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) 
(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 
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(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
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.