What are the responsibilities and job description for the Personal + Executive Assistant position at The Cole Group?
Hi! I'm looking for an exceptional Personal Executive Assistant for our family and my business.
This role is based in North County San Diego. While I'd love to consider candidates from different locations, the nature of the role requires someone to currently reside close to our home in Encinitas. Thanks for understanding.
The majority of the role will serve as the operational backbone for our family of four — my wife Taylor and our two daughters (ages 7 and 10). That means house management, vendor coordination, local errands, and logistical support for everything that keeps a busy household running. Some days that's a straightforward task. Other days it's a genuinely creative problem that requires you to just figure it out.
Travel is a meaningful part of the role. We take 3-4 substantial family trips a year, and I travel half a dozen times a year for work. Beyond booking, I need proactive end-to-end coordination during every trip — monitoring flights, managing timing across all touchpoints, and handling whatever comes up in real time so we never have to scramble.
About a third of your time will support my work life as co-founder of The Cole Group (www.colegroup.com), a boutique executive search firm.
Your primary mission here is owning my calendar and proactively navigating all of my stakeholders. You'll coordinate with internal and external parties, participate in a few ops team meetings each week as my representative, and join the firm for 3-4 in-person events per year in Northern or Southern California (all travel covered). I have a very dynamic schedule, and keeping that rhythm intact requires someone who can play aggressive calendar Tetris without dropping the ball on relationships.
You'll need all the core skills of a great assistant — organized, discreet, adaptable, strong communicator — but what I'm really after is extreme ownership. When something lands on your plate, you handle it. Make it happen, no excuses.
Responsiveness is non-negotiable during normal business hours, and a general "I'm on it" mentality is the baseline expectation for everything else.
One hard requirement: you need to be genuinely tech savvy and increasingly AI-forward. Our firm operates that way across the board, and this role is no different. If you're not using AI tools daily and open to building simple automations to improve your own daily life, this probably isn't the right fit.
This is a full-time role with very flexible hours. Many weeks will be well under 40 hours, but peak project periods will require more.
I'd love to find someone great and invest in a long term partnership. I absolutely recognize that the best people deserve to be compensated like the superstars they are!
I look forward to meeting you!! :)