August 13, 2021

Shedding Hats as a Founder

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In most SaaS startups and businesses you’ll often hear, “We all wear multiple hats here.” I have yet to talk to a Founder who carries less than three hats. Hats, in this context, means roles and responsibilities. A Founder is often the CEO, carrying a bag on the sales front, leading the product vision and sometimes a developer.

However, having that many jobs across different functions can only last so long, as you can face burnout from spreading yourself thin (here are some best practices to avoid burnout). So the big question is, when and how should you be shedding those hats?

The honest answer is: It depends on what your goals are for the company.

Identify your company and employees’ goals

If you want to grow, you’ll likely need to shed your hats as you reach certain milestones. You’ll know when because these milestones tend to be peaks in your growth that can turn into stagnation. It may show up as a decline in growth, or it could show up as unwanted employee turnover. As you continue to wear more hats, your employees tend to share that burden, and it can create an environment that isn’t sustainable for employee growth and development.

If your goal is to run the company flat (little organization structure) and harvest cash flow, you may need to look at what your customers’ reactions might be to you not investing in the business. That could mean customer turnover resulting in a decline in revenue and profit in the business, especially if your competitors choose to employ a different strategy. This won’t happen overnight, but can over a longer period of time.

Think through the positive and negative before delegating tasks

When looking at where to start shedding hats and delegating responsibilities, I like to think through who will be impacted most, and how your time should be allocated. Impact implies both positive and negative reactions. For example, if I choose to stop acting as a salesperson and hire someone to backfill my responsibilities in that role, the positive impact is that I may have more time to focus on other areas in the business that need attention, whether it’s developing an awesome team (which I’m currently training), or providing guidance for some of the companies we’ve acquired thus far. 

The negative impact would be short-term, but new sales and revenue could take a hit as the new sales rep begins to ramp up the learning curve. When initially thinking, look at what areas you can shed responsibilities where the negative impact can be mitigated in some way, either by time, dollarization or anything else that may be top of mind.

Anytime you’re in a position where you’re shedding hats, start small to gain momentum. The hardest part of this process will always be starting because we tend to expect immediate results. However, once you see some early wins, you’ll find yourself getting more comfortable with doing it again and again until you’re at a point where you begin to question what it is that you’re doing. That invested time will turn into a full-fledged strategy. A strategy that we will cover more in my next post!

Give it a try and let us know what you think. If you have any questions, feel free to contact us.


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