45. Part 1. The future of work through the eyes of a lead engineer | Derrick Franco, Co-founder of Counterpart


Derrick Franco | Co-founder of Counterpart


Today we catch up with Derrick Franco, an engineer and entrepreneur with over a decade of experience in startups and software engineering. He is currently lead engineer at Counterpart as well as the host of the Future of Work Project podcast.

Our podcast with Derrick has been broken down into 3 parts, this is part 1 of our conversation with him. Check out part 2 & part 3.


Derrick Franco-1


As an engineer and entrepreneur, Derrick Franco has a track record of building and scaling organizations from the ground up. These include co-founding Jumpstart, an AI-powered recruiting platform focused on helping college students find jobs and internships, in addition to building out the technical divisions at InvestorsAlley and Phinaz Media Group. In 2019, Derrick and his partner launched Counterpart, a management liability InsurTech for the 21st century that is striving to help companies become the best version of themselves, he currently leads engineering there. He also is the host of the Future of Work Project podcast, where he focuses on bringing together today's business leaders, researchers, and entrepreneurs who are experimenting with new and unique ways of working.




[00:00:00] - Derrick Franco
You have full permission to look at me, to look at our CEO, and tell us that is the stupidest idea I've ever heard. And the only thing I'm going to say back is, okay, why?

[00:00:16] - Doug Foulkes
Hello, and welcome to Episode 45 of The Future of Work. It's the podcast that looks at every aspect of work in the future, and it's brought to you by WNDYR. I'm Doug Foulkes, and as always, I'm sat here with Claire Haidar, the CEO of WNDYR. Claire, how are you doing?

[00:00:34] - Claire Haidar
Hey, Doug. It's autumn. It's good to be here. I'm happy the seasons are changing, and it's good to be doing another episode with you. How are you today?

[00:00:45] - Doug Foulkes
I'm good. Our seasons are changing into summer, here in South Africa.

[00:00:52] - Claire Haidar
But I've been hearing a lot of rain in the background when I've been on calls with you this week.

[00:00:58] - Doug Foulkes
It's been raining a lot, which is good because we've just had a new lawn put in. So anyway, that's enough of my life in the garden. This week, we're catching up with Derrick Franco. He's an engineer and an entrepreneur. He's got 10 years of experience in startups and software engineering. Why is Derrick on the podcast?

[00:01:21] - Claire Haidar
So I think there's two obvious reasons. I'll start with the very obvious one. He's doing something really interesting in the future of work space, which is about to become a book. And it's actually called The Future of Work Project. And what Derrick has done is he's gone and found, really, sort out business leaders who are trying to change the game up in terms of how they hire, how they recruit, how they structure benefits, and most importantly, how they're building mostly virtual teams in this new reality that we find ourselves in.

[00:01:51] - Claire Haidar
So we're going to be talking to him a little bit about that.

[00:01:53] - Claire Haidar
But then also, I really wanted to bring an engineer onto the podcast, because we know that product teams and engineering teams, and the way they go about shipping code and building products, and actually getting customers to use them, is a lot more progressive than if you look at, for example, an HR department or a finance department, and how they produce work.

[00:02:17] - Claire Haidar
And I think as we look at the future of work, there's definitely a lot for companies to be learning from engineering and product teams in terms of how they work. There's a whole work style, called Agile, that a lot of very progressive product companies use. And I want us to delve into that topic a little bit because I believe our audience can really benefit from that.

[00:02:41] - Doug Foulkes
Yes, we certainly had a very interesting chat with Derrick. What are the key takeaways from our conversation?

[00:02:49] - Claire Haidar
So Doug, we've broken this podcast down into three very specific sections. The first section is what products and engineering can be teaching the rest of the business world and the business team inside the company. The second one is tapping into that Future of Work Project of his. So looking at some of those leaders that he's been interviewing. What are some of the common threads that are coming through there today? And what are they doing differently? What can our audience be learning from them?

[00:03:21] - Claire Haidar
And then the last one is very much the practical application. So okay, I listened to the podcast, I like the idea of Agile. But how do I actually go and implement that in a finance team or an HR team? And then just again, from a practical lens, just delving in with Derrick in terms of what are some of the things that they've been experimenting with at Counterpart? What's worked, what's failed, et cetera?

[00:03:44] - Doug Foulkes
Awesome. Let's not beat about the bush. Let's chat to Derrick.

[00:03:49] - Claire Haidar
Derrick, it's so good to have you with us today. And it's so good to be having this conversation with you. You're doing a project that both Doug and myself are actually really excited about and really interested in. And so can't wait to dive into that with you today.

[00:04:06] - Derrick Franco
Yeah, excited to dive in, and happy to be here. Thanks again for having me.

[00:04:10] - Claire Haidar
Okay. So Derrick, just to give our audience a little bit of background in terms of why we invited you onto the podcast today is you're a technologist. And very importantly, you've built startups from the ground up. And that means that you come at transformation inside companies, which pretty much every single company is going through right now, from a very specific angle. And that is technology, and how technology, actually, in many ways, speeds up transformation and really drives it.

[00:04:43] - Claire Haidar
I'd like to make a provocative statement, and that is that goals are dead.

[00:04:50] - Derrick Franco

[00:04:50] - Claire Haidar
And I also think that technology figured this out a long time ago, and moved on from Waterfall into Agile. Tell us a little bit, from your perspective, why this is so critical. And why, in this current environment that we find ourselves in, it's such a critical mindshift that companies need to be making.

[00:05:10] - Derrick Franco
Yeah, that's a great question. And it's a great statement, the goals are dead statement, because it really does ring true. And from a technology side, things have been adapting so quickly every single year in technology. It got to the point where even five, 10 years ago, things would completely shift their patterns in the way that people worked, where people were driving towards, how they worked. Every, it seemed like, six months to a year.

[00:05:38] - Derrick Franco
So people on the engineering and technology side got used to that idea of constantly having to shift their mindset and rethink on, what are we building and why are we building it? And so that's why you see a lot of these companies that are full-tech companies able to deliver so quickly. That's their mindset all the time. It's, this is what we wanted to build towards. Something has shifted, and we've got to pivot right away.

[00:06:01] - Derrick Franco
And when we hit this age of Corona, and everybody being forced into shifting and changing, everybody got a little bit of taste of that in a different way. The world changed so much every month during 2020 and 2021. Especially, even now, as some companies have tried to figure out, do we go back to the office? Do we stay remote? Do we make this hybrid approach? People are changing their minds all the time. And big companies are making different decisions all the time. And so we're seeing everybody being thrust into that mindset of continually having to adapt in order to just, basically, survive.

[00:06:38] - Derrick Franco
And it's something that is uncomfortable at first, for sure. But especially as you dive into it, and you get more comfortable in that uncomfortable environment, you see that it actually allows you to have your organization thrive and grow much quicker, especially in all of the uncertainty.

[00:06:56] - Derrick Franco
And if there's one thing that this has shown right now, the uncertainty in the world, in the way that people are working, in what people want, even, it's going to continue to change. And if companies set one particular goal of, oh, we are getting back to the office. If that is the end goal, or if there's another piece, they just got to know that that's likely going to change. No-one can predict what's going to happen in the next six months, let alone a year timeframe, when some of these companies are coming back. So yeah, it's been very interesting to see everybody have to shift to that mindset that, most of the time, engineering organizations are in 24-7.

[00:07:31] - Derrick Franco
And so I think one big thing with this kind of mindset, to take one step back, you mentioned this idea of the Waterfall versus an Agile mindset. One thing that this applies really well... And for anybody that doesn't really understand those, in an old Waterfall mindset, that would usually mean that you were setting these are the end-deliverable goals that we are focusing on. And everything is, okay, let's split out the exact tasks that need to be done in order to get there. How do we do it? And okay, we thought through everything, let's go and execute.

[00:08:04] - Derrick Franco
The world changes too much. Things change too much now in order for that to happen. So this Agile mindset is more along the lines of, this is what we want to build towards. But if things are changing along the way, we can adapt our patterns. We can adapt what we're working on, and change course in the meantime. And so that's really where a lot of today's work is as well, in this more agile and adaptive mindset.

[00:08:28] - Doug Foulkes
Derrick, nice to meet you.

[00:08:30] - Derrick Franco
Nice to meet you too.

[00:08:32] - Doug Foulkes
You said something earlier, and I want to take it back a step. You talked about Waterfall and Agile. Why then is the Agile mindset more critical to the future of work, for the company and the employees?

[00:08:46] - Derrick Franco
Waterfall is very... I guess you could say it's basically linear. You are thinking of the end-goal state that you want to get to. And you're breaking it up into individual chunks, and thinking through all of the different things that need to happen in order to get to that goal.

[00:09:02] - Derrick Franco
And so Doug, taking a step back to what you were saying is, why would somebody want to focus on a Waterfall method? Well, if there is a complicated goal that you are trying to get to, and you have a lot of people working on that one goal, then it makes perfect sense that you want to think through every little piece that needs to be done, and how they'll communicate, and who will be working on it, when they'll be working on it, et cetera.

[00:09:25] - Derrick Franco
And so you really end up with this... If you think of almost a Gantt chart of different lines of, we're doing this, and then we're doing this, and then we're doing this. And that's great. It's an amazing way to really plan out a project, and make sure that everybody's aligned on what needs to happen.

[00:09:42] - Derrick Franco
The downside to Waterfall is when things inevitably go wrong. It's going to happen at some point. And if you're along the lines, and the website was dependent on the marketing team finishing with the design team, and they're behind, well, what are they going to do in that meantime? You don't really know what to do. They can't start development. If they've started development, and now they're behind, and the launch schedule gets pushed back, there's nothing they can really do.

[00:10:08] - Derrick Franco
Or in our situation, if you're in the middle of meeting with the designers, and a global pandemic hits, and you can no longer meet in person, how do you adjust those timelines and the pieces that need to happen?

[00:10:22] - Derrick Franco
And even taking a step back towards the goal mindset, if the goal has shifted, if the goal was we are going to launch a new website and a new rebrand. And halfway through, you learn that one of your competitors has now created a brand-new version of your core product, and they're doing it better. Well, realistically, who gives a crap about what your website looks like? You need to get all hands on deck to go and fight back. And the Waterfall mindset really... You've got all your resources stuck in this project.

[00:10:54] - Derrick Franco
Versus more of an Agile mindset, which is what a lot of developers go with. There's different types. But just sticking in a more general sense, in Agile flow, it is more that you are setting things up in a similar way where it's, this is what we want to do, and this is what it'll take to do it. But it's more abstract, and it's more flexible where, if you look at things in chunks of time versus a very long period of time, you're able to adapt.

[00:11:21] - Derrick Franco
So in most organizations, engineering organizations, we work in a timeline called a sprint, and that's usually about two weeks long. And usually what we'll do is, we'll have a timeline of something that we want to get to, but we're really just planning the next two to four weeks. What are we doing the next two weeks that gets us towards that? What are we doing the next four weeks?

[00:11:41] - Derrick Franco
So in the same situation where, in those two-weeks cycles we're working on design, and then we find out that our competitor launched a product that competes with us, and is doing it better, well, you can bet that the next two weeks on are now no longer about anything with the design, and we're getting a new plan in place to go after and basically, fight back with a new product.

[00:12:02] - Derrick Franco
And so that's the differences between Agile and Waterfall and how they work. And like I say, it's not that you're not planning for the future in Agile, it's more that, instead of planning every single chunk and adapting it out for three to six months, you're having that more as an abstract concept and breaking it down into two to four week chunks.

[00:12:23] - Claire Haidar
Yeah. And I think, Derrick, the one piece that I want to go into next is you've really drilled down into some specifics. But one piece that I want to highlight, and I want us to tease this out a little bit is, there's a huge component about Agile that's about value creation.

[00:12:38] - Claire Haidar
So you've used the example of the competition, which is a reactive, defensive move, to go and level up with competition. But I think the overarching thing that should be driving the whole Agile process is, what is the next piece of incremental value that I can offer to the business?

[00:12:58] - Claire Haidar
And why this is so important, not just from a technology perspective is, if you think about somebody sitting in finance or HR, it's very easy to lay out a financial team's working world, and say, okay, every week we have to do this with the invoices. Every month we need to do month-end and close out. Every year we need to do taxation. But the reality is that, that's not necessarily adding value to the business.

[00:13:22] - Claire Haidar
Whereas if I have an Agile team, which in our company we do have, which I'm so grateful for. We actually had a situation just this week where I was able to go to the team and I was able to say, new, unexpected potential customers have come to us. We can fill our pipeline with these deals. But I'm going to have to do some modeling here that wasn't planned. Can you guys potentially please work on a few models for me?

[00:13:48] - Claire Haidar
And so Tracy and myself literally just sat, we looked at the sprint that had been planned, and we said, okay, we're going to pull out these activities, and we're going to plug this modeling into that. And so all of a sudden, instead of the finance department just being this back-office function that makes sure that it's ticking boxes for the business, it, all of a sudden, becomes an extremely valuable team contributor.

[00:14:11] - Derrick Franco
Yeah, exactly. And not only that, but I think that one thing that, especially organizations that are more focused on this very long-term, goal-oriented mindset, when they first hear of Agile, one thing that is almost scary to them is, well, I need to know what's going to happen in the future. How am I going to tell the investors that, oh, don't worry about it. We're going to figure it out in a phase-by-phase basis?

[00:14:33] - Derrick Franco
And the one thing I'll say is, we still do chunk out and plan, hey, for the quarter, these are the three main goals that we have. What are the three main goals that we have? Okay, well, we want to increase our business in this new market that we just built up. We want to focus on building out this new technology suite, and we want to build a new website and rebrand. Okay, amazing. So you've done those. What are the projects that need to be done to do it?

[00:14:58] - Derrick Franco
So we'll list those projects out. And then we'll say, okay, roughly how long will they take to do? What do we need to do?

[00:15:03] - Derrick Franco
But it's a very high-level version of chunking those phases out. And so yeah, we can put down a Gantt chart of roughly when we think it'll happen. But the nice thing is, now, just like you said, if a new thing comes in, that we have to do all hands on deck, we can just adjust those Gantt charts around. It's not messing anything up. We just know that certain projects won't be done.

[00:15:25] - Derrick Franco
And not only that, but it allows us to really keep track of what is the most important thing at the company. And I think that that's one thing that a lot of people can't answer, even in the department. If you said, what's the most important thing to your department right now? You don't really know, because usually you're working between four or five different projects that are all in this strict timeline.

[00:15:46] - Derrick Franco
And that's a hard thing to rally people around when things go wrong. No-one's ever going to be there and be like, oh, man, Doug didn't turn in the Excel spreadsheet last night. So now, this, and this, and this, and this. No, you're going to be like, all right, well, he didn't turn in the spreadsheet. Why? Oh, he found an error. What was the error? And you can get people to rally around that too.

[00:16:04] - Derrick Franco
So that's the nice thing with the mindset is, you don't have to just think this short. You can think about where you want to be, but you're not defining a strict path to get there.

[00:16:15] - Doug Foulkes
So my take on that would be, it sounds as if it's something that would be easier for a small company or a start-up company to do, because you've got less parts in it. Can big, massive companies and big corporates use the same method effectively?

[00:16:33] - Derrick Franco
Yeah. I think the way that you can look at this is, large tech organizations do this all the time. The biggest difference is they do spend a little more time on the abstract component to really start putting it into a roadmap. So they will define a roadmap and say, oh, we're going to build this during month one and two of the quarter. And we're going to be testing in month three.

[00:16:55] - Derrick Franco
The only difference is, as they're going through and breaking it up, if something new comes up, they're fine with saying, okay, stop that project. Here's the new one. And continue on there. And it's something that is very scary to think about. If you're a month into a project, that's an expensive project.

[00:17:11] - Derrick Franco
But like I said earlier, the tech industry is used to moving so fast, to having to adapt so fast to just keep up. That sometimes, it's proven over the years, to be the best way to adapt and continue fighting with the competition. It's not just stick to, we're a month in right now. We have two more months to build this project. Let's just keep going.

[00:17:32] - Derrick Franco
Maybe you've learned that that's not going to be the big hit. Your competitor just put out a product, and for lack of a better term, it just completely bombed. You're not going to want to put in two more months to that. Some organizations would because they've got that sunk cost into it. And that's the biggest piece that companies need to get past, is it can work at big organizations, you just have to remove yourself from the mindset of focusing only on this sunkcost fallacy.

[00:17:55] - Claire Haidar
And Doug, I think it goes back to what we actually started the conversation with, is you have to let go of the idea of establishing this goal that you're just married to. Which is why we opened with goals are dead. Which really freaks big companies out because big companies, right now, you talk to anybody who's sitting at a big company right now, they're doing financial 2022 planning. And it's months, and months, and months of planning, and then we're going to roll it out. And then by the time January comes around, everything that they've been speaking about today, three months prior to the year actually starting, is mostly going to be irrelevant.

[00:18:35] - Derrick Franco
Yeah. And I think one thing that we can say with that too is, it's more about just what are the three most important things? That's the question that every company can just put down. If you had to list what are the three most important things for the next year, for the next quarter. If you can't answer those without listing out 48 different goals and projects that you want to do, you don't have any kind of foresight into what you want to build, or what you want the company to do.

[00:19:03] - Derrick Franco
And so that's really the better way that we look at it, is just what are the three most important things? Figure that out, and you're able to work back iteratively very easily.

[00:19:11] - Doug Foulkes
So that brings us to the end of part one of this podcast. Be sure to check out the other two main points we discussed with Derrick in our next episodes. You can catch them on Spotify, Google, or Apple Podcasts, or on WNDYR's website, wndyr.com. From Claire and myself, we'll see you soon.

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