Navigating a Startup: Challenges and Triumphs of Tech Startup Operations at

Navigating a Startup: Challenges and Triumphs of Tech Startup Operations at
  • 5 min read

Welcome to the inner workings of, where innovation and exploration define our trajectory through the ever-expanding passion for customer success. 

As the Director of Operations, I’ve been at the helm of a very dynamic and successful startup, navigating through challenges, redefining support structures, streamlining billing processes, and charting a course for success. In this extended blog post, I’ll delve deeper into the challenges encountered and the strategic solutions we’ve already implemented as we prepare for the next phase of growth.

1. Support Team Redefinition: Striking a Balance for Maximum Scale

In the vast expanse of a startup’s early stages, organizational structure is typically very flat. It’s not uncommon to see the entire team working in various parts of the business to ultimately achieve the same goal – customer success.

As your startup continues to grow, reshaping the support team’s operations is crucial when it comes to sustaining growth especially when your customers  need quick responses and nimble problem-solving.

There’s an old saying “if it ain’t broke, don’t fix it” which if you’re not able to plan ahead, this may very well seem relevant… but I promise you it’s not. The reality is, a flat organization can only scale so far and as your business grows, you have to adapt.

“One of the keys to success, is being able to stay ahead of your current state by anticipating growth and planning ahead of time before it’s too late”

Danielle Hardy, Director of Operations

As I joined, our CEO Ben Gabler was well aware of this need, in fact sometimes I think he has a crystal ball! In any case, I knew exactly what we had to do; scale.

In order to properly scale our support team, I came up with a strategy that involved  a slight restructure of our support organization with a new role: WordPress Engineer, Team Lead. By introducing an official leader on each shift, it allows us to empower our WordPress Engineers with comprehensive training and autonomy in resolving issues swiftly. 

As you can imagine, this is a very delicate situation and new concept to a team, not to mention I’m the newest member of the team, so I had to be extremely careful on how we started implementing change.

With full support of our CEO, I was ready to implement the first part of our new structure, but first I wanted to get to know the entire team, not only to help provide comfort during some of these changes, but to get to know the team as best as possible since I was relatively new.

As I got to know the team better, it was very clear to me that I was surrounded by some amazing individuals with some incredible experience and a common passion for our customers. In fact, before joining, I worked for a competitor and I knew how great their customer support was at, so it came to no surprise that we already had members of the team naturally executing the majority of this role. 

For me, this was huge as it made what seemed to be a big change, not so big… just official. Fast forward to today, we’ve successfully implemented our WordPress Engineer, Team Leads and things couldn’t be better. As expected, this approach not only enhances our customer service but also fortifies our team for future challenges.

2. Billing Challenges in a Bootstrapped Startup 

When it comes to billing in a startup it often involves grappling with manual processes and ever-evolving systems.  For most successful bootstrapped startups, it always starts with an MVP, including how we bill our customers. For example, “We don’t need to worry about auto-suspensions yet, we don’t have any customers, let’s launch!”, this is not a bad thing at all, in fact it’s amazing, the goal should always be get to market as quickly as possible to validate your product.

So as you can imagine, when I first joined, there were a lot of manual processes in place. With that said, our team has years and years of experience not only in hosting, but in business, so while there were a lot of manual procedures in place, there were also a lot of things already in place that you wouldn’t typically expect at a startup… but there was one major thing missing; documentation.

As continues to grow, it’s crucial to have as much billing automation and documentation in place as possible. From service suspensions, to account cancellations, we’ve had to implement many different solutions to ensure a smooth billing operation.

When I first started here, many of the processes in place were brought to my attention. As I was accessing the billing situation, I began documenting every process to properly cover how billing is handled at 

As we are nailing down these processes and workflows, it is showing us the many ways we can automate these processes further and is providing us with a clear pathway of what all will be automated next year, for a smoother experience internally, and externally.

3. Solo HR Navigator and the Startup Culture

As the solitary HR figure in our company, aligning HR practices with the incredible growth of has presented a unique set of challenges. Balancing employee needs, fostering a positive company culture, and ensuring compliance demands strategic navigation through the vast expanse of human resources.

We are in the process of Implementing an integrated HR management system that allows for efficient employee onboarding, streamlined performance reviews, and simplified leave management. This upgrade not only enhances overall HR efficiency but also ensures that our growing team remains connected and aligned with’s mission to provide the best possible experience on the planet.

When working with a start up and joining an already bonded team, introducing new internal policies and procedures is not always easy. Luckily, the team at knows that some change can be a good thing! With slight adjustments to how we all take our breaks, our time off, and our scheduled shifts, we are able to operate a bit more comfortably and ensure we are not understaffed during the higher volume times in Support. Not only does making adjustments like this help keep a nice response time for our customers, it helps the team remain stress-free with the amount of customers they are talking to.

One of my favorite things to say is: “You can’t provide good customer service if your employees aren’t happy”. As the company grows, new policies and procedures need to be put into place to help things flowing well internally and externally. Many people feel uncomfortable with the terms “policies” and “procedures”, but it’s really not the words that make people feel that way; it’s the implementation of them. That is the biggest thing I have focused on here at; Implementing changes smoothly, slowly, and compassionately.

4. Continual Exploration: Propelling Through Challenges

Like any industry and business, improvements internally are an ongoing effort. At, we’ve learned that innovation and adaptability are a necessity  to ensure the best possible experience for our customers and our employees. By addressing challenges head-on and implementing strategic solutions, we not only become better as a team but also stay ahead of the growth curve to sustain the massive success we’ve seen thus far. 

The journey may be challenging, but the rewards are astronomical as we continue to propel to new heights in the WordPress community; Always reaching for the stars to take our teammates and customers to the next level.

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