Virtual assistants aren’t just for inbox zero and calendar Tetris anymore.
The savviest entrepreneurs we know aren’t hiring task-doers—they’re recruiting strategic partners in disguise.
But most people don’t know how to find (or leverage) one. They burn out trying to “manage a VA” instead of empowering someone who can think, anticipate, and take ownership.
This blog breaks down how founders are building leverage through smarter delegation—and what kind of assistant actually scales with you.
Spoiler: it’s not the cheapest one on Fiverr!
Pro Tip: If you want to skip the trial-and-error phase of finding executive-level support, schedule a consultation with ProAssisting to see how fractional executive assistants can accelerate your business growth.
Why Entrepreneurs Need More Than Just a Virtual Assistant?
Entrepreneurs operate in a fundamentally different way from traditional executives.
While a corporate executive might focus on one company with established processes, entrepreneurs often:
- Work across multiple ventures,
- Deal with constant pivots, and
- Face situations that require quick thinking and adaptability.
The Reality of Entrepreneurial Work
Context switching is the entrepreneur’s biggest challenge.
One minute you’re discussing marketing strategy for your SaaS product, the next you’re handling supply chain issues for your e-commerce business.
This constant mental juggling requires support that goes far beyond simple task completion.
Traditional virtual assistants aren’t built for this reality. Most VAs are trained to handle specific, repetitive tasks like:
- Data entry and basic administrative work
- Social media posting and content scheduling
- Basic customer service responses
- Simple research tasks
What Entrepreneurs Actually Need
A virtual assistant may be a good partner for an entrepreneur in the beginning of their relationship, or the beginning of their journey, or when a business is just an idea.
But most entrepreneurs need someone who can think like a business partner.
When you’re in the middle of a crucial investor call and suddenly remember you need financial projections prepared for tomorrow’s board meeting, you need an assistant who can:
- Understand the urgency,
- Gather the necessary data, and
- Create professional materials without requiring step-by-step guidance.
The spectrum of assistant support has changed significantly.
Today’s executive support options range from:
- Same time zone international VAs
- $5-per-hour overseas virtual assistants
- US-based virtual assistants at $11.54-$33.89 per hour (averaging $24 /hour)
- US-based fractional executive assistants with corporate experience
- Full-time executive assistants commanding six-figure salaries
- Full-time administrative assistants
- Chief of staff level support
Smart entrepreneurs recognize that their first hire should be high-impact support. Many successful business owners credit their executive assistant as their most valuable team member.
This isn’t because they handle the most tasks, but because they free up the entrepreneur’s mental bandwidth for strategic thinking and decision-making.
What Most Virtual Assistants Can’t Do for Founders?
The fundamental problem with most virtual assistant services comes down to basic economics.
When virtual assistant companies charge $40-60 per hour but pay their assistants only $20-26 per hour as independent contractors, they’re not attracting experienced executive assistants with proven track records.
This compensation model creates a problematic dynamic.
Virtual assistants in these arrangements typically work with multiple clients simultaneously to make ends meet. Some juggle 8-10+ different clients, which means your “urgent” request competes with everyone else’s priorities.
The results speak for themselves:
- Generic, one-size-fits-all solutions
- Slow response times during critical moments
- High turnover rates as VAs seek better opportunities
- Lack of investment in understanding your specific business
What makes this even more challenging is that founders need team players who can touch many different aspects of the business and can represent them at a very high level because they are a reflection of the company and the founder.
Unlike traditional employees who focus on specific departments, entrepreneurs need full-time or even part-time executive assistants who can seamlessly move between:
- Financial coordination and reporting
- Personal scheduling and life management
- Marketing tasks and campaign coordination
- Customer service issues and relationship management
When it comes to representation, this becomes even more critical for entrepreneurs than corporate executives.
When you’re building a brand and establishing credibility in your industry, every interaction counts.
Your assistant becomes an extension of your professional reputation.
A poorly trained VA who responds slowly or provides subpar communication can damage relationships you’ve spent months building.
Beyond representation issues, complex project management falls outside most VAs’ capabilities.
Entrepreneurs often need support for initiatives that:
- Span weeks or months
- Need strategic thinking and adaptation
- Evolve based on changing business needs
- Require coordination with multiple stakeholders
The batching problem significantly impacts response times as well. Many virtual assistant services encourage their workers to batch similar tasks together for efficiency.
This means your email might not get answered until “email time,” and your research request waits until “research time.”
For entrepreneurs who need immediate responses to capitalize on opportunities, this system creates costly delays.
What Sets a Corporate-Trained Assistant Apart From the Rest
Corporate-trained assistants operate at a fundamentally different pace. In corporate environments, especially compared to non-profit or educational settings, the pace is usually faster.
These assistants develop the ability to process information quickly, prioritize effectively, and deliver results under tight deadlines.
Training makes the crucial difference. Corporate assistants receive ongoing professional development in both hard skills and soft skills departments:
- Advanced Technology Proficiency: Corporate assistants master complex software systems, project management tools, and communication platforms that entrepreneurs rely on for business operations.
- Professional Communication Standards: They learn to craft executive-level correspondence, manage sensitive communications, and represent their principals with appropriate tone and authority.
- Valuable Knowledge Base: Experience provides a knowledge base that the client or the principal can mine and get from them, which can be applied to their business. A corporate-trained assistant has likely worked with multiple executives across different scenarios, seen various business challenges, and learned effective solutions that they can apply to your unique situation.
- Project Management Methodologies: Corporate training includes systematic approaches to handling complex initiatives, coordinating stakeholders, and meeting critical deadlines.
- Proven Consistency: If an assistant has been corporate trained and has been in a company for a long period of time, that consistency speaks to the work ethic and allows you to ask questions about their abilities. When you see an assistant who has stayed in a corporate role for several years, it demonstrates their ability to build long-term partnerships with demanding executives and grow within their position.
- Emotional Intelligence Development: Corporate environments teach assistants to read situations, adapt their communication style, and build relationships across different personality types and organizational levels.
- Speed and Efficiency: Corporate environments demand quick turnaround times and efficient processes. These assistants learn to handle multiple priorities simultaneously while maintaining high-quality standards, which translates perfectly to the fast-paced entrepreneurial environment.
There is something to watch out for, though. If someone’s been in a role for a long period of time and they’re looking to make a move, you need to assess their adaptability.
You need to determine if they’re open to embracing the entrepreneurial environment’s dynamic nature and handling diverse responsibilities.
You want someone who’s adaptable to varied business needs and comfortable working beyond traditional corporate boundaries.
How to Identify an Assistant Who Truly Understands Your Business
Business understanding goes beyond industry knowledge. You have to ask them the right questions.
Sometimes getting an assistant who understands your business and industry can be helpful.
But we would also caution not to overlook an assistant who doesn’t have an understanding or knowledge of your business or your industry, even though they’re an excellent executive assistant.
Being an assistant, an executive assistant is industry agnostic and principle agnostic. Great executive assistants are going to get up to speed quickly.
They do outside training and research beyond anything that you’re doing from an onboarding perspective to get up to speed in your business and industry.
- Focus on Learning Initiative: Great assistants will go beyond your onboarding materials to research your industry. They understand your competitors and market position. They familiarize themselves with your business model and revenue streams. Most importantly, they take initiative to educate themselves rather than waiting for explanations.
- Assess Strategic Thinking: During the interview process, pay attention to whether candidates ask thoughtful questions about your business challenges. Do they inquire about growth plans and operational needs? Do they suggest potential improvements based on their experience? Look for candidates who demonstrate understanding of how their role impacts business outcomes.
- Evaluate Business Fundamentals: An assistant who understands financial statements and budget management can adapt to almost any business. The same goes for those who know project management principles and methodologies. Customer relationship management systems and basic marketing and sales processes are also key assistant qualities. These foundational skills transfer across industries and business models.
- Listen to Communication Style: Pay attention to how candidates discuss their previous roles. Do they describe how their work contributed to business outcomes? Do they understand the connection between daily activities and broader objectives? Look for specific examples of problem-solving and initiative. They should demonstrate knowledge of their previous industry and company.
- Watch for Red Flags: Be cautious of candidates who focus only on tasks they completed. Avoid those who are unable to explain the business impact of their work. Watch out for candidates who lack understanding of their previous company’s goals. Generic responses that could apply to any role are another warning sign.
- Check References Strategically: While many hiring managers skip reference checks, they can reveal important information about how an assistant handled challenges, grew in their role, and contributed to their previous organization’s success.
Top Virtual Assistant Tools Every Entrepreneur Should Use
Think about tools as part of a technology framework rather than individual solutions. The specific platforms matter less than having systems that work together seamlessly.
Your assistant needs to understand how different tools connect and support your business operations.
Content Management Systems
Content Management Systems form the foundation of your online presence:
- Website platforms like WordPress or custom solutions
- E-commerce systems like Shopify or WooCommerce
- Basic technical maintenance and content updates
- Coordination with developers for complex changes
Project Management Platforms
Project management systems create alignment between you and your assistant.
Popular options include:
- Monday.com for visual project workflows
- Trello for simple board-based organization
- Asana for task tracking and team collaboration
- ClickUp for comprehensive business management
There are also Notion, Airtable, and Basecamp among the popular options!
The key is choosing one system and using it consistently rather than jumping between multiple platforms.
Communication and Scheduling Tools
Email, contacts, and calendar integration enable seamless communication.
Popular platforms include:
- Gmail or Outlook for email management and filtering
- Google Calendar or Outlook Calendar for scheduling coordination
- Calendly or Acuity for automated booking systems
- Slack or Microsoft Teams for internal communication
- Zoom or Google Meet for video conferencing
The micromanagement trap destroys the value of assistant support.
If you’re still approving every email and double-checking every calendar entry six months into the relationship, you’re creating more work for yourself rather than saving time.
The goal is to train your assistant once and then trust them to execute.
Flexibility in tool adoption shows professional maturity. The best assistants adapt to whatever systems you’re already using rather than insisting you switch to their preferred platforms.
They recognize that disrupting your established workflows creates more problems than it solves.
How ProAssisting Supports Entrepreneurial Vision
At ProAssisting, we like to meet our clients where they are and use the programs and technologies that they’re leveraging. We become experts in that vision before offering up any suggestions.
That’s how we view the executive assistant relationship. We put the least amount of stress and pressure on a client to adjust or acquiesce to an assistant. It should be the other way around. The assistant needs to meet the entrepreneur and principals where they are.
- We Assess Your Current Business Stage: Different entrepreneurs need different levels of support. Some early-stage founders benefit from basic task-based support, while scaling businesses require executive-level strategic partnership. We help determine the right fit rather than pushing everyone toward the same solution.
- Timing Matters More Than Most People Realize: Bringing on fractional executive assistant support when you only need task-based help creates unnecessary costs. Conversely, trying to scale with basic VA support when you need a strategic partnership creates bottlenecks that slow growth. Flexible part-time executive assistant support that scales with your business is a good middle ground in such instances.
- Our Three-to-One Ratio Ensures Quality: Unlike virtual assistant services that spread their workers across 5-10 clients, our ProAssistants work with a maximum of three clients. This focused approach ensures prompt responses and personalized attention.
Ready to experience the ProAssisting difference? Hire a U.S.-based executive assistant who understands your entrepreneurial vision.
Want to learn more about maximizing your assistant partnership? Download our free book “The 29-Hour Work Day” to discover the five performance multipliers that can transform how you work with executive-level support.
Frequently Asked Questions (FAQs)
Let’s address common questions entrepreneurs have about virtual assistant services and executive-level support:
Do Entrepreneurs Really Need Executive-Level Virtual Assistants?
The answer depends entirely on where you are in your business timeline and current season.
If you’re just starting out with a new business idea, basic virtual assistant support might work perfectly. You need help with simple tasks and don’t yet require a complex business partnership.
However, once you have employees and revenue, the equation changes. When your team members get pulled away from their core responsibilities to handle tasks that a high-level assistant could manage, you’re creating inefficiencies throughout your organization.
This is when transitioning to executive-level support makes financial sense.
Growth creates natural transition points:
- Basic VA support → Fractional executive assistance
- Fractional support → Full-time in-house executive assistant
- Each stage serves different needs and budgets
How Is a Strategic Assistant Different From a VA?
Strategic assistants think beyond task completion to business impact. Virtual assistants focus on executing specific instructions. Strategic assistants consider how their work fits into your broader business objectives and can suggest improvements or alternatives.
Can ProAssisting Work with Early-Stage Entrepreneurs?
We can work with early-stage entrepreneurs, but timing and fit matter. Our assessment process during the free consultation call determines whether:
- Fractional executive assistant support matches your current needs or
- If you’d be better served by other solutions.
If you need basic task-based support that overseas VAs can handle effectively, we’ll recommend more appropriate options that fit your budget and requirements. Our goal is to find the right solution, not forcing a sale.
What Tasks Can a High-Level Assistant Take Over for a Founder?
The five performance multipliers framework covers the full scope of executive assistant capabilities.
These include:
- Project management,
- Business partner functions,
- Chief of staff responsibilities,
- Assistant/scheduler duties, and
- Personal assistant tasks.
Conclusion
The biggest mistake entrepreneurs make isn’t hiring the wrong assistant—it’s settling for someone who can’t grow with their business. ProAssisting bridges this gap with elite-level support at fractional (50-80% less than hiring in-house) costs.
Our ProAssistants bring five years minimum experience from globally recognized brands like J.Crew, Fidelity, and Oracle. With 75% of your monthly retainer going directly to your assistant, we attract top talent who build lasting partnerships, not just complete tasks.
Get started with ProAssisting and experience what true executive-level partnership looks like for your entrepreneurial journey!
