Name: Upile Chasowa
Current position: Co-founder and CTO


I am a business and software development entrepreneur with over 8 years of commercial experience in Retail, Insurance, Finance and Real Estate.

My hunger for innovation, knowledge and determination to turn ideas into consumer driven products, has contributed to my most recent success at WorkClubHQ. In less than 9months I was able to build a product from nothing to the point where it’s now valued at just over £1.5million.

WorkClubHQ reimagines the idea of how we use space in an urban environment by transforming unused space into productive working areas for people to work, network and share ideas.

Since obtaining a Degree in Computer Science back in 2012, I’ve founded 3 startups and gained vast amounts of exceptional computing and product development skills. Meanwhile, I’ve very hands-on development experience spanning software, design, R&D and product strategies for big data and online marketplace applications.

My secret ingredient to building a killer remote team is get to know your team, learn about them, figure out what makes them laugh, what makes them tick and pay attention to every concern they have. Productivity is very important for me, I enjoy implementing strategic project management methods and ensuring a work-life balance.

I am originally from Malawi, and currently based in London since 2001. I enjoy cooking, reading, and if I am not spending time with my friends or family, I am probably planning for my next big trip abroad.

Tell us about your life before leadership – what kind of roles and projects did you work on?

  • Graduated in 2012, University of Leicester BSc degree in Computer Science
  • Along the way, I also worked with a well established charity helping the homeless and was featured on ITV to help raise awareness. 
  • Further, worked on a side project called – LetMeView – 2015 – 2016  – an on demand property viewings service – a Deliveroo like service – for Real Estate Agents and Private Landlords across the UK.
  • Previously a Software Engineer for an Insurance & Finance company based in London. Created a data warehouse system, maintaining and processing over 230 Million of data.

How did your first leadership position come about, and was it intentional on your part?

I ran a startup called propertyGroup that registered and managed over 200 private properties, working with a number of private homeowners looking for residents across the UK. propertyGroup partnered with Zoopla, which allowed me to have access to a pool of residents across the UK looking for rental properties. 

How did you manage the transition? What came easily / what was difficult?

  • propertyGroup’s success enabled me to gain support from Virgin Startup, which opened further opportunities to enhancing the initial business model.
  • Following the success of propertyGroup, I was able to identify an enormous opportunity with AuctionShelter and was able to raise some funds to help build the initial product. AuctionShelter, realised that online home-selling technology was woefully out of date and making things more difficult than necessary for buyers and sellers alike. So I decided to fix it.

What was your biggest failure in that first leadership role?

Inability to understand my market and test my given assumptions with experts and clients; I just assumed that there was a magic bullet to success.

What made you keep doing it?

Surrounding myself with the right people and I networked hard, at least 5 times a week at one point – helped to expand my knowledge, confidence and determination to achieve something great  – I saw the world from a different perspective.

Tell us a fun fact that (nearly) nobody knows about you

I was once an aspiring songwriter.

What are the three key skills you think every lead needs?

Everything starts off with assumptions, which are then further refined. 

  • Be patient, 
  • Be persistent, 
  • And be ready to fail 

But, never give up and always be ready to learn from your mistakes. That’s how you build your experience and those are the tools you need.

What have you learned about acquiring and retaining talent?

  • The success of any team depends on the key stakeholders e.g. CTO, Project Managers, Business owners etc. to fully be involved and engaged. It’s not about micromanagement, but being able to foster and build an open environment.
  • Creating clear project guidelines for productivity, teamwork, and accountability is very important.

How do you motivate your team and manage their stress levels?

  • Set clear tasks and give detailed answers. Review the project requirements document attentively to make sure all business functionalities have been clearly defined. It’s wise to break development down into iterations and also define a CI/CD pipeline process, to ensure that code is easily stored, automated and accessible in one place. Automate as many processes as you can, this will help increase productivity.
  • My secret ingredient to building a killer team is get to know your team, learn about them, figure out what makes them laugh, what makes them tick and pay attention to every concern they have. 
  • Before diving into work – a simple “how are you doing today?” gesture or an icebreaker offers an opportunity for everyone to speak at the start of the meeting, which greatly increases the chances of engagement and a highly productive team.
  • Over time, icebreakers can help you get to know people and add a layer of fun that helps the team bond in a very unique way.

How do you manage your own stress levels and productivity?

  • Looking after my health – Exercise is a great stress relief for me. Also making time for hobbies and favourite activities. Getting enough good-quality sleep is also important for effective stress management. 
  • Setting boundaries – As a CTO, it’s easy to feel pressure to be available 24 hours a day. Establishing some work-life boundaries is very important for me. I try to avoid checking emails, Slack messages etc. from home in the evening, or not answering the phone during dinner. 
  • Taking time to recharge – taking short holidays, I do love to travel as it helps me to switch off from work by having periods of time when I am neither engaging in work-related activities, nor thinking about work. 
  • Relaxing – e.g. sauna –  allows me to observe present experiences and thoughts without judging them, definitely helps melt away stress. 
  • Accepting help from trusted friends and family members.

How do you stay in sync with other parts of the business?

  • Daily and weekly standups. 
  • Daily chats with my co-founder & team – might be 5mins, 10mins – frequent communication is very important

Most of our work is managed and stored online. Organisation is as much about process as it is about the tools we use. We bring everything from documentation, notes, product ideas, research insights, project trackers, and much more all into one place using tools such as G-Suite, Slack, Notion, Trello, Jira and more. No more exporting, syncing, or redoing work, and even less time keeping track of what’s where.

Where do you see yourself in 5 years’ time?

Building our current startup, WorkClubHQ into a multi-million pound business.

What product do you wish you’d invented?

My aim has always been about building a marketplace, an ecosystem, to enable buyers to buy from the comfort of their own home on a selection of exclusively available real estate.

Thanks very much, Upile!