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The art of juggling many roles in a bootstrapped eCommerce business

Every business starts with someone, be it a solo founder or large group of board members and investors. Most small businesses begin with just one or two people at the start, which inevitably means the founders constantly juggle dozens or hundreds of different tasks each day.

Learning to effectively manage the constantly changing duties of the founder’s or owner’s role can be incredibly challenging, and is one of the reasons so many small businesses do not succeed. Anyone who wants to start a business, be it eCommerce or anything else, needs to first appreciate the challenge they are taking on with the sheer number of roles they will need to fill, and hats they need to wear.

Learning to balance the responsibilities of running a business takes time and can only come through experience. You begin by knowing little more than the product or service you’re trying to build, and then slowly acquire new bits of knowledge and skill sets as the business develops. Over time, if you are to survive as a business, you become really good at taking care of the tasks that have to be done; even those that you dread doing. It’s that or fail as a company.

When Sandhills Development was first started, I was the developer/creator of the products, I was the website manager, and I was the customer support agent. I was also the marketer, the writer, and even the accountant. I did the company taxes, I managed payroll (for one person, myself), and I took care of setting up company insurance plans. It didn’t matter what the role or obligation was, I took care of it. That’s simply the nature of running a bootstrapped business as a solo founder.

It is out of necessity that founders take on all of the roles demanded of them, but it is through experience that we learn how to best prioritize our focuses and begin growing our teams and delegating the tasks that once landed solely on our own shoulders.

In 2012 or 2013, when Sandhills Development was in its infancy, I learned first hand that I should not be responsible for handling the company accounting and tax filing. This came through a nearly very expensive mistake where I miss calculated the income tax I owed through the company to the tune of $80,000. I had always managed my own taxes as a freelancer so in my mind it only made sense that I should take care of the company taxes as well. I was wrong and thankfully was able to recognize that so immediately hired a CPA (Certified Public Accountant) to assist me. I have never made the mistake of filing taxes for the company again. We always pay a professional tax firm to take care of that for us.

That was one of the first times I recognized the value in hiring someone, be it part time or full time, to help take care of specific challenges. Business owners hire new people when there are too many tasks to complete on their own, or when the needs of a role are beyond the skill set of the owner.

Easy Digital Downloads was the first product from Sandhills Development that grew beyond the scope of what I could manage on my own. It was a product I had begun building out of my own need. At the time I was the lead (and only) developer for numerous other products, including Restrict Content Pro, and I needed to have a better way to sell and market my own products. I was juggling the role of developer, marketer, and customer support with my other products and I wanted a better solution that would enable to bring all sales and communication with my customers under a single roof. Easy Digital Downloads was built to help serve this purpose and to help make my jobs easier.

As the platform grew, the demands put on me to manage customer support grew along with it. This forced me to spend more time helping customers than working on the product. To account for this, I decided to take on a new task, one that I had very little experience with: hiring. I brought on my first full time employee to help with Easy Digital Downloads support.

The first part of hiring that business owners often focus on is the cost. How much is it going to cost to hire a person for this role? The cost of a team member is one of the very obvious challenges a business owner has to take on, but it is far from the last or the most difficult when beginning to grow a team. At first, your role as “boss” is to ensure the new team member gets paid, and that they have something to work on where they can provide value. But that role quickly changes as a team grows.

At two people, the roles a founder juggles aren’t much different than before the first hire, save for the two mentioned above. As the team grows, a lot of the owner’s time is spent simply taking care of people. The team needs to be paid; the team needs insurance; the team needs ample communication; the team needs to be reassured; the team needs resources; the team needs feedback; the team needs approval; the team needs more help because they are overburdened.

These are all examples of needs that typically fall on the founder to take care of, at least initially. As companies continue to grow, founders tend to bring new people on just to help take care of needs. First there were people brought on to take care of customers’ needs, then there are people brought on to take care of the people’s needs whom are taking care of customers.

While not always the case, a good founder, CEO, boss, or whichever title is preferred, should be capable of diving into any role within the company. If there’s a role they are not personally capable of handling, they should be well equipped with the means and know-how to find a person that is capable of handling the responsibilities of the role.

The Sandhills Development team has grown from one to 18 over the course of five years. While that is in no way “rocket ship” growth that many start-up companies see, it is more than significant enough to highlight all of the various roles and challenges that are faced by those roles.

At the beginning, I was predominantly a developer and the only developer. The products grew and my focus was shifted to taking care of customers. That made it necessary to supplement the loss of my development time with new team members dedicated to development. This is a common trend seen as companies grow and is just part of learning to adopt to ever-changing roles as a founder.

Along with being the developer for Sandhills Development in the first couple years, I also managed all of the marketing efforts for our products. While I was quite good at building products and producing content for or blogs, traditional marketing channels were never one of my fortes. Once we had grown to a certain scale, it began to be painfully obvious that my rudimentary marketing skills would no longer suffice, nor did I have the bandwidth to handle marketing on my own. To ensure our products were given ample marketing efforts, I expanded the team to include multiple people whose primary job and skill set was marketing.

After less than three years from the start of Sandhills Development, I had removed development, support, and marketing tasks from my primary focuses. I still included tasks related to those jobs for several more years, and still do today, but the amount of time spent on them continued dwindled as new challenges popped up that needed attention. Recently my role changed again as new team members were brought on to take over social media and many of the company administration tasks that have typically always landed on me. This, along with hiring for other roles over the last two years, left me in an interesting position because it freed up enough of my time that I had the freedom to re-discover what my role at the helm of the company was.

Founders are generally good at taking care of things they’re required to do. It’s just part of the job. When all of the “required” tasks have been reassigned, however, a founder’s role transitions into one where they get to be more selective of the tasks they focus their time on. This is both a great luxury and a terrible burden. Business owners that succeed get there by completing the un-glamorous grunt work, and they tend to get really good at that work. When all of that work is moved off to the shoulders of others, it’s very easy to feel lost because suddenly you, as the founder, are no longer needed for the daily operations of the business.

The art of juggling the roles as a founder really comes down to being able to adapt well to rapidly changing needs and environments. One moment you’re intensely writing code for a new product, then abruptly your focus moves to server configurations because word just came that all the sites are down. In a single day, founders will often jump from acting as customer support reps, to being product creators, then on to being marketers, followed by being accountants. One month your only job is to hire new people to take care of jobs that need to be done, then the next month you spend twiddling your thumbs trying to figure out what to do because you just hired yourself out of a job.

Learning to balance all of the things that pull on your focus as a founder comes with practice. Through the last five years, there are four main lessons I’d like to share with anyone considering starting their own business and those already juggling.

First, be willing to do any job in your company. A lot of times, operating a successful bootstrapped company means getting your hands dirty and doing the work no one else wants to do.

Second, learn to recognize when someone else, either on your existing team or a new hire, is more able to perform a job than you. It’s easy to let pride get in the way and tell yourself that you’re the best person for the job even when that’s not the case. Remember, it’s cheaper to pay someone well to do a high quality job than it is to not pay someone and allow yourself to do the job poorly.

Third, adapt to change. Your role will change hourly, daily, and over months and years. To survive the constant change, you must be willing to adapt.

And lastly, 90% or more of the job of a founder or owner in an eCommerce business is to help address needs, whether those be the needs of your team or your customers. This means your job will constantly change, and that’s okay and normal.

A good founder or business owner is really good at taking care of needs. A person that can jump in and help address needs, whatever they are, is one that will do well at juggling the many roles in a bootstrapped eCommerce business, even when it’s the role of janitor.

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  1. Pippin Williamson

    Excellent post Pippin packed filled with wisdom from your own personal experience.

    Thanks for sharing.

  2. Pippin Williamson

    Thanks Pippin! Our team is a couple of years in and I relate to the founder’s responsibilities a lot. Customer support and success is extremely important to me and it’s been tricky to organize the team to consistently deliver excellent customer support.

    Would love to learn more about how your team organizes for the process of customer support and if you’ve seen any particular methodology work well for you. For example, how involved are developers in customer-facing support communication?

    1. Pippin Williamson
  3. Pippin Williamson
  4. Pippin Williamson

    Excellent insights Pippin!

    I can relate this to me as well. We have to address the needs of our team or the customers whether they need a soap or towel in the washroom or your customer needs to address an urgent issue on their site.

    But being a developer founder, Sometimes, you feel bad when you don’t touch the code for few months 🙂


  5. Pippin Williamson

    Thank you very much, this is helpful. I’m probably in the same situation you were in years ago. I’m currently working on my own (I have several products). I hired someone in the past for support but I was too scared by the cost and put an end to it myself. I feel like the business could grow but somehow I’m not allowing it to grow. I don’t know if that makes sense, but it’s really how I feel it’s going.

    1. Pippin Williamson

      I think that’s exactly what most business owners go through when they’re first looking to hire people. When budgets are already tight it’s difficult to see how paying someone to do the job you already do could raise budgets.

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