Alicia Diamond

I’ve been the figure-it-out operator and right hand to five CEOs.

Join me as I share lessons learned from my time as a COO and Chief of Staff in fintech, software, CPG, and professional services.

 
 
 
 
 
 
 
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ABOUT ME

Welcome! I’m an operator and business builder - I’ve partnered with 5 visionary CEOs to translate bold missions into clear, actionable strategies and measurable operating plans.

My sweet spot is building new capabilities, teams, and scalable operating systems for companies that have outgrown their old way of working. Read more about my background.

I’m a lifelong student and voracious reader. I’m grateful to everyone who inspired me by sharing their journey and I’m committed to doing the same. Check out my latest articles and if you find them helpful, sign up for my monthly newsletter full of actionable advice for operators.

 
 
 

I’VE BEEN FORTUNATE TO WORK WITH INCREDIBLE PEOPLE

Ridiculously organized and efficient! Alicia works well under pressure and across many teams... she has an amazing skill at translating the CEO’s thoughts to make them meaningful throughout many groups in the organization. She loves people and is a wonderful mentor and collaborator. It’s been a privilege to lead and learn alongside Alicia!
— Annie G. via LinkedIn
Time and again, I have personally seen her tackle difficult problems that don’t have clear solutions. She’s the kind of leader who can see the big picture, plan for the future, and then adeptly communicate and execute on those plans to make sure every detail is accounted for... She is the most organized thinker I have ever met and will often ask questions that make you wonder how she manages to think of everything.
— Liz H. via LinkedIn
Alicia always clearly communicated the CEO’s vision and provided clear and logical direction for our team’s strategies. On Alicia’s team, I was encouraged to be autonomous and creative in how I completed my deliverables, and I always felt challenged and appreciated. Alicia pushed me to be confident when reporting to leadership, and she always encouraged me to ask questions and dig deeper to get to the true root of a problem.
— Jeff P. via LinkedIn
 
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I write to learn and to pay it forward. Here’s my latest: