Giant Robots Smashing Into Other Giant Robots

411: Civic Innovation with Jay Nath

February 17th, 2022

Jay Nath is the Co-CEO of City Innovate, a govtech company streamlining procurement through enterprise software and innovative frameworks.

He talks with Chad about how he focuses on helping governments be more effective, responsive, and zeroed in on helping their constituents whether on a small city or a big state scale.

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CHAD: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel, and with me today is Jay Nath, Co-CEO of City Innovate and former Chief Innovation Officer of San Francisco. Jay, thanks for joining me.

JAY: Yeah, Chad, thank you for having me.

CHAD: I assume based on the name and the fact that I've done my research...but I assume based on the name of City Innovate and the fact that you're a former Chief Innovation Officer of San Francisco that what City Innovate might be. But why don't you give everybody an overview of what it is?

JAY: Thank you, Chad. So City Innovate is focused on helping governments be more effective, responsive, and focused on helping their constituents, whether it's a small city government or a big state. And the way that we've been doing this is really sort of an interesting; I'd say wonky place. We found that there's a pressure point in government around documents and specifically on procurement.

And why is that interesting? Because what I've seen is if you want to work with government and collaborate, whether it's even volunteering or you're a startup, and you want to work, procurement is often that channel. And it's not really a channel; it's more of a barrier, a byzantine process. You can think of this from a technical frame, creating an API, a read/write API to make that process much more streamlined on both sides, helping governments be able to find the best partners to solve their big challenges.

And on the other side, folks from all walks of life, whether you're a massive company or you're a founder in a garage, how do you actually connect those two? So we're really working at that intersection, and it's something that I find a lot of value in and importance in. And surprisingly and maybe not surprisingly, there's a lot of need for technology to help connect those dots. And ultimately, I think what I can do is make that process more inclusive and lower the barriers of entry so that people from different communities can participate and help make their communities better.

CHAD: So your clients at City Innovate are cities and governmental organizations. Are you just delivering a product to them, or are you often helping them work better too?

JAY: It's a bit of both. From a product standpoint, we're really in the B2B space and very much enterprise, if you will. And part of that standard enterprise SaaS offering is also support services, and that can be training, that can be professional services to help them in thought leadership in different ways. And that's exactly what we do. So we not only have our product, but we help them through something called agile procurement. So it's really borrowing from the software development methodology and applying the same principles and approaches to developing and finding the right partner and being more agile and iterative through that process.

And historically, it's been very waterfall and very stilted and overly structured. So really being more focused on outcomes, really being focused on getting data into the process so that you can actually do, let's say, a bake-off and get more information before we make that decision. And it's surprising, Chad, folks in government are often buying multimillion dollars, tens of millions of dollars technology systems without actually trying it out. And think about your personal life. You test drive a car. You look through a home. You make these big decisions with a lot of data and evidence.

And in government historically, they've been using paper documents to make that decision, RFPs responses, and marketing material. And it's hard to sift through and say, "Hey, what's real and what's not?" So we've been really helping them think through a more agile evidence-based approach, and our software supports that. And so yeah, it's really leading a movement about changing how they think about partnering with the vendor community or contractors.

CHAD: So one of the things that is probably interesting about this and maybe a little bit meta is that this is what you help them do. And so you have to go through that process with them of being procured. [laughs]

JAY: It is meta. You're absolutely right. [laughs]

CHAD: In order to become the vendor that they use.

JAY: That's right.

CHAD: What are the challenges inherent in that, and does it ever get in the way? And how do people, either your clients, come to you, or how do you find them? And how do you work through that challenging process of government procurement?

JAY: Well, the thing is, since we know this space really well, we know how to navigate those different channels, the byzantine processes I mentioned before. I think one of the things I worked on when I was in the City of San Francisco was a program that brought startups and governments together, and we had an educational component. We'd help founders better understand that exact question.

How do you actually get contracts with government? And there are no books that are out there. There's no real knowledge out there. And so, we help them talk about the ten different pathways to doing that. So it's a bit of a hidden art, if you will. And I think there needs to be more conversation and more resources for founders if they're looking to go into the public sector to be able to navigate that. So we know that really well. And we're trying to really help broaden access to that knowledge.

CHAD: I assume that the clients you end up getting are people who are...or are governments who want to be better. Otherwise, they wouldn't choose your solution. [laughs]

JAY: That's right. Well, I think their motivations are multifold. Some of the governments want a process that's more efficient. They know that they can be more productive. They have maybe staffing constraints, and they have a lot of work, so we can help them on the productivity side. There are other governments that are really focused on hey; we need to get better partners out there. We've been working with the same folks over and over again. How do we work with those innovators in our community? So there's that crowd.

And then there's, I think, another group of folks who are saying, "Hey, we wanted to make sure that this process is more inclusive. We want to work with folks who are from different backgrounds who may be underrepresented. How do we make this process more streamlined, more efficient so that they're able to participate more effectively?" So I think the motivations can be different, but it's really at the end of the day centered around this idea of digital transformation and service design that allows these two different worlds to be able to communicate and work together more effectively.

CHAD: How long is the typical sales cycle for a client?

JAY: Man, yeah, [laughs] it can range from weeks, I would say to months and going over 12 months. It can be 12 to 18 months, trying to get in, doing a trial maybe, giving them that certainty, and then securing budget and that annual process of waiting for that budget approval to happen. So it is not for the faint of heart, especially enterprise software within government is really something that requires a lot of different approaches.

So partnerships with bigger companies that have the distribution channel, that might have those relationships, that might have those contracts, how do you actually work with them to shortcut the long procurement process? How do you leverage folks like AWS and other cloud providers that may already have a relationship so that you can, again, piggyback off of that? So I think there are a number of different ways to try to compress that timeframe. But it's not a walk in the park, Chad.

CHAD: So, in that environment, how did you get started with City Innovate? How long was it until you were able to get your first real customer? And how did you bridge the gap between founding and being in the market?

JAY: That's a great question. So being in the public sector, I knew that procurement is a huge challenge and also a pressure point and a leverage point to unlocking a lot of value. And so the work that we had done with startups and government the first experience that we had was amazing. We had a startup that came in and helped blind people navigate through the airport here in San Francisco SFO in four months and truly a collaboration with the startup and the airport staff. And unfortunately, when it came to procurement, it took two years for them to actually get into contract.

CHAD: Wow.

JAY: For a startup, that's like dog years. That's like an eternity. And so we really knew that we had to tackle that. So we introduced a methodology called challenge-based procurement that, as I spoke to earlier, is more agile, evidence-based, and outcomes-based. And that really leveled the playing field for these young companies to show that hey, we can actually go in here and help you solve that problem. You don't have to work with a big publicly-traded company to do this work and spend a lot of money. We can be more nimble and agile. And so that's really where I started to dig in deeper into procurement.

And that work got federally funded because it created a lot of jobs. And we've had hundreds of startups all across the U.S. It's an international program called STIR, Startup In Residence, and really proud of that work. Our mayor, unfortunately, died unexpectedly. So we looked at hey, where do we move this program? And it did make sense for a city to manage a multi-city program, and so City Innovate came to mind.

At the time, they were a non-profit. I'd been working with my co-CEO co-executive director at the time. It was a nice, beautiful transition into that. And at that time, I said for myself personally, where do I see impact, and what can I do? And for me, the idea of entrepreneurship, the idea of products making impact in government, I saw how much impact was being made. And so City Innovate has really become that vehicle for myself and the organization to really scale that idea out.

CHAD: You mentioned you have a co-CEO. How did that come about? And how do you split the responsibilities between the two of you?

JAY: Well, the good thing is we're really great complements. So his focus is really on go-to-market and focusing on how do we get this in the hands of our customers or prospective customers? And I've always been very interested on the product side. I was formerly a VP of product at a startup before my time in government, and so that scenario I find keen interest. And I deeply understand the personas and the use cases of government, having spent a lot of time there.

And so that empathy and understanding and building a product around that and having somebody who can help get that product in the hands of government navigating through those difficult processes. It really does take that. You can have a great product, but without that ability to get it in the hands of your customers, especially with governments, it's really challenging.

CHAD: Is there any in, why Co-CEO and not two other C-level roles, one of you CEO, one of you CIO?

JAY: I don't think we've spent too much time debating that. And that might change, I think to your point to better describe our focus areas. Maybe my role changes to chief product officer and his to a different role title. I think if you're starting a company, you've got a lot of things to worry about. And it just seemed like a...yeah, I don't think there was much thought in it.

CHAD: Yeah. That's interesting, though. You alluded to what you were doing before the City of San Francisco. Well, let's dive into that a little bit more. And specifically, what were you doing, and then why did you join the public sector?

JAY: So I was VP of Product at a company called SquareTrade. It was a wonderful journey. We were working with, again, something kind of wonky and a space that was anti-consumer. It was around warranties, specifically electronic warranties. And we were in the eBay marketplace and expanded way beyond that in later years. But when I was there, we really took a contrarian perspective and being inspired by Zappos and many companies that are really focused on the consumer.

We changed that value proposition to say, hey, can we build a product that people love, a warranty that actually works? And so we did crazy things like we would actually give you the money before you returned the product. We would have the shipping label. And we wouldn't ask any questions. We did amazing things. But that wasn't just because we were focused on the user experience. We also had data to back it up.

We knew that, hey, there are a certain percentage of people who are going to return rocks. And there's a certain percentage of people who are going to do certain things. So we had a lot of information going in. The other thing we knew is that we could own the whole stack, the underwriting, the retailing. And we also knew the business. So that was a great experience.

But I really was missing this connection to the public good and doing something that was having impact in a really tangible way. That's when I saw why don't I work for a city I love deeply and care about? And that really drove me into thinking about public service. I had some friends who were in it, and they convinced me that I should take a look at that.

And I definitely have found the work that I had been doing in public service to be extremely rewarding and just a unique opportunity. Especially if you're a technologist or a product mindset or an engineering mindset, that is such a rare perspective in government, and being able to bring that in, you can do amazing things.

We all know the and how that was imploding and exploding. It almost brought down a presidency and administration, and it was saved. I think many people know the story, especially in your audience. That was really folks in Silicon Valley saying, "Hey, I'm going to raise my hand and volunteer my time. I might be working at a big company and making a lot of money, but I will take my time out and try to help." And they did. They turned it around.

And I think that ethos and that mindset of giving back is something that's animated my interests in public sector and the fact that there's so much need, especially from the tech community, in helping the government out.

CHAD: Now, you didn't get started as the City Innovation Officer. [chuckles] So you got started as the Manager of Enterprise CRM for the City of San Francisco.

JAY: That's right. Yeah, it was interesting. Yeah, definitely.

CHAD: I think that public sector work is maybe a little bit of a black box for people. I know it is for me. You mentioned you knew some people, but I assume that was not a political appointment job.

JAY: It was not.

CHAD: So, how does one get into that, find it, and get that job and that kind of thing?

JAY: I think I took a very rare and uncommon path. So as you noted, I came in helping stand up a call center. So a 311 one call center which is, for the folks who don't know, 311 is for non-emergencies, potholes, et cetera, starting a business, how do I do that? So yeah, set up a CRM system 24/7. It was a great experience and actually much harder than I thought. I was working harder there than I had at the startup, so breaking some stereotypes or at least some ideas that I had in my mind.

But I quickly found myself saturating that opportunity and saying, hey, what do I want to do? And this was at the time that Obama had just come into office, and he had a call to action. His first memo in office was around openness and collaboration and that I felt was really compelling to me. I had the opportunity to say, "Hey, let me reach out to folks in White House. I don't have any relationships there, but I have this badge of San Francisco." And that started me on a journey of innovation, civic innovation.

And I did some really interesting things with great startups like Twitter at the time. We created a read/write API, the first of its kind in local government. Almost got fired by the [inaudible 16:45] [laughter] and trying to explain just like, why are you opening a channel into government to let people do horrible things? And so it was an interesting conversation. But Gavin Newsom was the mayor at the time then, so you can see it's going back in time.

CHAD: [laughs]

JAY: But my journey then sort of said, hey, let's continue building data standards and doing good work. And I was recognized by the mayoral campaigns that were running. And so they wanted to sort of say, "Hey, we need somebody in innovation in the mayor's office." So I got recruited into that role, the first of its kind in San Francisco and in the U.S.

So it was just a great opportunity to really help define and set a foundation for what does civic innovation mean? What does that look like? And we had a small office, and we did some really interesting work at the nexus of collaboration. That's really what I think is what we tried to do is make government more permeable, more accessible for people who are driving innovation in their communities to be able to participate in government.

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CHAD: If someone's interested, how might they get involved in contributing to the public sector?

JAY: I think there's a couple of different ways. So one way, Chad, is that governments are often putting a lot of data out there. There has been an open data movement that we had led, and it's now a national global movement. So you can find data, and you can create a data product around that and giving more insight into visibility and into issues. You can volunteer with a specific department. They're looking for those skill sets, so you can do that.

You can also look for digital services offices. So those are becoming much more commonplace in governments if that's your thing. There are definitely ways to raise your hand and try to contribute. Folks are always looking for it. And if you don't see that opportunity, make that opportunity happen. Reach out to your council member. Reach out to a department head and say, "Hey, I've got this great superpower. I want to help you do better." And I guarantee they will listen because they're often strapped for resources.

CHAD: How do you know when you should pursue a more general product that might be useful to governments versus like, oh, if I could get in there and contribute? How do you make that distinction in your mind?

JAY: Well, I don't think there needs to be. So you can come in and have maybe a frame of hey, let me help my local government. And you might find opportunities while you're working there. They're using Microsoft Word and Excel to do something that really should be productized so you can think about it from that frame. Or you might have built a product for an adjacent market or for another need and say, "Hey, is there an opportunity to actually reframe this product that I have in the government context?" It might be a content management system. It might be a lot of different products can be reframed in that context.

So the way that we actually became a product company from a non-profit was just doing that. We got invited to bring our methodology of agile procurement. And so we had in the back of our mind this idea that I bet if we go there, it's going to be kind of dusty. There's going to be a lot of broken tools, and that was the case. They were using 40-year old technology to manage sometimes billions of dollars of purchasing. And so we saw something that you normally wouldn't have that vantage point by really collaborating and working with them. And that led to product ideas, and that we were able to co-design and co-develop that with our partner governments.

And then something that I think is also unique is that they're often eager to work with you because they don't get that opportunity often to work with vendors and folks who can conjure magic in their minds, that they have a vision or idea. And you can come back in a week or a month, and you might have a working product, not just wireframes. And for them, that ability to move so quickly they haven't seen that before.

And I saw that firsthand in bringing startups and governments together, the velocity and speed that startups can work with is so different. We all know that. But when they see that, they get excited. They want to work with them. They want to lean into it and figure out, hey, can I give you data? Can I give you other ways to better understand the space? Because no one's cared about this space before. So there's often a willingness to grab a hold of anyone who can actually help them solve their problems. But you have to listen, and you have to come in humble.

And I'll share a story here. I created a program called Civic Bridge that brought in pro bono services from big companies like Google and McKinsey, and many others. And some folks from Google came in, and they were sharing how they have to serve everybody. Their product is really ubiquitous and has to serve everybody. They quickly got reminded that government has to serve everybody, people who don't have technology, people who aren't online, people who don't have English as their first language, and people with different disabilities. All of them are constituents.

And so technology is one way to reach people. But you have to think broadly about how do you make that service or what you're offering accessible to everybody? And I think that was a humbling experience for the folks there at the table. But what I loved about that program is really this cross-pollination and also breaking down stereotypes in both directions that people sometimes have in the public sector of private sector folks because they often don't hop back and forth. If you're a public sector person, you're often in the public sector.

And so being able to actually see that they're not just a bunch of capitalists, [laughs] that they're your neighbor, that these are people who do care about the community, and they're making an impact in a different way. And vice versa, that there are so many talented people in government. And the problems seem simple or seem simple to solve on the outside, but they're often wicked problems or just have a lot of complexity to try to solve. So it's great to be able to have that empathy on both sides.

CHAD: Yeah, that's maybe one thing. Are there other things that you would point out that are different when creating and shaping products for the public sector versus the private products?

JAY: Yeah, I think that idea of being inclusive is really important. The other one is around...and this is, I think, true even in the private sector but more so in the public sector because of the demographics that you're working with. The demographics are folks who are closer to retirement. They are not digital natives. So when you're building products, you really need to leverage mental models and use that as a way to bring them into a new experience or a new tool. And as an example, there are obviously a lot of government forms that you see, right?

CHAD: Mm-hmm.

JAY: And I think as a technologist or a product person, you might say, hey, let's move away from Microsoft Word or Adobe PDF or whatever you're using. We have this thing called HTML, and we can bring this online and have all these beautiful affordances. Well, that's really hard for those folks to wrap their heads around and move from something they may have been using for 20, 30 years.

And so maybe that first step is not that; maybe it's online fillable PDFs that you can actually store the data in a database and shift that back. And maybe that allows them to actually move more quickly because there's less resistance both internally and for the public as well. And so we've seen that time and time again, is that hey, is there a way to make that shift into a new paradigm but do it in such a way that there's a clear connection point?

And then maybe the next step after that is, yeah, we need to make sure this is mobile-ready. Let's actually make that into a responsive design and move away from that PDF. And that's something that we've learned in our own product that, hey, we need to understand deeply the products and tools that they're using today. And how do we draw those parallels and bring them into the current modern set of technologies that we're offering? So it's not always easy, but it's something that we found a lot of success leveraging those mental models.

CHAD: Are there other things that you might call out as things you got to keep in mind?

JAY: Well, security is often, you know, we see that everywhere with SolarWinds, et cetera. I think there's just a deeper concern of supply chain attacks, ransomware, et cetera. So you're seeing, I think across the board in enterprise as well but in government even more so really focusing on that. And I think the challenge for folks who are building products is how do you find that balance when you have to make sure that you're NIST-certified and all of the SOC 2, et cetera? How do you build a great product that is accessible that doesn't make you go through a bunch of hoops to try to get access to it? And it's not easy.

So that adds a layer of complexity trying to build that out. And, Chad, I'm sure you've worked with a lot of folks who have thought about government or may have had some success with it. So it might be interesting to hear from you if there are certain patterns or product sensibilities that you've seen that have been successfully applied in the public sector realm.

CHAD: Well, I think you're right about that inherent complexity or that the bar is pretty high in order to have a product which is accessible and secure. If you're building a product for consumers, you can do some of that stuff iteratively. It can be difficult to work in an agile, iterative way in a highly regulated space. And so there's maybe not even one set way that you do that. It might be different for the space that you operate in.

But it is important to take a step back and say, what can we do iteratively, or what can we leave off right now because we have to do this other thing? And those will be different for every product. And I see the real mistake being not taking that step back and not really being thoughtful about how you're going to do that in the complex, highly regulated space.

And this is true for healthcare and finance as well. There are certain things you've got to do. And really, you have to approach it pretty thoughtfully in order to make sure you can still work and not just default to doing everything agile. We have this concept of like the 80-20 rule, and that is sometimes really difficult to do in the public space, right?

JAY: I think you're absolutely right. And I think people recognize that highly regulated markets or industries are tough to crack. And I think you're absolutely right, Chad, that you have to find that entry point where maybe you can come in and the regulations are lower for that problem that you're solving initially. And use that as a place to land and then better understand where you fit into the overall workflow. And you're able to go upstream and downstream from there.

And that's a lot of what we've seen success with these young startups, and the work we're doing will come in where there's maybe not so much regulations and provide value there, build trust, and then look at the broader ecosystem or processes to say, "Hey, where can we add more value?" Yes, it might be highly regulated. But we now have a better understanding, more resources, and customers to help us educate climbing that mountain together.

But yeah, I want to make sure that...the flip side of all if I were listening, I'd say, "Well, it sounds like the public sector is really tough," [laughter] and it is, but it's also truly rewarding. I think being able to know that you're able to help at the scale that the government does its work is really, really rewarding.

One of the founders that we helped get her first product was to help foster kids, and that foster process that we've probably all heard is really, really tough. And they brought that online, and they went from one city...they're in so many different states now serving so many people across the U.S., and they're doing really well. They're, I think, Series B or C. And it's amazing. But it took that one government to take a chance and to be able to bring all this value. So that's something that excites me is the level of impact is so significant.

CHAD: On that note, you started the conversation saying that procurement was the area where you felt like you could have an impact. Do you see expanding beyond that in the future, or is that not on your roadmap?

JAY: I think we have a lot to chew on. But like a lot of product folks, we've got ideas that are further out. What I'm seeing in the government space when we talk about digital the government context, you're often talking about PDFs and Microsoft Word documents, et cetera.

So I think for us, we're really excited about is there a new way to think about documents in a way that works for governments? They're used to Microsoft Word. But is there more that can be done there to create more affordances, to create more powers that they just don't have today? And they're using Post-it Notes or whatever it might be to try to address those shortcomings.

CHAD: Everything is going to be marked down in GitHub eventually. [laughter]

JAY: Yes, we do need to introduce Markdown or just plain text, maybe. Why are these contracts locked up in Microsoft Word? Yeah, that's something that's a pet peeve of mine as well. I spend a lot of time in open data. And let's not use proprietary formats. Let's use something that folks understand. But the world is changing, which is great. We're seeing more governments using JSON.

And one of the things that I'll share is that when you're building a product for government, you do have to think about the data component because that data doesn't belong to you; you're really stewards. That data belongs to the government and its constituents. So that's a different way of thinking because often, private companies are trying to monetize the data that they're having. So you have to have a much more sort of a frame that you're a custodian.

CHAD: I think that's one of the things that can get a little lost, whether it be bureaucracy or politics or whatever but this idea that there is a community here. It is the community in which you live. You said that what inspired you to get involved was wanting to contribute back to a city that you love. It's easy for that to get lost in everything.

JAY: Yeah. And that's my call to action to your audiences. Sort of touching upon our earlier points in our conversation, find a way if you have that means, and ability, and interest to make your community better. It might be something just for your city, or it might be something bigger. And I've seen so many people have good ideas. But to your point, how do you actually convert that good idea into something that's valuable and used by the community?

And hopefully, this conversation is helping people and inspiring them to raise their hands and knock on the door. I think you'll see folks on the other side giving you a warm reception. They're very hungry and eager for people who have the capabilities of product and engineering and that type of talent to come to the table and help them.

CHAD: That's great. If folks want to get in touch with you or find out more about City Innovate or STIR, too, where are the places where they can do that?

JAY: They can go to our website They can also go...I've got my own personal website, And I'm very open. I have been since my days in public service. I'm still very accessible, maybe not as responsive as I used to be, just with all that work of being a founder. But if you're interested in this space, I always want to give back because we need great people with great talent working in the public sector, whether it's for government or within government or building a product for government.

CHAD: Awesome. Jay, thanks very much for stopping by and sharing with us.

JAY: Thank you so much, Chad, for the opportunity to share the work that we're doing.

CHAD: You can subscribe to the show and find notes and a transcript for this episode at If you have questions or comments, email us at And you can find me on Twitter @cpytel.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening and see you next time

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