If you're interested in following this strategy, don't hesitate to reach out to [email protected] -- I'd be happy to help on both fronts.

As for your concern about logistics being not sexy enough - I've found that the best programmers (and the ones you'd want) are more interested in the technical aspects of the problem and business and customer impact, rather than the sexiness of the business domain.

Just want to heartily agree with this point here. Certainly many of us do get excited about particular business domains from time to time, but in my own experience, I get more excited about technical challenges, and -- critically -- solving real problems for real customers that I can see first- or nearly-first-hand. The customers for this "product" would be internal to OP's org, so the people who end up building this would have front-row seats to how it's being used, what's good, what's bad, etc.

Even with all the good words he wrote how company can improve by doing own dev - reality is that company makes money in logistics and as a software dev I would be second class citizen and cost center.

That is why I much rather work in company that makes money on software, because here I am money making.

At Meta, I hear Ads has one of the more toxic environments for SWEs, even though Ads make money.

If software can make the company provide better logistics more efficiently, it's not a cost center, it's an enabler. It pays for itself in reduced costs and increased revenue.

A smart management team can figure out that investing in IT, Software, etc is going to have a positive ROI overall by increasing efficiency among other things.

Unfortunately my experience (and many others') is that only the balance sheet will be considered and the goal will always be to reduce the costs in cost centres as much as possible.

Even in a company that doesn't fall fully into that trap, often times a lot of effort needs to be expended to keep funding at current levels, never mind the rituals involved in getting increased funding for new projects, hardware, staff, etc.

Generally the more obvious the connection between your work and company revenue, the easier your life will be.

Which means that if investing in IT is an enabler for gaining revenue or profit, it's not a cost center by this definition--it's necessary to gain revenue or profit. As you note, many companies don't appear to be smart enough to see this, but that doesn't make it wrong.

None?

It's a cost center in the same way the janitorial staff or legal are. The company won't be there without contracts or with overflowing trashcans, but it doesn't mean the company is making money off of janitorial services or drafting contracts.

Everyone’s a cost. The myth of revenue centres was made up by sales & marketing.

But it still doesn’t make company dynamics not true. Logistics company will have bunch of logistics specialists as management and they will see it as revenue center and will see „their own kind of people” as more important.

That idea of costs and profit centers is bullshit that only bad manager believe in. It may or may not be the case with the one company of the OP, we don't nearly enough information to judge.

(But the fact that the OP is reaching into IT with the goal of improving their people's productivity is a very weak indication that they are better than that.)

I am only pointing out my view on it based on my years of experience working in different companies. Looking by up votes it seems my experience to be applicable for other people as well, so I guess it might be useful for the OP.

Funny that sales and marketing sells and markets itself.

All the devs in this comments can do what I share below. 1000%. It’s a different way to make an impact and help make healthier spaces for technical teams to do what they want.

I’ll share one example. Clever architecture and leverage can beat most coding especially in the B2B space. I find I am fast at both architecting and uncovering useful system integration paths for the short and long term along with the flexibility in mind.

That being said, I have also seen a team of 100 devs flown in to write an ERP from scratch and it worked too because the process was fixed.

I won’t rule out a world beating team where 5-10 senior devs can beat a team of 50-100. I have got to be a part of those kinds of teams and also lead them. The caveat is being able to deliver world beating stuff is different than aspiring to it as well. It’s just not always sustainable way to live.

Since A company usually sells to companies the same size or larger. Anyone who comes from scratch can have their goose cooked pretty quick when a new client demand a different level of scrutiny in systems and data if coding from scratch.

Having deep enough experience to poke my head out in this thread both on my own as IC leading the charge, or or taking in my team, the orchestration of internal and third party vendors and resources is a big part of this. I deeply believe in external vendors operating in a client side platform I help implement and leave them with training that works.

A technically functional CTO who is still technical en putty to simplify and leverage to help deliver impact helps bring in different kinds of architectural and framework approaches.

I loving call it what management consultants talk about it don’t do. I’ve made learning and implementing that my craft to leverage solutions for anyone I put my time towards. It’s a life changer. Everyone wants the kinds of devs on YC to help their companies if they can learn a little bit of business.

It works well enough that I don’t need to pursue a public profile (although that is not changing), and warm introductions are a reality.

I share this because it’s possible for anyone who wants it instead of downplaying it. I help clear the path for the doers and builders, as one.

You have a fair indirect point that there’s a lot of different kinds of CTOs too.

If a business wants steady operation while switching over it will ultimately place a heavier loads on their teams.

If a business wants capacity to operate more smoothly to either grow capacity or increase flexibility for other things with their existing workforce.

This kind of thing may not always be built to success with the number of surprises and landmines discovered along the way.

Part of a transformation can become agile, parts of it water fall, all while holding the business and staff increasingly hostage while deciding to do a big bang switch over or daring to run in parallel.

Lots of people side things come up as well when changes happens to them instead of with them. It’s not uncommon for subject matter experts choose not to share information what itself can take some time.

It could have been shorter as it's not my target audience, not really able to edit it now.

Either the freelancers work out and you begin hiring a permanent team (hopefully converting some freelancers to full-time) who will promptly rewrite / revise the prototype or you will go back to paying for software. Either way the prototype code should die or be taken over.

It's rare for anyone to be around to look after the code they write for you forever. Ironically you might have more chance of a good long-term relationship with some of your freelancers - having a few good clients who come back to you from time to time is an excellent strategy as a freelancer.

So you always need the system and processes to be designed with future maintainability by other people in mind. Good developers will do that whether they're employed or freelance. Bad developers will mess it up either way too. Choose the people you work with wisely and try to make sure when you do bring in new people they have a good way to get up to speed so they can naturally take over as others leave. There's not much else you can really do.

Why throw away software when you can iteratively improve and build on it? Unless the tech stack was wrong.

Incrementally, it might make sense to hire an independent audit on occasion. This might be hiring a senior to jump into the codebase for a week or two to see if they can make sense of it or see any glaring red flags. The important part is them knowing this will take place and them not knowing exactly when or by whom.

I recommend caution with this kind of approach. Even if you're bringing in a team of freelancers instead of hiring employees trust is still an essential foundation for the relationship. Clients who play silly games tend to get fired abruptly because it creates a toxic working relationship that isn't good for anyone involved.

You should be able to have an open and ongoing conversation with your team of freelancers about the long-term intentions for the system they are building for you and they should transparently and proactively work towards your goals without being nannied. If that's not happening then you don't need some kind of surprise audit - you need to find different freelancers who are on the same wavelength as you.

Freelancers don't inherently write better or worse code than FTE's. Some of the most braindead, unreadable, undefendable code I've seen has been written by FTE's while contractors are leaving them in their dust.

And even if that succeeded you often end up with fear of change because the complicated architecture can't be touched.

It's really important to have the right balance here, but KISS and YAGNI are often easier to scale when you need it, than the reverse. If you don't have the mentality that the MVP must never be rewritten.

That, plus "they're probably going to fire us in a year anyway, who cares" thinking

And "we don't need to understand the business domain, let's just MVP", which they get away with because they would get accused of not being agile if they did boring stuff like trying to understand the business

I refer more to bigger off shore consultancy shops than individual freelancers

My company does exactly this. We build and maintain an open source project (SpiffWorkflow, for process automation) and help our clients build internal skills to deploy it and use it. No license fees or SAAS lockin - and no team of developers that walk out the door when things get difficult.

I don't know why you think they won't stick around long-term. I've seen many freelancers maintain relationships with clients for a decade or more - not necessarily full-time as if they were employees of course but with a genuine connection and coming back to do more work with the same client from time to time. If you want to retain access to the knowledge and insights of your early developers but also want to bring things more in-house - often because you don't need an all-star team to do every little thing once the system is in production and hiring a more mixed team is sensible financially - then this kind of occasional recurring contact can work well for everyone.

Identify a part of this system that can work somewhat in isolation and is non-critical if at all possible. Then document the requirements for this part thoroughly. This allows you to:

- Have something smaller for your new team to cut their teeth on.

- Ensure you have collected all the diffuse domain knowledge for this part in one place in the form of structured requirements.

- Forces you to think in terms of what you need and what is acceptable delivery,

If need be you can bring in a Senior/Staff level engineer to help you through this discovery and definition phase.

In my experience the most common difference between success and failure for a project often comes down to clear requirements and expectations. Your employees are the domain experts. You need to collect that expertise and document it in a way that this team can reasonably consume. This is difficult and time consuming so start now.

They will still have questions and get things wrong but this gives you a roadmap. They are going to be learning your industry while you are learning how to build software.

Best of luck

EDIT: formatting

A specific difficulty you are likely to face:

Your expert employees are busy doing their jobs. Writing requirements means taking attention away from that work - a difficult proposition, especially if they have managers who will ask why their KPIs are slipping.

I imagine the complicated part would grow wordy enough to stick out like a sore thumb.

Perhaps eventually have a freelancer turn it into technical documentation. The stuff we admire (if done right) but hate to do. (or in my case clueless how to)

(disclaimer: I know nothing, im just reading the comments.)

You can solve or mitigate these problems, but it takes experience and expertise that most coming from more pure software development backgrounds may not have. From experience, someone coming in with some consulting experience will tackle the situation differently.

Writing stuff down isn't always the best approach. Having a written record may be a good end goal. It may be better to have the small implementation soak up that experience through co-location with the experts. That way they are close by for interviews (probably too formal) but more likely sit and observe as the experts work. OP can then focus on building relationships between the experts and dev team. On this foundation you can add in more formality.

As part of the relationship management, OP will have to help the experts free time by working with their management. Without details of the company, we can't give real examples, but it might include supporting their requests for contractor support or giving their leadership political help.

When you can't come to some sort of co-location situation, you have seriously undermined your ability to execute the project. You will not have a true picture of the situation. Getting PMs or user experience people to engage with the experts will be lower value and require more clarifications. Developers can be low threat to the experts versus other types of people you can bring in.

It could be due to many different reasons. One the personal spectrum, they can overvalue themselves or have fear of loosing their jobs.

On the technical spectrum, they can be stuck in old tracks without computer knowledge and not thinking outside of the box. For example, in their eyes the objective is to move PDF file from directory A to directory B. In the ideal automated world, why is there a PDF in the first place? Basically "if you asked what they wanted they would have said faster horses...".

You need personal access to talk to the experts anytime some question comes up. This means 1-2 experts work part time as PMs more or less, which will impact their regular work.

Costly, but I don't trust any other way.

What you need is someone with significant dev experience, but enough outside exposure to step into the PM role. Ideally, it'd be someone with interest in user experience research, or a personality that connect outside of a dev team. They should be able to perform this role in a mechanical fashion to avoid a dedicated PM.

Doing this will be effective enough until things are at the point where a dedicated PM can be justified. If there is a struggle with the user experience aspects and getting knowledge out of the experts, you can get expertise from an agency on a short-term basis.

Adding a pure PM is going to significantly slow you down unless are one of the rare switchers who flip between dev, PM, and dev manager roles. People don't know what to make of these people, but they exist, especially in the freelance contract world. People will only full-time experience tend to look down on them because they can't understand it.

Here you are just copying an existing system. Reverse engineering requirements from domain experts unnecessarily turns this into a green field project.

I was fortunate in that I, for the first part of my career, joined teams that were structured like this.

Some additional thoughts:

- keep things small at the start - task your team with at least two goals for the first 90 to 180 days

       i ) to define a small but critical piece of work (actually designing and coding something related to what you need to do). Cannot be part of your core platform but will need to eventually be in the platform. Picking the right piece of work here is critical.

      ii ) to define a design, roadmap and project plan for completing everything you want done with cost, staffing, tech and effort estimates

    i) if the folks and team you have put together works:

        a) as a team and 

        b) with your existing business ( can they do the work, can they work effectively with the rest of your business, is the design the come up with solid and does it give you confidence that they can tackle the real core work you need done)


   ii) if you can get a sense of what it will cost (what did the 90 day project cost and was it delivered on time and budget per the team's estimate )

   iii) if the team can put together a road map with support of the business for the broader objective in parallel to executing the piece of work chosen

   iv ) if the solution if palatable from a cost perspective ( money, people, tech, disruption ) 

   v) if the staffing model , architecture and integration proposed for the project by your new team could work (get feedback from the rest of the business about what is proposed by your new team ) 

    vi) if your business can work with this new tech team ( feedback from your existing staff about the folks doing the work and their product for the small piece of work they tackled )

- it is critical that your freelancers not just be developers: they have to be "business-goal oriented". Consider asking for references who are not developers and consider filtering your freelancer hires through their networks in LinkedIn - do they have a good mix of senior and non-senior people in their network who are NOT developers? That is a good indicator they worked effectively enough with other non-software parts of the business that the people on that side of the fence (marketing, ops, finance etc etc ) are comfortable being associated with them. Pick the areas that matter to you.

- Consider filtering for delivered results when you talk to candidates and in resumes: look for achievements / projects / work delivered rather than work done as this 'could' be a signal that the person is focused on actually 'owning' projects (not work ) and closing out on projects / goals (could also be a signal that the person did not not consider put delivered work in their resume so there is that - so, if you don't see it, just ask something like "what projects have you owned start to finish and how did you architect, design and execute on them" and interpret the response ).

- Key skills to look for in free lancers:

               - systems integration (making systems 'talk' to each other - you will have to make your existing system talk to your new system + you will eventually have to get your data off wherever it is now to your new environment and you will have to make the new system work with all the other tech systems you have now)

               - system architecture: designing software solutions

               - database architecture & design

               - project & program management 

               - lean six sigma / green belt ( means they have may have worked with ops people to optimize operations )

You will definitely find folks who have the right profile who will work with you - the key is decent (not crazy) pay, benefits and elements of stability attached (contracted duration with pay guarantees for performance, performance bonuses if possible etc etc).

- Plan on developing a bench from the freelancers so hire some mid-level junior folks to work alongside them for when the freelancers inevitably move on. You will have to hire from outside (try and get mid-level people in the industry, not senior folks, so that it is clear that your senior freelancers are the leaders / owners of work ) but try really hard to source at least a few of these folks from existing staff if possible ( people in other job functions - and are good at those jobs - who are programming inclined ) as they are a good source of how things work to integrate into the team or as new hires. They do not have to be as as senior but they have to be able to keep up. These people start as grunts for your freelancers and learn the system as it is built - they are your future tech staffing.

- Plan ahead for what WILL go wrong. I strongly strongly strongly recommend reading two books

                - The Phoenix Project - https://www.amazon.ca/dp/0988262592
                - The Unicorn Project - https://www.amazon.ca/dp/1942788762

Any given operation may not be able to follow all of it to the letter, but all of it is really sound advice and can be tweaked/customized for a variety of settings.

I'm probably thinking about this at a different level, but when I start something new I like to find the core pieces and the most difficult pieces and see if I can tackle those first. Everything else builds on top of that. I'm assuming you mean to start at a higher level piece that will need to use all of the lower level pieces. That's good too because it may help identify what those difficult core pieces even are that I'd like to go after first.

If they produce some big mess you will find out much quicker than if you set them loose on the big project. Small deliverables which incrementally get larger is how you roll on a new team. It allows you to get fast feedback and make small calibrations as you go. Hopefully avoiding the “fire them all” failed project scenario

I’d love to do that again. It was by far the most fun I’ve had working on software. These days I do pretty boring work that’s significantly below my capabilities, but it pays the bills and there’s not much else to pick from at the moment.

As for if someone hypothetically did choose to build a new solution in this scenario, it would almost certainly make sense to build it in tandem with your existing process. Going totally greenfield and trying to port your business over in 6 months would be misery. I’d look at ways to incrementally build a new system which you adopt gradually, probably starting with replacing the no/low code pieces you’ve already built.

Any kind of monolithic approach to replacing an existing system gives me deep, deep tingly creeps due to past disasters.

The approach of "I'm going to hire someone to build me a team" only works if you know someone excellent. It is a very low percentage strategy if hire #1 is from the market.

That doesn't mean you can't find excellent people through the market, but you'll have to see them work first, and it might take a few tries. You won't be able to spin up your own interview funnel and get good results. Hiring freelancers and seeing who gets it is probably the only way your organization can reliably detect talent (whereas a software company would have an interview funnel as a core competency). Once you have a freelancer who gets it, you can ask them if they want to join, or if they want to get paid to interview for you. Talent likes to work with talent, and the freelancer will be better at interviewing than you. Repeat this process until you have a team.

Eventually you may want management, but by the time you need management, you should have a pool of engineers large enough that one of them would be willing and able to manage the rest. They will be more competent than any manager you try to hire from the market by a mile.

If you don't have a 'trusted wrangler' freelancers won't build anything worthwhile as they're not interested in the long term unless forced.

There must be somebody you know, or friend of friend, to get a warm intro to an experienced developer you can pay to oversee said team on an interim basis. No consultants, agencies etc. they'll fleece a non-tech like you, save your money and drop it on somebody good who can actually help execute your vision.

Freelancers' careers live or die based on where future work is coming from. Happy clients are good for repeat business. Happy clients refer other potential clients. Happy clients are good for portfolios or case studies. Smart freelancers are all about keeping their clients happy in the long term. It's just good business.

Of course there are people in the freelance world who are hopeless and will never build anything useful just like there are people in the employment world with the same problem. But it's much more career-endangering to be incompetent as a developer and/or as a communicator in the freelance world because freelance gigs can often be terminated relatively easily if the client isn't happy with the work.

Maybe this is different in the parts of the US where compensation for tech employees can be way higher than anywhere else but in most of the world freelancers tend to be relatively good at what they do and part of the attraction of going the freelance route is that it doesn't have the glass ceiling on compensation that being an employee often does so if you're good enough to justify higher fees then you can actually charge what you're worth.

Not a freelancer, but this is a classic "market for lemons" situation: designing things for the long term takes a significant amount of extra thought and expertise. If two freelancers give two different quotes, one of which has a higher hourly rate and will take a longer time, there are one of two possibilities:

1. The more expensive quote is way overpriced, trying to extract money out of the buyer and possibly double-dip

2. The cheaper one is a low-quality "cowboy" job that's going to cost way more to maintain in the long run

If buyers in general can't tell the difference, then the market will end up pressuring even the high quality people to cut corners and produce "cowboy" jobs. In other words, it may not be 100% the freelancer's fault they're "not interested in the long term unless forced".

So part of the job of a "wrangler" is to understand what's worth investing in and what's not -- to know that it's worth spending double in this particular area because it's a long-term win -- and to be able to evaluate the output of the work, to make sure that what was delivered actually is higher value.

There are enough buyers who can tell the difference. Good freelancers just gravitate towards good clients and vice versa.

A pattern I commonly see is that they are heavily technology focused and don't really care about the domain, because domain-specific skills are not transferable. They are snake-oil salesmen, every problem can be solved by adopting some hot new piece of technology which can be added to their CV and increase their market value. What's frustrating is that their contribution is in the end often negative rather than merely zero - adopting over-architected solutions looking good on CV will result in great costs. If you have a strong technical leadership, you can catch their bullshit, but in the op's situation, they would be pretty much relying on freelancers' good will and abilities without much of a chance to verify their claims.

To be fair, I've met also a number of very good freelancers, usually staying with the company for years.

This same danger exists also with the normal employees, but I think this "pad the CV, move on" is more common in freelancers since they generally operate on shorter timescales.

Software needs to be designed with an understanding of the business needs and goals. You need someone who understands how to keep the software well designed (ie. Easy to debug, update and extend in the future).

Judging solely as a user of the software gives you no insight into whether or not a plate of spaghetti code could be holding behind the scenes.

Good code has two traits: It does the job it was designed to do. It is easy to update and maintain.

Everything else you read online is nonsense. And you need someone trusted inside your company to ensure the second trait is being adhered to.

Why? There are many terrible everything out there. Eventually you are always relying on the quality of your developers' output and their honesty in explaining it whether they are hired as employees or working freelance.

Crucially that is as true of the technical in-house person as the outside freelancer. I've seen scenarios with my own eyes where an experienced freelancer was better - sometimes much better - than the in-house "senior" people but the latter made critical reports about the freelancer to management. Maybe they were defensive because someone better than them was brought in. Maybe - and I suspect this is more likely in at least some of the situations I'm remembering here - the in-house person was so far below the outside freelancer in ability that they simply didn't realise how much better the freelancer's work was than their own or understand the reasons the freelancer was following certain good practices and the risks they were mitigating by doing so.

So my question to you is this: Why do you believe you can trust someone to evaluate the quality of the work more accurately and honestly just because they are inside your company?

I think there's a big difference between bringing on a boutique consulting shop and hiring freelancers who sit together in your office. The sense of ownership and professional responsibility is way higher in the latter case. In fact I'd even go as far to say that many freelancers have MORE professional pride than permanent employees, many of whom just want to draw a paycheck and live their life.

YMMV of course!

My company worked with freelancers/consultants for years, it just delayed the inevitable. You need to start building your in house team.

Find the ONE. See if he can build anything on their own. If they can/thinking is good, then scaling with freelancers seems good because you retain knowledge and long-term vision/oversight.

- small team hired (via a well regarded agency) - small team creates and releases initial, limited POC - company retains the freelance lead to staff up an in-house team - in-house team takes over and starts moving to a more complex phase 2 product - initial project ends up being maintained by an offshore team while in-house team goes gangbusters on everything else the company needs.

We had a freelance team for each major product (web, iOS native and Android native). In house teams existed for backend and devops but freelancers create all of the customer facing products for at least phase 1.

It was useful to have an architect level person involved at the start but once development was moving everyone had enough experience to make the need for a higher level tech person a non-issue (the freelancers ranged from senior dev level to architect level). It helped to have someone in-house overseeing things (timelines, scope, etc.), of course, but someone at the CTO level would have probably not moved the needle much in that first year of work.

The "move fast, break stuff" phase benefited from a small crew of experienced devs without too much bureaucracy while later phases needed more structure.

Quality isn't always easy to find - avoid agencies, hire the kind of freelancer who dares to work on complex / hard projects (there aren't that many of them) and ideally.

The pitfalls are mainly hiring:

a) Inexperienced people who happen to work for themselves. b) Agencies, they have an incentive to sell bodies: two mid-level bodies are 1.5-1.8x the cost of 1 senior and they do less work. Especially if they sell you a team of them.

Pick a small vertical slice or process and have them implement that. Run in parallel (the costs in these projects is when operations are negatively affected). Treat it as a learning process. Iterate. Then grow based on what you learn.

I'll disagree with Dave on one thing: I personally prefer not having a single lead developer. I've come to appreciate the advantage of having multiple, aligned leaders in a team. Teams like that are absolutely awesome to work on and you can specifically hire for it.

You will absolutely need buy-in from your company, you'll need to give them access to the people doing the job and likely have one of your senior employees do the job. Based on my experience the best internal people are the same people who you'll be putting through a management development program - the type where they get to know the entire business. They'll have the right attitude (can-do, hard workers, personable) and ideally are good with people / nice to work with.

Have the team as a whole report to you. It's a small team (3-4 devs + 1 internal full time).

Also make sure that the team are in control of their own destiny. You'll need backend/frontend/ops/dev-ops skills covered in that team, you don't want them crying for the sake of having a server made available for them. Give them an AWS / Azure account and let them work there.

I had a similar experience working with a large agricultural company, where we developed a track-and-trace system to manage their entire workflow. This system provided them with insights into all aspects of their processes. They gained full insight into their margins, mass-balance and quality control, from field to fork.

Our agreement included the agreement that we would own the system, with the option to eventually resell the system in the market, ensuring we could establish a company to support the system after development was completed. As you don't want to loose the knowledge after the system is finished and don't want to have a complete team of developers on your payroll.

We only developed the components that were crucial to the business process, relying on existing software packages, such as the accounting system, and ensured seamless integration between them.

One approach that worked really well for us was working on-site and providing support to the people using the system. This was invaluable in resolving issues that users were experiencing, and it also kept us focused on delivering quality—otherwise, we would be the ones responsible for providing support.

Please note that if you begin development, don’t expect the first version to be the final one. This was a major pitfall for us. The first version was good but not future-proof. Only after developing the second version, essentially a complete redesign and redeveloped from scratch, did we achieve the best solution for the business.

Ensure you maintain an open dialogue with the development team and allow for quick iterations. For us, a significant challenge was aligning expectations. Budgets were tight, and expectations were high, which created a high-pressure environment, that worked great for us and helped us focus. However sometimes this led to a lack of appreciation for our work, as expectations where not met. Keep in mind that developers think differently from business owners. We addressed this by having a technically proficient, data-savvy production manager in the company who understood most of our challenges and helped realign expectations.

Unfortunately for us, the company we built this system with didn’t respect our contract, preventing us from distributing the system and killing future opportunities. This resulted in legal action, which didn’t end well for us, as the company was much larger. We were naive in thinking we could make it work, assuming it would be in the best interest of both parties, but they didn't share the same intention.

Probably the best way to think about this whole project is not as a project, but as a capability to grow internally. As a big project, you'll get stuck at 80% and never deliver. If you start small and deliver continuously, you'll get stuck at reducing the pain by 80%, which is probably a huge win.

Software is grown. Start small and focus on delivering value quickly to build momentum and credibility, but make sure that the team lead knows that your vision is to eventually replace the other systems.

In short, please no. No documentation, awkward separation of inhouse/external employees (regardless of team setup, you have different access to resources), there is just no creativity, everything is done loveless and cookie cutter.

If you plan long term, hire long term.

Where I’m at we brought some software in-house and that part was skipped, or ignored. Years later, in talking with the lead on that project, he will admit that was a big miss. On the one had, to make change he didn’t want to be tied down and pushed around by past politics and issues, but on the other hand, some big fundamental problems were carried forward from the old solution to the new, and there was no way to really fix them after the fact, without effectively starting over.

- How does this team with just a lead determine the business and domain rules? It sounds like the application is quite complex. Letting some freelancers go at it is the worst thing you can do for an application that is meant to handle hundreds of millions in revenue - Long term maintenance. Who is going to do the knowledge transfer and maintenance of this application as it grows and the freelancers leave? - Who is interfacing with the clients? With the existing software developers? Do you really think devs are going to be doing this?

So many things wrong with this approach. Please stop telling the guy to adopt this? And top sending him your emails when he is just asking for advice. Just because you want to jump onto this project as you see $$$ signs. Jesus.