Ep. 56 Behind the Scenes of Growing a Team as an Online Business Owner
Building a team for your online service business can feel overwhelming. When should you hire your first employee? How do you know if you're ready? What mistakes should you avoid?
After nearly a decade of growing my brand and web design business from a solo freelancer to a thriving micro-agency, I've learned that team building is less about following a playbook and more about understanding what works for your unique business model and life goals.
In this comprehensive guide, I'll share my complete journey of hiring, the costly mistakes I made, and the systems that ultimately led to a sustainable team structure. Whether you're drowning in client work or just starting to consider your first hire, this post will help you navigate the complexities of growing a service-based team.
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The Solo Freelancer Stage: When One Person Is Enough
My business journey began in 2016 when I landed my first freelance Squarespace design job through Upwork. Like many service providers, I started without an official business structure—no LLC, no business name, just me taking on graphic design projects wherever I could find them.
During this phase, I wore every hat imaginable: designer, project manager, bookkeeper, and client support specialist. This is normal and even beneficial in the early stages. Working solo allowed me to:
Learn every aspect of my business operations
Develop my service offerings through trial and error
Build initial client relationships without overhead costs
Establish my design process and standards
The Mindset Shift That Matters
Early on, I operated with the mindset that my value was directly tied to output—the number of hours I worked and deliverables I produced. This is a common trap for service providers. The reality? Your value lies in the strategy and expertise you bring to clients, not the quantity of work you can personally produce.
Understanding this distinction is crucial before you hire anyone. If you're still in the "trading time for money" mindset, you're not ready to effectively lead a team.
Recognizing When It's Time to Hire (Before Burnout Hits)
In October 2018, I left my corporate job to run my business full-time. Initially, having 40 hours per week available instead of 5-10 felt like more than enough capacity. I wasn't eager to build a team—part of leaving corporate was escaping traditional team dynamics.
But by summer 2019, barely eight months after going full-time, I was experiencing severe burnout.
Warning Signs You Need Help
Here are the red flags I ignored that you shouldn't:
Time allocation problems: I was spending 60% of my time on client management and administrative tasks, leaving only 40% for actual design work—the service I was selling.
Anxiety about work: I dreaded sitting down at my computer because I felt perpetually behind.
Marketing abandonment: I had completely stopped marketing my business, not by choice but by necessity. This is dangerous for long-term sustainability.
No time for business development: I couldn't work on my business because I was too busy working in it.
Physical and mental exhaustion: Despite loving my work, I felt drained instead of energized.
The 80% Capacity Rule
Based on my experience, start your hiring process when you reach 80% of your maximum capacity. Here's why:
You'll have time to properly vet candidates
You can create training documentation without rushing
You won't make desperate hiring decisions
You can gradually onboard your new hire while still available
Waiting until you're at 110% capacity (like I did) leads to rushed decisions and inadequate training—a recipe for disappointing results.
Your First Hire: The Virtual Assistant That Changed Everything
My business coach finally intervened: "You have to hire help. You're going to crumble if you don't." She connected me with Sadie Prestridge, her own VA at the time, which eliminated the hiring and vetting process entirely.
Why Start with a Virtual Assistant
For most service providers, a VA should be your first hire because they can:
Handle client onboarding and offboarding
Manage invoicing and payment follow-ups
Coordinate scheduling and communications
Maintain project management systems
Free you to focus on delivery and strategy
The impact was immediate and transformative. Hiring a VA allowed me to refocus on my zone of genius—designing brands and websites—while ensuring clients received better support. This capacity increase enabled me to take on more clients without working more hours.
Overcoming First-Hire Hesitations
Even with a trusted referral, I experienced common concerns:
Financial pressure: At the time, I was earning solid five figures monthly, and investing 10% of that in a VA felt significant. While I knew the value would be there, I suddenly felt responsible for someone else's income. This pressure actually motivated me to market more consistently.
Delegation anxiety: I worried I wouldn't know what to delegate or how. Fortunately, Sadie had established systems and essentially told me, "Here's what I'll take off your plate." This taught me an important lesson: hire experts who can lead in their domain, not just execute your instructions.
The Seven-Year Partnership
Sadie's business has since grown into Prestridge & Co., a full VA agency. I've worked with them continuously since 2019—seven years and counting. This longevity demonstrates the value of choosing the right people for your team.
The Costly Mistakes I Made Hiring My First Designer
A few months after hiring my VA, I approached burnout again. Even though I was only doing design work, I was so busy I couldn't work on business development or marketing. I needed a graphic designer.
This is where I learned my hardest lessons about hiring.
Mistake #1: Waiting Too Long to Start Looking
I waited until I was completely overwhelmed before beginning the search. This created several problems:
I felt desperate to fill the position quickly
I had unrealistic expectations for how fast they'd become productive
I lacked the time and patience for proper training
I made the role and requirements less clear than they should have been
The fix: Begin your search at 80% capacity, not 110%.
Mistake #2: Prioritizing Culture Fit Over Skills
I posted a basic job description in Facebook groups and interviewed a handful of candidates. I ultimately hired someone without formal design training who was eager to learn and enthusiastic about working with me.
Here's the nuance: I believe it's important to like the people you work with. However, at that time I was still working through people-pleasing tendencies. I prioritized finding someone I enjoyed talking to, someone who validated my work, over someone who could independently deliver results.
The truth: When you're already overwhelmed, how much you like someone won't compensate for skill gaps you don't have time to address.
The fix: Create a balanced scorecard evaluating both culture fit AND hard skills. Being a 5/5 in personality fit doesn't make up for being a 2/5 in technical ability.
Mistake #3: No Test Project
I never asked candidates to complete a paid test project. This meant I had no evidence of their:
Actual design skills
Attention to detail
Ability to follow a creative brief
Time management
Communication style
The fix: Always conduct paid test projects using real work from your business. More on this below.
Mistake #4: Insufficient Documentation
I had no standard operating procedures (SOPs), recorded processes, or training materials. Everything I knew was in my head, and I didn't have time to extract it properly.
The fix: Document your processes before you're desperate to hire. Create Loom videos of yourself completing common tasks.
What I Learned From This Experience
Despite these mistakes, the hire worked out reasonably well. They helped me through a tough season, and when business slowed down, we parted ways amicably. The key lessons:
Don't wait until you're drowning to hire
Create systems and SOPs before bringing someone on
Prioritize culture fit AND skills equally
Excellence in one area doesn't compensate for deficiency in another
These lessons completely transformed my next hiring experience.
The Leadership Skills Nobody Talks About
During my first year managing team members, I grappled with significant emotional and identity challenges that nobody had prepared me for.
The Emotional Complexity of Becoming a Boss
I felt responsible for someone else's livelihood, yet questioned whether I was qualified to be anyone's boss. I was hesitant to give direct feedback because I didn't want to hurt feelings or come across as a micromanager. Simultaneously, I felt frustrated when deliverables didn't meet my standards or timelines.
I was caught between maintaining Specht Co.'s quality standards, building a positive relationship with my new team member, training them without adequate time, and stepping into a completely new identity as a business owner rather than a freelancer.
We don't discuss enough how the first year of full-time business ownership—especially with your first hires—is an emotional roller coaster. Even with excellent support (business coach, supportive spouse, capable VA), the transition is challenging.
Developing Leadership Skills
I have a design degree but no formal leadership training. Leadership development became something I had to prioritize independently. I'm still developing these skills and have significant room for growth, but I recognize that leadership is crucial and often underestimated when people begin building teams.
What I've learned about effective leadership:
Clear communication is kindness: While it might feel uncomfortable to say "This needs to be completed by this date, we can't be flexible on this timeline," or "I don't like this approach, let's revise it"—this is exactly what your team needs from you.
Boundaries protect relationships: Setting clear expectations and boundaries isn't harsh; it's the foundation of healthy working relationships.
Your team wants direction: Team members aren't looking for you to be their friend first and boss second. They want clear objectives, honest feedback, and confident leadership.
Feedback is a service: Providing thoughtful, direct feedback is the most supportive thing you can do for someone's professional development.
Case Study: Hiring to Support Maternity Leave
In 2020, business slowed considerably and I became comfortable with the idea of remaining a solo business owner with just VA support. I envisioned keeping operations simple and low-key.
Then I got pregnant.
The Strategic Imperative
If I wanted to continue earning during maternity leave, I needed someone handling client work while I was unavailable. This non-negotiable deadline forced me to approach hiring with much more preparation and strategy.
At the end of 2022, I went through another hiring process—this time with dramatically better results.
The Improved Hiring Process
Job description with clear requirements: I specified exactly what skills were non-negotiable because I wouldn't be available for extensive training.
Multiple interview rounds: From approximately 70-80 applicants, I filtered based on rate and availability, then narrowed to four finalists.
Paid test projects: This was the game-changer. I took an actual monthly newsletter I created for a retainer client and asked each candidate to design the next month's edition based on previous examples.
This revealed:
Who understood the aesthetic and brand
Who had appropriate attention to detail
Who could complete work within reasonable timeframes
Who could follow creative direction
Gradual onboarding timeline: I hired at the end of 2022 for a March 2023 due date, giving us several months to work together while I was available for questions.
Trial period: In early March, I told my team, "Pretend I'm not here. Run the show. I'm available for emergencies, but this is your test period."
This preparation proved invaluable. They rarely needed to reach out, giving me confidence that they could handle situations independently during my actual maternity leave.
The Results
I took a three-month maternity leave, opening my laptop occasionally to work on business development and respond to Slack messages, but I was genuinely out of day-to-day operations.
When I returned, clients consistently complimented how well my team had supported them. They said things like:
"We felt completely taken care of"
"The quality never wavered"
"We didn't even notice you were gone"
This was the biggest professional win of 2023—proof that with proper preparation, you can build a team that truly runs without you.
The Unexpected Identity Shift: From Doer to Director
The plan was for this hire to cover maternity leave only. But when I eased back into work in June 2023, I realized something surprising: I didn't want to reclaim the work my designer was doing.
They were handling ongoing design work for retainer clients—what has since evolved into my Six Figure Brand Society membership. This was primarily maintenance-level graphic design rather than high-level branding or web design.
With a newborn at home and extremely limited time, I felt pulled toward:
Working ON my business instead of IN it
Being the creative director who guides projects
Conducting brand strategy sessions
Connecting with potential clients through marketing
Overseeing work rather than producing every pixel
This realization was significant because when I had hired my first designer years earlier, I desperately wanted to keep all design work for myself. The evolution of my role preference reflected business maturity and life stage changes.
Considering the Agency Model
This shift got me thinking seriously about an agency model. This structure would allow me to:
Focus only on aspects I loved and excelled at
Hire specialists for areas outside my strengths
Continue growing without proportionally increasing my hours
Build a sustainable business that didn't solely depend on my production
In contrast, keeping all design work for myself while caring for a newborn simply wasn't sustainable. There aren't enough hours in the day.
Team Transitions and Maintaining Relationships
My designer worked with me until 2024 (1.5-2 years) before pursuing a different direction for her business. This departure was completely amicable.
Here's a valuable lesson: I reached back out to one of the candidates I had really liked during the initial interview process but hadn't hired. I asked if she was available, she said yes, and she's still on my team today.
Pro tip: When interviewing candidates, if you have multiple people you'd love to work with but can only hire one, maintain those relationships. Keep their contact information and stay in touch. Your business will likely grow to the point where you can hire your #2 and #3 choices later.
My Current Team Structure: The Micro-Agency Model
Today, Specht Co. operates with three core team members, and I genuinely believe we've found the sweet spot.
Role #1: Founder, CEO, Creative Director (Me)
My primary responsibilities include:
Marketing and business development
Taking sales calls with potential clients
Conducting Standout Brand Strategy sessions
Creative directing all client projects
Brand strategy and positioning
For brand design projects specifically, my involvement includes:
Strategy session facilitation
Mood board creation
First draft of logo concepts
Review and feedback on all subsequent work
Client presentation and relationship management
This structure allows me to maintain quality standards and stay involved in the creative work without spending hours on production tasks.
Role #2: Graphic Designer (Paige)
Paige has been with us for nearly a year and handles:
All day-to-day design requests
Six Figure Brand Society member design work
Building client websites
Developing full brand kits
Producing marketing materials
Implementing the creative vision I establish
I review everything, provide feedback, and approve final deliverables, but Paige handles the production work. This structure maintains quality while freeing my time for strategic work.
Role #3: Virtual Assistant & Studio Manager (Taylor - Prestridge & Co.)
Taylor manages everything outside of design:
Client onboarding and offboarding
Invoicing and payment processing
Scheduling coordination
Client communication and questions
Six Figure Brand Society training coordination
Podcast guest management and logistics
Project management system maintenance
Taylor is the organizational backbone of Specht Co. While I consider myself organized, she elevates systems to a completely different level, freeing me to focus on what only I can do: connecting with potential clients, marketing the business, and providing strategic creative direction.
The Micro-Agency Advantage
You'll notice we're only three people. I'm not building a massive agency, and I don't aspire to. The micro-agency model works beautifully for me and my clients because:
For the business:
Lower overhead and complexity
Easier team coordination
Maintain consistent quality control
Sustainable work-life balance
Higher profit margins
For clients:
Direct access to senior-level expertise
Consistent team (no rotating junior staff)
Personalized attention
Quick communication and decisions
Cohesive brand vision
Occasional Specialist Contractors
We regularly bring in contractors for specialized needs:
Social media management
SEO optimization
WordPress development (we work primarily in Squarespace)
Copywriting for specific projects
These contractors work alongside our core team on specific projects but aren't permanent team members. This flexibility allows us to offer comprehensive services without the overhead of full-time specialists.
The Reality of Team Management
To be completely transparent: growing and maintaining a team requires significant mental energy and emotional labor.
The Ongoing Pressures
Financial responsibility: These people count on me for their paychecks every month. I must consistently market the business and maintain client flow to meet payroll obligations.
Professional development: I want my team members to feel fulfilled, continue learning, and want to work with me long-term. This requires attention to their growth and satisfaction.
Leadership development: I have no formal leadership training. Everything I've learned about managing people has been self-taught through books, courses, mistakes, and reflection.
Decision-making weight: As the team leader, major decisions rest on my shoulders. This responsibility can feel heavy, especially during challenging periods.
Why It's Still Worth It
Despite these challenges, I'm genuinely happy with where my business is now. For example, there was a time when I was sure I didn't want to grow a team or build an agency. Now that I've figured out what works and what doesn't, I'm actually excited about potentially adding one or two more team members in the coming years.
The key insight: it's important not to grow your team too quickly. Although I experienced burnout, I'm grateful for the years I spent managing every aspect independently. This hands-on experience helped me understand every component of my business, ensuring I wouldn't find myself in a position where I had hired multiple people but no longer understood my own operations.
The Loneliness Factor
One underrated benefit of building a team: online business becomes significantly less lonely when you have people working alongside you. The collaborative energy, shared wins, and mutual support create a completely different experience than solo entrepreneurship.
5 Essential Principles for Building Your Service Business Team
1. Balance Culture Fit with Hard Skills
You need both. Don't hire based on personality alone, and don't hire based solely on technical ability. Create evaluation criteria that weight both factors appropriately.
Use a balanced scorecard approach:
Technical skills and experience (40%)
Portfolio quality and relevant work (30%)
Communication and cultural alignment (20%)
Problem-solving ability (10%)
2. Hire at 80% Capacity, Not 110%
Once you reach 80% of your maximum capacity, start your hiring process. At this level:
You can afford to be selective
You have time to create proper documentation
You can conduct thorough interviews
You won't make desperate decisions
You can provide adequate training
Waiting until 110% capacity creates rushed decisions, insufficient training time, and potentially misaligned hires.
3. Document Everything Before You're Desperate
Start building your operations manual now, not when you're drowning:
Record Loom videos of repetitive tasks
Write step-by-step SOPs for common processes
Document your quality standards and brand guidelines
Create templates for common deliverables
Maintain a list of tools, logins, and resources
Future you (and your new hire) will be incredibly grateful.
4. Always Use Paid Test Projects
Never skip the test project phase. This is your opportunity to evaluate:
Actual work quality (not just portfolio pieces)
Ability to follow your specific brief
Attention to your particular details
Communication style during revision
Time management and deadline adherence
Pay candidates fairly for their time. Use real work from your business—a recent client project, a typical retainer task, or an internal need. The investment is minimal compared to hiring the wrong person.
5. Build Your Team Around Your Life
Stop comparing your business to others. The team structure that works for someone else may not serve your goals.
Ask yourself:
What lifestyle am I building this business to support?
Which tasks energize me vs. drain me?
What does sustainable growth look like for me?
How much complexity am I willing to manage?
What does success actually look like in my life?
My micro-agency with three core team members works perfectly for my life stage and goals. Your ideal structure might look completely different, and that's exactly right.
The Reality: Why Building a Team is Worth the Challenge
Building a team is hard. It's messy. You will make mistakes. You'll probably have difficult conversations and relationships that don't work out as planned.
But it's still worth it.
When you get it right—when you crack the code—it's transformative. Team building doesn't just increase your business capacity; it fundamentally changes your relationship with your work. You move from production to strategy, from execution to leadership, from working IN your business to working ON it.
The collaboration, shared victories, and mutual support make online business feel less isolating. Having people who are invested in your mission alongside you creates energy that's impossible to generate alone.
If You're Hesitant About Building a Team
I encourage you to remain open-minded. There may be a way to structure a team that aligns perfectly with your vision for your business, even if traditional agency models don't appeal to you.
Consider:
Could hiring just one VA change everything?
What if you started with a contractor for your least favorite tasks?
How would your business and life improve if you weren't doing everything yourself?
If You Already Have a Team and It's Harder Than Expected
You're not alone. Leadership is a skill that requires practice and continuous development. It is difficult, but it's also one of the most rewarding aspects of running a business.
Keep learning, keep communicating, and keep refining your systems. The investment in developing your leadership abilities pays dividends throughout your entire business and life.
Final Thoughts on Team Building for Service Providers
The path from solo freelancer to team leader isn't linear. It's filled with false starts, learning experiences, identity shifts, and hard-won wisdom. The key is approaching it strategically rather than reactively.
Start documenting your processes now. Begin thinking about what support would make the biggest difference in your business. Calculate what 80% capacity looks like for you. Most importantly, recognize that building a team isn't about following someone else's blueprint—it's about creating a structure that supports both your business goals and the life you want to live.
Your perfect team structure is out there. It just might look different than you expect.
🔗 Links & Resources Mentioned In The Episode:
➡️ Follow me on Instagram @spechtand.co
➡️ Book Your Stand Out Brand Strategy Session (use code SFBPOD for $100 off)
➡️ Book A Brand Chat➡️ Book Your Stand Out Brand Strategy Session (use code SFBPOD for $100 off)
➡️ Connect w/ my VA Agency, Prestridge & Co.
🎧 Listen to episode 56 of The Six Figure Brand Podcast on Spotify, Apple Podcasts, Amazon Music, and YouTube
