Entrepreneurs share about growing from 10 to 50 employees

Anthony Mongeluzo

Anthony Mongeluzo

President of PCS

Growing from 10 to 50 employees was a MAJOR change for PCS.
I cannot emphasize that you must begin to view your company differently, with a more strategic view, supported by infrastructure.

For instance, we started tracking time off, which we never did previously.

We discovered that team members were taking advantage of our generosity.

We created policies and procedures to handle the growth and incoming work in a more predictable, measured fashion.

We ensured that employees knew what they were by creating an employee handbook.

No more random, by-the-seat decisions.

Then there was the delicate part of navigating promotions.

With 10 people, I was the boss and knew everyone’s first name.

We lacked a reporting structure, and people become upset when their “friend” was now the boss.

We ensured that when we made a promotion, we were able to explain why.

I found that if you choose Joe for a prometon and explain why you were doing it with specific examples, people accept it more readily.

For example, if you say, “Joe always comes in one hour before everyone else and continues to take online courses was a factor in our decision,” people get it.

As I look back, it’s clear that we might not be in business today had we not implemented these changes.

The is clear cut: If you fail to add structure to your organization and communicate the reasons for implementing those changes, you will stunt or halt your potential growth.

It begins with the president — in this case, me — recognizing that I could no longer manage my company with a style that was fine for 10 employees but ineffective for a company with 50 employees.

It was a struggle and mental challenge to implement this new company view, but it worked.


Arjun Pillai

Arjun Pillai

Founder & CEO of Insent Inc + Insent.ai

How I changed:

  • Started deferring decisions. I count the number of times I use the word ‘defer’ a week to make sure I’m on track.
  • No pride of ownership – I keep using this phrase to show that I’m vulnerable and people could call out my mistakes as well.
  • Revised JD – I asked all my direct reports to write their new JD for the next 12-18 months. I’m also writing my new one. This will help everybody to be on the same page.
  • Started firing me from roles: From a 90% individual contributor, I’m resetting myself to 50% first. and then in a few months to 30%.

  1. Specialization
    From being generalists, all of us started becoming more specialized. Mid level leaders or seniors were brought into the company for handling individual departments.
  2. Documentation, Tools & Processes
    We started spending more time in making clear documentations right from requirements, developer documentation, bug tickets, customer documentation etc. More meetings, all hands meetings, 1:1 and sync ups came in (especially coz of Covid). We also bought the right tools to support this.
  3. Focus on HR, and Culture
    We had quarterly full company offsites when we were 10. Now, there are smaller meetups in teams or cross functionally. The full company offsite is only once a year. We have started documenting best practices, value, culture etc.

  4. Insent.ai

Ronnie Teja

Ronnie Teja

CEO of Softwarekeep

In 2016, when we started, things were easy.

I was the CEO, the HR, and the accountant at the same time.

However with ten employees we could fit around a coffee table.

Easy to manage.

Nonetheless, things took a twist between 2018 & 2019 when I acquired ten more e-commerce stores.

The acquisition meant more employees, more headaches.

In 2019, I realized a downward trend in terms of sales and performance from the team.

What I didn’t know, I was the cause.

The team was not motivated, and no one seemed to care or take responsibility.

Plus, I was also overworked and couldn’t think straight.

In the last quarter, we lost close to $500K in revenue.

As a last resort to save the situation, I turned to one of my HR friends to carry out an audit to determine what was causing the issue.

It turned out my employees were no-longer motivated nor interested in serving the company; thus, the clients weren’t getting good service.

We quickly devised a method to relinquish some of my powers.

We promoted some of the employees to a management position to help in governance.

I’m happy today my business has realized double-digit growth due to good and management.

Lesson: You can’t do it alone once your company surpasses 25 employees.


Anastasia Dyachenko

Anastasia Dyachenko

CEO of Cadabra Studio

There are three main points that changed in my work as CEO and our company in general as it grew:

  1. Delegation is a must. It becomes harder to control all processes in a middle-size company; that’s why it’s essential to trust people and delegate different tasks to department heads. To do that, the company leader has to accept that people might do things differently, and there’s no need to interfere with their workflow if the end goal is achieved.
  2. Make all processes clear and automated. The bigger a company is, the more important it is to write guidelines for all company processes. This helps to solve any issues during one working day and avoid situations when one department blocks another one’s work. Plus, keeping a simple hierarchy is crucial..

  3. CEO is not the only head – they are one of the heads. Compared to small companies, where the CEO is the primary decision-maker, the middle or big company leader stands in line with other department heads.

    At least, this is how I feel, and this position helps our company grow. Because if you feel above all others, why hire such people to your team?

    Cadabra Studio

Matthias Treutwein

Matthias Treutwein

Co-Founder & Managing Partner of enpact

The times of team members deciding on how to conduct their meetings are over.

The times when neither personal nor project-level objectives are set, tracked, and evaluated are over.

The times where annual appraisals and feedback loops are a “nice-to-have” are over.

The biggest challenge when growing a business is to establish standardized processes.

Without them, your company lacks efficiency and effectiveness.

In our case, this became painfully evident last year.

We had to break old habits and jointly develop and embrace a new way of working together.

We had to re-establish the identity of our organization to professionalize our work.

Getting there is all about communication.

Is this change process difficult?

Hell, yes.

It is probably among the most difficult things a growing company can face.

But it is urgently needed to improve the workflow and to maintain a supportive and co-creational workforce.

It is the management’s task to clearly explain the “why” in this process.

This we do by stressing the benefits this has on everyone’s work.

If both the management and employees buy into the new standards, we can play out our organization’s strengths, shift resources, and provide training and recovery time where needed.

How do we get there?

By requesting our people to speak up.

By empowering them to take ownership in the process.

By introducing new intermediate management levels and clarifying roles and mandates for everyone.

Finally, we mutually need to discipline ourselves.

Regardless of tenure or title.

While this seems awkward and uneasy in the beginning, it is probably the most important duty of everyone.

In the long term, it will make everyone’s life easier, by ensuring a high level of transparency and accountability.

Finally, there must consequences.

Just like Ken Kesey wrote: “You are either on or off the bus.”