Executive Assistant Personal Assistant Jobs in Santa Rosa, CA

I am the founder of a busy trial consulting business in the San Francisco Bay Area and am looking for an exceptional Executive Personal Assistant to become my right hand across both business and personal administration.

This is not a traditional administrative assistant role.

I am looking for someone who is exceptionally organized, resourceful, detail-oriented and proactive—someone who genuinely enjoys taking things off another person's plate and carrying them all the way through completion.

The right person will be comfortable sending a client retainer agreement in the morning, following up with a contractor about missing time entries, dealing with Adobe support, returning items to Amazon, arranging business travel, ordering replacement equipment and solving an annoying household/vendor problem—all in the same role.

The Role

My highest-value work is strategic and creative: working directly with trial attorneys, analyzing cases, developing strategy and helping clients prepare compelling courtroom presentations.

I need someone who can take ownership of the administrative and operational work surrounding that work—and a variety of personal administrative tasks—so that I can stay focused on the things only I can do.

This person will work directly with me initially to learn my business, preferences and systems. My goal, however, is not to hire another person I have to manage.

The successful person will increasingly anticipate, own, track and complete responsibilities independently.

Business Responsibilities

Responsibilities will include:

- Prepare, send and track client retainer agreements

- Follow up until agreements are signed

- Track retainer payments

- Maintain regular client invoicing

- Follow up on outstanding invoices/payments

- Track contractor time and obtain missing time entries

- Follow up with contractors regarding assignments, deadlines and outstanding communications

- Coordinate contractor schedules and trial coverage

- Draft/send routine administrative client communications

- Coordinate client onboarding

- Maintain client/project administrative checklists

- Coordinate business travel, including airfare, hotels and ground transportation

- Maintain audiovisual and technology equipment inventory

- Research and order replacement equipment

- Manage software licenses and renewals

- Handle Adobe/Microsoft/vendor support issues

- Coordinate routine technology administration

- Track recurring subscriptions and renewals

- Coordinate client gifts following trials

- Maintain business-development/contact tracking

- Help maintain and improve internal administrative systems and workflows

- Identify administrative matters that need attention before I have to remember them myself

Personal Responsibilities

This is a true Executive Personal Assistant position and will also include practical personal tasks such as:

- Amazon, retail and other returns

- Dry-cleaning drop-off/pickup

- Household/vendor calls and follow-up

- Scheduling appointments and services

- Coordinating repairs and household projects

- Purchasing gifts

- Ordering household items

- Researching products/services and presenting a concise recommendation

- Local errands

- Following administrative problems through to resolution

The personal component is primarily about removing errands, administration and unfinished projects from my plate.

You Might Be My Person If...

- You are exceptionally reliable.

- You have excellent common sense and judgment.

- You naturally notice what hasn't been completed.

- You take pride in making someone's life easier.

- You are unusually good at follow-through.

- You enjoy bringing order to complicated situations.

- You create systems when you notice recurring problems.

- You can handle multiple moving pieces without dropping details.

- You communicate clearly and professionally.

- You are comfortable interacting with attorneys, clients, contractors and vendors.

- You don't need constant direction or reassurance.

- You are comfortable making reasonable decisions independently.

- You know when something genuinely needs to be escalated.

- You are equally willing to deal with a software vendor, send an invoice or make a return.

- When something doesn't work the first time, your instinct is to figure out another way rather than simply reporting that it didn't work.

You Probably Won't Enjoy This Role If...

- You prefer receiving a defined list of tasks every day.

- You need detailed instructions for routine assignments.

- You routinely require reminders about follow-up.

- You consider errands beneath your professional level.

- Your default response to an obstacle is to return the problem to the person who assigned it.

Qualifications

I'm much more interested in demonstrated capability than a particular degree.

Ideal candidates may have experience as an:

- Executive Assistant

- Executive Personal Assistant

- Senior Administrative Assistant

- Operations Coordinator/Manager

- Personal Business Manager

- Legal Assistant

- Real Estate Executive Assistant

- Family Office Assistant

Experience supporting a founder, attorney, high-volume professional or other demanding executive would be particularly relevant.

You must have:

- Exceptional organizational ability

- The ability to work independently

- Reliable transportation and ability to complete occasional Bay Area errands

- Excellent references

- Excellent written communication

- Strong technology skills

- High discretion and comfort with confidential information

Schedule

Approximately 15–25 hours per week initially, with the possibility of expanding the role for the right person.

This will be a hybrid position involving both remote administrative work and in-person work/errands in the San Francisco Bay Area.

Some flexibility is important because my business involves trials and occasionally unpredictable schedules.

Compensation

$60–$75/hour DOE, with compensation reflecting experience, judgment and demonstrated ability to operate independently.

I am willing to pay well for someone exceptional because the purpose of this role is not simply to complete tasks—it is to reliably remove responsibilities from my plate.

How to Apply

Please send your résumé to caitlin@pptrialtech.com, along with a brief answer to this questions:

What interests you most about this line of work?

Please don't send a generic cover letter. I'm much more interested in understanding how you think, solve problems and take ownership.