Canvas Rebel Feature: Meet May O'Connor
- Magnolia Ad Co
- 4 hours ago
- 4 min read
Alright – so today we’ve got the honor of introducing you to May O'Connor. We think you’ll enjoy our conversation, we’ve shared it below.
May , thanks for taking the time to share your stories with us today How did you scale up? What were the strategies, tactics, meaningful moments, twists/turns, obstacles, mistakes along the way? The world needs to hear more realistic, actionable stories about this critical part of the business building journey. Tell us your scaling up story – bring us along so we can understand what it was like making the decisions you had, implementing the strategies/tactics etc.
People assume my business “took off” because my work got better or I got luckier, but the real scaling moment was when I stopped doing everything manually and started building infrastructure.
For the first stretch, I was the bottleneck. Every lead lived in my inbox, every follow-up was in my head, every onboarding step depended on me remembering it, and every project started from scratch. I was busy, but it wasn’t scalable.
The shift happened when I invested in automation and built a real client journey. I created a streamlined intake form that captures the info we need upfront, then connected it to a calendar system with specific days and time blocks for design, interviews, and onboarding. Once someone books, the system guides them step-by-step, sends the right emails, assigns the next tasks, and keeps everything synced across the tools I use.
Then I layered in AI to remove the hidden time drain: call notes and recaps. Now my calls are recorded, transcribed, and summarized automatically. I can ask the app to pull out deliverables, key decisions, and next steps, and even generate a proposal outline in minutes. That alone gave me back hours every week.
Scaling wasn’t a single viral moment. It was building systems that created time, reduced friction, and made the client experience feel polished and consistent. If time is money, scaling starts by creating more time.
May , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I’m the founder and principal designer at Magnolia Digital, a website design agency I launched in 2014. I build conversion-focused websites and automated client journeys for service-based businesses who are ready to look as premium online as they are in real life.
The twist is- I did not start in tech. I spent eight years working on yachts as a private chef, where I learned the art of high-level service, calm execution, and delivering an experience that feels effortless. That background heavily influences my approach. A great website is like a great dinner. It needs the right ingredients, the right structure, and a presentation that makes people trust what they are about to invest in.
Today, I help clients clarify their message, position their offer, and build websites that guide visitors to take action, whether that is booking a call, submitting an inquiry, or making a purchase. My work combines strategy, copywriting, design, and backend systems like forms, calendars, CRM, and automations. I love making businesses run smoother behind the scenes while looking elevated on the front end.
What sets me apart is that I am not just designing; I am building a sales tool. I am known for strong messaging, especially headlines that speak directly to a client’s pain points and drive action. I am also deeply hands-on. I can look at a business and quickly identify what is missing digitally, then build the plan and the system to fix it.
What I’m most proud of is helping founders go from “my website is fine” to “my website is stunning, and bringing me business.” More clarity, more qualified leads, more consistency, and a lot more time freed up because the process is finally automated and professional.
What’s a lesson you had to unlearn and what’s the backstory?
I had to unlearn the idea that charging less makes you more desirable, or that being “more affordable” somehow makes you easier to say yes to.
In reality, doing things for less attracted the wrong clients, the ones who nickel-and-dime, question every line item, and treat expertise like it is negotiable. The best clients I’ve ever worked with are the opposite. They come in with a healthy budget, they value speed and quality, they respect my years of experience, and they are happy to pay my prices because they understand what it saves them in time, stress, and costly mistakes.
Once I stopped trying to prove my value with discounts and started pricing based on outcomes and expertise, everything got better. The work, the process, the relationships, and the results.
Are there any books, videos or other content that you feel have meaningfully impacted your thinking?
Yes, Building a StoryBrand by Donald Miller is my go-to, and it has influenced how I approach nearly everything: websites, messaging, sales, and positioning.
It gave me a simple framework for clarifying what most businesses struggle to say in a clean, customer-centered way: who they help, what problem they solve, and what the next step is. It also reinforced something I believe deeply: most businesses don’t have a marketing problem; they have a clarity problem.
When you can make your message instantly understandable, your website converts better, your content performs better, and your sales process becomes easier because people “get it” faster.
Contact Info:
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