“8 Questions with Playfair” ft. Rich Waldron @ Tray.io

This is the fourteenth in our “8 Questions” series — in which we sit down with founders in the Playfair portfolio who share their entrepreneurial journey.

We first invested in , the global leader in low-code automation, in 2015. Since then, the company has experienced incredible growth, winning numerous Fortune 500 companies as users, and in late 2019 which valued the company at more than $600m.

Today, we sit down with founder and Chief Executive Officer, Rich Waldron, to hear his story from the beginnings of Tray.io. We hope this can help other founders and aspirational entrepreneurs in their own ventures.

1. What inspired you to be an entrepreneur?

I’ve had an interest in technology for as long as I can remember. Specifically, I’ve always been fascinated by the potential of technology to help people achieve things they couldn’t otherwise. I’ve been fortunate enough to work in a variety of roles in and around technology, including product management and sales, and experience different sides of a technology business.

I’ve also been fortunate enough to work with co-founders (Alistair Russell and Dominic Lewis) who, in some ways, have very complementary personalities to mine, but we all share the ambition to build something that will stand the test of time.

2. Can you take us back to the beginnings of Tray.io?

We officially founded the company in 2012, but I had been working with Ali and Dom for several years prior. We had previously attempted to build and launch several projects prior to Tray.io, including a web agency, a media company, and a mobile app for social gatherings to help groups of friends and family members make group decisions, which we noticed would get bogged down in lengthy email threads. Our initial prototype included a rules-based API service that made it easier and faster to handle incoming emails.

Our mobile project led us to the beginnings of what would become Tray.io, as we realized over time that accessible, rules-based automation could be of great value to many potential users. However, as of 2012, there wasn’t much of a venture capital community in and around Southampton. At the time, I was literally selling Wellington boots on eBay to keep us afloat.

Since we needed more runway, more team members, and more resources, we moved to London to join an accelerator program, which would be the start of a multi-year rollercoaster ride of highs and lows as we engaged with accelerators, sought funding, and ended up high and dry in San Francisco, in the wake of a funding round that had fallen through, just as the mid-2010s SaaS boom was getting underway. We returned to London, eventually raised a modest round, and, in fits and starts, began building our team. From there, we focused on building the best possible product to solve the growing challenges of data management in the rapidly-growing API economy. We eventually went to market with what I would consider to be a strong product-market fit, and by the time we raised our Series A, we were off to the races. Things haven’t slowed down in the slightest since then.

3. What is the hardest lesson learned since day 1?

Product development versus go-to-market. As a recovering product manager, and someone who has used thousands of products of varying quality in my time, some part of me believes that every organization should, in an ideal world, develop and ship best-in-class products of the highest quality. It has also been my experience that organizations that have superior go-to-market strategy and execution, even if they don’t have the best product, tend to win.

Bottom line: While we all want to build the best products the world has ever seen, any company that neglects its GTM does so at its own peril.

4. What has been your strangest day as a founder?

The pandemic has led to plenty of strange days. In early 2020, both our EU and US teams were outgrowing their respective office locations. One moment, we were urgently searching for new workspaces on both sides of the world. The next moment, we were asking everyone to stay home.

5. What have you learned from your investors since you first fundraised?

We’ve been fortunate enough to learn an enormous amount from our investors. Because they’ve been doing this for some time and have a strong sense of what works and what doesn’t at startups, they’ve offered perspectives on larger industry trends, competitive analysis, financial modelling, hiring, and many, many other important topics that have been invaluable to us. They’ve also been extraordinarily helpful for networking to connect with potential partners and customers.

6. As a founder, what is your proudest achievement to date?

I’m most proud of the incredible team we’ve assembled. I believe strongly that a company’s team is one of the most important assets and competitive differentiators it can possibly have. I’m grateful every day for the diverse and incredibly talented group of people who have somehow decided to join us.

7. Crystal Ball: What are your plans for the future?

We’ve built products that meet some of the most important business challenges of the modern workplace, including integrations for the ever-expanding tech stack and automation for business processes which, more than ever, require scale and speed. Given how software is eating the world, as they say, the challenges for which we support our customers will clearly continue to persist and profoundly affect the future of work for years to come.

Because the average enterprise uses more than 1,000 different cloud-based applications, every company needs some way to connect their tech stack to flow and manipulate their data to solve their unique business challenges. In particular, every software company also needs to provide integrations to its customers’ tech stacks, so that those end-customers can also execute faster and at scale.

I’m incredibly proud, and humbled, that we’ve already built industry-leading products and count Fortune 500 firms and some of the fastest-growing companies in the world as our customers. We also have a massive opportunity to reach even more top organizations all over the world, particularly with our recent expansion to EMEA and APAC. So, our focus for the foreseeable future is on growth and execution. And because we have such an exceptional team to help us hit our goals, I’m beyond excited to continue the journey.

8. #1 piece of advice to an aspirational founder?

Be bold. Take the risk.

As a founder, it’s common to be constantly bombarded by people with highly varied and frequently conflicting opinions. At many points in your journey, you’ll hear a lot of advice to hold back, avoid taking risks, that sort of thing. And while you should absolutely consider advice from experienced domain experts, as a founder, you will ultimately have to make the call on difficult, risky decisions yourself. It’s my fundamental belief that throughout history, people have accomplished the most incredible things when they decided to go out on a limb and actually take a shot. It’s certainly been my experience, anyway.

You can find out more about Tray.io on their and follow them on and .

You can follow the Playfair team on , , and and here on . If you would like to pitch us, please submit your application on our .



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Chris Smith

Managing Partner @PlayfairCapital | Class 25 @KauffmanFellows | Contributor @Forbes