How to build a personal dispatch system for gig and hourly workers?

David Pickerell, Co-Founder & CEO ● Aug 8th, 2023

The full transcript

Stephen May

David, good morning! Welcome to the Devico Breakfast Bar! Glad to have you here as one of our guests. I wonder if you could start for our audience telling us your full name and the name of the organization you're currently with.

David Pickerell

Yeah. Thanks for having me here. I'm David Pickerell . I'm one of the Co-Founders and the CEO at Para. At Para, we're trying to build a personal dispatch system for gig and hourly workers. So what that means is a tool where one can get all their pings in one place and also use their work profile to access lots of other opportunities. And the way I really view it is we're sort of building a bot or preference engine for the, you know, individual worker.

Stephen May

I had a look at your website. Some fascinating stuff going there, and lots of challenges in the organization, which we can talk through as we progress. How about telling us a little bit about your journey to where you got to today as CEO and the role you currently undertake?

David Pickerell

Yeah. There's sort of a long story and a short story as to how I got here. I guess. I never thought I would work in the gig economy again. Back in an old life, I'd helped launched Uber in Las Vegas, actually. So that's how I got my feet sort of wet in the gig economy. Uber was a fascinating market, as I'm sure you can imagine. But essentially sort of was on the operations team that launched and helped oversee a bunch of the desert states for Uber, as Arizona, Nevada, New Mexico.

After that sort of went my own way, sort of worked at a startup, worked at an early stage VC fund. But I think, I heard from a lot of people that ideas targeting gig workers essentially, right? So kind of here's FinTech, trying to target gig workers, here's InsureTech, trying to target gig workers. And I guess from my time at Uber I've always had the idea that, you know, I've always sort of about nobody comes home after driving 16 hours and wants to find your FinTech product. And I think just always had this philosophy that the way to build tools and services for the gig economy is to build a tool that puts dollars in pockets, that puts people in charge. And I think sort of fast forward a bit, had this realization at the beginning of Covid that when I'd worked at Uber, 20% of Uber drivers worked on Lyft, but none worked on DoorDash.

So the average person worked on one point something apps. But Covid forced that change in behavior, right? So the average gig worker suddenly had to work on three plus apps. And I think it was sort of a realization that the world was changing. And what I'd learned previously at Uber – this idea of a platform that sits holistically across multiple platforms or across multiple opportunities made more sense now. And that's sort of how we started working on this.

Stephen May

Thanks very much. And again, I think the Uber experience must have been very interesting. But around that and others, perhaps, you could share with us what you feel has been your most important accomplishment to date then throughout your kind of career and different roles.

David Pickerell

That's a tough question. I do have a simple answer for that is we built one feature for our users. It was called Tip Transparency. And at that time we had, call it, 2000 or 3000 users on the platform. And over the course of like a three or four week period it went from a couple thousand users to over 300,000 users, basically, because we built a tool that made our users money and that they liked.

And I think that was the, you know, you always hear these things about finding product market fit, or exponential growth, or something like that. I think to me, that's something I was really proud of, which is for a while we were able to help lots of people make more money basically. So, I'm proud of that.

Stephen May

Okay. Yeah. I understood. And here's another question then a bit about you. I mean, within the concepts of something you are very proud about, what is it that you are really passionate about within the industry that you work within?

David Pickerell

Yeah, I think on my end it really is building these tools for individuals, right? I think I have a philosophy that a lot of the time the technology that we're building isn't rocket science. It just hasn't been applied on behalf of the individual, right? So a bot that will scan opportunities, a preference engine that will take into account what you want to accomplish, none of this is, you know, super technically challenging.

It just hasn't been applied for somebody. I think the other philosophy we always have too is that you just need to help people be able to make informed decisions. And to be able to do that, you just need to give people very clearly the data that they need to make that decision. So I think both of those sort of philosophies drives what we do.

Stephen May

Okay. Thank you. Here's a question we ask most of our guests. And when they look back on their career and the projects they've been involved in, there are those moments when we say, "Wow, that was a bizarre experience," or "That was a kind of scary, funny experience." Any stories to share with us when you look back at the past?

David Pickerell

That's a good question. Like scary... let me think about that. I think it ties back to that sort of first initial crazy user growth. At that time we had three people at the company. It was Jeff, my Co-Founder and CTO, myself, and then Jimmy, who at that time had just joined us. His first ever job was working for us at the company, here basically. And what I always said was, you know, we'd wake up and do what I call fight the tidal wave, right?

It was really, you know, 300,000 daily active users, 1% error rate at 300,000 people is a lot of angry people yelling at you. We would just wake up and at that time the only way we had to communicate with our users, we had a website, simple web form, and we had a Facebook group. We just lived in that Facebook group, 18 hours a day, basically, and just fought the tidal wave. I think we called it fight the tidal wave on purpose, right?

Because there's this realization that no matter how much we did in a given day, we were only chipping away really slowly at it. And I actually think that that's probably bringing it back to sort of Devico here quickly once that's around that time. I think just before that, that we started working more closely with Oleg and the team at Devico.

Stephen May

Okay, good. We're gonna get into that sort of working with different resources and then meeting your aims. But thanks, that's a really interesting story. Thinking about the industry in the space we're in, right? People often say that there's no more constant than change nowadays, and things move very quickly, but particularly in our space, right? How do you go about keeping yourself up to date with the latest developments in tech?

David Pickerell

That's a good question. I mean, I try to read a whole bunch of things and I try to play with things when I see them. But I'll admit that as a founder of a early stage company, I probably don't have as much time to play around with some of the things as I would like. So I guess it really is sort of reading, playing with things, and talking to friends that I trust, and just staying in touch. But I'll admit that I'm probably behind the ball a little bit. Just most of my day is sucked up by what we do.

Stephen May

Yeah. Understood. Well, within that context though, give any advice for us on how you would go about choosing what computer language or development framework to use.

David Pickerell

You know, on my end it really was. We went through this sort of back and forth, right? And I'm not the technical co-founder. So I'm probably not the right person to speak super deeply about this. But at the end of the day, for us, speaking at the earlier stage of the company, that's whatever it is that we can do to get something out in front of people as quickly as possible.

So at that time we went with Google Cloud because it just had a bunch of ready made components when there was just the two of us, which could just let us do things. I think at multiple times we tried to switch over to AWS and tried to rip things out, and even had solutions consultants, because we're spending a lot of money on that. But we still just kept sticking with what we have. Because I guess, there are certain projects where, obviously, these decisions matter a lot deeper. There're more technically challenging problems.

But on our end it really is, at the end of the day, with our users, the only way we know if they want to do something or to use something is by putting it in front of them and seeing if they actually use it.That's something we've learned again and again and again. So really on our end, what we're really optimized for is. Does it perform the function that we think it does, that we can put in front of our users and see quickly what they like. Just because that's the only way we know if something's gonna stick or not.

Stephen May

Thanks. I think you've alluded to this. I heard you used the word "user" a lot so from UX/UI perspective. But in addition to that, what other characteristics would you say are essential for a good IT system or a software design?

David Pickerell

Yeah, that's a good question. I think it really depends a little bit, going back to the first thing, on sort of like the philosophy of the company and the philosophy of the people that you're working with, right? So I think when we first started these projects, we probably overthought some of this. We did a bunch of like data aggregation showing what you think you could earn on a map and doing all these sort of like fancy, slick looking things.

And I think what we realized when we went out and we drove with a bunch of our users was frankly most of what we built was nice to have, not need to have. And we ended up having to go back to the drawing board and throw a bunch of stuff against the wall to see what happens. I think really, I'm thankful that Jeff's my Co-founder and CTO.

I think we both share a similar philosophy there, which is, you know, for our use case, quick and dirty, prove it out and keep iterating from there really is what's right for us. If you're building a slick B2B SaaS tool, probably a different thing, right? But just for our users, you know, simple design, big buttons, does it do the thing, and do they use it, really. And whatever, we can keep pushing that out.

Stephen May

Okay. Thank you. You alluded before around your relationship with Devico, and I want to come to that a bit later. But I'm kind of interested as well around this whole point on efficiency in teams and working with teams. I just wondered if you had a view on what tools you prefer to use in your organization to drive efficiency in your teams.

David Pickerell

I think that's a good question. I mean, I think we've gone through a lot of the usual natural cycle of like there is no tracking whatsoever when there's just a couple of people at the company. It's just you tell everyone talks, and you know what you need to do. You know, we've then gone from that to, I don't know, sort of slack check-ins. And now I think we are onto the Asana board. And I'm sure we'll move on to, I don't know, Linear or something at some later point. So I think it really is what works for the people at that stage of the company, and just don't lock it in, really. I think that's what it comes to for us.

Stephen May

Tell us a bit about your team. What kind of specialists do you have? Typically what sort of specialists do you choose at present for the project you've got going?

David Pickerell

Yes, I think the team is still pretty heavily engineering and design heavy. So I think primarily the backend, we have sort of a couple front end folks, and we have sort of two designers. Other than that, we have sort of a smallish ops team. So we have sort of a three-person ops team. One of the ops team members was actually one of our users, which has, actually, worked out very well. He's really been doing a great job for us.

And outside of that, we sort of have one lady who does growth and another lady who does sort of like marketing and product operations, basically. But I'd say sort of the bulk of the team is engineering, and we sort of split it, I guess, between two different projects. One is what we call Driver Tools, which aggregate all your pings in one place and help you accept and decline them. The other initiative is what we call Para Works, which is to take your driver profile and unlock other good opportunities.

So I think even though the team is sort of split down the middle. I mean, they still work closely with each other because the beauty of what we're trying to build is when you're able to cross those silos at some point. So even though those two systems live separately right now, we want to make sure that they're built in a way where they can interact with each other at some later point.

Stephen May

Thanks. And typically when you're looking for specialists to join your organization, what kind of profile and competence are you looking for from those people?

David Pickerell

Yeah, I think a lot of the time in what it really just comes down to like if you're looking for somebody with a super, super, super specific skillset, that's a different story. But I think from our end, it really is does somebody have a core competency in it. And I don't know if I can swear on this, but I think our hiring philosophy has always been like "does this person give a shit," basically. Right, I think that's what we've really learned is like, you know, if somebody has the based competency and they're motivated, that's really all you need to look for at the end of the day, right?

And I think really if we had to distill our hiring philosophy down to one phrase, it would be does this person, you know, assuming that they have the based competency and do they give a shit. Because what we've just found is, especially on the engineering side, if somebody is just motivated to keep trying, and figuring out, and pushing, and doing it, that's worked out well for us. So I think when people ask us about our engineering hires and our engineering team, we don't have, you know, as per some other Silicon Valley startups, a bunch, you know, we don't have five ex-Google engineers sitting in San Francisco. Really, on our end we have engineers from all over the world, different age brackets. I'd say one of our best engineers, actually, right now he's like 21 or 22 years old, basically. And you know, we have older engineers too.

But I think what we've basically found is that is sort of that unifying thing when somebody's good or not, right? We even I think have one or two sort of our front end developers who started off as like French. They're at engineering school in France, and they started off as interns. But what we've learned as, if somebody's really motivated and is smart and competent, they outperform really. And I think that's what we look for.

Stephen May

And I guess, there's that cultural fit piece that we 'll come to a bit later, right? But you know, for those developers out there, who are wanting to put themselves in the shop window, give themselves a better chance of getting a role, what advice would you give to them about developing their skills portfolio and general competence?

David Pickerell

Yeah, I think it really is just doing things, I guess, right? So like, you know, do the practice projects, spin up things, you know, like that sort of a thing. But when it comes to like actually getting your foot in the door, I think the story I'll tell is like this 21, at that time 21-year-old engineer we hired, right? He reached out to us actually when our system had crashed.

And he's like on Instagram of all things, and he's just like "Hey, I heard your system crashed from my girlfriend, who's one of your users. Like, I can fix your problem." And we're just like "No, you can't. Like, our problem's pretty hard. I'm pretty sure you can't fix what we're doing." And he's just like, "No, send me your phone number and I'll start texting you the answer." So I did. And we went down, and started driving, and we started getting the answer in my inbox.

And of course immediately I like "Where are you? Where are you based? Can we go get coffee and dinner tomorrow? You're a five hour drive tomorrow, I'll drive down and see you." But it was, to me, sort of that's the difference between, I guess, sort of like okay, and good, and great. It wasn't a "I think I can fix your problem." It's a "I've fixed your problem." I think that to me was, I mean, for us it was a no-brainer to immediately hire the guy, basically.

Stephen May

Yeah. And thinking about kind of style and behaviors, how important would you say it is to have somebody who is a developer who has strong interpersonal skills, these people relational skills, as well as their technical knowledge?

David Pickerell

Yeah, I think it's important. I think if you're just working in a silo or you're responsible for one thing ,or it's super early on as a company, you can do it all. Sure, maybe, you don't need that many interpersonal skills. But as a company grows and as a team gets more complex, like sort of what I was talking about earlier. It's like we have these two different silos or stacks that we're building, but eventually we need them to be able to talk to each other. It's super important, right? I think in that, if you want to go beyond just being an entry level engineer and progress beyond that, those interpersonal skills are super important.

Stephen May

And how difficult have you found it recently trying to get that talent? People talk about the talent war and talent scarcity. How have you found that?

David Pickerell

Yeah. I think where we've really gone is, you know, at our end, we have three engineers, including my CTO in the US, Co-Founder, and CTO, of which one, actually, only recently immigrated to the US. I think what we've really found is if you're looking for a very specific skillset set, or somebody with scaling experience, or something like that, might make sense to hire in the US. But what we found in general is that our hiring philosophy is we want to go to other countries, we want to go and pay near the top of the pay bracket one.

And really that's what we're looking for. Like can we hire top 5% talent somewhere else that is super motivated? And our philosophy isn't "let's go to another country and save a lot of money." Ours is "we're already saving money not hiring in the US. We want the best, basically. I think that's really how we approach it. So we've worked with Devico, we've worked with online job boards, we've worked with the referrals.

But on our end, we've heard other people say, "Hey, you're hiring people in these countries. You're paying them what?" And we're happy too, right. At the end of the day, as you talked about, if they have the interpersonal skills, if they have the motivation, if they have the technical ability, you know, I know there's always this sort of like hack need or oversaid thing of the 10 ex-engineer. What we found is people who are great are just much better than people who are good.

Stephen May

Yeah. What was it that took you down the route of considering some kind of IT outplacement, outsourcing, to help with your resourcing model?

David Pickerell

Yeah, that's a good question. I think from my end, it was pretty simple. So at that time Jeff and I had started the company. And we didn't really have a lot of experience with hiring out that initial dev team. So I went to a friend of mine, his name was Ulf. And Ulf had founded a company. He'd sort of founded a couple different companies, basically. One's called Descript. So he was the founding engineer of a company called Descript that does sort of audio translations and cutting, basically.

That's actually quite popular. But Ulf was experienced. He was a technical Co-Founder of a bunch of companies. So I went to Ulf and I said, "Hey Ulf! I want to hire some engineers, one or two engineers, to start off helping on the project. Like if you were me, what would you do?" And he's like "I've got the person for you ". And he introduced me to Oleg, and through Oleg, we ended up hiring our first one or two engineers there. So it's really was I went to a guy I trusted and said, "Who should I talk to?" And he just, he said, "Devico."

Stephen May

Okay. And If I obviously said to you, we stood at the bar and I said, "Hey, you're doing IT outsourcing. Tell me in three words, what pain points does it solve for you?" How would you summarize that?

David Pickerell

Yeah. I think for us, what I've heard from a lot of friends who've done outsourcing is just not knowing the quality bar, or the talent bar, or the motivation bar. And I think the other one is something that you've highlighted too, is the sort of EQ or ability to talk to people or like "Do I have to clearly lay out what needs to be done or can we have a conversation, and you understand what needs to be done?" So for me, it really was, you know, the first person we hired with Devico ticked all of that and more. I think we realized that we really struck gold there.

There's a sort of crazy moment where he was actually supposed to go on a holiday to Egypt with his mom and his girlfriend. But we had some big release date, and stuff just really wasn't working. And he didn't go to Egypt to make sure that we pushed that thing out. And I never would've thought that would've been an option on his mind. But I think for us it really was. I've heard a lot of outsourcing horror stories of people not working well, things haven't gone right. But from our end, it was smooth since day one.We got exactly who we needed. And he was great.

Stephen May

Yeah. Well, there're always pros and cons with every solution, right? I mean, what would you say could be some of the organizational risks or drawbacks to taking an outsourcing model?

David Pickerell

Yeah. I think as I've told a lot of friends, who've started companies, if you don't have a strong US-based CTO, or Co-Founder, or technical lead, who is willing to work closely to make sure that relationship works, et cetera, that's hard. So if you're a solo founder, no technical background, overseeing this, probably not the right step for you at first. On the flip side, I really think at the end of the day, it's like can you build a rapport, can you build a relationship, can you check their work, can you provide some guidance? As per a lot of things, you know, the first couple months to onboarding somebody is important. And I think really that's, you know.

What is our cultural fit? How do we do the work? What are our expectations? All of that I think is important. And I also think on the longer term, at the end of the day, we treat the people we work with abroad. They are part of our team, right? Some of these people have been with us for two plus years, for most of the journey of the company. They're team members. We have given them equity. We have done an offsite in Portugal to make sure that some of the, our sort of European developers could show up. So I think that's important to us too. It's like if somebody comes to the team, and they're really doing a great job, to make sure that they know that they really are truly part of our core team.

Stephen May

Okay. I mean, I don't know if you spoke to lots of other organizations as many competitors offering outplacement, outsourcing, body shop type service. I wondered if you engaged or had conversations with some organizations where you heard things or experienced things that you thought, "That's why I wouldn't work with that type of organization." I don't want you to name them, but I just wondered if there was an experience you had.

David Pickerell

I haven't. I've heard sort of other people mention bad experiences with some people. So I think, you know, to stay away from that. At the end of the day, what matters to me is, I think, it goes back to the same hiring philosophy. If somebody's good, we want to pay them well, we want to treat them well, we want them to be part of the team. So for me, if I hear that people are unhappy the place they're at, if people don't feel like they're respected. That stuff matters to me.

Stephen May

Okay, thanks. Listen, I just wanted to finish off. You said, obviously, your relationship with Devico and that's obviously we wanted to talk to you because of your experiences in working with us as an organization. You have alluded to it, but I'd like to ask again if you reflect and someone said to you why have you chosen Devico, could you give us a summary of what that would be?

David Pickerell

Yeah, for me it was a smooth experience, the ability to scale up the different roles that we needed to.With the end of the day, it was the talent bar, right? I think where it really comes down to was the people that Devico helped us find were motivated, they had the skillset to do it. We were able to talk with them. They were able to understand our needs. And really, at the end of the day, I think that's what differentiate. As you said, there's a lot of talent shops or body shops out there.

At the end of the day, it's the quality of the person, really. And I think from my end, at the end of the day, actions speak louder than words. You know, I've referred multiple of my friends who started companies to Devico. I have had sort of, in an old life I was a VC, and some of the companies we invested in have start hired their first couple engineers through Devico. And to me, I get to hear from anyone that's been unhappy with that. So it really comes down to, you know, talent, and getting the right talent, training the right talent, and keeping that talent happy.

Stephen May

Thanks. The last question for you. There will be people listening in who may be in a startup environment growing quickly and might be at the step of considering working with an outsourcing partner. What might be your tips to anybody who's at the stage of maybe stepping into that world?What might be some of your early advice for them?

David Pickerell

I think, you know, what you're gonna want to say person to do, right? Have it, I think, very clearly defined goals, very clearly defined projects. And I think you also can't hire somebody and just expect. At the same time, like even though you have something super defined what you want to do, you can't expect somebody remotely, without a lot of context to figure out all the details. So I think it's important that you spend the time. You spend the time giving the context, you spend the time working together, and it's not just a "Hey, I'm going to shoot you a bunch of tasks to do." And I think a lot of people run into that sort of an issue.

It's not like you're, you know, if you're hiring a growth marketing person remotely, or if you're hiring other sorts of people remotely, maybe you can just say, "I needed to do X, Y, Z." But if you're depending on this person to build something that's core to your business, you just can't manage them with a "Hey, do X today, do Y tomorrow." Maybe that'll get you one step ahead, but to get to where you need to, it just takes the time and effort from your end also.

Stephen May

Hey, listen, David, it's been really interesting learning a bit about you, and your organization, and what you guys are up to, and more importantly, your experience with outsourcing. Thanks for sharing that. Wish you all the best and every success in the future.

David Pickerell

Awesome. Thank you. No, thanks for having me.

Stephen May

Cheers, man.

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