How to Implement ClickUp for a 200-Person Agency: Lessons from Hawke Media
Key Takeaways
- Build deep platform expertise before leading a company-wide migration - Lauren spent 18 months learning ClickUp before the Hawke rollout
- A six-month implementation timeline is realistic for a 200-person agency when you invest in interviews, process building, and training
- Replacing a disparate array of tools with a single platform eliminates context-switching and creates a shared source of truth
- Team interviews during the discovery phase reveal how people actually work, not just how leadership thinks they work
- Process templates and documentation are the bridge between a configured tool and a team that actually uses it correctly
- Implementation is never truly done - build a roadmap for ongoing optimization after the initial rollout
Gray MacKenzie is joined by Lauren Makielski, Chief of Staff at Hawke Media, to discuss the realities of implementing ClickUp at a 200-person agency. Lauren is a certified CSM and PMP who led Hawke’s migration from Wrike to ClickUp - a project that touched every team, process, and workflow in the organization. Outside of work, she collects cookbooks and builds mechanical keyboards.
Life Before ClickUp at Hawke Media
Before adopting ClickUp in 2020, Hawke Media managed projects using Wrike alongside a disparate collection of other tools. The result was what Lauren describes as “general chaos” - information lived in multiple places, teams had inconsistent processes, and there was no single source of truth for project status or workload.
This is a pattern that many agencies experience as they scale. A tool that works for 20 people starts breaking down at 50, and by the time you hit 100+, the operational friction becomes impossible to ignore. For Hawke, the tipping point came when the cost of not having a unified system - in missed handoffs, duplicated work, and lost context - exceeded the cost of a full platform migration.
The decision to move to ClickUp was driven by the platform’s flexibility and customization capabilities. But choosing the tool was just the first step. The real challenge was designing a system that could serve the needs of a large, multi-disciplinary agency while being simple enough for every team member to adopt.
The Six-Month Implementation Journey
Lauren’s approach to the migration was methodical and thorough. She had already spent 18 months using ClickUp personally and developing a strong expertise in the platform before taking on the Hawke rollout. That personal experience proved invaluable - she understood the platform’s capabilities and limitations from a practitioner’s perspective, not just from watching demos.
The implementation unfolded over an intense six-month period. Lauren conducted team interviews across the organization to understand how each department actually worked - their workflows, handoff points, pain points, and communication patterns. These interviews revealed important nuances that would have been missed if the implementation had been designed purely top-down.
From those interviews, Lauren and her team built process documentation and ClickUp templates for each workflow. Data migration from Wrike required careful planning to ensure nothing was lost in the transition. Then came the training phase - getting 200 people comfortable with a new system requires more than a single training session. Lauren developed training materials, ran workshops, and provided ongoing support as teams made the switch.
Results and Lessons Learned
The outcome was a meaningful shift from chaos to clarity. Teams moved from managing work across disconnected tools to operating within a structured system with consistent processes, clear ownership, and visible project status. Process templates and documentation gave every team member a reference point for how work should flow through the organization.
Lauren is transparent about the fact that the initial rollout was not the end of the journey. With 200 people using the system, there are always opportunities for improvement - workflows that need refinement, new use cases that emerge, and team members who need additional support. She discusses the roadmap for continued optimization of Hawke’s ClickUp instance and the importance of treating the platform as a living system rather than a one-time setup.
For agencies considering a similar migration, the key takeaway is that successful implementation at scale requires significant upfront investment in discovery, process design, and training. Rushing through these phases to “go live” faster almost always creates more work on the back end when teams struggle to adopt the system.
Resources Mentioned
- Lauren Makielski on LinkedIn - Chief of Staff at Hawke Media
- Hawke Media - outsourced CMO and marketing services
- Gray MacKenzie on LinkedIn - Founder at ZenPilot