How We Started

Henry, founder of Digital Contractors, leads a marketing agency focused on Facebook and Instagram ads for outdoor living contractors. As his client list grew, so did the operational headaches. Day-to-day management was handled through Slack messages and memory, with ClickUp sitting idle as a neglected list of content ideas. Henry admitted he was always “firefighting,” unsure if tasks were completed and unable to delegate effectively. The lack of structure meant he couldn’t confidently bring on new employees, even as the business grew.

The Process

Why Workshop

We began our engagement with Henry by running a focused “Why Workshop” to uncover Digital Contractors’ true operational challenges and define what success would look like for him and his team. We asked questions such as:

• What’s the biggest bottleneck in your current project management?
  
  

• What’s working well, and what needs to be carried over to the new system?
  
  

• What would make ClickUp a total success for your agency?
  
  

• How will this impact your day-to-day and your ability to scale?

This session ensured we aligned with Henry on priorities from the very start and set the stage for a solution that fit his goals.

How Workshop

Next, we mapped out the entire client journey at Digital Contractors, from initial lead to testimonial worthy result. We documented every key step, tool, and handoff, giving Henry his first comprehensive, high-level view of how work actually flowed through his business. This process surfaced hidden inefficiencies and manual tasks, many of which Henry hadn’t realized were draining his time and bandwidth.

DRTT Chart & Process Prioritization Review

We worked with Henry to define his agency’s core departments, roles, and responsibilities. Together, we prioritized which processes needed to be in ClickUp from day one, focusing on the 20% of workflows that would drive 80% of results. We also identified process owners and took stock of existing documentation, ensuring that every critical workflow had a clear home in the new system.

The ClickUp Blueprint

Over the following week, we mapped out a ClickUp hierarchy tailored to Digital Contractors, defined system rules and permissions, and planned out custom dashboards and automations. This blueprint became the foundation we used to implement the system.

Henry noted that seeing the system blueprint forced him to think more deeply about his business and realized his previous ad hoc approach of adding new lists whenever something new came up to Clickup was actually creating more problems than solutions.

Implementation

Initial Setup and Feedback

We rebuilt ClickUp from scratch, migrating all essential workflows and building out templates for recurring processes.

Team Rollout and Training

With the foundation in place, we rolled out the new ClickUp system. Henry and his team received video training not just on the system but on how best to use the system. This training became a key part of the onboarding of Henry’s growing team so they could quickly hit the ground running.

Ongoing Support & Iteration

After launch, we provided ongoing support, including two office hours 1 week and 3 weeks after launch to keep the system adoption high. We also provided Henry with best practices so that he could manage future improvements on his own.

Key Features

Centralized Task Management: All client work and internal tasks are now tracked in ClickUp, replacing scattered Slack conversations.

Custom Dashboards: Henry and his team have instant visibility into what needs to be done and who is responsible.

Process Templates: Recurring workflows are standardized, making onboarding new clients and employees seamless.

Automated Reminders: Routine check-ins and deliverables are automated, reducing manual follow-up.

Scalable Team Structure: With clear processes and accountability, Henry can now confidently add new team members.

Results

• Clarity and Control: Henry knows exactly what needs attention each day. No more second-guessing or missed tasks.
  
  

• Confident Hiring: With structure in place, Henry was able to bring on two new employees and delegate work effectively for the first time.
  
  

• Time Savings: Henry saves 5 hours per week on admin which means more time for sales, marketing, and strategy.
  
  

• Process Awareness: Henry discovered hidden inefficiencies and automatable steps, leading to ongoing improvements.
  
  

• Sustainable Growth: Digital Contractors is now positioned to take on more clients without operational stress.
  
  

Insights from Henry

Henry shared that the biggest shift was realizing how much mental energy he had been wasting trying to keep track of everything himself. The mapping and blueprint process forced him to examine every aspect of his business, revealing the value of having a system that works for the whole team. He noted that even with his technical background, the expertise and outside perspective were essential to building a system that could actually scale.

“I thought I could set up ClickUp myself, but I kept putting it off. Bringing in an expert brought clarity I didn’t know I was missing. Now, everything’s organized, nothing gets lost, and I finally feel in control of my business again. For the first time, I can bring on new team members without worrying things will fall through the cracks.”

Henry Shalom, Digital Contractors Founder

Conclusion

Henry’s experience highlights the power of process mapping and custom system design when it comes to implementing a project management tool in a service business. By investing in structure and operational clarity, we helped him move from daily chaos to a scalable, confident business, ready for the next stage of growth.