PIM Tax Services is a boutique tax practice primarily serving active-duty military and veteran families. We’re growing, and we need an Executive Assistant to support Paul Allen, founder of PIM Tax Services and founder of the Military Qualified Financial Planner –(MQFP®) Certification Program. 

The Role 

This role touches everything: calendar management, inbox organization and prioritization (triage), travel booking, client document handling, and drafting responses on Paul’s behalf to an audience of clients, team members, and other financial professionals. You’ll move between strategic support and hands-on execution, adapting as the day requires. Judgment, problem-solving, and attention to details counts for more here than any single software tool skill. We can teach systems; we can’t teach discretion. 

We’re a small, highly collaborative team working across both virtual and in-person settings. The person in this seat communicates proactively, works independently with light supervision, and treats every request, whether from Paul or a teammate, as an open loop until it’s closed. 

Who Thrives Here 

  • Self-motivated in a hybrid (primarily office + occasional remote) setting with minimal oversight 
  • Sharp attention to detail and strong written communication 
  • Builds processes, systems, and structure to manage complexity 
  • Adapts quickly, picks up new tools fast, and takes initiative without being told 
  • Finds genuine satisfaction in a long to-do list and the follow-through to clear it 
  • Reads what someone actually needs, not just what they asked for 
  • Favors direct communication and takes feedback as readily as gives it 

Prior executive assistant experience supporting a founder or working at a small business is preferred. Customer service or operations backgrounds with a demonstrated record of ownership and follow-through are also welcome. A genuine drive to help people get what they need to succeed translates directly to this role. A passion to serve the military community  

If you’ve taken either assessment: traits that tend to fit include high Follow Thru on the Kolbe Index and high S and/or C on DiSC. Not required knowledge, just useful context. 

Expected Qualifications 

  • Authorized to work in the US and able to pass a background check 
  • Outstanding grammar, writing, and editing skills 
  • Genuine interest in personal finance, tax preparation, and military life 
  • Working knowledge of military life and terminology (PCS, TDY, TSP, DFAS, LES, SGLI, CZTE, SBP) 
  • Customer service experience (prior executive assistant experience a plus, not required) 
  • Strong emotional literacy: naming and processing emotions, handling feedback and conflict directly and constructively 
  • Independent task and calendar management, with the judgment to know when to ask for help 
  • Comfortable in a small, hybrid team; resourceful and willing to wear multiple hats 
  • Tech-savvy with strong problem-solving instincts 
  • Proficient with Microsoft Office (Outlook, Teams) and comfortable exploring AI tools 
  • Uncompromising attention to detail and absolute discretion with confidential information

Responsibilities (Training Provided)  

This position initially supports Paul’s work at PIM Tax Services, with responsibilities expanding over time to include MQFP and other roles. The Executive Assistant will: 

  • Manage Paul’s calendar across three organizations, coordinate meetings, protect focus time, identify scheduling conflicts, and ensure he is prepared for upcoming commitments. 
  • Coordinate travel arrangements, itineraries, reservations, meeting logistics, and related documentation. 
  • Monitor and organize Paul’s inboxes, distinguish urgent matters from routine correspondence, and maintain a reliable follow-up system. 
  • Draft, proofread, and format routine emails, letters, announcements, and other communications for Paul’s review or approval. 
  • Track requests, commitments, deadlines, and delegated work until each item is completed or intentionally closed. 
  • Prepare concise daily or weekly summaries of priorities, upcoming meetings, unresolved questions, and items requiring Paul’s attention. 
  • Organize information from emails, meetings, documents, and conversations into clear, accurate, and current summaries. 
  • Prepare meeting agendas, gather relevant background materials, take notes when requested, and distribute action items and follow-up reminders. 
  • Serve as a communication link between Paul, team members, clients, vendors, professional colleagues, and other stakeholders. 
  • Handle sensitive personal, client, business, tax, financial-planning, and compliance information with absolute discretion. 
  • Maintain organized electronic and physical records using consistent file names, folder structures, and document-retention procedures. 
  • Learn and maintain working knowledge of the systems used across the three organizations, including Microsoft Outlook, Teams, and organization-specific client and workflow platforms. 
  • Identify incomplete information, conflicting instructions, approaching deadlines, and potential problems before they require Paul’s direct intervention. 
  • Develop checklists, templates, standard operating procedures, and other systems that make recurring work more consistent and efficient. 
  • Assist with special projects, research, event coordination, presentations, forms, spreadsheets, and other administrative needs as they arise. 

Compensation and Logistics 

  • Part-time to start, with growth toward full-time within a year 
  • Primarily in the Virginia Beach office with occasional remote work as needed 
  • W-2, $22-24/hour based on experience, plus bonus potential 
  • Currently supports PIM Tax, with the role envisioned to eventually support Paul across multiple organizations  
  • Multi-part interview process  
  • Initial written interview after resume submission 
  • Virtual interview 
  • Paid sample work 
  • Final interview  
  • Expected start date in October  

Ready to take the first step?

How to Apply

Applications close August 24th. First-round interviews follow shortly after. 

  1. Complete this Executive Assistant Application with a few background questions and upload your documents as PDFs. 
  1. Submit a resume and cover letter. In the letter, name three qualities or experiences that make you a fit for this role and for PIM Tax’s mission. Specifically outline why you are interested in working HERE.  

Skip the boilerplate. We want to know what excites you about this role, not a polished version of you. 

 

PIM Tax Services provides equal employment opportunity to all applicants without regard to race, color, religion, sex, national origin, age, disability, or any other characteristic protected by law.