From Freelancer to a CEO with Jack Thorogood

Earlier this month, Hackernoon published an interview with our CEO, Jack Thorogood.

In the interview, they discussed how to build a better working environment for freelancers and remote workers. Jack shared his insights on leadership, mentorship, and building a successful remote team.

Read the whole interview below!

Hackernoon Interview

How did you start with Native Teams? 

It all started with a problem we experienced ourselves. Alex, my co-founder, and I both faced challenges with work payments, taxes, and the friction that often exists between talent and opportunity - especially when working internationally.

What drew me to Native Teams was how tangible it is. We’re addressing something very real and practical: helping people get more value from the work they do while removing unnecessary barriers.

At the same time, I was searching for the right business to build with Alex. Native Teams was the perfect fit for both of us - a chance to solve meaningful problems while building something rooted in our shared vision.

How has your leadership journey shaped the company’s vision?

Most directly, I can say that the business absolutely carries the DNA of Alex and me. If I look at the culture we’ve built and the approach we’ve taken - for example, putting values and decency ahead of money - then it is true to what we set out to achieve.  

Of course, it ‘takes a village’ and it ceased to just be the business Alex and I wanted to build and shape since the moment we began to work with a wider team. I hope it’s true that we continue to guide the business through our actions, though.

Who were your key mentors throughout your career, and how have they influenced your leadership style?

Right back when I was 13 and grew up working on the farm with my dad, I learned about the importance of hard work. My mum was also a key mentor in a way because my parents divorced when I was young, and having two single parents with very different outlooks on life made me realise you have to hear all arguments and then take the best path forward for you.

For the last year and a bit, I’ve had an excellent mentor, Hristo Manov, (LinkedIn). He’s the smartest - real smart, not just book-smart - guy I know and has been instrumental in helping me make better decisions.

Finally, my co-founder Alex is the best mentor I could have asked for.

How do you define effective leadership in a remote-first or distributed work environment?

Where everyone is doing what should be expected of them, it doesn’t really matter when they do it - flexible working is a great thing - but if colleagues are working remotely or on a distributed basis and their output is what one would expect, then that is success. It means trust in people is being repaid.

What strategies do you use to foster trust and collaboration within a remote team?

The best way to build trust in a remote team is not to always be ‘remote’! Once a year, we have an all-hands in-person weekend, and for a month, we hire a couple of villas and have as many people as possible work from there for a couple of nights.

We also do all we can to actively encourage friendships to blossom. The more people are working with friends whose company they enjoy, the more they’ll be accountable and give their best.

How do you balance maintaining productivity with ensuring team members feel supported and valued?

The simple answer is by picking the right people in the first place. If you have the right people on the team, this balance is self-regulating.

How important is mentorship for freelancers and remote workers, and how does Native Teams address this need?

In my opinion it is vital if you want people to be the best they can be, for their benefit as well as ours. We run a series of external and internal mentorship programmes for our team. Finding the right people to be mentors isn’t always easy, but it's possible with some hard work and patience.

The best advice I had about helping find the right mentor is to ask the mentee where they want to be in 5+ years and then find a mentor with the profile that is already there.

Can you share a success story where mentorship played a pivotal role in the growth of a freelancer or remote worker?

Without meaning to sound like an egotist - and not least because one of the most important aspects of a mentor/mentee relationship is confidentiality - I can say that I’m a good case study.

I’m fairly certain that if I hadn't really embraced the concept of having a mentor, my leadership capabilities would not have grown sufficiently fast to keep pace with the demands of our business. As it is, I think I’m just about able to keep the plates spinning!

How can experienced professionals in tech better mentor the next generation of freelancers and remote workers?

This is only half-right as a question to ask. My answer to it is that potential mentors should realise that they have a lot to give. It is easy for people to have ‘imposter syndrome’ and to, therefore, undervalue their worth as a potential mentor.

The other half of the question, though, is how professionals in tech can be better mentees. In my opinion - and I can say this from personal experience when I was much younger - people don’t always have the self-awareness to realise how much a mentor would benefit them. This should change!

How do you see leadership evolving as remote work becomes more prevalent worldwide?

I see a more progressive, trusting and less egotistical form of leadership emerging as remote work becomes more prevalent.

The ‘return to the office’ approach is really favoured by less trusting, more micro-managing leaders who can’t let their people go free to fly.  

It’s inevitable that more and more companies will embrace remote work - even if there are a few high-profile return-to-the-office types - and therefore, the requirements of trust, flexibility and confidence in your team to do the right thing will become more to the fore.

What role does technology play in enabling effective mentorship and leadership for remote teams?

Technology, of course, plays a pivotal role in enabling effective mentorship and leadership.  Without tools such as video meeting software, text chat (e.g. Slack) and cloud-based project management tools then modern leadership for modern teams cannot work.

The chat and video tools are obvious of course, but a solid project management tool such as Asana is the best way to help people stay on track and for everyone to be abreast of progress.

How is Native Teams helping to shape the future of work for freelancers and remote professionals?

Every time we help a freelancer or remote worker engage with a client or employer with less friction, which we do via the payment tools and employment options we can provide, we can call that a win for remote workers.

We help our users work on more exciting projects (by removing international barriers), and we help them keep more of the money they earn (by looking after their tax-free allowances and tax-efficient remuneration).

Fundamentally, we help our users get all the best of remote work opportunities with the benefits, for example a local employment contract, of a non-remote career.

What steps are you taking to ensure diversity and inclusion within Native Teams and the freelancer community you serve?

We founded the business with this premise: I knew that if I founded the business with Alex - a girl from a different country and perspective - we’d have a far better business than if there wasn’t a diversity of views.

Since then, we have taken steps to ensure that not only does the business have a great diversity of gender and ethnicity, but we also reward that fairly. For example, this means monitoring salaries to check that women and men are paid the same average salary.

I cannot stress the value that diversity brings to the business: Over and above our gender parity, since we decided to build out our core team in India and the Philippines, as well as in Europe, we have only become a stronger and better business.

How does Native Teams build a sense of community among freelancers and remote workers?

We are beginning to offer some of the best-practice we have within our business to bear with our wider user base. This includes informal dinners and drinks, and also a ‘work from a location as part of a wider group’ approach. These have been great for us as a company, and we’re sure our users will benefit from this, too.

What advice would you give to aspiring leaders in the tech industry, especially those focused on remote work?

Work hard and be persistent. Lead by example and be open-minded. Trust people. They might sometimes let you down, but if you don’t trust people, they’ll always let you down.

What leadership qualities do you believe are most critical for navigating the challenges of the gig economy?

Flexibility, trust and a lack of ego.

If you could mentor one aspiring entrepreneur or leader, what would be your top piece of advice?

Don’t be afraid to say you don’t know something and that you could do it with some help and support.

Jack Thorogood, Founder and CEO

With an impressive track record of over 11 years, Jack excels in software development and remote team management. His passion for innovation and dedication to fostering collaborative environments have played a key role in the success of numerous projects. Combining a solid sales foundation with technical prowess, Jack brings a unique entrepreneurial insight to the table.

As the visionary behind InPlayer and NOVP, Jack encourages businesses to embrace streaming and visual communication, infusing humanity into the business world. His latest venture, Native Teams, offers businesses and remote workers opportunities in the global community.

Known for generously sharing knowledge, Jack actively participates in fintech events, showcasing expertise. Jack's commitment to education goes beyond the boardroom, embodying the spirit of a true mentor empowering others.