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Hey, listeners. Welcome back for another episode of Pivotal Conversations. My name is Dorme

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Andrewitz, and this week I'm happy to bring you an interview with Terry Miles and Jason

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Nash of Entrato. This interview was actually recorded back in April of 2019 when Terry,

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Jason, and their colleague Don gave a presentation at CF Summit about modernizing and migrating

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170 plus applications in 18 months. Now, a lot's changed since April of 2019. One, you'll

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notice that Terry and Jason refer to West Corporation. West Corporation has since rebranded

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to Entrato, so you'll just have to map those types of references in your head, and you'll

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be able to find ongoing information if you look for Entrato. Second, you'll hear Jeff Kelly

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as the interviewer. Jeff Kelly was one of our esteemed co-hosts here at Pivotal Conversations.

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He's now an esteemed Pivotal alumni, but we get to hear his great interviewing skills one

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more time. And finally, there's been an update in the form of Terry's presentation that he

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actually gave in October of 2019 at SpringOne Platform. And it's got a very similar title

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to the talk that he, Jason, and Don gave back at CF Summit. But I got to tell you, they're

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very different presentations, both worth listening to independently to get different levels of insight.

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And on that note, I hope you enjoy this particular interview because there's a lot of great insights

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for teams that are working on large-scale transformation. So with that, enjoy.

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But why don't we start with, just if you could introduce yourselves, just kind of your name,

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your title, what you do, and then we can get into a little bit about the story of the application

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transformation that you're doing.

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Sure. Terry Miles, product manager with West Corporation, the platform owner for PCF. Responsibilities

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include that, and also the broader aspect of change management for the entire enterprises that

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adopts PCF and related services.

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Great.

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And I'm Jason Nash, product engineering manager, and I lead a dev team that was the first or

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one of the very first to jump onto the platform and shake loose what wasn't bolted down.

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Got it. And for those listening who don't know too much about West, tell us a little bit about

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the company. I understand you were acquired and kind of changing your model from a holding

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company model to more of an operations or operational model. Tell us a little bit about that and

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how that impacts your application portfolio.

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That's exactly the case. We average about $2 billion annual revenue. That has been primarily

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historically through a series of acquisitions. We have always let those acquisitions lie.

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And while there have been previous attempts before the adoption of Pivotal Cloud Foundry to

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at least unify some of our infrastructural resources, we haven't gone very far in that

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direction. And it's not just a matter of practice, but a matter of policy. We just saw it to be more

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efficient to leave those lie as they were. We are now owned by a private equity group.

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And among the mandates they brought is greater platform consolidation primarily for the purposes

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of efficiency. That is the first explicit phase, the justification for the adoption of Pivotal

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Cloud Foundry at West. But there is also the greater idea of platform consolidation, greater

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efficiencies, more rapid release cycles, and the usual types of business value.

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So that's our size. That's our lineage to a certain degree. Offices in, I think I counted about 14

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different countries. Time zones all over the world. Distributed teams, not just by business

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unit, but many of our project teams are distributed around the globe too.

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Okay. And so I understand, you know, part, as you mentioned, it's part about gaining efficiencies.

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You've got quite a fairly large application portfolio. So a lot of folks that I talk to, they often start

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very small and they'll pick one or two applications, kind of experiment, learn the culture a little bit

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there, and then kind of expand to the larger application portfolio. Tell us a little bit about

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your approach because you're coming in knowing, you know, hey, we have a mandate to really move all

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these apps over. What's, what was the strategy?

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I think Jason's going to have a good story to tell in there, but I'll start with the broad strokes.

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We tried for a combination of initial application selection for A, low-hanging fruit, B, bang for

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buck, value, size, impact. And the commercial outbound platform that Jason manages is one of

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those early candidates because they fit both criteria. Is that how, from your experience,

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how it went, Jason?

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Yeah. I mean, we were really trained to kind of kill two birds with one stone on it. We wanted

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to get the, the developmental efficiencies and, you know, not have to worry about that stuff. But we

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were also dealing with a ton of operational sprawl and snowflakes all over the environment that really

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slowed our dev cycles down and made our systems fragile. And, and even if you were just lifting

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and moving something that was fully functional and you weren't really transforming it into something

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that was more cloud native and we took advantage of the platform, there was still benefits to us

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for doing that. So we pushed really hard on anything that will fit, let's shove it in there and we'll

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figure it out after.

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Okay. And, and so I know you're, you're speaking tomorrow at the conference. So, and you're going

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to share some lessons learned. I mean, if you give us a little preview of that. So what, what,

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actually, why don't you tell us a little bit about where you are now in the journey? I think it's

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about a year and a half. I've, if I'm reading correctly, tell us a little bit about where you

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are now and then maybe we can get into a few of the lessons learned.

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We're gaining traction now. We have gone from about a total of, with a, with a, with a final

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projected total of about 5,400 AIs in our respective founders. That's the end state that we would expect

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near the end of this calendar year, sometime first quarter of the next. We had struggled for a large

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part of 2018. We were sitting only at about six, 700 AIs through last October. And that number had

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been static through most of the summer and the early fall. But now we are to the point of 2200

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application instances. We've seen rapid growth in the first quarter of this year. And it was just due

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to a lot of hustle, you know, a lot of, you know, product, project management driven, um, making teams

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identify why they can't get through and doing whatever we had to do, begging, borrowing resources,

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but getting as creative and as pragmatic as possible to at least get them in to their first initial

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customer cutovers. So in terms of our project status, we, uh, we, we saw things darkly about

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six months ago. Things were a lot better than they used to be. Most of it was due to just our own

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organization's ability to lift itself out. And a few of the people that sit around this table that you

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don't hear that work for pivotal too. Um, we feel it's a particularly good client relationship,

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professional services story to tell. Great. Um, so yeah, why, why don't you tell us a little bit

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about why you think you were kind of stuck around that 600 AI mark? What were some of the things that

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were making it challenging to kind of take that, that leap to the next level? We really had a lot of

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problems with last mile, right? Like you got all the way through and then there was something in the

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greater ecosystem that was missing, right? Whether it was database, whether it was, um, you know,

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caching layer, whether it was logging and, you know, those types of things, like we made it work. And then

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when it was time to productionalize it and take it to scale, there was some piece of the external

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ecosystem that had to be brought online. And as an organization, we did a pretty good job about six

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months ago of really, um, identifying what those blockers were and creating like executive level

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kind of task forces to go knock those blockers out as enablers for the rest of the team. I think

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that's what broke the dam. That's, that's, that's when you started to see the AI count really go up.

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So getting that executive buy-in?

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It was, you know, it was, it was, uh, uh, acknowledgement that there were holes in our

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solution stack and they weren't pivotal holes, right? They were, they were, they were things

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that you needed in order to make your applications run, you know, an acknowledgement that, man, we really

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need to address those. And then the executive will to kind of do those because a lot of times those

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things tend not to have owners, right? Like who owns this thing that doesn't really exist? That's a

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really difficult question to, to, to answer. But if you can put it in an executive who's got the

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ability to form groups to attack those problems, then that, that's a huge enabler. Adopting

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Pivotal Cloud Foundry was not the most radical transformation going on at West in 2018.

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Right. So there was more of a culture and, and process and, uh, approach to computing versus

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the actual technology that was underlying it. That was more of the challenge, sounds like.

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Correct. Any, any re-platforming project of this scale, um, must impact all parts of the business

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and must, you know how Jason referenced, uh, prying loose anything that isn't bolted down.

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You could sort of extend that analogy to fixed processes, um, functioning relationships cross-functionally

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within West. So it's not simply a tale about moving to agile. It's, it's, it's not even that

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simple to say, but it's, um, process of, of governance of, uh, workflow of change control. Every single

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thing about that last mile that involved people and or technology has been changing. We had preceded the

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PCF adoption with the, uh, continuous integration, continuous deployment effort, a very familiar

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tool stack to most, um, and enterprise-wide adoption of New Relic is also concurrent to all

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of these. So all of these are change agents to that culture and process. Meanwhile, a lot

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of turnover and a lot of churn among our existing teams. So that's a lot to manage. Yeah. When you've

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got a, the kind of history that we had of all these snowflakes in this environment, all these

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systems that were different, right. It's really difficult to throw, to throw automated process

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and technology at a problem like that. Right. So our, our governance mindset became slow down,

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think, get everybody in a room before you touch anything and make sure that everybody agrees

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that it's safe to do it. Right. And that our, our gut response to stability was to slow down

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and think, and then to flip that on its head and say, the way to get to stability is to go faster

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and be able to react faster to problems. It was, it was just a real kind of epiphany that a lot of

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people had to go through. And some people really had trouble with that, right? People are wired different

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ways. Um, but the, that, that tide is turning, right? The culture is starting to, to wrap their head

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around going faster is how you actually get the stability. Even one other layer to that change,

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I forgot to mention, but I think it's significant is we've migrated from, from our, uh, from service

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desk to service now. And just switching tools is not the half of that story that, um, a much more

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comprehensive form of managing our time tracking, our respective projects, how we handle all of these

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related processes is another layer and opportunity. It's, it's, it's complexity, but it's also

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opportunity. But we, we created a lot of chaos for ourselves, but looking back, I'm not even sure

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how we could have avoided it. Yeah. It was, it was good because it forced us to examine the

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organizational structure and the processes that we had put in place and that we're enabling with this

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old tool and then go, man, do we really want to repaid that cow path in the new tool?

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No, let's simplify things. And that kind of broke a lot of logjams.

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Mm-hmm. And talk about how you extend the culture change throughout the enterprise. I mean,

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it's a large company, uh, you mentioned there was some turn, turn over because some folks just

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kind of couldn't, couldn't grok the, uh, the fail fast and agile mentality. Um, but how, what were

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some lessons learned in terms of reaching out and winning the hearts and minds, uh, of those

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different constituencies within the, within the enterprise?

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It's an essay question to me. I'm trying to think of the right way to sequence it, but

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some little wins, some early wins, um, basic responsiveness. Um, the people who would manage

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the legacy platform for application teams might not easily be available to teams trying to push

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an application through. And it could sincerely have been, I mean, Jason and I know, and his team have

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often had to wait several weeks for somebody to push a deploy button that they knew dang well was going

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to work, right? The first time. But, um, so that kind of access, um, and real-time responsiveness

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by the operators team of Pivotal Cloud Foundry at West is probably the most significant early win.

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Um, um, even if the answers weren't always there and weren't always right, they knew that somebody

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was engaged in dialogue with them. And I think you take a little win like that and then you apply

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something beyond West or beyond Pivotal, uh, lots of different ways to look at it, but how an innovation

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diffuses itself across an organization. There's lots of different handles and disciplines can, can use the

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language differently, but basically the mechanics are you find eager adopters, early adopters, you

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enable them, you put the machete in their hands so they can hack the forest floor a little bit, and

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then you try to learn from their lessons and keep publishing, stay responsive throughout, even if that

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responsive means taking it on the chin one day. And, you know, some very ugly system failures. I can think

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last year of a, uh, dev test site failure, you know, that took a few days and we were all just, it was

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just, every day was fingernails on blackboard all day long. But we, we had to face that fire and keep

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communicating. So I think that's the, the single most important tactical factor. Since then, it's been a

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little bit more of an enterprise change management approach. Um, we talk to each other a lot better

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than we used to. There's lots of different discussion forums that are now, because our project is far enough

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along focused and detailed. We don't just bring in somebody who worked for Pivotal,

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works for Pivotal talking about the value propositions of the platform. We can now bring

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in survivors like Jason and his team who can tell their specific tales about it. We've had enough .NET

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applications try to go through where we now have kind of a support group there that can talk to the

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next ones who are going to come through it. So it is pretty much an oral tradition.

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You know, there's a, there was a lot of cultural drive kind of from the top down, from the bottom

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up. The way we tried to drive it is just winning cures a lot of ills. You know, you know, we were

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a good candidate to go first because we already had full CICD. We already had, you know, a lot of

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those tooling in place, but we were holding it all together manually, right? We spun up our own

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Ansible instance, you know. Things like that, you know. The dev team doesn't want to deal with,

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but we were dealing with it. So moving from that environment into, you know, our managed,

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foundry-based, you know, corporate CICD, all that kind of stuff, made our developers really happy,

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right? Because now they didn't have to deal with all that stuff that they used to have to deal with.

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And now all of a sudden we were going faster, and we were pushing things into product faster,

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and we were getting scale that was difficult to achieve because it took me two weeks to get

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a VM before, and now I could not get the smash button and get more instances, right? And then we saw

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groups that were less down the path of kind of being cloud native and ready for that kind of thing go,

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"Oh, there's a path of least resistance. I'll follow that," right? So somebody has to be a wake-breaker

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and make a wake for those behind them. Finding a good candidate that's willing to take a couple

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shots on the chin and make a wake and who's probably going to see immediate benefit from just being in

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the ecosystem is a really good strategy. Right. Well, and it sounds like you picked a good

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candidate because, as you said, you had a need there. So it was definitely going to benefit your

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group. Your developers were going to have a better experience. And so that sounds like one

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criteria in terms of when you're looking for that early win,

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a potential group to embrace would be someone like that or a group like that.

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Yeah. I mean, we really, you know, we needed to learn PCF, but we didn't need to learn

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agile concepts. We didn't need to learn how to use Jenkins. We didn't need to learn, you know,

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all those kind of things. Like, it can be really overwhelming for a new team. So having a team that's

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gone through a bunch of that kind of learning already, so that their delta in learning is pretty

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small and that it makes what they're already doing easier, like that there's no friction there,

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right? One other aspect of change management I think important to bring up is we made sure we

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walked everything through the front door. And what I mean is the team operating and building PCF

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in early stages was part of a transitional authority. So on an org chart, it's isolated,

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but that isolation could have lent the opportunity to change the way we push applications through

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to production to avoid existing processes like our change control. The back door was there. We could

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all see it, but we committed at a very early stage to, if we want to see procedural reform within West,

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we had to have existing authorities and existing procedures see and confront again and again these

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decisions to have to make. So that by about the 15th or 18th time they're saying no to something,

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they might ask themselves, "Maybe there's a different answer here." We had to let them decide

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to make that change and give them the confidence that they were going to be able to be in control of that change.

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And I thought that was, engagement is control and interest. And to get engagement from these teams,

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to be able to take this project seriously because similarly large investments have fallen to dust

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before, to know that this one was not going anywhere, I think that engagement was important.

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You know, little things that facilitated that, like the original PCF box group that was putting

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together at the initial counters, we sat them right next to my team. And my team's on the progressive

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end of the spectrum as far as managing to process and things like that and being able to pick up

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and have a conversation human to human and challenge, "Is that really how we want to do this again? Or man,

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this is a real pain, can you help me?" There were some real wins on just having human face-to-face,

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working together kind of stuff going between the app team and the Foundry team.

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Got it. And so, as we wrap up, I wanted to hear a little bit about your experience working

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with Pivotal. My understanding is you also worked with Cognizant to help with some of the scaling.

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Cognizant and Stark and Wayne. And Stark and Wayne. Tell me a little bit about the role.

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Maybe we start with Stark and Wayne and Cognizant and those kind of consultancies. What role did they

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play and how did they help you take this approach from kind of those that first successful engagement

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to starting to scale this out throughout the enterprise? Stark and Wayne has provided through

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Pivotal generally a series of platform reliability engineers at different stages of the project,

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particularly early on. They were there. They have also staffed a recent platform dojo

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hosted by Pivotal but involving some Stark and Wayne resources. Cognizant has been on the application

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transformation side, leading a series of dojos, particularly when the location of those dojos

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is a little bit far afield for say Pivotal resources or our own West resources. I should add to

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Cognizant leading dojos, Pivotal leading dojos. We use the engagement plan with Pivotal. There's also

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been our own West internal center of excellence team that we call the cloud native enablement team,

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that it's the same idea as the center of excellence. They went through pal training at Pivotal and they

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represent different disciplines, different business units. They and so they are a third and ongoing

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source of the dojos. Pivotal has supplied ongoing account people, product managers, a general

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platform specialist, human spackle and polyfill that fills almost any possible role for us at any time.

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Including ventriloquism too and a zero-diversion X style that I greatly appreciate from time to time.

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So the help from all of those groups has been vital to success. I think the closest to home has been

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primarily pivotal and secondarily Stark and Wayne because they have had a direct impact on what the

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platform looks like now, how we automate, how we push things through and how we deploy.

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Right. And so it's a lot about, as you mentioned, enablement. The dojos are essentially helping you,

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helping your teams learn some of the concepts and how to run the platform, those kinds of things. And

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then they can take that and hopefully spread that throughout the rest of your organization through

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some of your enablement, internal enablement efforts.

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Great modeling. They model. They show you how they modeled. They're willing to tell you explicitly why

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they do the things they do. And they're willing to walk with you to sell the concepts to your supervisors and

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senior leadership. And like any sophisticated mature service provider and professional services organization,

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which Pivotal is in part to us, is it's a consultative practice, at least as much as it is a technology

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platform for us to adopt, that they have successfully engaged West at all levels, analyst to C-suite,

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up and down. The Rolodex is there and they know who to talk to. And they, and so I greatly appreciate

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their ability to pragmatically help us manage change within our own organization.

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Um, that's, that, they'll sound like broad strokes. A couple of more specific things I'd say is, uh,

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um, when things were dark, I'd say about six to eight months ago,

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they weren't shy and they behaved like a very responsible project manager in much the same way our

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own project management team responded very ably and, and valiantly at times to identify critical blockers

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and remove them. And I could think back to every one of those critical blockers, a list of about 13 to

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15 that we've mowed down since then. Um, every single one of those were either identified by

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at least partially a pivot and resolved by at least partially a pivot. Great. Um, so as we wrap up,

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what's, what's the future hold? So you're about a year and a half into the journey, maybe take us

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another six months to another six months to a year out. What, what's, what are you hoping to accomplish?

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Let's go with the app first and then I'll go to the platform.

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Yeah. I mean, you know, as we've, as we've completed app migrations, right, to differing degrees,

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we've also become more cloud native. Um, and I think probably less transformation than,

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than, than we probably anticipated that we would have, right? More, more lifted move than,

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than actually taking advantage of what's there. So there's, there's a lot of stuff in the platform.

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It's like auto scaling, um, that a lift and move application just doesn't really do very well.

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Um, so the transformation of what is in the foundry to take advantage of the, the stuff that,

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that the platform offers, I think is kind of the next, the next big iteration, the next transformation

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that, that teams that have adopted will be there. Like, okay, now I'm here. Like, I, I got my CICD

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stack working. I, I, I, I still, I still have, you know, all these shiny things that I want to take

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advantage of that I can't yet. So let me transform my app to do that.

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Mm-hmm. And do you have a plan to, uh, kind of, kind of determine and prioritize which, which applications

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and which, which, uh, suite of applications get, you know, get top, top billing and are going to go first?

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And how do you think about that? Revenue wins the day in general. So you look for revenue

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and you look for, um, the direction of that revenue too. And you make sure that we're going

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to get the return of investment, um, for the choices that we make, because we know that, um,

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while we are definitely not a homogenous portfolio of applications, there are lessons to be learned

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from an app transformation adventure by one team that could be shared to others. There are enough

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commonalities where even to the teams we don't target for that immediate, um, next level at

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transformation opportunities are there. Tactically, uh, what we're doing with the center of excellence

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team internally, the West is looking into the rest of this calendar year and doing, um, second dojos at

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transformation dojos with them. Let's pick a fight. Let's pick one about auto scaling, for example.

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And let's see if we can get you to avail yourself of that important service. So that's kind of where

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we are in a, in a, in a project perspective. We have metrics that we look at, uh, not just the

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applications we've onboarded, but application teams. And just as a change management metric, have you,

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have you had a representative from this team attend a dojo or had significant correspondence,

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um, to be able to get ready to conceive of how to transform their application. We've talked to all

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but two of the teams that we know exist in the project of West, almost everybody in the two teams

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that remain. We know very well, and we already know how that conversation would go. So we are

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at a relative luxury now of being able to focus on those second dojos with us. Yeah, I think the,

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the reality is that this migration has consumed a lot of development cycles, um, over the last year

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and a half. And that's created a pent up demand for product features. So I think, you know, our

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success going forward will be dependent upon our ability to, to prioritize applications that have

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both a combination of pent up feature demand to take advantage of revenue and are ready to take

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advantage of the transformative steps. Right. So like when you squeeze, where are you going to get

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the most juice? When we're fortunate, we'll have a backlog item that aligns with the transformation.

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That's exactly right. Those are the ones that should bubble to the top because again,

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they'll make a wake for the ones where the transformations are harder behind them.

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All right. Well, I think that's a great place to wrap up. Thanks so much for joining us.

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Appreciate it. And perhaps next year at this time, we can do this again. And I would love to hear how

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it went. You're most welcome. We'll do the next one from the beach because all of our apps will be in.

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Exactly. We'll be sipping pina coladas and having a grand old time with our feet in the sand.

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All right, gentlemen. Thank you so much. Thank you.
