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JASON: Hello, everyone, and welcome to another episode of the webdev podcast. Today on the show, we're going to dig into something that's been a thorn on my side for the entirety of my career as an agency owner, freelancer, and now as a company founder, which is the busy work that comes with any type of project that just sort of really bogs you down at the beginning. It's the sort of thing that I feel like has been inescapable, but in recent developments, it's starting to feel a lot more like maybe it can be automated in good ways. And today, I want to talk to somebody who is an expert in doing exactly that. So please, welcome to the show Raileen Del Rosario. How are you doing?

RAILEEN: I'm good. How are you?

JASON: I'm happy to have you on the show. I have a million questions relevant to my interests, but before we dive into that, I would love to talk about who you are and what you do. J.

RAILEEN: Sure, yeah, my name is Raileen, I'm a developer, advocate, and program writer with Docusign, I've been with them since 2022, and I kind of just do a lot. I jump around to all of these different things. I love writing code samples, I love writing tutorials. I do reference implementations for any new things coming out just to teach people how to use them. But yeah, it's kind of my main role is to teach developers, which is a lot. [ Laughter ]

JASON: Yeah, I mean, I think the challenge, especially today, of figuring out how to teach people when -- I mean, it feels like the material goes out of date every six hours.

RAILEEN: I know.

JASON: How are you approaching that just as a quick aside before we dive in?

RAILEEN: Yeah, so part of it is my experience before I was a developer, advocate, and program writer, I ran a dog training company. And so there was a lot of tutorials to be written that I wrote, there was a lot of automation I really was interested in doing, and organization. And so part of that is how I approach it where I think about kind of what needs to be explained and what doesn't. And part of that is, you know, knowing what the use cases are. The nice thing with dog training, I knew them pretty well because I have my own dog, but with developers, it's a little bit trickier, right? Because you have all of these industries, these use cases. So -- it's kind of -- I'm a little bit of a completionist in that way where I try, every industry and have a tool for them. Tall order, but I try.

Yeah, yeah. I mean, especially when you're working in something like Docusign where it truly is like a tool that it's not a developer tool, it spans everything. And, you know, everybody needs contracts and I think Docusign is really one of the only options I've seen that feels good to use. Like, I get a lot of -- it seems like everybody sends me Docusign, I don't get a lot of nonDocusign contract stuff unless they're like, hey, can you scan this and send it back to us?

[ Laughter ] Um -- but so, so thinking about, like kind of the concept of what we're talking about today, this is a space that has felt a little bit stagnant for a really long time. Like contracts are something that kind of haven't changed, you know. I'm actively in the process now of -- of doing some paperwork, and I found out that I have to print off and sign and like ink sign and then scan the thing and send the scan back. And this is something that I think, you know, it's only in -- this is a real estate thing. But the majority of things seem to be moving to esignatures. But it also sort of feels like that hasn't changed a lot in the last 15 years. You know? Like you've been able to e-sign things for quite a while. And Docusign has been sort of the core of at least that's how I became aware of people being willing to accept Docusign for actually legally binding contracts. That's what I use at CodeTV now, but I think the thing that's been interesting about it is like, where the rest of the world is sort of in active turmoil because all of the new tools that are coming out, I haven't really -- I've seen people talk about LLMs coming to, you know, law, but I haven't seen a lot of it in practice. And so, I imagine this is something that you end up talking about a lot. And I guess, maybe my first question is just, how are you seeing the landscape shift in and around the space that Docusign occupies?

RAILEEN: Yeah, definitely. I think part of it is like, you know, this AI evolution coming out, right? Where people are realizing the data is, in specifically agreements, is something that is now accessible, right? Because even with that first wave of innovation when paper contracts became like digital contracts, even still, it's what -- what we call it is the agreement trap, right? I know with me, when I have contracts for various things, you know, someone working on my house, I don't know, anything. They get stuck in like some folder on my desktop or email and it's always like organize later and it's got random numbers. And I have no idea what it is. And it would be nice if, you know, we had something like a dashboard or a system where we could see with our own eyes what we're actually looking at. And not only that, but extract the data from it to keep us organized and in compliance. I actually wrote a piece on this called the Agreement Trap. There's two articles, one is more the problem statement, one is more the solution. It's over on the news stack. I think you can find it on my LinkedIn, actually. But -- it kind of now that this like AI evolution has come in, it's sort of opened the door where that's now possible, right? Where we're not manually opening these files. There is a way even if it's not completely defined yet to look at this data that's stuck in these things. And so, that's when Docusign became, you know, started becoming this platform, right. It's not just, you know, e-sign and you're done, now it's become this thing where it's that agreement is part of that workflow. And then, what happens after the agreement is signed, we have a -- API called navigator, which is building up to be an AI analysis of contracts. So things like if you have renewals coming up, right? You can flag those in the metadata and actually pull them and, so you have this consolidated organized view of here's this client, here's this project, here's the renewal date, make a ticket on JIRA soon, you know. So, yeah, that's how I'm kind of seeing it evolve. It's turned into this thing where it's not paperwork drudgery, and it's becoming something that's, you know, extractable and actionable. And I think that's really, really neat. >> JASON: Yeah, I think, and this has been a big point of -- drag for me. Like, I find that, you know, the challenge of running a business or being independent tends to be that you -- you're responsible for everything, right? And so your to do list is sort of growing, not just vertically with like the projects you're working on, but horizontally with the related things, the metawork that needs to be done, contracts, taxes, bookkeeping. You've got to coordinate things or scheduling, there's, you know, like you said, file organization, making sure you can actually find stuff later when you get asked about it by your accountant. All of these things that need to be done. And what I've found is that I don't love doing that stuff. And as a result, I tend to procrastinate it, and then, it turns into this massive chore, and I don't even know if I'm doing it right because the likelihood that I actually found everything I did over the last year, it's so much of it is sort of like, OK, I've procrastinated too long on this, it's now an emergency. I'm going to do it or I'm going to miss a deadline for something. And so, you know, there's also these other sort of metatasks that happened where -- in a transactional relationship, like if I am running an agency, if I am doing client work, if I'm a contractor, in all of those scenarios, there's these sort of phases that happen. There's the sales phase where you're talking about what's possible and how it might work and you're defining the scope of work together. And then, there's the contract phase. Where you actually send the formal agreement and say, this is what I'm going to do, this is the timeline, this is what it's going to cost. And everybody sort of works back and forth to agree on what that thing is. And you kind of can't do anything else until everybody hits that agreement, or at least, a little word to the wise to the contractors out there who are saying, well, I just go off and email. Stop doing that, get a contract. [ Laughter ] Ask me how I learned that lesson.

Yep. Don't learn it the hard way. [ Laughter ] But so, once you get that contract signed, then it kicks off all of this other busy work. You have to set up, you know, if you've got a project management tool, you've got to create the new project. You probably have templates that you used to give you baseline stuff about what's going on in that project to make sure you hit all of the right things. You need to maybe set up a calendar. Maybe you need to turn the timeline that's in your SOW into an actual like set of calendar deliverables or a Gant chart or something that helps you visualize where you are. Maybe you've got to set up a GitHub or JIRA or Trello whatever you use. Maybe a private Slack in Discord. All of these things start to add up and that horizontal growth of the Admin play list is really extensive for every project. And that makes me, personally, resistant to starting new projects. Which is really counterintuitive to the idea of I operate this business to make money. [ Laughter ]

RAILEEN: Yes.

JASON: So, as you're working on these new tools, you're talking about the ability to sort of organize your contracts and stuff. Is there -- like what's happening in the world of kind of taking away some of this other stuff? Like my project templates and my various things that have to get spun up after the contract is signed?

RAILEEN: Yeah. I mean, even the entire flow you described from sales to agreement to Admin work is all something that is automatable within the Docusign platform. And so, that's something -- >> JASON: Interesting.

RAILEEN: Yeah. That's something I think about in the busy work, right, I try to look at these different industries. Like, I really liked working on the things we're covering for the stream today because it is an interesting kind of industry I've never touched as far as like tooling goes. And it is building it you kind of see the value. And part of the daunting part, right, is the how big the Docusign platform tooling is. So, a lot of people don't know that you can automate the CRM portion and the agreement, and the Admin work. >> JASON: Oh, interesting, OK.

RAILEEN: Yes. So handling that, you know, is really nice, like I wish I could automate taxes like we were talking about earlier. Not yet, though. But yeah, it really helps, obviously, it doesn't eliminate completely that horizontal growth when it comes to tasking, but it picks up a lot of the slack. A lot of the repetitive mindless busy work that a lot of us don't really like to do, you know, like something like building the notion page template. If it's the same every time, it kind of stinks to do every time.

JASON: Even if the checklist is like open this web page, create from template, open this other web page, create from template. It just creates 30 minutes, an hour of drudgery that's not necessarily -- it's the sort of stuff that feels like chores. Doesn't feel like progress. And historically, it's the sort of thing that led me when I was younger, well, I don't need these templates, I'll just remember. And why would I do this paperwork? And of course, that works if you're doing maybe one project. But hopefully, your business is doing well. And hopefully, you are busy enough that you can't hold all of the context for everything you're doing in your head. Which means that these become necessary evils. Like, you have to be doing some product tracking. You have to have reminders of what you've promised by what date to which person. You need to know when it's time to check in with a client. You need to keep track of who's in charge. Your racy or DACI whatever you're using to figure out who needs to know what things are happening, approve things, there's a million little things that happen and as you're working with multiple clients, you can't track all of that in your head anymore, you need a system to keep it organized. And like, the problem of organizing your organization is this sort of perpetual thing that, you know, there's millions of systems out there. Everyone's got their own personal organization system, getting things done, and you know, the cost. Everybody's thinking about how they track information, store information, use information. So I think the thing that is really interesting to me is this idea that, like, it's not going to replace the need to design your system, but once you've designed it, it sound like we can lean on Docusign to sort of have these automation triggers. And so, if I can repeat this back just to make sure I'm understanding it correctly, you're saying that, like, as I'm doing miss sales process, I would write my proposed scope of work and the proposed contract language, whatever it is, whatever the documents are we're trying to agree on as the sale continues. I can put that into Docusign and send it back and forth for the red lines is the term that I always hear lawyers use, but basically, feedback and edits. And once we hit a point where I -- where everybody agrees, I can say, all right, Docusign, send this for signatures. That's the signed contract, which actually kicks off things. That, then, can hit an automation that would say go to my notion and create a project from the template and populate with the client's data and go to my CRM and update them to closed 1 or whatever it is. It could go to Discord or Slack and create a channel and invite -- basically, anything with an API, I can theoretically have Docusign kick off these workflows for me?

RAILEEN: Yeah, anything with an external API is something you could absolutely add, you know, to your system. And I like to think of it, too -- setting up a system is, you know, a lot of work. And I like to think of it as, I am grabbing all of the time I'm spending doing these Admin tasks over the course of my business's life or whatever. And I'm just putting it all in the same day. And so, I kind of get -- I guess, get through it, get over it really quickly and really speeds up my day-to-day tasking, right? But yeah, you've got the flow right on the money. Something as simple as like changing a client on Salesforce to like a contract sent can kick off that workflow, right? Because we've got that. >> JASON: Right.

RAILEEN: Extensibility, and so, automating as much of this as possible, but also, keeping a human in the loop, right, like during the red lining moments is something that is super important for businesses is to continue to scale, right? Because I know for me, one of the things I try to automate is my Google Calendar, and I'm horrible at it, because I keep changing how I want to do it and doesn't stay consistent. But something like that, right? Having a trigger on there that's like, hey, you have this email where you have to sign something or reply with something, whatnot. And it just spits it out on the calendar. Yeah, you can absolutely have access to all that information. But consolidating it and organizing it into one spot is something that is just as valuable, I think, as having that system. >> JASON: Right. Yeah. I couldn't agree more. I think the part that is really hard is that generally speaking, the system has to be simple enough that -- I mean, there's that XKCD comic, where how much time you can spend automating it than you would save. And it's honestly, you've got to save a lot of time to make it worth building a really complex automation. And so, the real magic in automation is when you can sort of -- you've built out the system because you have to do the same thing every time anyway, so whether or not you're intentionally building a system, you're building a system, right? The process is there. And if you already have a process, being able to quickly plug it into one central place, and in this case, we're talking about Docusign to do that. You are then minimizing the amount of effort required to actually create the automation, which means that you do get to reap the benefit of it, right? You can't spend 6 weeks on building an automation or you're absolutely not going to see the benefits of that time until years later, right? It's got to be something you can put up pretty quickly. We're going to get into it -- we're going to do a companion episode of Learn with Jason here where we'll actually live code one of these things. So if you are interested in that, make sure you head over to the CodeTV website, look at Learn with Jason and you'll see the episode where we will live code using the Docusign API. I guess, can we talk at the high level about, what is -- what does it take to set up one of these automations? For somebody kind of coming in fresh, like me, what am I in for? What am I going to do to make it happen?

RAILEEN: Yeah, you know, there's a few different ways you can get started with this, right. So the first kind of tool I would use is the Maestro Workflow Builder, right, I call it the bones of your automation. It's what tells it what to do. It's the foundational, right? And then, going from there, it's -- and this is part of the -- this is the tricky part, right? It's so big. So going from there, you can, let's say, make an e-signature template, and you can do that also on the UI. The beginning part is a good amount of UI, right, before you get to the nitty-gritty coding. And it's basically set up, right. So it's quick, I think it's pretty simple, it's a matter of matching variables to variables, which is nice because that's just spell check really. And so, going from there, you can trigger the workflow if it's something like your smaller scale business, you maybe don't need something to trigger programmatically, you can do that in the UI, trigger the workflow, send it out. Even though it's still manual, that's like 100 million less clicks, still. >> JASON: Well, yeah, an automation that means I can click one button to do five tasks is still an automation. Even if -- I think human in the loop stuff is good, personally. I'm a good fan of being intentional about what you're doing because, like, I don't know, I get a lot of automated things that are clearly automated and no one has looked at them. And we see the jokes about how recruiters will send out the emails that are like, you know, dear applicant name here, we saw your experience mat company name here. We do want to avoid, I think, depersonalizing the work and moving to the point where we're not aware it happens. But I think that there's a way to be mindful of what's being done and to keep yourself, as you said, a human in the loop on everything that's happening without requiring all of the busy work that goes into that. You can sort of look at it and say, yep, this is ready, click the button, and off it goes.

Exactly. On the other side of this. Once I get signature, that starts to reach into the other things that I would want to do. And so, is this something -- so to get into the maestro workflow that you were talking about, I know there was a Docusign developer portal and that's all in there. Are there also like integrations? Am I hand coding this? How are we hooking this up into other tooling in the workflows?

RAILEEN: Yeah, there are built in integrations within Maestro which are really nice. Salesforce is on there. Google Drive is another one for storing files. You can also build your own integrations, like something like notion, right, can be kicked off -- I just saw -- [ Laughter ] But yeah, anything like that can be kicked off by it will Maestro workflow, and that's the nice thing, too, is that any kind of builder from low code to high code, whatever your preferences can utilize this tool and use those integrations. Maybe you just need a Google Drive, and so you can plug that in and you're all good.

JASON: Right. And there's a gradient here, too, on the one hand, things simple as in the UI, I can build out quick automations that move data from review to signature and then, use the Salesforce automation to like put that signature data back into the CRM or put the -- the signed contract into my Google drive. But then, you've also got support for like a webhook if I say have an existing automation pipeline, I could have the webhook trigger certain things to kick off in existing pipelines. And then, we also have the ability to custom code inside of Docusign, is that correct? I can like write my own actions that live in the Docusign pipeline?

RAILEEN: You can, yes, so we have an extension apps, like platform, as well, where you can create your own. And whether, we have different ones available right now. So something like data input/output, data verification, custom field verification. So if you instead of like, I don't know, checking email, you can check like VIN, if you built that extax app out, then you can take that. It'll pop up on the Maestro workflow UI, you can take that and find your extension app and put that in as a step. >> JASON: Nice.

RAILEEN: Very, very handy, for sure. And regarding the webhooks, yeah, we do have like the connect webhooks, as well, which you know, if there's an event like agreement signed, something like that, it can kick off the workflow. I know something I was playing with earlier this week was a webhook kickoff.

JASON: Nice.

RAILEEN: That's nice because you can -- you can take -- you can call the set that as your trigger. It'll kick off the workflow appointment is made.

JASON: Somebody goes to Calendly and click they want to meet with you. A waiver or something?

Yes.

JASON: Those are the little things that you either, you get lazy because it's a lot of work or you get -- you get, like, you know, you don't want to deal with it, right? That's the sort of stuff that -- those little things, if you're doing them all manually are death by a thousand cuts.

RAILEEN: Oh, yeah.

JASON: And being able to automate those little things that just burn your -- you know, they just burn your time, right? That's the sort of thing that I desperately want in my life. I'm really, really excited to hear about this. I guess one other question in the abstract about this is like, how does it fit into a business? I'm going to make the assumption that this is for Docusign customers, right? And if you're running a business, I think it is probably very reasonable to be a Docusign customer. But am I upgrading? Am I signing up for a new service? Is this like a separate SKU I have to get if I want to use the automations?

RAILEEN: Yeah, with a developer account, you can try these things out, for free, right, the only thing limited right now is Navigator, the agreement analysis via AI, that's the only --

JASON: That tracks, AI tokens aren't cheap.

RAILEEN: Yeah. So as far as trying it out, it is free to do on the Developer Center. As far as plans go, you know, two weeks ago, I was like, I really should learn what the plans are. Because I'm not in sales and how much they cost. I know what they are, but like the nitty-gritty, I'm not sure of. As long as I'm correct, yes, there's a separate plan, the IAM plan, you can utilize extension apps, Maestro, and Navigator, as well. >> JASON: Got it. OK. Cool. So this is the sort of thing that -- I guess, in the companion episode, we can peek at that in the pricing page to see what somebody's getting into it. So you can start on a -- is there like a free tier for low usage? Like if you're an independent contractor who doesn't have a ton of contracts, but like awe few automations? Or does it go free trial and then when you want to go live, you have to get a plan right away?

RAILEEN: Yeah, so you can actually just build your workflow out in a Developer account for free, right. Try it out, yeah, anything -- I mean, it'll say like for demo purposes only on the email, so it's not like an official live --

JASON: Sure. Sure.

RAILEEN: Workflow, but after that, you don't have to buy the plan and rebuild the whole thing, you can just talk to, I think it's support, and they can talk about usage rates and things like that for smaller scale businesses and promote the workflow you already have to a production account.

JASON: Nice.

RAILEEN: Which is really nice, you're not building two different things.

JASON: Very cool. Yeah, that's definitely handy. OK. Well, I think, that's -- was there anything that you wanted to talk about on this that I didn't ask you about?

RAILEEN: You know, I think you covered everything. I think the only thing to mention is that it is a tool that is very general, and so, it's very use case specific. So I think a little bit of a call to action is that building and finding out what the use cases are in building these tools is something that is really helpful for me because, like, you were saying with regards to the automation and the time investment it takes to even build it, I want to try to lower that for developers as much as possible, right? So it's -- because of how big Maestro is, all of the options you've got, it's tricky. So, I guess like, you know, trying this out, going to the developer center, trying to build something for the use case, and then, reaching out to, you know, the Docusign community something, the developer community is something we just launched recently, which is similar to Stack Overflow forum. And just got LinkedIn, I'll get back to you really quick. I am curious to see how people want to use this. >>

JASON: Cool, Raileen, thank you for taking time to talk to us about all of this today. I think as a business owner, this is the sort of thing that is just, you know, it's not maybe the most exciting thing to think about. But it's a drain and weight on my shoulders. Being able to see. It would be wonderful. So thank you so much for spending time with us today, and don't forget if you're enjoying the webdev podcast, subscribe to it. You can get us on Spotify, Apple Music, whatever we're using, you're probably there. And watching on YouTube, make sure you like, subscribe, HR share, leave a comment, make sure you're enjoying it so we can make sure more people are able to find us. We have a companion episode where you can watch us live code something with this automation workflow. That's at CodeTV.dev, and consider becoming a supporter, that helps us make more content just like this. Thank you for watching the podcast, we'll see you next time.