Project Management for Web Design Agencies: My Circle Day 2025 Talk
As part of Squarespace’s Circle Day 2025, I had the great opportunity of presenting two in person sessions and an online session on project management for web design agencies. In this talk I shared how I grew September Design Studio from a solo practice into an award‑winning creative agency, and outlined the systems and strategies that keep our multi‑location team aligned.
One of the key points I covered was the importance of mapping out your services and workflows. Taking the time to define what your agency offers—whether it’s copywriting, ecommerce builds, marketing, SEO or another specialization—helps you structure your processes and ensures nothing falls through the cracks. I walked attendees through our project systens, which uses detailed checklists to track every step, from preparing contracts and welcoming clients to executing branding, copywriting, design, SEO and accessibility tasks. Checklists make it easy to visualize the entire process and free you up to focus on higher‑level creative work.
We also talked about recognizing when it’s time to expand beyond a solo practice. Hitting a bandwidth cap, feeling overextended or wanting to reclaim personal time are clear signals that you might need a team. When you do decide to hire, the people you bring on should align with your studio’s aesthetic, communication style and culture. I explained how I inventory our existing skills and identify gaps, then recruit designers, developers or specialists who complement our brand and can operate autonomously.
Another area we explored was project pricing and team member compensation. My approach is to estimate the cost of delivering a project—including the team’s time—and then add a 50 % markup to ensure profitability. Most clients prefer a flat fee so they know exactly what they’re getting, while team members are paid hourly. This transparent model has allowed us to grow sustainably while rewarding our contractors fairly.
Throughout the session I emphasized that project management isn’t just about tools—it’s about building a business that supports your vision. By defining your purpose, systematizing your workflows and hiring thoughtfully, you can scale your agency in a way that preserves your creativity and delivers incredible results for clients. Thank you to everyone who joined my Circle Day talk and asked such thoughtful questions. If you missed it, you can catch the recap on the Circle blog. I’m excited to continue sharing resources that help creative entrepreneurs elevate their brands with confidence and style.
During my in-person session at Circle Day 2025, we hosted a round-table discussion around the four pillars of scaling from a solo practice to a multi-location team—Mapping, People, Communication and Pricing. To keep the conversation broad enough for every stage of studio growth, I asked attendees to reflect on these prompts:
Capacity Clues – What signs—workload, missed leads or burnout—have told you it’s time to bring in help whether it would be your first hire or expanding your team?
First Hire, Best Hire – If you could add just one collaborator tomorrow, which skill gap would you fill first, and why?
Process Templates That Stick – What single checklist or template would most reduce chaos for you or for your team?
Tool-Stack Sanity Check – Which one tool keeps your client communication clear today, and which platform did you abandon (or would abandon) after outgrowing it?
Money Math – How do you structure your pricing to protect your margins whether you’re preparing to hire, currently working with contractors or growing a full team?
Remote Onboarding Wins & Misses – If you onboarded a remote collaborator tomorrow, what would be your biggest worry—and how might you pre-solve it? If you have hired one, what worked well? What didn’t?
Next-Level Delegation – If budget weren’t an issue, which task would you delegate to free up creative time? Why?
