When Aaron Reimann found himself alone with a handful of hosting clients after selling his first agency in 2019, most would have seen it as starting from scratch. Aaron saw it as an opportunity to build smarter.
Five years later, Clockwork Web Dev employs 15 people, maintains 30% annual growth, and manages complex WordPress projects for clients like the Georgia Department of Education—all while avoiding the typical agency growing pains.
In our latest Scaling Smart episode, Aaron shares the unconventional strategies that made this rapid growth possible, from his “anti-sales” approach to technical training for non-technical staff.
The technical founder advantage
“I’m kind of like an anti-sales guy. I don’t like salesmen,” Aaron admits with a laugh. It’s an unusual confession from someone responsible for all sales at a growing agency. But this apparent weakness became his greatest strength.
Unlike traditional agency salespeople who promise the moon and check feasibility later, Aaron brings 25+ years of technical expertise to every sales conversation. When prospects ask about API integrations or security protocols, he doesn’t need to “circle back with the team”—he provides real answers in real-time.
This approach does more than close deals faster. It sets realistic expectations, prevents scope creep, and builds trust from day one. Clients know they’re talking to someone who understands both their business needs and the technical realities of fulfilling them.
Building through strategic hiring
Aaron’s growth strategy defied conventional wisdom in several ways:
Start with contractors, not employees. Every key hire at Clockwork began as a contractor. This “try before you buy” approach eliminated costly hiring mistakes and ensured cultural fit before making long-term commitments.
Hire for aptitude, not experience. When Aaron needed project managers, he didn’t search for WordPress experts. Instead, he hired smart people and trained them. “I think none of them had any WordPress experience when they started,” he notes.
Create teaching systems from day one. Every two weeks, Aaron personally trains project managers on technical concepts. This investment means PMs can answer client questions about CloudFlare, custom post types, or plugin selection without constantly interrupting developers.
The power of transparent operations
With 15 people across multiple time zones, communication could easily become Clockwork’s biggest challenge. Instead, it’s their competitive advantage.
The team meets three times per week—Monday, Wednesday, and Friday. These aren’t lengthy strategy sessions but focused standups that keep everyone aligned. The structure is intentional:
- 9:30 AM: Team members working on Georgia Department of Education projects
- 10:00 AM: Everyone else joins for general updates
“We try not to get in the weeds,” Aaron explains. Detailed discussions happen in separate meetings, like the weekly design check-in where designers and project managers coordinate workloads.
This transparency extends to resource allocation. Despite having multiple project managers competing for developer time, Aaron notes they “haven’t had many fights yet over resources.” The credit goes to their systematic approach to communication and clear project prioritization.
Scaling in both directions
Perhaps the most valuable lesson from Aaron’s journey is the importance of building a business that can contract as easily as it expands.
When 2024 brought industry-wide slowdowns, many agencies faced impossible choices. Clockwork simply reduced contractor hours temporarily. No layoffs. No broken relationships. No loss of capability.
“It’s nice to not have to fire people because we don’t have all the work,” Aaron reflects. This flexibility came from intentionally mixing full-time employees with fractional talent from partners like Quickly Hire.
The model works because everyone understands it from the start. Contractors know their hours may fluctuate. Full-time employees have job security. And Aaron maintains the ability to scale up quickly when big projects arrive—like when the Georgia Department of Education “threw projects at us.”
Lessons from the journey
Aaron’s path offers several key takeaways for growth-stage founders:
1. Recognize when you’re too busy. “When you are always busy, it should be a no-brainer that you need to bring on someone else,” Aaron says. He wishes he’d learned this lesson sooner in his first agency, which waited seven years before making its first full-time hire.
2. Document your expertise. Much of Clockwork’s operational knowledge lived in Aaron’s head until he systematized it through training programs. Now, that knowledge multiplies across the entire team.
3. Embrace your weaknesses. Aaron readily admits he’s “not good at project management.” Instead of forcing it, he hired experts and let them own that crucial function.
4. Build for flexibility. In an industry notorious for feast-or-famine cycles, Clockwork’s hybrid staffing model provides stability without rigidity.
Looking ahead: the AI question
Like many agency owners, Aaron views AI with a mixture of excitement and concern. He recently used Claude to build a WordPress plugin in three hours—a task that would have taken days of developer time.
“I feel like a lot of people are going to just become great AI prompt engineers,” he predicts. But he doesn’t see AI replacing developers entirely. Instead, he envisions developers who use AI to work faster while maintaining the expertise to debug and secure AI-generated code.
His advice? Stay curious but grounded. “I wish I had a crystal ball to see what engine I should be investing time in,” he admits. For now, Clockwork uses AI as a rapid prototyping tool while maintaining human oversight for production code.
The bottom line
Aaron Reimann’s journey from solo founder to successful agency owner offers a masterclass in pragmatic growth. By focusing on sustainable hiring practices, systematic knowledge transfer, and operational transparency, he built an agency that thrives without the chaos that typically accompanies rapid scaling.
For founders facing similar growth challenges, his story provides both inspiration and practical blueprints. Sometimes the best path forward isn’t the conventional one—it’s the one that honestly acknowledges your strengths and systematically addresses your weaknesses.
Ready to scale your team the smart way? Listen to the full episode to hear Aaron’s complete story, including specific tactics for training non-technical staff and managing complex client relationships.
Want to learn more about flexible staffing solutions? Explore how Quickly Hire can help you scale like Clockwork Web Dev.