one coffee and gelato cafe into a regional chain of cafes and wholesale gelato distribution. It was my dream job: building something from scratch, hands-on ownership in every aspect of the business, working for wonderful people on a product I genuinely loved. 

Since those humble (and very sticky!) beginnings, I’ve worked with teams on world-changing ideas: I worked with seasoned advertising executives who recognized an opportunity to completely reinvent the 1960’s client service model. From there, I joined a family office/startup incubator focused on investing in homegrown portfolio companies. Today, I’m a proud Chief of Staff at a venture-backed SaaS/Daas company.

I get my energy from passionate leaders and their teams. I believe in the power of capitalism to be a positive force for good. I believe in the power of experimentation and rapid learning. Most of all, I believe in the passion of people. I’ll bet on a passionate, hungry team over a well-funded team any day of the week. 

Don’t be shy… I want to get you to know you!

Advice, tips, and thoughts from my journey as a Chief of Staff