Replacing production help with strategic partnership
The Problem
The Brand Studio team at ClassDojo was paying $6,000 per month for an agency partner that required 80% of the team's effort upfront. The agency had been working with the company for nearly three years—responsive, communicative, growth-minded—but their skill set was purely production. If we provided detailed guidelines and assets, they could recreate. But as we emerged from an internal rebrand with solid creative direction but amorphous solutions that needed heavy stress testing, they couldn't help us get there.
The mismatch became costly. We were exhaustively solving every edge case before handing work off to them, which meant we were doing the hard part anyway. Meanwhile, our workload was insane. We were moving quickly across five different brands (ClassDojo, Sparks, Islands, Tutor, Districts), each needing varying degrees of updates post-rebrand. Quality was suffering. Design debt was accruing. We were paying monthly for a partner relationship that didn't multiply our capacity—it just redistributed the work.
The real problem wasn't the agency. It was that we were drowning in strategic work while paying for production help.
The Approach
I outlined three options in a resourcing memo to leadership: pause everything else and focus on one major project (unrealistic, would take 3-4 weeks minimum), hand everything to the agency (guaranteed quality drop and more design debt), or bring in a senior freelance designer who could think and make simultaneously. The resistance was budget—we'd just tightened spending the year before.
The strategic play was advocating to replace the agency, not supplement it. We'd run a 2-week trial with a freelancer at the same monthly cost, then make a call: move forward with the freelancer or return to the agency. No wiggle room, clean comparison.
I wrote a creative brief that would stress-test whether a freelancer could handle both strategic exploration and production execution. The project focused on the Districts brand system—our most challenging work requiring exploration across paid ads, e-books, one-pagers, homepage designs, and pattern systems. The brief explicitly asked for strategic rationale, not just execution: Why this approach? How does the team use it? What are the resource implications?
What I Did
Wrote the brief: A deliberately amorphous project that required divergent exploration of fundamentally different strategic approaches, then convergent development into a refined system. This wasn't "make these three ads"—it was "stress-test our creative direction and tell us if the system itself should evolve."
Set clear parameters: 2-week trial, ~32 hours total (half the monthly allocation), flexible timing (could work 2 full days or 4 half days), regular communication expectations (tell us when you're working, when we'll see rounds).
Defined evaluation criteria: Quality of work, strategic rationale behind decisions, volume delivered in the timeframe, interest in our mix of exploration and production, mindset (growth-oriented, curious, open, respectful), and willingness to learn new tools (Figma vs. Adobe Illustrator, web design vs. print).
Presented to leadership: Problem we face, options with impact and trade-offs, open discussion. The turning point was hearing "this is your team that you lead, so you have the ultimate call."
The Impact
The freelancer delivered. Across the 2-week sprint, she produced strategic exploration of different directions with clear rationale, stress-tested the Districts system across multiple surfaces, and created production-ready artifacts. She demonstrated both sides of what we needed: the senior design thinking to explore solutions holistically, and the craft to produce final deliverables.
We made the offer February 12th, the day after her final round. Not full-time—60 hours per month, part-time, same cost as the agency.
The projected impact based on the trial work: our team will be more balanced, delivering higher quality work that's thought through holistically. The freelancer can take on projects we'd otherwise have to exhaustively figure out before handing off. She'll deliver exploratory design across homepage heroes, PDFs, paid ads, websites, and one-pagers while also handling the universally not-fun production work like creating 20 email graphics for a campaign. Quality improves. Production still gets met. Strategic work becomes possible again.
We're no longer paying for help that doesn't help.
What This Demonstrates
This case study exemplifies how I help founders make resource allocation decisions that multiply team effectiveness:
Diagnosing mismatched needs: The problem wasn't the agency's quality—they were excellent at production. The problem was paying for production help while drowning in strategic work. Recognition that "help" isn't helping if it doesn't address the actual bottleneck.
Reframing the conversation: Rather than asking "can we afford more help?", I shifted to "what kind of help actually multiplies our capacity?" Part-time senior judgment delivered more value than full-time production when the constraint was thinking, not execution.
The trial as proof: A 2-week sprint with clear deliverables gave us evidence to make the case, rather than hypothetical arguments about what might work better. The brief was designed to reveal capability across both strategic and production work.
Building the business case: Presented options with explicit trade-offs and impact, used data from the capacity system to show we were paying monthly for work we were already doing ourselves, made the decision reversible (clean 2-week comparison, then choose).
Strategic advocacy: This required recognizing when an existing relationship wasn't serving the team's needs, making the case to leadership with clear alternatives, and designing an evaluation process that would prove the model. The real deliverable wasn't hiring the freelancer—it was establishing that creative teams need senior partnership, not just production bandwidth.
This is the approach I bring to creative direction: identifying where resource allocation is undermining creative effectiveness, designing evaluation frameworks that prove better models, and advocating for decisions that shift teams from reactive execution to strategic partnership.
Role: Creative Director
Company: ClassDojo (EdTech, Series D, 50M users)
This case study is part of my creative direction work helping founders translate brand instincts into decisions their teams can execute. Learn more about working together →