Cashflow Diary Virtual Assistant

Please Note: This job is being posted on behalf of J. Massey (cashflowdiary.com) by Great Assistant (www.greatassistant.com). Great Assistant is a company that works with entrepreneurs to match them to assistants.

J. Massey is the CEO of West Egg Enterprises, Inc. dba Cashflow Diary, a real estate education and consulting company focused on short-term rental investing. Through Cashflow Diary, J. has trained thousands of entrepreneurs and built a business centered on helping others create financial freedom through systems, strategy, and operational excellence.

We are looking for a Virtual Assistant who is proactive, steady, highly organized, and works well with a visionary, fast-moving leader who communicates primarily through voice and operates in a high-clarity environment where feedback is frequent, direct, and focused on outcomes. The ideal candidate is comfortable in a straightforward work culture and can adapt to different communication styles, including neurodivergent work environments.

As our assistant, you will support day-to-day operations, help protect our CEO's time so he can stay focused on high-value work, and translate direction into clear priorities, next steps, and follow-through while helping keep operations moving smoothly.

The right person will align with the company's Core Values and be able to bring clarity, structure, and follow-through to a dynamic environment.

Core Values

• Ownership
• Excellence Without Apology
• Clarity Over Cleverness
• Stewardship
• Growth as a Practice

Some of your responsibilities will include:

• Email triage, inbox management, and routing client communications
• Calendar management, including scheduling and calendar confirmations
• Managing incoming requests and setting appointments
• Meeting prep and follow-up, including recaps and action items
• Reviewing daily priorities and helping keep the day on track
• Social media scheduling, posting, and direct message management
• Supporting coaching and consulting calls through preparation and follow-up
• Document creation and formatting
• Research and data compilation
• Project and task coordination
• Travel and logistics coordination
• Assisting with occasional evening and weekend virtual events
• General operations and administrative support

In addition to the above, the ideal candidate must be/have:

• Proactive, anticipates needs, and stays one step ahead
• Accountable, takes ownership of outcomes, not just tasks, and presents solutions and recommendations
• Works independently and handles tasks end-to-end with minimal oversight
• Tracks details through completion and reliably closes loops
• Captures direction quickly, learns fast, and executes without repeated instruction
• Detail-oriented, highly organized, and creates structure
• Calm under pressure, flexible, and adaptable to change
• Comfortable in a fast-paced environment with frequent, direct communication and shifting priorities
• Emotionally mature and steady in a direct work environment
• Assertive, direct, and clear in communication
• Comfortable asking questions or pushing back when needed
• Takes verbal direction and translates it into clear priorities, action, and follow-through
• Understands priorities and protects the bigger picture
• Comfortable supporting a visionary entrepreneur
• AI-fluent and highly comfortable using AI tools in day-to-day work
• Tech savvy and quick to pick up new tools and software
• Professional, polished, personable, and trustworthy
• Growth-oriented, curious, and open to learning new things
• Neurodivergent-aware and respectful of diverse cognitive and communication styles

Experience with the following tools is a plus!

• Google Workspace
• Microsoft Office
• Gmail, Substack, and Kit.com
• Slack
• Motion
• GoHighLevel
• Social media platforms (LinkedIn, Instagram, Facebook, YouTube, TikTok, X, and Pinterest)
• AI tools, with Claude experience as a plus

Position Details

• This is a Remote W2 position
• The position will be 40 hours per week
• Hours are flexible and based on workload and deliverables
• Benefits include:
  • Medical, dental, and vision
  • 3 weeks PTO, Birthday off, and unlimited sick time
  • 15 paid holidays
  • Employer-paid life insurance, AD&D, Short-term and Long-term disability
  • $150/month wellness stipend
  • $1,500/year learning stipend through Fringe
• Availability required for virtual event moderation:
  • Twice monthly on Thursday evenings, and occasionally Wednesdays, from 7:00 pm to 9:00 pm EST
  • One Saturday per month from 11:00 am to 2:00 pm EST
• The pay rate is $35/hr. USD
• You must be able to pass a background check
• We are looking for someone to become a long-term (3+ years) team member

**Please do not contact J. Massey or Cashflow Diary directly; doing so will disqualify your application***