I’m Rich Waldron, Founder and CEO of Tray.io. AMA!

In 2012, after years of experimenting with product ideas, I took the plunge and started a company with my two friends, Alistair Russell and Dominic Lewis, in the UK.

Our goal was to build a technology that people loved; we were inspired by reading Techcrunch and learning about all of the amazing technology created in Silicon Valley.

We created Tray.io, which offers a low-code automation platform to give people the capability to build powerful apps, supercharge processes, embed native integrations and connect any service that their heart desires.

The past ten years have been quite the journey; we started in an environment that had a small technology scene and venture community and ultimately ended up (literally) bootstrapping the business by selling Wellington boots on eBay.

From there, we embarked on a rollercoaster ride of joining a variety of startup accelerator programs, identifying what we thought were opportunities, and a series of stops and starts that led us to San Francisco at a time when the city was entering an unprecedented startup boom period.

Through blind faith, stubbornness, and more than our fair share of luck, we managed to stay afloat long enough to hone our vision of a technology platform with a robust product-market fit. We somehow started assembling a team of unimaginably talented people and, over the next decade, raised more than $100M in funding while acquiring customers such as Cisco, FICO, EventBrite, Segment and many others you may have heard of. To this day, I’m still in awe of both how far we’ve come and of the size of the market opportunity that remains in front of us.

I’m excited to participate in this AMA and happy to answer questions on a range of topics; a few that comes to mind are…

  • From idea to paying customers, the overwhelming breadth of advice and why patience is critical
  • The phases of hiring (and identifying your core value)
  • Finding the right investors, and the impact on the value of your board
  • The scale mindset

I’ll be answering questions on February 24th between 8:30-10:00 AM PST, looking forward to it!


Note: This AMA is closed for questions, but you can check out the existing conversations below.

This February 24th, we’re really looking forward to hosting Tray.io’s founder and CEO, Rich Waldron. From finding their footing well outside the valley a decade ago, pivoting early with great poise, doggedly navigating the arduous first few years of hitting PMF, and cracking the ever-exacting mid-market segment, Rich and team have passionately built and scaled a platform that serves 47,000+ customers such as Cisco, Eventbrite, Segment, and others.

AMA Index (Rich’s brain-pickings) :brain:

(Hard-won insights, opinions, and observations; thoughtfully examined and articulated)

How Tray untangles what some have called the “mid-market briar patch”
The “forever iteration" of org design
Making strategic decisions when advice points everywhere
How should one think about US expansion
How Rich allocates his time; “Some of the most effective time spent is really trying to diagnose and unblock anything that is slowing us down”
The “founding pillar” in Tray’s approach to building out integrations
Why founder openness dictates a team’s scaling capabilities (and investors’ trust)
“I’m sure there many experiences that were exceptionally painful at the time that I look back on through a different lens today”
On patience and the scale mindset
Weaving the product’s vision with customer learnings; “I don’t think this challenge every really fades away it just seems to evolve over time”

Further reading/listening/pondering from the interwebz :open_book:/:headphones:

(Other insightful excerpts drawn from blog posts, interviews, and conversations)

On time and investor relations:

I’m not saying you want to fill your schedule with hanging out with investors all the time. But regularly meeting people that can add benefits to the business, and could ultimately invest or become partners with the company, makes a lot of sense.

From our perspective, spending time with investors also leads to customer intros, or partner intros that are extremely useful from their portfolio companies or the organizations they’re meeting.

I think an investor relationship isn’t developed in a heartbeat. You want to have met that person well ahead of time. You as a founder want to understand how they think, where their fund’s at, and the position they’re going to take in the company. And you’re not going to do that by compressing it down to a number of weeks.

Where I feel setting those deadlines and creating that competitive tension is important is when you actually go out to fundraise. So there’s two sides to this: one is you always want to be building relationships, you always want to be meeting people and ensure that people are aware of you as an organization and your opportunity to grow through that network is there.

But secondarily, when you actually get down to the hard yards of fundraising, you do want to make sure that you have that competitive tension going. And you’re getting people to work against deadlines, so there isn’t an ongoing opportunity for decision after decision after decision that will ultimately likely lead to a ‘no.’

Source: Startup Grind | 2019

On building from the gut in the early days:

I guess I have a slightly different view to the way many products are conceived, or even best practice is considered. [Getting] a well thought-out and executed product idea through to delivery involves a lot of analysis, a lot of customer interviews, a lot of other stages that effectively will reduce risk as you go through to launch.

For us, we really didn’t do much of that. We were so passionate about the problem we were solving and we were so clear on how we wanted this product to be, we sort of ignored most of the fundamentals and kind of built exactly the way you’re not meant to.

Whilst I’m not a complete advocate of that, I think it is important in some ways. I think there are many products that wouldn’t exist if people listened to the exact logic of people around them.

Or perhaps weren’t very good at asking the right questions. But you kind of have to build the things that your gut tells you to get this thing off the ground.

Source: Product School | 2020

On reexamining a knee-jerk hiring recommendation:

If you hire somebody that really obviously not a good fit, is detrimental to culture, and you have a fairly mature process. Say marketing or sales or whatever else.

The absolutely, you need to make the change quickly. And you need to protect the health of the team and ensure that you have the right kind of progressive talent in place.

I think where we get this sort of knee-jerk culture is where you’re still defining a lot of those things. And somebody is coming in and is under pressure very quickly to make a change in the next quarter or the quarter after that.

When you actually need to allow a bit of time for them to embed in. And as long as you have a very open line of communication as to what your expectation is, what the goals are, and that you’re working together on it. I think a little more patience is certainly required.

I think it’s easy advice to dish out and there are some very obvious situations where it should be applied to.

But I think there’s a nuance in…a company is scaling fast, they may not have developed the perfect go-to-market or inbound lead strategy. Or they may not have developed the perfect sales process yet.

They feel putting somebody under the gun straight away for a strategic reason. Then it’s probably not the smartest move. If it’s a cultural issue, then absolutely, that’s when things can go south very quickly.

Source: Startup Grind | 2019


Thanks for doing this, Rich!

Looking forward to learning more about the amazing Tray.io journey.

WP Engine’s Jason Cohen once wrote (The mid-market briar patch) a scathing critique of the mid-market segment, stating that it’s the worst of both worlds and that startups are better served either by targeting only SMBs or enterprise companies.

This view is from 2012 and a lot has changed in the market since. There is a narration from the past that it is not cost-effective to sell to this segment.

Tray.io seems among the rare few that aimed at and successfully scaled for the mid-market segment from the outset. What would your advice be for early-stage founders targeting this segment? What did you and the team get right in those early days? And what were some of the challenges that you’ll tackle differently today?


Hey Rich,

Glad to have you on Relay!

I’ve read about Tray.io’s move to SF within the first few years and the concentration of GTM-focussed teams there and the scaling of more technical teams back in London. And also how there were almost two different cultures, not just geographies, enabling those teams.

I’m curious to learn how the decision making between these two geographically separated functions works (worked?) out? Also, with the remote-first necessity of the past couple of years, how has your thinking evolved around this unique division?


Thanks for doing this AMA, Rich!

There’s something universal about the “overwhelming breadth of advice” bit you touch upon. I’d also add “often conflicted,” as a qualifier there. And I would love to learn what helped you navigate conflicting truths during the early days? Any particular instance that stands out?


Hey Rich,

Thanks for doing this AMA. How would advise a Series A stage, London based b2b SaaS company think about US expansion in 2022?

I feel like 3 years ago a presence in SF would be table stakes. In post-pandemic 2022 that idea seems like a relic!

I think our biggest market will be the US and probably tech companies in the US. We’ve got another 12 - 18 months until Series A, but I do wonder what scaling up our US presence might look like when the time comes.


Hello there, Rich!

I’ve always been curious what it’s like running the size of team and handling the level of growth you’re seeing at Tray right now…

How are you spending your time on any given day right now?

And how (if at all) do you wish you could spend your time differently?

I ask because I’d imagine that balance of time has changed phenomenally since the early days of you and your co-founders huddled around a few desks in Shoreditch.

Much love,



Hey Rich, so impressed with the immense success (and stubbornness) of you and Tray so far!

Integrators or middleware like Tray in the early days often have to choose between building all the integrations or empowering other developers to build upon/with your API.

Would love to hear how your integration-development strategy evolved over the Tray journey, and what your biggest ‘gotchas’ were along the way.


Hi Rich,

Thanks so much for doing this AMA with us. Its great to hear your story and your amazing success!

I love your statement of building from the gut. We, Kriyadocs, are a document workflow platform for book and journal publishers. We certainly believe in our mission and have succeeded in convincing our wonderful customers to adopt our perspective. My question is related to scale and investors. How did you back yourself to scale up in the early days and what are some of the strategies/techniques you used to get to the early majority? At what point did you connect with investors and how did the investor search process help in your scaling effort?

Thanks and best wishes for your continued success.
Best regards


Hey Rich,

Appreciate you taking out the time. What have been your personal challenges/beliefs that were the hardest to change but were most rewarding in your journey as a founder so far? Specifically interested in learning more about your transitions in the 0 to 1 phase to PMF to scaling and hypergrowth.


Hello Rich,

Glad to connect with you here…!

As patience is critical. Paying for patience adds up a lot to bootstrapped organizations. How should any business see this patience? What should be the primary focus in a venture during the phase of patience?

On scale mindset - How challenging is scaling in aspects of multiple products in parallel while target customers are different? When both are in the stage of tractions and being a bootstrapped organization.


Hi Krish, thank you for the question!

A few things to unpack here, initially we were very open minded about who we sold to (there are pro’s and con’s to this for sure), we felt we had a platform that covered a wide breadth and interesting expansion opportunity, so ultimately there were parallels between the use cases that were stage agnostic. In fact one of our first 10 customers ended up being a 350k employee organization.

I think on both fronts it’s dependent on what you’re selling and the potential revenue growth that is available. I do think the world has changed somewhat from the MM perspective shared above, many of those orgnizations are not only growing faster, but have become more enlighten by what SaaS can provide for them - they key (IMO) is to ensure you have the functionality to grow with them.


Hey Rajarman this is a really interesting question, in my experience there are some real benefits to having locations that have a central x-functional discipline (ie Product+R&D) this has benefits in how the days are designed, what the working environment is like, how collaboration occurs - they key is that the underlying value set is aligned with the teams in other locations, who in turn benefit from environments that best suit their work.

The drawback here is that is certainly creates additional headaches with communicating between teams, although as you point out the remote-first environment many of us have found ourselves in has been a real accelerant of that.

Ultimately I think that regardless of geo it really comes down to org design, process and communication channels which to me feel like a forever iteration to meet the needs of an org at its given point of scale.


Hi Aditi, oof this is a topic that is near and dear to my heart. The conflicting scale of advice is one of the most paralysing things a founder faces, handled well it’s a rich source of information, handled poorly it’s a major timesuck. I try to take everything as its own data point and ultimately process and come to a decision that is in the best interests of our overall vision, and the path to getting there.

An example I can think of (in early 2012) was the misrepresentation of the lean startup approach, as with anything it’s best consumed as a guide to support decision making but the emphasis at the time was essentially to create extremely lightweight prototypes of products. This didn’t sit well with me at the time as I feel there is a balance between setting out your experiments correctly and having the conviction to commit to an idea that you believe it.


Hi Neil,

I would think about this based on where the majority of your audience is today (and where it is growing the fastest), in my own experience it was vital that we built a GTM in the US (and HQ’d there) given the penetration of our customer base.

Over time this expands into new territories and that in turn requires a playbook for building out those channels, but in the near term I would be focused on where we expect to acquire the majority of our customers and build around that.


Hello James (great to see you!)

Well this certainly changes a lot through the various stages we’ve experienced so far (and I’m sure continues to do so). I think the best answer is optimizing around the things you’re best at, and hiring people that are great at the things you are not.

In reality there are some commons themes between how my day is spent, it’s typically a split between recruitment (significant %), strategy, and being in tune / supporting the core priorities we have as a business at any given time. Some of the most effective time spent is really trying to diagnose and unblock anything that is slowing us down.


Hi Hector,

Thank you for the question. A founding pillar in our approach to product was to focus around flexibility, our frustrations with what existed in the market were often related to hitting a roadblock in building out a solution because the connector or logic wasn’t available out of the box. A ‘connector’ in our world is really the opportunity to create a great experience around using a specific API, but what’s important is that there is always a way to pull or push the data that you need to be successful.

There have been plenty of gotchas along the way :slight_smile: I think it’s easy to underestimate how quickly these integrations can scale and finding ways to make it easy for new team members to get up to speed with the mission-critical workflows that exist in their realm.


Hi Ravi,

I hope I’ve interpreted this question correctly, but I’ve read it as the approach to ‘scaling’ with the business as a founder, and how looking for/working with investors supported that.

I’ll caveat this with the words that many smarter folk have said before me, ultimately imposter syndrome is very real and realising that everyone faces this challenge in many walks of life is a great reflection point.

Speaking to this personally I believe it’s important to be very open to being wrong, and being able to adapt and learn from those with differing levels of experience. Ultimately I think capability to scale is directly tied to openness to be taught. The best investors look for this in the founders they back and it’s a case of finding that fit in the process.


Hi Divyansh,

Super interesting question, it’s funny how reflection often leads to us feeling very different about a prior experience - I’m sure there many experiences that were exceptionally painful at the time that I look back on through a different lens today.

For me personally it was accepting that just being the best product isn’t enough, and that ultimately great GTM trumps having the best offering in the market. I still dislike that I believe this to be true (and hope to change my opinion someday) but the perfect storm is being the best of both - that is unstoppable.


Hi Deepika,

Well I think that patience is an individual thing and ultimately is determined by how long you can be patient for. If it’s clear to the business what the expectation is, and the measurement of success in this timeframe then it’ll be well setup for a healthy culture - misalignment here leads to trouble.

From a scale perspective I would assume (and hope) that the multiple product lines are aligned by vision and therefore the narrative that is being developed (which can take time) is supported by the strategy.