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July 5, 2022, 7 a.m.
Omni Roadmap, July 2022

Ken Case, CEO, joins the show to break down his post-WWDC 2022 Roadmap.

What’s the latest? What’s amazingly cool? And — the annual question — just how much work will we be doing this summer?

With continual OmniFocus 4 progress, OmniFocus for the Web updates, single sign-on (SSO) authentication for enterprise customers, and more - there’s plenty of exciting stuff to talk about. (And thankfully, nothing announced at WWDC 2022 derails the current OmniFocus 4 milestones already accomplished.)

Show Notes:

Andrew & Ken also speculate on what just-announced features might be useful in Omni software down the road.  Listen in for all the latest details.

You can find Ken Case on Twitter @kcase.

Some other people, places, and things mentioned:


Andrew J. Mason: You're listening to The Omni Show, where we connect with the amazing communities surrounding the Omni Group's award-winning products. My name's Andrew J. Mason and today we have CEO Ken Case with the Omni RoadMap 2022 post WWDC update.

Andrew J. Mason: Hey everybody, welcome to another episode of The Omni Show. My name's Andrew J. Mason, and today we are hanging out with the Omni Group CEO, Ken Case, unpacking WWDC and all the announcements that come out of Apple and how it intersects with the Omni Group. And we're honored to have the Ken Case in the house. Thank you so much for being here, Ken.

Ken Case: Oh, well, thank you. It's my honor.

Andrew J. Mason: Well, let's jump right into it. And when reading through the Roadmap blog post of 2022, early January, you gave some air time to the world around us, this context surrounding us before moving forward. And over the last three years we know that a lot has changed. What was on your mind over the last six months since you last checked in with the Roadmap?

Ken Case: Yeah. Well, our hearts go out to all of the people in Ukraine who are dealing with much harder circumstances right now than anything I feel like we're having to go through. We're relieved to be finally hitting the tail end of COVID, and people feeling comfortable going back into the offices so far, starting to travel again, and so on. Thanks to vaccinations. Very happy about that.

Ken Case: I don't think we're going to go back to exactly what we had before. Life is not exactly the same. It shouldn't necessarily be. So for example, when a lot of our work we're still doing from home, rather than going back into the office every day the way we used to, and we're not expecting that to change anytime soon, or ever really. I think people are enjoying being able to work from home, but to have the flexibility to go into the office from time to time if they want to change of pace and just want to see people.

Ken Case: And as a result we've had to think a little bit differently about what it's like to work with a mostly remote team and how meetings work, and so on. Where now, if you're in the office and it's time for a meeting, instead of everybody getting together in a conference room to get in the same place, we all scatter and go to different corners of the office. So that everybody can be on the same playing field in the video conference, whether you're there in the office or remote. So yeah, there are definitely some changes in the world.

Andrew J. Mason: And I love how the fact that there are changes in the world are not keeping you from moving forward in this. The first part of your Roadmap talks about OmniFocus 4 and the progress that's being made there and the different phases or freezes, I guess I should say, of the development process. So there's feature design, usability freeze. Can you talk us through that process and where the team finds itself?

Ken Case: Sure. For those who haven't been following the test builds closely since we started this process a little over a year ago now we've shipped 133 test builds at the time of this recording with more than a thousand changes and improvements over that time. If you look at the release notes, the release notes are pretty long right now. I don't think many people are reading through all of that at this point. And so it's easy for these to get buried in and we have to, from time to time, call things out. And of course, when we get closer to actually shipping or introducing it to an even wider audience as we hit some of these milestones, we'll need to consolidate that and say, "Here's what you should be looking for. Here's the summary of all of these thousands of changes or what enhancements, improvements we've made so far."

Ken Case: But where we are right now is the public test itself was a milestone that we were reached last year. It was a little bit before the summer. And then that public test grew and we were working towards our feature freeze, which is the milestone where we feel like all of the features are in place and we can describe now what the app is about, what it's doing. Start writing the documentation for it at a conceptual level.

Ken Case: But not everything looks the way it's going to look or is usable as it will be when we finish that milestone. So we finished that milestone feature, freeze milestone. We had resolved about 1500 issues a few months ago. And then we split our team to start bringing the Mac app up to date with all these features and to start working on the... Actually, we call it the design freeze milestone.

Ken Case: And that's where the app is not just ready to describe in terms of its feature set, but it's actually ready for our screenshots and so on. That the interface is stable enough that we can start taking pictures for their documentation, and so on and continue on with that part in parallel.

Ken Case: When we hit design freeze, which we're still working on right now, then after that we'll turn our attention to the usability milestone. This is where some of the things may look correct, but they don't actually work the way they're supposed to yet. And from there we'll also be looking at stability performance.

Ken Case: Of course, finishing the documentation that I mentioned. That's something we can do in parallel with usability, stability and performance. And then localization works where we translate it to different languages, make sure that it's ready for people to use in different locales. It speaks their language. And then eventually it all comes together and do code trees.

Ken Case: So we still have quite a bit of work ahead of us, but we are well on our way and feel like we've been making great progress.

Andrew J. Mason: Now that's interesting to me. I'm not super familiar with software development cycles, Agile, or how anything standardized is done. I wasn't aware that this process was in place before this. Is this something that the team has always used, these milestones, or is it something that's been developed over the last couple of years, almost in response to the changing environment?

Ken Case: This particular layout of our milestones, I think really is how we've always approached development. Some of it has changed over time. I think it used to be that we also had some stages of, well, at what point are you burning CDs, and at what point are you printing boxes? And those have also had to have screenshots, they had to have documentation.

Ken Case: And then there was this whole manufacturing process involved. Now we're assembling the boxes and shipping them out, and so on. And obviously, that's another change in the last few years that was... That's a change in the last 15 years as more and more people have moved to online purchasing in the app store, and so on.

Ken Case: So the process was definitely more fixed in the past where you really wanted to hit that code trees in time to now burn these CDs and then get them assembled into the right boxes at the right time, and everything out there. And it was a closely timed process. Now it's easier to be more flexible about that stuff. Also, you don't have to worry about when retailers are wanting to put things on their shelves, and so on. That whole purchasing and stocking cycle, that was a major factor in the past.

Andrew J. Mason: So no more boxes?

Ken Case: Yeah.

Andrew J. Mason: Man, there is a part of me that's just nostalgic for walking through and finding things in boxes. I feel like I need to go track down a Blockbuster Video somewhere, if there's any in existence left. Maybe the metaverse will solve that. Maybe I can virtually walk around and look at the software I buy before I actually... Anyway.

Andrew J. Mason: But the collaborative nature of something like Slack that allows these tighter and tighter iterations of being able to see, okay, somebody likes that, they don't like this, and this is how we can change. That's really cool. I knew that feedback loop has tightened a little bit more over time.

Ken Case: Yeah, we love, we've always loved working with our customers to show them here's what we're working on. Now how does this actually work in practice when the rubber meets the road and you're using it in your own lives?

Ken Case: We had a long public beta process, even for the very first release of OmniFocus 1 back through '96. And so when 1.0 was ready to ship we had a lot of people that were right there ready to say, "Yes, I know it meets my needs and I'm ready to buy." It's a nice way to work.

Andrew J. Mason: Now I do want to roll back just a couple of sentences because something you said I'm afraid people might gloss over it if we don't draw extra attention to it. You mentioned OmniFocus 4 being released simultaneously on iPhone, iPad, and Mac all at the same time?

Ken Case: Yeah. So obviously, we want OmniFocus 4 to be available not just on one platform or another. And one of the major shifts that we started with OmniPlan 4 was toward delivering our products as a universal product, which I think was how a lot of customers were thinking about it anyway. It wasn't the way we were building it so we weren't thinking about it that way. But it's important for us to adapt to our customers rather than the other way around.

Ken Case: So we are now building OmniFocus 4 not just for iPhone and iPad at once and then for the Mac later. Or actually iPhone and iPad used to be separate apps as well. But we're building it all as one synchronously developed project that when we're ready to declare 4.0 is ready to ship, it will be available across all the platforms at once. Not, "All right, here it's available for this platform, and now in a few months it's available for the next," and so on. The way we've done in the past.

Ken Case: And then it can be a single purchase and people just download it and use it on whichever devices are available to them at the time. Or if they switch to a different device they don't have to worry about, "Oh, do I need to now buy it again?" Because they already have a license that covers them everywhere.

Andrew J. Mason: That's phenomenal. And along with all of this still developing for OmniFocus for the Web. Can you catch us up on what's been happening there?

Ken Case: Sure. So of course, we've been thinking a bit about how the changes in OmniFocus 4 will affect OmniFocus for the Web, because we want it to be ready the same time as well. But OmniFocus for the Web, it started much later than all of the other products, and so it didn't have support for things like attachments. So that's the latest feature that we're bringing over there.

Ken Case: They're currently available in the public test versions of OmniFocus for the Web, which anyone can get to at And when you sign in there now you can view your attachments and download the attachments, and have them available on Windows rather than only available on your Mac and iPhone.

Ken Case: So whenever we get a pause in terms of other things that are going on we continue to build that on OmniFocus for the Web's feature set so that ultimately we want to have close parity there.

Ken Case: We really wanted to do even more with attachments, being able to upload and have them on OmniFocus for the Web. We haven't finished that yet because we wanted to make sure we turned our attention over to getting the version 4 feature set up and running.

Andrew J. Mason: Definitely. And now there is something that you're catching folks up on that is really significant for enterprise customers. This is a feature that if you're a consumer may not change your day or your life, but if you're enterprise this could be huge. What's this about?

Ken Case: Sure. Well, this is not maybe a surprise, but I don't know that we've shared it very broadly yet. For enterprise customers we've been rolling out licensing support for site licenses that include single sign-on support or SSO authentication. So it's for people who are technically minded, it's called SAML authentication.

Ken Case: And many thousands of users are now signing into our apps using their organization's single sign-on accounts, rather than having to create and maintain separate Omni accounts on our account server. So that makes it much easier for our largest customers to manage their thousands of licensed users.

Ken Case: When they hire a new employee they add it to their authorized list, and they're obviously not just working with us, they're working with other vendors to do the same sort of thing. So those users come in and sign into any Omni app using their work email address, but they could also sign into maybe an Adobe app or a Microsoft app or whatever.

Ken Case: And that also means that as people come and go from different teams it's easy to replace one account that was active with another, and so on. And to only do it once in one place rather than having to say, "Okay, well now I've got to go through every piece of software that that employee was using and update whether they should have access to it or not." The way it works, if you're managing a team on our account system.

Ken Case: So it does take more overhead to set up in the first place, and it's not something we do yet as a self-service option. But for large customers who are interested in... We're happy to work with them and see what we can do to make their lives a bit easier.

Andrew J. Mason: Oh yeah. If you're managing multiple Excel sheet rows with user names in it and you're copying them in and out every single day, this is a lifesaver for you.

Ken Case: Yeah. We have one customer who's already up to over 7,000 seats and that would be a lot of users to be managing through a website interface rather than through their own existing accounts interface.

Ken Case: For everybody else this isn't the only work that we've been doing to try to simplify our licensing and account system. We've also been looking at getting rid of the distinction on our account system between team licenses and individual licenses. So that's one less decision you have to make when you go to our site and purchase our products. You don't have to decide is this a team license versus for me personally? And they're just licenses and you can assign them to team members if you want, or you can hang on to them yourself if you want.

Andrew J. Mason: And of course, OmniFocus isn't the only software that's getting attention these days. What about the other apps on the Roadmap?

Ken Case: I think I hinted probably two years ago now that we were going to be redesigning and rebuilding multiple apps, not just OmniFocus. OmniFocus was the first one that reached a public test phase just because of where our development cycles were. But we've also been hard at work at Omni on OmniGraffle, and the features that we're looking to bring there are some things that customers have been asking us for decades. And in fact, at this point it's funny to think that OmniGraffle is now 20 years old.

Ken Case: And so some of the features that other people have been asking for are the ability to theme, to apply themes to a diagram so that you don't have to think so much in advance, or on a shape by shape basis about what is the theme for this thing going to be? We had something similar in the diagram styles that we've had for years, but we really wanted to make something that's even easier for somebody to use and switch between, and not have to spend a lot of time thinking about.

Ken Case: And then another, it's kind of a power feature, that customers have been asking for for years is the ability to have reference objects, where you build a shape or a group of shapes and you say, "Well, this is now designed the way I want it to be." Like we have in stencils now.

Ken Case: But the big difference between reference objects and stencils are that when you put your stencil on the canvas and then you make some changes they're no longer linked in any way to the stencil, they're just a copy of the stencil. And so if you go to change that stencil later on and then you want to apply it to an existing document, you have to go back through and change every instance in the document to match the changes you've made in the stencil.

Ken Case: With reference objects, when you make the change to the reference object it now applies anywhere within the document at your choice. Because we don't want to... You want to be able to have different versions of a document where you see what it used to look like before you made that change. So there's a bit of trickiness around that as well.

Ken Case: And so we're getting to the point where we're very interested in feedback, especially from people who've asked for this feature over the years. And we'd love to hear from anyone who's passionate about OmniGraffle and interested in giving this new stuff a go.

Andrew J. Mason: All right. And so WWDC rolls around and I love this phrase that you use. Let me pull up your... Let me pull up your blog post here. You say, "WWDC often brings us both gifts and homework sometimes wrapped up in the same feature." Can you break down what that means?

Ken Case: Yeah. So the easiest example of a combination gift and homework was something I posted about. A few years ago Apple made some great improvements to the document browser that initially iPad didn't have at all, and the iPhone for that matter, or there wasn't a files app. There wasn't any sort of document browser that you could use in your own apps. So when we brought OmniGraffle over to the iPad for its launch, we had to build our own. Like so many things at that time.

Ken Case: But over the years when Apple did introduce their own we compared it with ours and we're like, "Well, that's great, but you can't actually rename documents very easily." There were lots of limitations around it and so we didn't think it was ready to switch over to. But a few years went by and then they finally did have a Version 2 of their document browser that was ready to adopt. And so we decided it was time.

Ken Case: So it was a gift in one sense, because now we have these great capabilities that document browser provided to the app. Like being able to work with iCloud more easily, being able to work with other third party syncing solutions, like Dropbox and so on, also more easily. But it was also a lot of homework because we had to go back and do a bunch of work, reworking our app in order to take advantage of this new thing. We had to rip out all of our old document browser and figure out how we were going to fit into the new architecture, and so on.

Ken Case: So the good news about this year is at least we're not having to look at doing that for anything in OmniFocus. Put it that way. We are looking at that for some of the things that OmniGraffle does. Apple has now provided us with some great new technologies for doing layout in Swift, which is much more efficient and much more customizable. And we are very interested in taking advantage of that in the new version of OmniGraffle.

Ken Case: So we are going back and we're looking at, okay, well, what's some of the code that we have spent time on this last year, laboriously working around the limitations of where SwiftUI was in the currently shipping operating system. And now looking ahead, okay, here's how we can do that much simpler in the new operating system, but it does mean we're going to have to throw away a bunch of that old code and rebuild it and put it on top of something else.

Andrew J. Mason: Ah, that's such a hard thing to figure out. How do I assess the risk of having this all move forward and develop something custom, knowing that they may eventually come out with the exact same thing? And then you're just ripping out code that you've already created. And that's taking away time, but at the same time you can't wait forever. There's no promise.

Andrew J. Mason: A flip side of that. Talk to me about, and this is no promise of future features, but what did you see that got you thinking like, "Oh man, that would be awesome to make its way into some of our products." We've seen WeatherKit, we've seen the lock screen widgets. Is there something in there that you're like, "Hmm, that would be interesting for us?"

Ken Case: Yeah. Well, the very first thing that came to mind when I watched the keynote was those lock screen widgets seemed perfect for OmniFocus. That you would love, of course, to have your tasks right there on your lock screen, to have the same thing available on your watch. It's great that they made it possible to share that code back and forth. So when we do the work for either one, now it's immediately available for the other one. And so we get twice the bang for the buck in terms of the investment we make and the value our customers receive.

Ken Case: So that one is a very obvious one. Another one that I saw that, "Oh yes, finally, we can do that," and of course, we're going to use it as soon as possible, was the ability to customize toolbars on the iPad, in the new iPad Quest. And so, we struggled in the past that we're deciding, "Well, what belongs in the toolbar, what doesn't?" We want to not overwhelm people with a lot of options that are visible at once, but we don't necessarily know which features different customers are going to want.

Ken Case: Some people really want automation in the toolbar. Other people don't want it at all because they never use it. And now that it's a standard feature of the operating system we'd be able to customize it to include the things you want, people will be able to make that decision for themselves.

Ken Case: We'll still get priority over what goes there by default in the initial setup and what goes there on the iPhone where you don't have that customizability. But it will at least make things nicer for people who are using the latest iPad at least, much like we've always had on Mac, I should note. We've always liked supporting customizable toolbars there because it lets you put the things that matter to you on it.

Andrew J. Mason: Yeah. Did you see anything else that got the wheels spinning?

Ken Case: There were so many other things that Apple... You mentioned WeatherKit already, but there were also things like Swift Charts and Passkeys, Focus filters. Apple introduced the whole new collaboration framework called Share With You. And of course, they made improvements to shortcuts in Siri, giving us a wealth of new capabilities.

Ken Case: So we look forward to building on that. As I mentioned in the post I'm a tiny bit jealous of people who are just starting out now and they have all of this to build on top of, instead of having to build or rebuild on top of [inaudible 00:20:05]. Not jealous enough that I'd want to start over from scratch, but...

Andrew J. Mason: Yeah. And this brings us, I think, to the question. This is maybe part of the central question that everybody has an eye on when they're watching WWDC is, is this going to affect the Roadmap for OmniFocus moving forward? Is there so much disruptive change here that we're going to have to reassess the way that things are going down the pipe?

Ken Case: No. Yay. Unfortunately. Yeah, that was, of course, the big question that was in our minds heading it to WWDC. We've done all this work over this past year. We're now quite a ways along in our design freeze milestone. We've already closed out our feature freeze milestone. Are we going to have to reopen that to add some new features?

Ken Case: Well, obviously we are talking about adding a new feature around the lock screen widgets, but that's something that we can't really ship until the new operating system ships. And we don't have to do a bunch of work that would make the existing code required of the new operating system. That was really the work.

Ken Case: So we can continue to ship the product on iOS 15, as well as 16. And if you're running on 16 you get to have some of these new features. And if you're still on 15, that's okay. And that means that we don't have to tie our development schedule to Apple's development schedule. And there's no extra delay caused by that.

Andrew J. Mason: Oh my goodness. That, in and of itself, such good news. And that's exciting too, to think, okay, we're plowing forward. This is good.

Andrew J. Mason: On behalf of the customers, I just want to say, Ken, thank you so much for all you do. The fanaticism with which you approach the customer service, just how you're popping... And just looking at Slack alone, how you're popping in personally to answer questions, I know that the customers are too. So thank you for that.

Ken Case: Oh, thank you. We certainly appreciate our customers. That's why we do what we do. We wouldn't be doing this if our customers weren't interested in using the results. So we appreciate everyone's support through the year. Anyone who's listening right now, thank you for listening.

Ken Case: And of course, to anyone who's testing all of these test builds, thank you for your patience as we try different things. And some of the experiments stick around and some we quickly find are just terrible ideas and they get thrown out. We appreciate your patience.

Andrew J. Mason: That's perfect. Thanks, Ken.

Ken Case: Take care.

Andrew J. Mason: Hey, and thank all of you for listening today too. As always, you can drop us line @theomnishow on Twitter. We'd love to hear from you there. You can also find out everything that's happening with the Omni Group at