🚀 What happens when you let your team run the company?

How keeping a bootstrapped team led to our company’s profitability, and what our Chief Appreciation Officer, Gary Willmott, is up to next.
🚀 What happens when you let your team run the company?
Gary Willmott

My Next Chapter 🚀

How keeping a bootstrapped team led to our company’s profitability, and what I’m up to next.


Hi5 was born in 2016 out of recognising a need for an easy way to manage a rapidly growing team. We’ve been fortunate to partner with some incredible clients such as Pep, Yoyo, M&C Saatchi Abel, ooba homeloans, Advanced Space, Lulalend, PayU, etc. who ultimately helped us become an overnight (profitable) success… 3 years later! In 2020, I decided it would be better to get away from the day to day and see how the company would run without me… read what happened 👇

Long Version

Almost 5 years ago, we founded Hi5 with a vision to help managers and leaders engage with their employees with ongoing feedback and recognition using a simple cloud-based platform. Our ambitious mission is to create an Employee Engagement platform that employees love so much that they actually want to use it.

Three years in, we reached profitability and had some incredible opportunities to scale, however we decided to steer a route most startup founders don’t go: We decided to stay bootstrapped and profitable.

I really appreciate that our Seed Investors (Ryan & Thomas) were open to this move.

When we took this step, I reflected and asked myself 2 things:

What do I really want to do?

I want to build stuff with smart, creative people. I’m a maker and I’m always running through new ideas in my head!

What don’t I want to do?

I don’t enjoy the day-to-day work of being a CEO, even though I love daily interaction with my team and being the visionary for the company.

With this in mind, I realised I don’t need to be at the helm every day. With our values at the core of this decision, I empowered the team to continue building without me. Two of the most important values driving Hi5 are:

1. Customer-centric: Listen to our Customers

2. Doer: Keep Shipping

This isn’t a copy and paste strategy; it isn’t possible without incredible core members such as Sharné & Enricko who have stuck through since the beginning.

Since Hi5’s inception I’ve led a bunch of great product people who went on to work for amazing companies like Luno, Booking.com, Amazon & Takealot.

After being inspired by Ricardo Semler’s book, Maverick, on giving autonomy to team members, I put this to the test in real life and left my day-to-day leadership position at Hi5. I started consulting to help other companies in the scale-up phase by empowering their teams with lean product principles.

On top of that, we decided to move to Jeffreys Bay, South Africa. It’s an incredible “Zoom Town” that has a mixture of a great community, lifestyle, surf and an incredible co-working place.

Guess what? When I got out of the way, the company grew!

  • Our revenue grew by 50%.
  • The team added and trained 2 new staff members (Kyla & Ofek) to assist with the growth of the company.
  • The existing staff were promoted to senior positions and were rewarded with Hi5 stock options.
  • We started implementing a new revenue sharing scheme based on the success of the entire company.

Fast Fwd

Hi5 is growing. The team is happy.
I’m enjoying helping other companies scale. I’m happy.

And then… GoDaddy reached out to me with an incredible opportunity to lead a product team within Mobile Ventures to Empower Entrepreneurs. We are brewing something really exciting and can’t wait to ship it 🚢

Famous last words

I’m honestly amazed how the counter-intuitive decision of leaving the day to day of Hi5 as the Chief Appreciation Officer, essentially leaving my company in the hands of my trusted team, blew up in an awesome way. I’m still fortunate to remain a majority Shareholder and Board Member within Hi5 to advise on strategy and growth.

I’m super pumped for this next season and incredibly excited to watch Hi5 grow from the sidelines!

If this story intrigues you, I’m keen to help others that might be on similar journey. Feel free to comment below with any Q’s or contact me or give me a Hi5.

P.S. I’m aware the team at Hi5 is looking for one more junior devs, apply here.

P.S.S. If you have a similar story to share, why not send your story to the Hi5 blog.

P.S.S. I’m aware the team at Hi5 is looking for one more junior dev, apply here.