C-suite career advice: Rich Waldron, Tray.io

What are some common misconceptions about working in IT/tech? “Traditional training and education for a tech career usually involves studies in mathematics, science… In my experience, working in tech has been the opposite. Be prepared to deal with ambiguity.”


Name: Rich Waldron

Company: Tray.io

Job Title: CEO and co-founder

Location: London, England

Rich Waldron is CEO and co-founder of Tray.io. He believes strongly in democratising the use of software and data for anyone – not just for engineers. He helped create Tray.io to lead the low-code general automation movement so that any business user can have the power to integrate their tech stack and automate mission-critical business processes by themselves.

What was the most valuable piece of career advice that you received? To not be afraid to take risks. You never know what you can do or what’s possible if you don’t try. Throughout history, we’ve witnessed incredible progression in many disciplines and astonishing success for the startups that were bold enough to try something new. Ultimately, I think much of the progress in the world comes down to someone, or a group of like-minded people, deciding to take a chance.

What was the worst piece of business advice that you received? At the risk of sounding cliche, some of the worst (but probably the most sensible) advice I’ve received was to give up on my goal of starting up a new company. Get a stable job somewhere working for someone else, take a good salary, that sort of thing. I’ve been lucky enough to have been offered a few such opportunities earlier in my career, but my co-founders and I refused to give up on our dream.

To be clear: Entrepreneurship isn’t for everyone. It’s one of the absolute hardest things anyone will ever try. For every billion-dollar “unicorn,” there are literally millions of startups that fail. The process is frequently stressful, occasionally terrifying, and eats up huge chunks of your time. But for those who are disposed, there just isn’t anything like starting your own company. Nothing else I’ve ever done compares.

What advice would you give to someone starting their career in IT/tech? Don’t give up. Succeeding in tech is about being tenacious. And there’s a constantly-growing library of community resources out there for technology beginners.

And don’t let the fact that you don’t have a computer science or engineering degree hold you back in your career ambitions. If you put your mind to it, you can learn a great deal through self-teaching. Also, the advent of low-code solutions has opened up a wellspring of opportunities for employers and job seekers.  

Some years ago, a career as a developer required formal certifications and degrees in the “correct” programming language of the moment. Now, it’s far less about which coding language you’ve studied and much more about whether you can use conventional technical tools to solve the challenges at hand. Having a fundamental understanding of key concepts such as data structure and programming functions (such as logic operators and data manipulation) positions job seekers – across specialties and backgrounds – to capitalise on low-code to launch their careers in tech.

Did you always want to work in IT/tech? I think my ultimate goal has generally been a career in technology. For as long as I can recall, technology has only increased in importance in the world as a means of empowering people to achieve incredible things and express themselves creatively.

I was fortunate enough to attend the University in Bournemouth, which not only has an excellent digital and engineering program, but also connected me with one of my co-founders, our CTO Alistair Russell. (To be fair, Ali is far more technically-minded than I am, having studied with Sir Tim Berners-Lee on the Semantic Web).

When we graduated, we spent that summer working out some of our ideas. We explored several different avenues, but we always came back to the theme of democratising technology for larger audiences, which ultimately led us to our inspiration for Tray.io.

What was your first job in IT/tech? After college, I took a job as a product manager at a local tech company, and spent three years getting a crash course in what it’s like to be part of a small team and what it’s like to manage an engineering team. I also led a sales team, which afforded me an interesting view into different departments across an organisation and how to best scale out different teams as a company grows.

What are some common misconceptions about working in IT/tech? Traditional training and education for a tech career usually involves studies in mathematics, science, and other subjects that may seem to indicate a future of exact calculations and known quantities. In my experience, working in tech has been the opposite. Be prepared to deal with ambiguity. At several points in your career, you’ll be expected to solve new, unforeseen problems that haven’t been well documented or explored. If you decide to go the entrepreneurial route and work at, or found, a startup, you’ll be tackling new challenges every single day.

In the same way, there’s no such thing as “knowing everything” in tech. Working in tech is fundamentally about change as you, your colleagues, your competitors, and your customers discover entirely new areas you couldn’t have imagined. Many of the best developers and technical experts in the world aren’t the ones with the most degrees or the most years of experience. They’re the ones who never stop learning because they understand there’s always some new challenge just around the corner.

What tips would you give to someone aiming for a c-level position? In my opinion, being a successful executive requires a combination of experience, strategy, and a way to synthesize the two into a vision. For example, good marketing leaders should have a great deal of real-world marketing know-how to inform a larger marketing plan each year to generate leads and pipeline, increase visibility via PR, and cultivate loyalty and advocacy among customers. CMOs should be able to forge a future path that dominates a category, breaks open new markets, and evolves the brand.

It may also be worth mentioning that being a successful executive isn’t simply about being a best-in-class worker in a specific field, especially in technical and engineering disciplines. There’s a world of difference between highly skilled and knowledgeable developers who excel at coding and highly competent engineering managers who successfully lead large teams. Each role can be crucial to an organisation and each can offer a long and satisfying career path, but each requires completely different skills.

What are your career ambitions and have you reached them yet? One of our primary goals has been to build a truly world-class company, a brand that stands the test of time. Have we reached that goal? I’d like to think we’re well on our way. We founded Tray.io in 2012 and have seen exponential growth since launch, but we have big plans for the future.

Another goal I’ve always had is to help other entrepreneurs to build their own world-class companies. I remain actively involved in the startup and VC community in the UK, and have been fortunate enough to be invited to events such as LDNSaaS and StartUpGrind to offer what perspective I can. I realise that I and my team have benefited immensely from the mentorship and support we’ve received from the startup community, so I’m always happy to pay it forward to the next generation.

Do you have a good work life balance in your current role? Balancing work and life is something every entrepreneur struggles with. (I also should mention that right now, I’m also juggling my duties as CEO with my duties as a new father!) However, I’m thankful to be able to work with an absolutely unbelievable team, which absolutely helps.

Then again, our team has always believed strongly in work/life balance. It’s a strong part of our company culture that goes back to one of our most fundamental beliefs: That in an increasingly competitive world, one of an organisation’s most essential competitive advantages is its people. Companies that unwisely burn out their teams can lose their edge as valuable team members move on to organisations that better understand how to set reasonable expectations, as well as how to build a culture and an environment that encourages people to stay.

What, if anything, would you change about the route your career path has taken? Let’s just say that throughout my career, I’ve made more than my share of mistakes. At the time, some setbacks seemed devastating (a few of them positively humiliating, in fact). However, in hindsight, every mishap led me down the path to where I am today. Tactically speaking, it seems like we could’ve benefited from moving our company’s headquarters to the US from the UK a bit earlier on, since startup funding was scarce about 10 years ago. Still, relocating our headquarters to San Francisco was an important move for the future of our business and it was likely the right choice to make.

Which would you recommend: A coding bootcamp or a computer science degree? I think both have their merits. We’ve hired engineers with computer science degrees and bootcamp graduates pursuing tech as a second career. What matters is a person’s drive to learn and advance their career. I think bootcamps will become increasingly popular and will be a critical component of the world’s reskilling efforts, because they provide job seekers an alternative to a four-year degree, which is going to become increasingly more important as our job market continues to evolve.

How important are specific certifications? The way we look at certifications depends on the specific area we’re talking about. For example, in specialised disciplines such as security, compliance, and data privacy, for which certifications are the industry standard, we’ll obviously want to look for team members with the appropriate training and accreditations. However, as mentioned, we’re more flexible in other areas.

One of the exciting things about working in low-code automation is that it gives us the potential to grow and evolve the job market. Today, having formal coding skills is still a significant part of landing a technical job. In 10 years’ time, when a significantly larger portion of the workforce may be using low-code platforms in place of writing traditional code, what will that new job market look like? Maybe we’ll see a totally new generation of separate certifications and complete educational programs based on working in low-code environments. Or, maybe we’ll see fewer certifications...or none at all, as low-code becomes the new normal.

What are the three skills or abilities you look for in prospective candidates? The top three attributes we look for in prospective candidates are the ability to support our teammates, the drive to do amazing things, and the understanding that we’re on a journey together – and that it’s a ride that’s to be enjoyed. We believe that humility and ambition aren’t mutually exclusive, and in fact, we’ve found that the best team members usually possess both qualities.

What would put you off a candidate? There are a few red flags that immediately come to mind for me. First, at Tray.io, we believe strongly in collaboration and stopping at nothing to deliver for our customers. The “hero” is the team – not an individual. I imagine I’d be wary of candidates who are much more interested in pride of ownership than they are in working with us to build something great.

I also believe that the future belongs to those who come up with creative solutions to big problems. Countless organisations have failed due to inertia, because teams did things “the way we’ve always done them.” I’d find it difficult to get excited about a candidate who doesn’t seem interested in thinking outside the box and didn’t have much of a track record of innovation.

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? Overthinking seems to be a common mistake. Of course, it’s a good idea for candidates to prepare as best they can. However, setting oneself up for a single, rigid talk track can leave candidates unprepared for even simple follow-up questions. Because interviews can go in so many different directions, it’s not productive to try to script out an entire interview in your head from start to finish. And trying to adhere to a script too rigidly also puts candidates at risk of misrepresenting themselves and their personalities to companies that are increasingly looking for candidates that will be a culture fit. By all means, prepare for questions you think might be asked, but remember you’re having a conversation with an actual human being.

Do you think it is better to have technical or business skills – or a mix of both? A decade ago, I might have made the case that it’s more important to start with technical skills. However, today, with the rise of low- and no-code technology, it’s becoming easier for non-technical individuals to interact with and use technology to drive competitive advantage for their business. Being technically savvy will surely benefit individuals in their careers, but I now believe a mix of technical and business skills will be highly beneficial, especially as we see more organisations embracing transformative technology, such as low-code automation, as a way of life.