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

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,

James

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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.

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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
Ravi

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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I’ve got another one, Rich. :slight_smile:

I learned that Tray.io managed to acquire some major logos quite early on. Were you deliberate about onboarding big-name brands from the early days? What did it mean for your product roadmap, as such companies are typically way more demanding than SMBs or startups? And how did this tie with your philosophy of building from the gut as much as customer development?

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Hi Krish - awesome!

Yes - we were deliberate about landing some key logos early on, we felt it would help to build trust with future prospects. I think in an ideal world you’re building a solution based on the experience you want to bring to the world, and weaving in what you’re learning about the challenges customers face - for us this was really split by stage. The pre-customer stage was heavily focused on constructing the foundation for that vision, and as we onboarded customers we were able to begin to weave in the learnings from them.

In our experience this was certainly tough (and initially a lot of learning on the job) to get that balance right, I think it requires the discipline to do the right thing for where you’re heading with the expectation on the direction from a customer. I don’t think this challenge every really fades away it just seems to evolve over time.

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Thanks for stopping by and casting a concise and thoughtful light upon the ideas that have shaped Tray.io, @richwaldron! Especially the messy (ripe with uncertainties) truths of scaling up. :sunflower:

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And, thanks, as always, to our ever-thoughtful Relay founders, @aditi1002, @ncameron, @jamesgill, @hector, @raviramani, @navydish, and @Deepika, for joining us! :raised_hands:

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That’s excellent, @richwaldron, thank you. To add to this, from what we’ve seen at Chargebee, I believe striving to build functionality that are must-have for the fastest-growing customers can be a brilliant accelerant for the roadmap. Your point about having functionality to grow with them resonates with me.

Of course, the challenge of deliberate learning and building in parallel, as you’ve said, never really fades away. And often it gets harder when when you’re building for different segments.

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Thanks, @richwaldron. As you’ve phrased it well, org design is indeed a ‘forever iteration,’ constantly being revisited as the org itself acquires new forms. To me, how you’ve thought about structuring different teams, seems like a great way of acknowledging the unique, function-specific sub-cultures that exist within a company.

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