Scaling Solo: When to Build Your First Team & How to Keep Clients

Scaling solo as a solopreneur or agency owner is an exciting yet challenging phase in your business journey. When you start as a one-person band, you might feel invincible, handling everything yourself from web development and design to client management and marketing. However, as your client base grows and projects become more complex, you may hit a wall where being “too good” solo becomes the bottleneck to your growth.

In episode 10 of the Bright Commerce Podcast, Judd Dunagan and John, two seasoned digital agency veterans, dive deep into the realities of scaling from solo to building your first team. They discuss the good, the bad, and the ugly of growing an agency, managing client expectations, developing systems, and making tough decisions like saying no or firing clients. Whether you’re a freelancer afraid to let go or a consultant hitting capacity, this comprehensive guide will provide you with a roadmap to scale your agency sustainably without losing your sanity or quality of work.

Table of Contents

Background: From Solo to Enterprise

John shares his extensive background, starting in the early 2000s with a digital agency focused on local real estate projects. Back then, web development was a different beast, building sites in Flash, using ASP Classic, ColdFusion, and early e-commerce platforms like ASP.NET storefront. John reminisces about the challenges and excitement of those pioneering days, including flying out to Amazon in 2008 to help launch George Foreman Grill’s online marketplace presence.

He explains how the early days lacked the sophisticated tools we have now, no streamlined platforms, no cloud backups, and security was the Wild West. For example, he recalls a client whose site was hacked with inappropriate content that stayed live for over a week because the developer who built the site was uncooperative. This story highlights the importance of owning your domain and infrastructure, a lesson he emphasizes throughout the conversation.

Owning your domain name and managing your infrastructure independently is crucial. John warns against shady developers who buy client domains and lock them in, creating headaches when clients want to migrate or change vendors. Fortunately, this practice has become less common as clients become savvier.

When and Why to Build Your First Team

Scaling solo means recognizing where doing everything yourself limits your growth and client service quality. John shares that it took him years of trial and error before realizing he had to build a team to handle bigger projects and enterprise clients effectively.

He stresses the importance of not trying to do it alone, especially when dealing with larger clients who expect faster turnaround, more complex deliverables, and structured project management. The sheer volume of work and client expectations make it impossible for one person to be everything: developer, designer, project manager, and client liaison.

Building a team allows you to delegate tasks, specialize roles, and maintain high-quality service without burning out. However, John warns that managing a team requires new skills, including hiring, training, managing workflows, and fostering a supportive company culture.

Building and managing your first team

Enterprise vs Mid-Size and Small Clients

John contrasts working with enterprise clients versus mid-size and small businesses. Enterprise clients can be lucrative but come with significant challenges:

  • Complex approval processes involving multiple stakeholders and departments.
  • Contractual rigor demands detailed statements of work and scope management.
  • Scope creep and budget control issues require constant vigilance.
  • There is a need for a whole project team, including project managers, developers, and Scrum masters.
  • Payment terms that often favor larger agencies, even if smaller firms do the same work.

He shares a story about a micro-site project for an enterprise travel client that had to be redone three times because approvals didn’t reach the final decision-maker. This experience taught him the importance of identifying the true stakeholder who signs off on deliverables and payments.

In contrast, mid-size businesses offer a sweet spot for agencies. These clients typically have fewer bureaucratic hurdles, more transparent communication, and faster decision-making, making projects smoother and often more profitable. Smaller projects also provide a sense of accomplishment because they have clear endpoints, unlike enterprise engagements that can drag on for months.

Systems and Tools for Managing Growth

One significant shift when scaling is implementing systems and tools to manage projects, clients, and teams efficiently. John walks us through the evolution of his project management tools, starting from Basecamp, moving through Jira, Monday.com, and Freecamp, and then specialized agile tools like Vivify for plugin development.

He emphasizes that while many clients expect agencies to use their project management systems, it’s often impractical for agencies to juggle multiple platforms. Instead, agencies should use tools optimized for their workflows and provide clients regular status updates via email or meetings.

John also praises Airtable as a robust relational database and reporting tool that integrates time tracking, billing, and project data into one dashboard. This helps keep team members accountable and provides billing and project budgeting transparency.

Client Management and Setting Expectations

Managing client expectations is a recurring theme in the podcast. John shares hard-earned advice on:

  • Documenting everything during discovery calls, including screenshots and recorded videos, to avoid misunderstandings later.
  • Setting explicit scopes of work and contracts to prevent scope creep and extra unpaid work.
  • Communicating regularly and clearly, especially with larger clients where multiple people may be involved.
  • Providing clients with weekly or bi-weekly status emails rather than expecting them to log into project management software.

He also stresses the importance of building a brand beyond just being “that one person.” Clients should hire your company, not just you personally. This helps future-proof your business to grow beyond your capacity.

Hiring, Training, and Letting Go of Team Members

Scaling means you’ll need to hire and sometimes fire. John shares his journey of hiring over 100 people to build a reliable team of about 20. He highlights:

  • The challenge of finding good talent and the importance of recruiting actively on platforms like LinkedIn and Upwork.
  • Using project-based hiring to test multiple candidates on the same task before making a full-time hire.
  • Training new team members with Standard Operating Procedures (SOPs), even if no one follows them 100%.
  • The necessity of monitoring time tracking to prevent abuse and ensure accountability.
  • Creating a culture of transparency where team members feel comfortable asking for help or admitting when they need assistance.
  • Using HR best practices such as 30, 60, 90-day reviews and respectful communication when addressing performance issues.

John also shares cautionary tales of employees secretly outsourcing their work or unethically using agency resources. He advises acting swiftly but fairly when such situations arise.

Challenges of enterprise clients vs mid-size clients

The Emotional Challenges: Empathy and Leadership

Being a solopreneur is often solitary, but managing a team requires a different mindset. John talks about the growth he experienced in developing empathy and emotional intelligence as a manager:

  • Understanding that everyone on your team has personal challenges that can affect their work.
  • Recognizing the importance of boosting morale by acknowledging and supporting team members.
  • Learning to step back emotionally from your work to avoid burnout, especially as creative projects can feel personal.
  • Acting as a buffer between clients and the team protects both sides and maintains professionalism.

He admits that it took years to develop these skills and that being a “happiness officer” is a critical but often overlooked role in agency leadership.

The Power of Saying No to Clients

One of the hardest lessons in agency growth is learning to say no. John explains that early in his career, he accepted every client because he needed the money, but now he is more selective. He shares criteria he uses to disqualify clients, such as:

  • Clients who expect you to finish work started by someone else only want to work after standard business hours.
  • Prospects who haven’t done any research or due diligence about what they need or the costs involved.
  • Clients who are difficult or toxic, even if they bring money.

John stresses that letting go of bad clients protects your team’s morale and your agency’s reputation. Sometimes, returning deposits and walking away early is the best choice for all parties.

The Impact of AI and Technology on Agency Growth

Technology and AI are reshaping how agencies operate. John shares his mixed feelings about AI: while it can streamline tasks like contract review or content creation, it still requires human oversight to avoid errors or “hallucinations.” He also warns about AI being used deceptively in hiring, such as candidates using AI-generated profile pictures or outsourcing their work without transparency.

Despite these challenges, John embraces AI to augment agency work, especially plugin development and managing complex projects. He notes how AI has accelerated plugin creation for his company, Bright Plugins, which has grown rapidly in recent years.

Conclusion: Scaling Solo the Right Way

Scaling solo is more than just hiring your first employee. It’s a transformative process that requires developing new skills in leadership, project management, client communication, and emotional intelligence. John’s journey from a one-man show to running a thriving agency with a strong team offers valuable lessons:

  • Know when to build your team and don’t try to do it alone.
  • Choose your clients wisely and don’t be afraid to say no.
  • Implement systems and tools that streamline workflows and keep everyone accountable.
  • Develop empathy and emotional maturity to lead your team effectively.
  • Embrace technology and AI as tools, but maintain human oversight and transparency.
  • Build a brand that stands beyond just you as an individual.

By following these principles, solopreneurs can break free from the bottleneck of doing everything themselves and scale sustainably while maintaining client trust and quality.

Frequently Asked Questions (FAQ)

When should I start building my first team?

You should begin building your first team when you notice that your workload is overwhelming, client demands are increasing, and you can no longer maintain quality or meet deadlines alone. If you find yourself turning down work or feeling burnt out, it’s time to consider hiring support.

How do I manage client expectations when scaling?

Set explicit scopes of work, maintain detailed documentation, communicate regularly via emails or meetings, and ensure the final decision-maker approves deliverables. Use project management tools internally and provide clients with digestible updates rather than expecting them to learn new systems.

What are good tools for managing projects and teams?

Popular data integration and reporting tools include Freecamp, Monday.com, Jira (for enterprise clients), and Airtable. Agile tools like Vivify work well for development teams managing sprints. Choose tools that fit your team’s workflow and scale with your business.

How do I find and hire good team members?

Recruit actively on LinkedIn and platforms like Upwork. Use project-based hiring to test candidates before offering full-time positions. Train new hires with SOPs, monitor time tracking, and foster transparency to retain top talent.

How do I say no to clients without burning bridges?

Be honest and professional. If a project or client isn’t a good fit, explain your reasons clearly and offer referrals if possible. Returning deposits and walking away early can protect your team and brand reputation in the long run.

What is the impact of AI on running an agency?

AI can speed up workflows by helping with tasks like contract review, content generation, and plugin development. However, human oversight is required to avoid errors. Be cautious of candidates or team members using AI deceptively, and maintain transparency.

Scaling solo is a complex but rewarding journey. With the right mindset, systems, and team, you can grow your agency sustainably and continue delivering exceptional value to your clients.

For more insights and expert services, visit Bright Vessel and Bright Code.