Should I Hire a Virtual Assistant (VA), an Online Business Manager (OBM), or a Chief Operating Officer (COO) for My Online Business?

Aug 5

Last year, I made a huge mistake.

When I start working with clients in my capacity as an Online Business Manager (OBM), we typically begin with what I call the Business Systems Overhaul: I take inventory of their current operational gaps, investigate how we might do things more efficiently, and implement long-term solutions to streamline their business systems and processes.

But in this particular scenario, I didn’t do that. I was so excited about the possibility of taking on my first long-term OBM client, I was determined to meet this business owner’s needs and priorities (even if they didn’t honor my own process or zone of genius):

She wanted support in developing and launching a new program, without investigating her current operational systems
She needed help with administrative tasks and customer service issues, but wasn’t sure where we’d draw the line between the role of a Virtual Assistant and an Online Business Manager
She wanted someone to take ownership of the finances—cutting business expenses, communicating with her bookkeeper, and helping her take regular owner’s distributions

Transparency is a key tenet of trauma-informed care that I hold myself to. Buuuuuuut—and I’m not proud of this—I really wanted this to work out. I wanted to be a REAL OBM, even if that meant “getting out of my comfort zone” (what I now recognize to be: “operating outside of my scope of practice + expertise”). I couldn’t untangle whether my apprehension meant I was being too rigid, or if I was experiencing Imposter Syndrome, or if I was truly outside of my integrity. Being a solpreneur is weird (and this experience is a big reason I chose to seek mentorship this year).

This potential client, too, wasn’t exactly sure what she was looking for: Is it time to bring on a COO? What exactly is the role of an OBM? What’s the difference between these and a VA? Why are there so many acronyms, and what do they all mean?!

It’s been a source of confusion for ME as I transitioned from supporting online business owners as a Virtual Assistant to an Online Business Manager. No wonder it’s nearly impossible when you’re a Founder or CEO with 64 other priorities and a to-do list as long as your left leg.

But here’s why it’s important to get clear before hiring:

Strategic investment. Understanding the differences between VAs, OBMs, and COOs (especially in the online business space) can help you find the right fit for your specific needs and business stage, instead of stalling out your progress and wasting money trying to fit a square peg into a round hole.

After a few awkward months, this client and I parted ways. We realized that she really didn’t need an OBM at this stage of her business and I couldn’t offer the specialized financial expertise she was craving. We completed a few projects. It’s not a “no” forever. But for now, it’s quite simply just not a match (and that’s okay! Normalize exploring multiple options and selecting the best one for your business).

Want to avoid this experience altogether? I present to you a humble guide about Virtual Assistants (VAs), Online Business Managers (OBMs), and Chief Operating Officers (COOs).

What is a Virtual Assistant (VA)?

This is often the first team member that online business owners hire to support them with specific, well-defined tasks. A VA’s role is to free up your to-do list from repetitive and often-boring action items. They follow your instructions to carry out well-established procedures or support projects that always seem to fall off your list of priorities.

When to Invest in a VA:

You need someone to take on the clear, repeatable tasks that are cluttering your schedule
You’ve documented your process or can easily explain what needs to be done
You’re ready to free up 5-15 hours per week of routine work
You’re happy to invest $25-$45 per hour (depending on skills and location)

Common Virtual Assistant Responsibilities:

Email management and customer service
Social media posting and basic content creation
Data entry and calendar management
Basic graphic design and administrative tasks

What VAs DON’T Do:

Strategic planning or business development
Remote team management
Systems creation (from scratch)
Decision-making or problem-solving without clear guidance

You Might Need More Than a VA If...

You find yourself constantly explaining context and struggle to articulate clear instructions
The tasks or projects you want to assign require business judgment calls
You need someone to manage your team or other contractors
You're spending more time managing than the tasks themselves would take to complete (”It’ll be less complicated if I just do it myself!”)

What is an Online Business Manager (OBM)?

While a Virtual Assistant is a helper who executes the tasks you assign, an Online Business Manager is your strategic operations partner-in-crime. Their core function is to manage and optimize the behind-the-scenes of your business—your systems, your projects, and your team. They don’t just check off to-do list items, but think about the business holistically and take ownership of how the outcomes of these actions feed into the bigger picture.

When to Invest in an OBM:

Your business has multiple moving parts that need coordination and systematization
While not strictly required, you probably want to be making $100K+ per year in revenue
You’re ready to step out of day-to-day business operations and hand over the reins of project management and remote team management to a trusted partner
Things are going “well enough,” but you’re far from the work-life balance you crave
You want someone who can support your business strategy, not just complete easily-defined tasks
You have your sights set on significant business growth, more easeful + effective marketing funnels, and/or successful launches for your products, programs, or services.
You’re happy to invest $2,000-$8,000 per month (depending on skills and experience), which will pay for itself through increased efficiency and revenue

Common Online Business Manager Responsibilities:

Systems & Process Management: Auditing your existing business operations for inefficiencies, implementing long-term tech and workflow solutions, and documenting business systems and processes in Standard Operating Procedures (SOPs) for easy remote team communication
Project Management: Taking ownership of timelines, resources, deliverables, launches, projects, team members, and contingency plans
Remote Team Management: Hiring and developing the team, onboarding new contractors or employees, facilitating communication, monitoring performance, and creating systems of accountability
Strategic Operations Support: Tracking business metrics, analyzing Key Performance Indicators (KPIs), recommending operational improvements for growth, managing tech tools, and supporting you as the Founder/CEO/Business Owner with high-level business decisions

What OBMs (Typically) DON’T Do:

Financial planning, business budgeting, or accounting beyond basic KPI tracking
High-level strategic planning or setting overall business direction, especially without your input and approval
Specialized skills like legal compliance, HR policies, or technical development
While they likely have experience with content creation and marketing (and may manage strategy execution), they won’t necessarily have the same expertise for strategy that a marketing professional will

How to Hire an Online Business Manager:

I mean, hey, I could help you out! My name is Sabrina Joan, and I’m an Online Business Manager who helps socially-conscious, values-driven businesses and creators build business operations in service of both their goals and their humanity. My work sits at the intersection of trauma-informed care, systems thinking, and online business operations. If you’re reading this and thinking, “Huh, I really feel like it’s time for an OBM!” I invite you to learn more about my services and submit an inquiry when you’re ready.

You Might Need More Than an OBM If...

You’re ready for someone to take full ownership of business functions, like the whole marketing department or ALLLLL business operations
You want a business strategy expert to make significant, independent decisions and represent you with C-level leadership in high-stakes meetings
You’re excited to step away from the business entirely for extended periods
Your business is large enough that you need someone to manage other managers and department heads

When is it Time to Bring in a Chief Operations Officer (COO)?

As the name suggests, a Chief Operations Officer can bring C-level operations leadership and strategic partnership into your business. Unlike an Online Business Manager, who serves as a collaborative coordinator for projects, team members, and processes, a COO makes major business decisions independently and is often a full-time, salaried employee. They usually bring a wealth of experience in finance, business strategy, and organizational leadership.

When to Invest in a COO:

Your business is an enterprise with complex operations, spanning multiple locations or big departments
While not strictly required, you probably want to be making at least $2M+ per year in revenue
You want a true strategic partner who shares big decision-making authority about the direction of your business
You have your sights set on major business expansion, acquisitions, or exits
You want to forget about day-to-day operations entirely so you can focus solely on the vision and growth of your business
You’re happy to invest $80K-$200K annually (depending on skills and experience), which will go towards unlocking dramatically-accelerated growth

Common Chief Operations Officer Responsibilities:

Strategic planning and execution for the next 3-5 years of your business
Building full departments, leading company culture, and developing new team leaders
Taking ownership of financial operations, including profits and losses, budgets, and investments
Developing the business through negotiating new partnerships and acquisitions

The Hybrid Approach:

Your business is unique. If you’ve reviewed the parameters above and find that you’re craving elements of multiple roles, you might find it beneficial to work within a hybrid model. Each professional’s boundaries and expectations will be different, but this might look like:

Hiring someone to fulfill VA and OBM roles as you grow your business (I’m open to this—fill out an inquiry form here to start the discussion)
Bringing on an OBM to manage multiple VAs
Enlisting an experienced OBM who can grow into a COO over time

Making the Right Choice for Your Business Stage:

These are by no means hard-and-fast rules. You know your goals and needs better than I, a random person on the Internet you probably found through Google, do. But the guidelines below represent common patterns that arise for business owners at each revenue level. May they be helpful as you consider the best folks to hire:

The Startup Stage is usually characterized by annual revenue below $100K and is most likely to benefit from a Virtual Assistant. Since I started as a VA in 2022, I’ve been multiple businesses’ first-ever hire and have noticed this is a great opportunity for business owners to learn how to delegate and complete lingering projects because they are accountable to another person.

The Growth Stage tends to characterize businesses that are generating $100K-$500K per year in revenue and could benefit from both VAs and an OBM. In this phase, I often see business owners experiencing a sense of overwhelm—perhaps they grew more quickly than they anticipated or have (up until this point) been able to get away with doing all of their operations manually. The business is “successful” from an outsider’s perspective, but feels chaotic internally. This is where an OBM’s strategic eye for streamlining systems and managing complexity can REALLY make the difference! And this is where I specialize.

The Major Scale Stage needs a strong operations team of multiple VAs and an experienced OBM to achieve the expansive and predictable growth they are ready for (or are rapidly experiencing!). This phase describes businesses bringing in revenue of around $500K-$2M annually and hiring new team members left, right, and center to make BIG waves in their industry.

The Enterprise Stage tends to be when we start leaving “small business” territory. These businesses are generating at least $2M in revenue each year and need a COO who can run the operations (with a team below them) while the business owner/CEO focuses on the vision.

Again, these are not strict prescriptions, but rather invitations to consider how your business might benefit from the support of a Chief Operating Officer, Online Business Manager, or Virtual Assistant(s).

The right choice will depend on: