There are really two schools of thought on this, and you can see the tension between them across the founder journey. You have the Pragmatic Delegator, who keeps things lean and hires to fill gaps, and the Organizational Architect, who builds a formal leadership structure to replace themselves.
Camp A: The Pragmatic Delegator
This camp is all about efficiency and staying lean as long as possible. The core idea is to offload the tasks you aren't good at or don't enjoy, freeing you up to focus on higher-value activities. Ashley and Ryan Reynolds of Cloth and Paper, on an episode of Honest Ecommerce, put this simply: they advise hiring employees for tasks you’re not good at. It’s a surgical approach. You identify a weakness, like graphic design or customer service, and you plug that specific hole with a person.
Lindsey McCoy of Plaine Products made a similar point on the same show, framing it as a way to avoid founder burnout. She urged founders to "let it go a little sooner" and bring in help, warning against the tendency to be a martyr who does everything. This model is practical, cash-flow friendly, and keeps the founder at the center of decision-making. It’s about making the founder more effective, not making the founder redundant.
Camp B: The Organizational Architect
This camp argues that to truly scale, you have to build a machine that can run without you. This isn't about offloading tasks; it's about delegating entire outcomes and building a leadership layer. On The eCommerceFuel Podcast, Bryan Croft shared how he grew his business past $20 million by intentionally building a high-performing leadership team. This allowed him to step back and focus exclusively on company culture and vision.
This thinking is crucial for breaking past growth plateaus. As Jenica Oliver explains on the Up Arrow Podcast, your team structure can be a "silent DTC killer." She questions whether the founder should still be doing tasks, even if they can. The goal is to hire leaders who are better at their function than you are. It represents a fundamental identity shift. Craig Shiesley, CEO of Yasso, even takes it a step further on Stairway to CEO, describing how founders can identify the right time to replace themselves in the CEO seat entirely for the next stage of growth.
I believe the Organizational Architect model is the only path to significant scale, but you can’t just start there. The Pragmatic Delegator model is a necessary first phase. Many founders fail because they get comfortable just plugging gaps and never make the leap to building a real system of leaders. They fail to make the crucial mindset shift from maker to manager that Jono and Nick Pandolfi discuss on Shopify Masters. They see delegation as getting things off their plate, not as building a team that can think for itself.
Your strategy should depend entirely on your current stage. If you’re in the early stages and wearing all the hats, start by being a Pragmatic Delegator. Write down everything you do for a week, highlight what you hate or what you’re bad at, and hire or contract someone to take over those specific functions. This is the heart of effective Delegation Strategies For Founders. This frees up your time and, just as importantly, gives you practice in letting go. If you are approaching the $5M to $10M revenue mark and feel like you’re the bottleneck, it’s a sign that this model has reached its limit. Your next hire shouldn't be another "doer." It needs to be a true leader, someone who can own an entire pillar of the business, like marketing or operations. That’s how you build a brand that can one day thrive without you.