Executive Assistant

I have a problem, and I am looking for the right person to help me solve it.
I am building a legal empire. I run a criminal defense firm in Boca Raton. I own a startup legal technology company. We are growing the firm statewide, and we will be building other law firm brands statewide as well. I teach high school pre-law in Plantation, Florida, five days a week from August through June. I have two boys under seven.
There is a lot of daily driving between all of it, and some days I will need you in the car for part of it. I am also unreachable from 1:30 to 3:45 every school day, and you will run that window without me.
The problem has two halves.
The first is volume. Every one of those things has a calendar, and right now all of them run through me.
The second is follow-through. I am good at deciding, and I am good at starting. What I commit to in a room does not reliably become something that finishes, and nobody's job is to notice that in week three while it is still fixable.
What I am looking for is a proactive problem solver who is genuinely excited to be the right hand while a legal empire gets built. Not someone looking for a stable seat next to one.
What will annoy you about me
I produce more ideas than any human can execute. I will hand you three on Tuesday that contradict the two I handed you Monday. Your job is to help me come to the right conclusion, commit to it, and then execute it.
I am still a trial lawyer by trade. Cross-examining people to figure out whether their recommendations, opinions, and context are accurate and make sense is part of my nature and one of my superpowers. So do not bring me option A or option B and ask which one I like. Bring your recommendation and the reasoning behind it, and be ready to defend it. If you bring me A or B, I will ask which one and why, every time, until you stop. That is not distrust. It is how I get to the right answer.
Some weeks I will not look at what you built. Make it impossible for me to ignore, and say out loud when I am the reason something is stalled.
Your first thirty days
The first thirty days are not about doing. They are about absorbing.
You lead your own onboarding. I will make every introduction and answer every question you bring me, but I am not building you a training plan, and there is no manual. Figuring this out is the first thing I am hiring you to do.
In your first month: figure out every aspect of my life, work, and home. Sit down with my wife. Interview everyone in the firm, top to bottom. Map how all of it connects: the firm, the technology company, the brands we are building, the teaching, the family. Then bring me what you learned, what you found broken, and what you are taking off my plate first.
If you are not curious by nature, this is where you will fail. The people who do this job well cannot stop asking why.
What I hand over, and when
Most people in this seat spend a year waiting on permission that never comes. This one is built the other way. The authority arrives on a schedule, and it is written into the job description before your first day.
Day 1: My personal life. The family calendar and school events, household vendors and projects, appointments, the standing fitness blocks, gifts and personal purchasing. You handle it without checking.
Day 30: My calendar, and committing me to dates inside stated rules.
Day 60: All travel booked inside budget and standards, no pre-approval.
Day 90: Speaking for me in rooms I am not in.
If I fall behind that schedule, say so out loud. That is part of the job too.
Do not apply if
You want a law firm operations role. This seat touches zero cases and manages zero staff.

You want remote or hybrid. This is in the Boca office and on planes with me.

You need consensus before you act.

You need a training plan handed to you. Building your own is the first test.

You are waiting to be told what to do. This seat anticipates. It does not react.

You need regular reassurance that you did well.

You think the personal side is beneath an executive assistant. Half the value of this seat lives there

One more thing
I am building something big, and it is getting built either way. The question is whether the person beside me is pushing it forward or keeping up with it. If reading this made you want in, apply.

Responsibilities:

Own my calendar and my inbox, with the authority to kill things without asking me

Book and manage all travel, business, and family

Prep me for every meeting I walk into so I never arrive cold

Log every person I meet at a conference or in a room, and follow up before they forget who I am

Carry every relationship I start from first contact through signature

Run my personal life in full: school events for two kids, household vendors and projects, appointments, gym blocks, gifts, personal purchasing. One calendar, not two

Keep my Rocks current and hold my numbers. We run on EOS. There is a Scorecard, and there is a Level 10, and you walk me into that meeting with everything already assembled

Flag a Rock that is going to miss in week three, not at the quarterly

Find problems before they reach me and bring the fix with them

Drive with me across Boca Raton, Plantation, and Fort Lauderdale on the days that call for it

Qualifications:

This is for you if
You have run point for a founder and liked it

You cannot stop asking why. You go find the answer rather than waiting to be told

You go looking for problems and solve them before they reach me

You make the call and report it

You notice the number moved before anyone announces it

You can sit across from a trial lawyer, an investor, or a contractor at my house and be equally at ease in all three

You can hold a line against a senior person who wants an hour I do not have

Discretion is most of this job, and you already know that

The words legal empire made you lean in rather than roll your eyes

What you need to have done before
3+ years supporting a founder, CEO, or owner directly

Real authority in a prior seat: booking travel, committing calendar, speaking on someone's behalf

A track record of following up on relationships without being reminded

Experience supporting an executive's household or family logistics, with references who can speak to your discretion specifically

Hands-on experience running EOS or a comparable operating system: Rocks, Scorecard, Level 10, IDS. Run it, not read about it

Non-negotiables
In person in Boca Raton. Not remote, not hybrid

Willing and able to travel with me

Comfortable with significant daily driving across South Florida

Culture Index survey completed before any interview

About Company
We Take Care of Our People:
Competitive pay based on experience.
A generous number of vacation days each year.
At Rossen Law Firm, we're more than just a team of experienced criminal defense lawyers. We're a family that cares deeply about people, not just cases. Our firm has built its reputation on trust, integrity, and relentless dedication to those we serve. We believe in ensuring justice and treating each client with the personal attention and compassion they deserve.
We love helping good people when something wrong happens. Our legal team understands what clients are going through, and we are committed to producing outstanding results.
With offices in Fort Lauderdale, Boca Raton, and throughout South Florida, Rossen Law Firm is a high-end criminal and DUI defense firm. Rossens 1000+ 5-star reviews tell the story of a criminal defense law firm that truly puts its clients first.
Rossen Law Firm is an equal-opportunity employer.

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