Bookkeeper Executive Assistant

Description

Work Arrangement:
Remote, preferably with an overlap of 2 hours PST (but not necessary)

Job Type:
Independent Contractor, Full-time

Salary Range:
Competitive salary

Work Schedule:
Monday to Friday, 8:00 AM – 5:00 PM
PST
, 40 hours/week (flexible, as long as coverage is consistent and results are delivered)

Locations:
Remote, open to candidates from the Philippines, Africa, and Latin America

About Pearl Talent:

Pearl works with the top 1% of candidates from around the world and connects them with the best startups in the US and EU. Our clients have raised over $5B in aggregate and are backed by companies like OpenAI, a16z, and Founders Fund. They're looking for the sharpest, hungriest candidates who they can consistently promote and work with over many years. Candidates we've hired have been flown out to the US and EU to work with their clients, and even promoted to roles that match folks onshore in the US.

Hear why we exist, what we believe in, and who we're building for:

Why Work with Us?

We're not just another recruiting firm—we focus on placing candidates with exceptional US and EU founders who prioritize the long-term success of their team members. We also provide retention bonuses at 3, 6, 9, and 12 months, as well as community-driven benefits like an annual retreat.

Role Overview:

As an
Executive Assistant
, you'll act as the client's right hand—removing administrative load, managing calendar chaos, overseeing bookkeeping cross-checks, and keeping key operational processes moving. This role combines strategic assistance, personal project coordination, and operational support, ensuring the client can focus on high-impact consulting and clinical work.

Your Impact:

Your work will create calm in complexity. By anticipating needs, structuring workflows, and maintaining operational excellence, you'll make a measurable difference in the client's ability to serve patients, legal institutions, and mental health providers. You'll transform administrative processes into streamlined, proactive systems—amplifying the overall impact of the client's mission-driven work.

Core Responsibilities:

1. Billing & Bookkeeping Oversight

• Cross-check entries from the bookkeeper
• Flag inconsistencies
• Generate summary reports

2. Calendar & Scheduling Management

• Manage complex scheduling across clients, legal teams, and practitioners
• Anticipate and resolve conflicts in real time
• Maintain alignment between personal and professional calendars

3. Document Drafting & Proofing

• Format legal and forensic documents, ensuring clarity and compliance
• Proofread for grammar, structure, and citation accuracy (APA preferred)

4. Daily Executive Support

• Run short accountability huddles
• Set reminders
• Organize and prioritize the client's task queue

5. Inbox & Task Management

• Triage and respond to basic client inquiries
• Flag urgent issues
• Ensure follow-ups are tracked

6. Operations Coordination

• Execute SOPs for billing, reimbursements, and insurance workflows
• Recommend process improvements where needed

7. HR-Adjacent Projects

• Build staff rosters
• Setting up payroll
• Track benefits usage, staff documentation, and credentialing

8. Personal & Business Admin Support

• Book travel, hotel reservations, and personal appointments
• Manage errands and personal administrative tasks

Requirements

Must-Have:

• Highly organized, proactive, and self-managed
• Experience with bookkeeping and cross-checking financial data (QuickBooks or similar)
• Excellent written communication, research, proofreading skills
• High discretion, trustworthiness, and HIPAA-level confidentiality awareness
• Strong Microsoft Office proficiency (especially Excel, Outlook, and Word)
• Able to own and execute personal and business tasks without excessive handholding

Nice-to-Have:

• Background supporting clinical, forensic, legal, or healthcare professionals
• Familiarity with billing cycles and credentialing, specifically in mental health clinics
• Prior experience in legal proofing, APA citation formatting, or medical reports
• Project management experience using Excel, Notion, or similar tools

Benefits

• Monthly Compensation:
  Competitive salary
• Remote Work:
  Fully remote, flexible work hours
• Generous PTO:
  15 days annually
• Holiday Adherence:
  U.S. holiday calendar
• Executive Coaching:
  Access to coaching and professional growth resources
• Infrastructure & Support:
  Fully managed payroll, HR, and compliance