When to Fire Your Team: The Truth About Scaling From 6 to 7 Figures

November 28, 202511 min read

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Broadcasting from our coastal offices in Mauritius and South Africa, we're Chanelle, Chantal and Jennifer - business strategists who've cracked the code on building thriving businesses while actually living the lifestyle most entrepreneurs file under "someday."

The Team Evolution Truth: Why 90 percent of Your Team Won't Make It to Your Next Revenue Milestone

What if we told you that 90% of your current team would have to be completely different when you get to your next revenue milestone?

The sad truth is most businesses outgrow their original team members, but few CEOs recognize the warning signs until it's too late. You're cruising along with your small, scrappy team that helped you hit six figures. Everyone's wearing multiple hats, things are getting done, and it feels manageable. Then you scale to $500K. Then $800K. And suddenly, the team that got you here isn't the team that can get you there.

After our last episode on the task ticking trap, we dove into telegram and started asking ourselves: what should we actually be paying for different levels of team members? What's fair? What's strategic? And more importantly, how do you know when it's time to evolve your team structure entirely?

Between the two of us, we've watched this evolution play out dozens of times with clients scaling from mid-six figures to seven figures and beyond. We've seen the CEOs who got it right and scaled smoothly, and we've seen the ones who held onto team members too long and paid the price in missed opportunities and drained energy. Today, we're breaking down exactly what different team levels should cost, when to hire up, and—the hardest part—when to let people go.

What Is Team Evolution?

Team evolution is the natural progression your business goes through as you scale, where the skills and roles you needed at one revenue level become inadequate for the next. The person who was perfect for answering support tickets at $100K is probably not equipped to build your customer experience strategy at $500K. The VA who helped you launch your first course probably can't architect your entire content ecosystem at seven figures.

This isn't about those team members being bad at their jobs. It's about your business needing different things as it grows. Think of it like outgrowing clothes—a jacket that fit perfectly two years ago just doesn't work anymore, no matter how much you loved it.

The mistake most CEOs make is trying to force the old team into new roles without properly assessing whether they have the capacity to grow into them. You end up with a bloated team where half the people don't know what they're doing, and you're spending more time managing than growing.

The Real Cost: What Should You Actually Pay Team Members?

One of the biggest questions we get is about pricing. What's fair? What's smart? What actually makes business sense? After working across dozens of teams, here's what we've seen work.

Task Tickers: $25-50 per hour

These are your boots-on-the-ground people handling copy-paste tasks, basic admin, simple scheduling. They're not project managing themselves, they're not thinking strategically, they're executing clearly defined tasks. On some teams, we've seen rates as low as $9 per hour for very basic tasks, and as high as $35-40 for task tickers who've been with a business for a while and know the systems well.

The key thing to remember with lower-level team members is that someone needs to train them. Either you're spending your time creating detailed SOPs with screenshots and step-by-step instructions, or you're paying a higher-level team member to do it. That cost needs to factor into your decision.

Tech VAs: $40-65 per hour

Once you need someone with actual technical skills—building funnels, setting up course platforms, creating checkouts and order bumps—you're looking at a different tier. These people have technical understanding, they're just learning your specific systems. They'll be much faster to train because they already know how things work conceptually.

A good tech VA at this level can save you enormous amounts of time. But they still need oversight. They're not going to tell you that your entire funnel strategy is outdated or suggest a better approach. They'll execute what you ask for.

Problem Solvers: $50-100 per hour

This middle tier is where people start actually solving issues rather than just executing tasks. They can troubleshoot, they can escalate intelligently, they can spot patterns. You might have a launch manager or project manager in this range who's coordinating everything but not necessarily setting the strategy.

Strategic Thinkers: $100+ per hour

This is your COO level, your funnel strategists, your high-level consultants. These are the people who will actually tell you when you're being stupid. They'll say "don't record that entire course before you've sold it" or "that offer doesn't make sense for your audience." They bring years of experience across multiple businesses and can spot trends you can't see.

We've seen VIP consulting days go for $18,000 because the knowledge and strategic thinking at this level is worth that much. When you hire someone at this tier, they often bring other excellent people with them through referrals.

Understanding Team Roles: Who Does What?

There's massive confusion about what different roles actually mean. Let's break it down clearly.

Virtual Assistants (VAs)

VAs handle specific tasks—social media posting, email management, basic admin. They need clear instructions and all assets ready to go. They're not project managing themselves. A social media VA needs you or someone else to tell them what to post and when, provide the graphics and copy, and set the deadlines.

Tech VAs

These are VAs with technical skills in specific platforms—ClickUp, ActiveCampaign, course platforms, funnel builders. They can build what you need, but they still need direction on what to build.

Project Managers/Online Business Managers (OBMs)

These folks coordinate everything. They create the task breakdowns, manage timelines, ensure deadlines are met, and task out to the team. They're in the weeds making sure the machine runs smoothly. Some teams separate this into a launch manager (overall launch strategy and timeline) and project manager (nitty-gritty execution).

Chief Operations Officer (COO)

This is the highest strategic level on the operations side. The COO works directly with the CEO to translate vision into operational reality. They're in planning meetings, they're brainstorming offers, they're creating the systems that allow everything else to work. They need team underneath them to delegate to, but they're setting the direction.

Most CEOs start out being all of these roles simultaneously. As you grow, you selectively bring in people to take these functions off your plate.

Warning Signs It's Time to Scale Your Team

How do you know when it's actually time to hire? Here are the red flags we watch for.

You're consistently missing deadlines or working until midnight to deliver on what you've sold. If you've got website builds backing up or coaching clients you can't serve properly because you're drowning in delivery, that's a clear sign.

Your marketing has completely stopped because you're buried in operations. This creates the classic feast-famine cycle for service providers. When you're delivering, you're not marketing, so your pipeline dries up.

You're experiencing the famine-famine problem where you have no time to both deliver and market, so both suffer. Your business starts feeling unsustainable, and you resent the team you do have because you're paying them while working yourself to death.

Warning Signs Your Team Is Too Bloated

On the flip side, how do you know when you've got too much team? This is where things get uncomfortable, but it's crucial.

Team members aren't hitting their hours

If you implement time tracking (which you absolutely should), you might discover that your full-time team members aren't even working their committed hours each week. They don't have enough to do. This happens constantly when CEOs keep hiring at the bottom rather than bringing in strategic thinkers who can actually streamline and eliminate work.

Team costs are eating your profit margins

When you start grumbling about team spend constantly, when you feel like you're not paying yourself enough because everyone else is getting paid first, that's a major red flag. You've probably got a bloated operations team and not enough investment in marketing and sales—the actual revenue-generating activities.

You don't know what half your team is doing

If someone asked you right now what each team member worked on this week and you couldn't answer, you've lost control. Time tracking by project can reveal shocking truths. We've seen clients discover team members spending 20 hours cleaning up Google Drive when that wasn't remotely a priority. It was just something someone mentioned would be nice to have done.

The Quarterly Audit That Changes Everything

Every single business needs a quarterly audit. The amount of waste that accumulates over just three months is staggering—wasted time, wasted money, wasted energy on tasks that shouldn't exist.

Sit down and review recurring tasks. Should this still happen? Can it be automated? We helped one client turn 80-90% of her business tasks into recurring automated tasks in ClickUp. The system became the project manager. She took a three-month sabbatical while her podcast, social media, and email marketing continued, and team costs were still covered.

Audit your software subscriptions. You're probably paying for tools no one uses anymore. That alone can save you hundreds monthly.

Review team assignments. Does everyone have clear ownership? Are three people assigned to one task with no clarity on who's actually responsible? That's pure waste.

Question your processes. Are you solving actual problems or just managing symptoms? If support tickets keep piling up, the answer isn't hiring more people to answer them—it's fixing whatever's causing them.

The Pricing Psychology That Changes How You Value Your Team

Here's something fascinating we've observed: CEOs value team input differently based on what they're paying.

You'll dismiss suggestions from someone you're paying $25 an hour, but if you pay $5,000 for a VIP consulting day and get the exact same advice, suddenly you'll implement it. We've watched this happen repeatedly. A team member suggests a strategy for a year, gets ignored, then the CEO hires an expensive consultant who says the identical thing and suddenly it's gospel.

Sometimes the solution is actually to book your existing high-level team for a VIP strategy day instead of bringing in yet another outside consultant who needs to be briefed on your entire complex business. Your team already knows everything—just properly value their input.

When It's Time to Let Someone Go

This is the hardest conversation, but ignoring it costs you everything. Here are the clear signs a team member needs to move on.

They're killing team morale

If someone is constantly negative, always talking about what won't work rather than solutions, they're poisoning your culture. Attitude is almost impossible to train, and one negative person can drain the energy of your entire operation.

They're consistently making errors

Lower-level team members especially need to be accurate and detail-oriented. If you're having to check every single thing they do because they're error-prone, they're not actually helping you. They're creating more work.

They're not teachable

Someone who's bright-eyed and eager but inexperienced is infinitely more valuable than someone with skills but a closed mind. If you give feedback and they don't implement it, or they resist every new process, that's a fundamental incompatibility.

The good news is that when you bring in excellent high-level people, they naturally raise the bar. Mediocre team members start feeling out of place because everyone else is operating at a different speed and quality level. Often they'll naturally transition to other clients where they're a better fit.

The Marketing-Operations Balance

One of the biggest mistakes we see in bloated teams is all the investment going into operations and delivery, with almost nothing in marketing and sales. You've got five people managing client delivery and course updates, but nobody actually driving new revenue.

Remember: marketing and sales are the engine. Without them, there's no business. You need people who understand what's working now—not what worked two years ago. Buyer behavior changes constantly. The strategies that converted well in 2023 might be completely ineffective now.

For example, cart open-to-close windows have shifted. People need more time to make decisions now. They want to talk to someone, see social proof, feel connection before buying. What worked as a three-day flash sale might need to be a week or more now.

Your Next Step

Team evolution isn't optional—it's inevitable if you're growing. The question is whether you'll be intentional about it or let it happen chaotically.

Start by implementing time tracking across your team. Use a tool like Timing App or similar to see where hours actually go. You cannot make smart decisions without data.

Next, honestly assess each team member. Are they operating at the right level for what you need now? Not what you needed when you hired them, but what you need today as you push toward your next revenue milestone.

Finally, ask yourself: am I investing enough in strategic thinking, or am I just hiring more hands? The businesses that scale smoothly bring in high-level strategic thinkers early, even when it feels expensive. Those investments save you from building a bottom-heavy, inefficient team that costs more and delivers less.

Your team should evolve with your business. And sometimes that means making hard decisions about who comes with you to the next level.

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Ready to dive deeper? In our next episode, we're exploring how AI is completely transforming team onboarding and training. Subscribe so you don't miss it.


The Leveraged CEO Podcast is hosted by Chanelle, Chantal and Jennifer, three business strategists with 30+ years of experience helping multi-six and seven-figure entrepreneurs build businesses that run without their constant attention. New episodes drop every Tuesday.


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Meet Chanelle

After shooting destination weddings across Europe and further afield like Bali and Mauritius, having her daughter in the Caribbean sparked a revolution in how she viewed business.

Now based in Jeffrey's Bay, she helps established entrepreneurs create businesses that look gorgeous AND run without them being chained to their laptops. Featured in Forbes, Thrive Global and Stylist Magazine, she's passionate about helping women escape the chaos of "successful" businesses through strategic systems that create true freedom.

She has a knack for building world-class teams and designing systems, processes and beautiful brands for globally based clients.

Meet Chantal

With expertise spanning one-day website builds to her revolutionary heyCEOflow all-in-one software, Chantal helps established business owners escape the chaos of "successful" businesses through strategic automation and recurring revenue models. Her clients benefit from the same systems that allow her to run an international business while enjoying boat days with her young daughter.

Known for her uncanny ability to simplify the complex, Chantal combines technical brilliance with creative design thinking to build businesses that work for their owners, not the other way around.​​​​​​​​​​​​​​​​

Meet Jennifer

Jennifer transformed her exhaustion on a packed London train into a multi 7 figure industry empire, then sold it.

Instead of just scaling her business, she built the entire infrastructure her industry needed. From Mauritius, she now helps successful but plateaued experts discover the ecosystem hiding in their expertise.

Having coached thousands while traveling 60+ countries with her young family, Jennifer proves that freedom beats hustle. Her clients work 15-hour weeks, turn competitors into customers, and build assets worth millions by architecting their industry, not just working in it.

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