How to Manage a Small Law Firm

Executive Assistant to the CEO/Founder

Miami-based, 50-something, entrepreneur seeks experienced, outgoing and extremely organized tech-savvy Executive Assistant to work full time from our office in South Florida.

We have a fast-growing and highly-entrepreneurial personal development & professional services company that helps some of the fastest growing entrepreneurs in the country manage their business, their mindset, and navigate their way.

Our core company employs more than 120 full time employees, has been named an Inc. Magazine “Best Places to Work” and has been named one of the 5000 fastest growing privately held companies in the country every year since we first debuted on the list in 2016. We service more than 600 clients and get nearly 1/3 of our new business by way of referral so we must be doing something right. With that being said, we are still “building the bicycle” as we ride it to keep-up with the fast-paced growth of our company. Our CEO/Founder requires an experienced and detail oriented Executive Assistant to make his professional and personal life easier. The candidate we seek has criteria, the intelligence, imagination and experience to “see around corners” and anticipate our founder’s personal and professional needs.

The successful candidate will be able to “pave the way” for our founder to focus on continuing to grow the company and keep him out of his own way. As the company grows and changes we anticipate his needs will too. The right candidate should have the experience to anticipate what those needs are likely to be and have enough flexibility to grow and adapt with the job.

We are looking for a long-term relationship with the right candidate. He or she should be a thoughtful and detail-oriented person, extremely organized and experienced with project/event management with good taste and high-standards. Very tech-savvy. If you are not very tech savvy our founder will not know because he isn’t tech savvy at all but the rest of our team who desperately want our founder to have the support of an amazing EA… we’ll know. So if you’re not very tech savvy please don’t try and bluff your way through this interview process because we won’t let you.

We are looking for a clear communicator (written and verbal) to help our founder keep up with our nearly exponential growth of customers, vendors and staff. Speaking of staff, separate and apart from the rest of the company, our founder has his own “Skunk Works” which you will be part of. This staff is headed by our founder’s own Chief of Staff, and includes a personal assistant, publicist, librarian/file clerk, videographer/editor, social media manager and hopefully soon, YOU.

Above-average-ability to learn and adapt as our business grows and takes on new dimensions. The successful candidate should know how to “get things done” with minimal supervision and doesn’t watch the clock…ever! In fact, we’d love to find the pro-active individual who can see the big picture and then make recommendations for all the nitty-gritty details to make things better instead of waiting around for instructions.

Good sense of humor. We take our business very seriously around here, but not ourselves.

Your compensation will be positively-affected by your willingness and ability to think outside the box (we hate that cliché too but it fits) and effectively identify opportunities, propose and then execute solutions to increase the leverage, productivity, profitability, and effectiveness of our founder. This may include investing your own time to learn and remain familiar with our business and how our founder interacts with it.

Part of your job description is also to be patient with our growing pains. This can be the best job you ever had or the most frustrating depending on your flexibility, team-spirit, commitment to our mission and your realistic expectations about what it’s like to work in a fast-paced growing business. If you have always dreamed of working in a highly-entrepreneurial and fast-paced business environment because you imagine it to be like one of those exciting montage scenes from a cheesy movie from the 1980’s, please, please, please do not apply for this job. On the other hand, if you have worked in a fast-paced, fast-growing, highly creative, things are always changing, priorities are always evolving, get-it-done environment and felt energized, inspired, and appreciated for your contributions… In other words, if you’re a grown-up and this job description resonates with you we would welcome the opportunity to meet you and if we may be so bold, you’d probably really like meeting us too.

The is a full-time position but with flexibility and freedom earned by performance. You need to run to the doctor, take care of some personal business or even go out of town for a family emergency on short notice? No problem so long as you take responsibility for things getting done. This is a double-edged-sword for slackers but we imagine great news for the right person...

Duties and responsibilities:

  • Keep our founder’s projects & project files organized and in front of him so he has what he needs at his fingertips when he needs what he needs to do what he does which includes staying on top of his goals, projects, and priorities.
  • Liaise between the founder, his personal staff, senior leadership of the organization, and a myriad of business relationships, potential business relationships and an ever-growing group of very nice people (and some who aren’t so nice) vying for his time.
  • Manage founder’s calendar & ever-changing schedule which usually extends 12-18 months into the future. This means being strategic about the calendar and not just dumping-in a whole bunch of appointments.
  • Handle routine correspondence in your own voice on founder’s behalf, not trying to pretend to be him. This includes responding to emails, proactively seeking information to support the calendar and project initiatives to keep things moving.
  • Manage complex and ever-changing travel arrangements (primarily domestic) which includes flights (private and commercial), hotel, car service, etc.
  • Help founder maintain personal and professional relationships by strategically and proactively sending thank you notes, gifts, books, etc.
  • Maintain a running list of all current and future deliverables so nothing falls through the cracks.
  • Keep founder apprised of short-term obligations as well as long-term implications of expedient decisions.
  • Coordinate with founder’s personal assistant to be sure the PA knows where the founder needs to be, what he’s supposed to be doing when he gets there, and making sure the PA makes sure the founder has what he needs (the right file, the right information, a rhinoceros, etc) to be effective at all times.

Qualifications:

  • 4 year degree from accredited college or university – we care less what your degree is in than that you have demonstrated the commitment and organization to complete it. Better yet, impress us with what you have accomplished and convince us not to care about your formal education.
  • Minimum of 5 years related experience supporting highly-entrepreneurial, fast-paced and disorganized individuals.
  • Excellent references. Yes, we really are going to check your references.
  • Demonstrated ability to prioritize executive tasks and multi-task effectively.
  • Strong communication skills, both written and verbal.
  • Very tech-savvy (have we made this part clear enough) including proficiency in all Microsoft Office and Mac products. Be enthusiastic about new technology and constantly on the look-out for ways to leverage technology to make life easier. And be able to assist founder in day-to-day tech issues (he is about a 5 on a 1-10 tech-savvy scale).
  • Demonstrated ability to organize complex meetings between people with busy schedules, travel between time zones, getting hotels, restaurants, and other venues to say “yes” when they would normally say “no” to mere mortals.
  • Professional mindset and the utmost discretion
  • Ability to work independently and troubleshoot with limited input & supervision
  • Detail oriented with exceptional organizational skills
  • Flexibility with hours and scheduling; available to work overtime as needed
  • United States work authorization

Qualities/Attributes of Preferred Candidate:

  • Self Starter/Responsible/Work Independently
  • Diplomatic/Tactful
  • Inquisitive
  • Assertive
  • Non-judgmental
  • Flexible
  • Problem Solving and Analytical Ability
  • Strong Communication Skills
  • Sociable & has a sense of humor
  • Tolerance for ambiguity
  • Comfortable working in a growth environment

Next Steps:

This is a critically important position and it takes more than one person to manage all of the details of our founders life so we need a team player.


If you’re still reading this and you’re put-off or annoyed, this is DEFINITELY not the job for you. If you’ve already called me a few names in your head (or out loud), please don’t waste my time or yours by applying.

If by now you’re thinking “ahhh, someone who thinks like I do!” please apply! If you’re going to apply, you need to do the following (in order):


STEP 1: Submit your resume, cover letter, and references by email to recruiting @ howtomanage.com

The subject line of your email should read “EA – Your Name spelled backwards” (you’d be shocked at how few people read instructions so this is our first screening test).


In your email answer the following questions in bullet-point form. It’s ok to have an opening and/or closing paragraph, but these are the specific questions we want answered.


a. Why are you a good fit for this job? In other words, what do you bring to the table?
b. Why is this job a good fit for you? In other words, what does this job offer that would meet your professional goals?
c. What compensation are you expecting and why?

d. What is your favorite book or movie that you have read/watched in the last 12 months and why?

STEP 2: Complete the Predictive Index Behavioral and Cognitive surveys

This is a recruiting tool specifically designed to develop high-performing teams by matching a candidate’s innate strengths to the requirements of the role.

Set aside 20 minutes in a quiet place to complete these surveys. Be honest and thoughtful in your responses. Don’t try to predict what you think we want to see or you may just end up in a job you hate…

You will receive a copy of your behavioral pattern which can be used to quantify and describe your own behavioral patterns and is an extremely insightful report for you, regardless of whether we are a good match for each other.

STEP 3: Complete a Technical Quiz

Once we receive your resume and Predictive Index survey and determine that you are a fit for our organization you will be sent a technical quiz to allow you to effectively demonstrate that you have the skills to do the job.

This quiz will take a few hours and is less of a “quiz” per se than showing us your work in action.

STEP 4: Interview rounds

In case you haven’t figured it out by now, this is a critically important role to our organization, and we take the hiring process very seriously. We invest a tremendous amount of time in both the recruiting and onboarding for this role and we don’t want to waste your time, nor do we want to waste ours by making an avoidable mis-hire.

Successful candidates will meet with several members of our Executive team to ensure we have a solid cultural fit – for us and for you. These are the people you will be working with day-in and day-out so we want to ensure that there is chemistry.

~ The RJon Robins team