How Three Elite Engineering Leaders Achieved Team Excellence | Best in Jellyfish

In this Jellyfish Illuminate Awards webinar, host Phil introduces the inaugural award program, highlighting three categories: Innovation (won by Submittable), Excellence in Engineering Operations (won by Loadsmart), and DevOps Metrics (won by Hootsuite). Phil emphasizes the value of sharing customer success stories and fostering community dialogue. Jess, representing Submittable, recounts the company’s strategic transformation from a sales‑centric to a product‑centric organization, driven by a post‑COVID focus on corporate social responsibility and a roadmap crafted by CTO Andy Wright. She explains how the shift required additional headcount, clearer metrics, and the use of Jellyfish to track investment categories, justify hiring, and sustain product development momentum. Phil probes deeper into the engineering management practices that supported this change, specifically the implementation of quarterly business reviews and other ceremonies to measure progress. Throughout, the discussion underscores common principles across award winners: data‑driven decision‑making, maximizing engineering investment, shipping early and often, and aligning metrics with business goals.
Chapters
Thanks everyone for attending this webinar. We're psyched to be here today, nestled in between World Cup football matches and with 3 distinguished guests here to talk about the Jellyfish Illuminate Awards. And how 3 engineering leaders and teams achieved excellence using data. I wanted to give context on, you know, why we're here and what are the Jellyfish Illuminate Awards. So this is the first year that we're actually doing this. We want to make it an ongoing thing. We think we see so much great, great work and great results with all of our customers that, you know, I think just sharing those stories in, in giving them the recognition they deserve and also giving, you know, getting them out and letting people, you know, bringing forums together like this so we can talk to each other about them is super high value. So we're really excited to do it. And the 3 awards that we did this year as kind of the inaugural Jellyfish Illuminate Awards, there were first, there was an innovation award. And so the winner there is submittable and Jess will be able to tell more of the story for, for, for Submittable winning the Innovation Award. So congrats to Jess and thank you. The second award is the Excellence in Engineering Operations Award. And so ironically, even though Jess is the engineering operations professional here, Loadsmart is the winner of the, of the Excellence in Engineering Operations Award. And Gustavo is here to help share that story. So congrats and thanks to Gustavo. And then last but not least, going back up to the upper left on my screen here, Alex and Hootsuite are the recipients of the DevOps Metrics Award. And so congrats and thank you to Alex and Hootsuite. So those are, those are the award categories. And in going through the stories for all of these awards, I think we, you know, one thing that I took away, I was a judge on one of the the award panels, we kind of like, we kind of did a divide and conquer thing. So, so I'm not even going to tell you which one I judged. But, you know, one of the things that I figured out after we came back together and organized this webinar is that in almost all cases, this stuff is such a team effort. And like, you know, if we're talking about, you know, a very, you know, like, I think Jess's story is very different than Alex's story, but like, you know, at the lowest level, but when you, when you kind of zoom out a little bit, like all of this, relates to, you know, kind of the fundamental principles of what we're all, I think, all trying to do with our software organizations, which is, which is, you know, get the most out of our engineering investments, build great software, ship it, you know, early and often, make our customers happy, drive the business forward. And whether you're, you know, coming at that from, you know, deployment, deployment frequencies and change failure rates, or whether you're coming at it from you know, managing deliverables, or whether you're coming at it from, you know, looking at all the stats and metrics in between, I think it all comes together to kind of tell, you know, in service of the same goal. So it's really interesting to like go through not even just the award winners, but even the other nominees and all the submissions that we had. So that's one thing that I really liked about this process and why I'm psyched that we're doing this award series. So with that, I think I would like to— and we talked about this a little bit beforehand— I'd love to also facilitate some crosstalk between people. So I don't want this to be like Phil asks questions of award winners and no one else chimes in. I really would love it if, you know, Alex and Gustavo and Jess are talking to each other as well. But I will kick it off and I'll start with you, Jess. I think a lot of, a lot of the— well, well, maybe can you give us a, like, maybe a brief overview of the story? I'll summarize what I, what I know from the, from the award submission, right? Like, the, the thrust of the story was that Submittable was making a, what, what counts as kind of like a strategic transformation from being a sales-centric organization to a product-centric organization. I can speak to that from past experience and maybe present experience when you're scaling a company, I think sometimes selling stuff is what you need to do in the beginning. And then to make that work at scale, you need to start doing things that are a little bit more repeatable. And so I've seen that transformation be kind of required, a required ingredient to success in the past. Maybe you could give us the submittable version of it, like what motivated it and and how you all aligned around it.
Yeah, definitely. So hats off from sales-driven to technology and product-driven work. Love it. But as far as Submittable goes, like I said, tomorrow is my 2 years. When I was hired at Submittable, it was a very small organization, lots of changes in the middle of COVID and Submittable as what the platform is, or was, excuse me, then, and still is today, is a kind of a grants-based application type of platform. And we had the pleasure of assisting and helping people all over the country and the world, whether it was their business, personal stuff, through COVID, and providing aid. And it just stirred up this whole idea with our CTO, Andy Wright, who had come in just probably a couple months before I started here, and wanted to try and take what Submittable was already doing and latch on to this idea of corporate social responsibility and dive even further. So he created this elaborate roadmap to start pointing our developers and where we were hiring and what we were putting our energy into as far as development and product work, um, and designers, to see how we can continue to build upon what Submittable already was and give even more back to the community in that way and have more stake in it. And so with that being said, you know, we have this roadmap, we need to have more headcount, we needed to have more metrics and data to say, yeah, we can hire this person, we're doing these things, we're building this. And that's how it became so much more than just a sales-driven company, because it was about the technology and the product and the people that we were delivering it to. So that's kind of my Long story short of how it went from A to B, here we are. And, you know, this greenfield project that we've been a part of now, we have volunteer as part of like that first phase that was on that roadmap. So it's real life, it's happening. And using Jellyfish to measure those metrics, continue to support the headcount and the forward momentum and enablement of this product work. And it's, it's pretty rad. So without going too much, if that helps.
No, that's, that's really cool. I, I appreciate— no, I appreciate you sharing the story. I think it's, um, in some ways it's like a necessity is the mother of invention thing. I think a lot of us kind of got thrust into interesting circumstances in 2020, and I think for those of us who are in tech, a lot of those ended up being surprisingly, surprisingly good. And so just It was all about how you respond to it and how you kind of play it forward. To your point about Andy's roadmap and the team's roadmap, as pushed by Andy, part of what we talked about in the application process was looking at starting putting process in place around quarterly business reviews and other engineering management ceremonies to really, you know, kind of drive and measure the change. Can you give a little bit more detail about that? And because I think, you know, for the people in the crowd like that, that kind of advice, like those kind of examples are worth their weight in gold. Like any, any lessons you can share?
Absolutely. And so as you Jellyfishers know, we have investment categories that measure, you know, within Jira what we're doing and We decided that we would have product roadmap work and engineering roadmap work so that way we can see the shift in how things change. Those are our two primary investment categories. No surprise there. And so for our QBRs, or quarterly business reviews, shortly after we finally got everything kind of synced with Jellyfish and Jira, and I was able to pull clean reports and metrics from that, I made a, I think it was like for like Q2 of 2021. I took, you know, like, what is it, April through July. And I was like, okay, here we go. And this is, or through June, excuse me, pardon me. And every single thing that shows up on that overall, you know, these are where your company's at that screen. I made a slide of that so that way our entire company, our board members, everybody that has some kind of investment, whether it's mental, monetary, you know, emotional, to see where we were, you know, in March and how it changed. Like that shift, you see those colors of those investment categories from being like maybe down here to like keeping the lights on to being like, holy lick, we are working so much in product-driven work. This is incredible. We're really doing what we're saying. And then I followed that side up to show like the exact— these are the 10 top epics of effort under product roadmap work. These are the 10 top epics of effort in engineering roadmap work for that same timeframe. So we could see where the FTEs were going, where the effort's going. It's like my receipts to say, hey, these aren't just pretty colors, this is real. And this is being measured from your work that you're not doing anything extra except making sure you're putting it in Jira so I don't go crazy. So It's just been phenomenal to see kind of like the insights and the feedback from people that maybe don't go into Jira for anything and have no need to, but they have an investment regardless. And it, I think it's helped quite a bit just for that high-level overview of we are doing what we said we're going to do and the changes are there. So that's kind of my quarterly investment that I give. [MUSIC] [MUSIC]
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