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Software Development Teams: Build vs. Contract

By In Technology

Almost every business is technology-enabled in some way these days. Hair salons do their scheduling online, powerline workers train in VR, and pharmacists use AI systems to check for contraindications. There are very few businesses out there that could not be made more efficient and profitable — or provide better services for their customers — through technology.

In most situations, buying software and customizing it makes the best sense. You need a word processor and an accounting system, but it would show boldness to the point of lunacy to build one yourself. Quickbooks and Microsoft Word are worth the few hundred dollars a year. They might not be perfect, but the cost to build and maintain your dream accounting software could run into the millions.

However, in many situations, businesses invent new ways to improve their internal operations or their customer experience. While a comparable off-the-shelf solutions may exist to fit those needs, a custom built product is likely the only way to deliver the required features and processes the company is looking for. Features like these become competitive advantages. Organizations want to own the intellectual property behind their competitive advantages. You don’t want to license these types of systems if your competitors can license them just as easily.

That leaves companies with one choice: Build your own custom software. But the question is whether you should try and build your business-changing application in-house or outsource it to a development agency.

Cost vs. Time

Most decisions in the professional space come down to the project management triangle. If you want to build software of any decent quality, you can pick two of the three corners to move: cost, time, and scope (the number and robustness of features the project has). If you want fast and cheap, you have to shrink the scope. If you want robust and cheap, you’ll have to wait a long time.

The decision to hire an agency or build a team hinges on these three corners. In business applications, scope is usually the non-negotiable — the requirements are the requirements. Building a team takes a lot of time and costs money. Hiring an agency will drastically reduce the ramp up time by comparison, but potentially cost more. If you are worried about quality, remember that you get what you pay for.

Management Structure

Deciding to build out your own development team is not for the faint of heart, but it can have serious benefits.

To build a basic, but healthy and functioning, software team you will need the following:

  • A CTO or CIO to handle strategy and management.
  • A Director of Engineering to manage the team, build out processes, etc.
  • A Software Architect to design the system. (This can be a senior developer for small teams.)
  • A couple of DevOps engineers to manage the environments.
  • At least one QA expert. (No, developers can’t check the work themselves, I’ve tried.)
  • Developers, including full-stack, frontend, and backend developers if you’re building out a product. A good mix of senior, mid-level, and junior developers would be my recommendation to make the team robust.
  • A product owner. Preferably someone with management experience
  • A scrum master (if you’re following Scrum/Agile).
  • UX expert. I cannot understate this role enough! (They can be outsourced if you have to, but are much better to have on the team.)
  • A visual designer. Depending on the product you are building, this is the one optional role.

This is the biggest reason to hire an agency. If you want something built well, you really need a team that looks like something similar to this. Depending on your budget and experience, it could take years to put a team like this together.

However, if you have highly technical and experienced upper management there are benefits to in-house teams.

But We Are a Lean Startup

That’s great! Then you don’t need any of the stuff I listed above. But if you are purely a technology startup, then you (I’m guessing you’re a founder), need to be building the tech yourself, or at least have a co-founder building the tech. As the company scales, you can bring on additional help and you will almost certainly start looking like the organize above.

How Long Does It Take To Build a Team?

It depends on if you’re talking about a good team, or just any team. Building an organization from scratch takes time. You need to recruit, hire people, onboard them, manage them, weed out the good, let go of the bad, hire replacements for those let go, etc. You also need to invent, document, and enforce the systems and processes that will lead to the best outcomes. You will need to build a culture of caring, accountability, and quality. So, basically it will take a long, long time. This is a lot easier to do if you have a top rated CTO or a Director of Engineering in place already. Someone who has gone through this process before will be able to get you up and running much more quickly. They will also be able to oversee all stages of the team building from recruiting to delivery.

Recuiting may be the hardest piece of all of this. Good developers don’t want to join companies without histories of good development practices. So if you don’t have someone for new hires to look up to, you’re going to be stuck with coders who are just looking for a job, and they don’t write good code.

In-House vs Outsourced — Conclusion

Unless you are going to go with the lowest bidder, there probably isn’t that much difference between a good internal team and a good agency. Well-run development studios partner closely with their clients and eventually start to act as part of the same company. The developers in agencies like this feel as much ownership in what they are building as full-time employees would — sometimes more.

Price is not going to be dissimilar either. Once you count things like benefits, office space, management scaffolding, training, hardware and software tools, payroll, HR, etc., etc., etc., it’s unlikely that in-house could be done cheaper than even the large agencies.

The real difference comes down to the level of control you want over the team and the type of product you’re building. If you are a small technology startup you would be crazy to hire a big agency unless your product needed to be really good from day one. If you plan on becoming a technology company, you might want try a hybrid of agency and in-house. Finally, if you are a small- to medium-sized company whose existing products or services are not predominantly tech-focused or delivered, I would suggest not doing development in-house.

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I help companies turn their technical ideas into reality.

CEO @Sourcetoad and @OnDeck

Founder of Thankscrate and Data and Sons

Author of Herding Cats and Coders

Fan of squash, whiskey, aggressive inline, and temperamental British sports cars.

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Don’t Fall Into the Trap: Why Startup Software Development Isn’t Like Corporate Development

In Startups, Technology

So, you’ve left the corporate world, and now it’s time to build your own startup. You’ve probably managed dev teams before, overseen product launches, maybe even helmed some fancy project management tools that made everything run like a well-oiled machine. You’ve done this before, right? Not exactly. When it’s your startup, everything changes—and, as I’ll explain, if you assume it’ll work the same way, you’re heading for a few surprises.

Startup founders often fall into a dangerous trap when starting a software project from scratch: thinking it’ll be just like building software inside an established company. Here’s why it’s not—and some advice on how to navigate the differences.

1. Switching from Product Manager to Teacher

In an established company, a software team already has two things that give them a serious edge: an existing market and a deep understanding of the business. They’re working within a proven model. Developers in that environment know what questions to ask, can fill in gaps intuitively, and likely understand why they’re building what they’re building.

At a startup, however, your devs are going to need a whole lot more context. They’re not working with familiar requirements—they’re working with your vision, which may be abstract at this stage. If your development team doesn’t understand why something matters, it’s a recipe for ambiguity and frustration on both sides.

Advice: Think of yourself less as a product manager and more as a teacher. Your job is to make sure they understand the core problems, not just the features. Teach them why each requirement matters, help them visualize the end-user, and create that shared language for decision-making. It might feel tedious, but it’s essential to avoid future misalignment and expensive rewrites.

2. Beware of Perfectionism — It’s the Budget Killer

In a large company, products with an existing user base often have to be polished. Features need to be rock-solid, invoices have to be perfect, and everything needs an audit trail. Startups, however, have a different goal: get an MVP in the hands of users fast. It’s a classic trap for first-time founders—focusing on “perfection” and “polish” before knowing if the business model even works.

Startup perfectionism is budget poison. It’s shocking how quickly adding “nice-to-have” features can chew through funding, especially if you’re paying a dev team to build things like automated invoicing or churn management before you’ve even proven people want what you’re selling.

Advice: Ruthlessly strip down your MVP. If a feature doesn’t help you validate your market, it goes on the “later” list. Keep the scope laser-focused on what helps you test your business assumptions. Let the non-essential features wait until you know you have customers who’ll use them.

3. Zen and the Art of the Startup Pivot

Building software for a startup means embracing one cold, hard truth: the business model will change. According to research, 93% of successful startups pivot at least once (and often more). Imagine being asked to go out and passionately sell something that you know might not look the same next year—or next month. It takes a level of zen acceptance that your original idea will likely morph, but that’s what keeps you flexible and ready to capture new opportunities.

For founders, that requires a mindset shift. You have to believe in your product, while also knowing you might be building the “wrong thing” in some way. The focus should be on preserving capital and brainpower for what’s next. The game is less about proving you’re right and more about staying adaptable.

Advice: Budget with pivots in mind. Set your burn rate assuming you’ll need to make big changes. Don’t let ego get in the way of listening to the market, and keep enough gas in the tank for at least one big strategic turn.

4. The Hard Work of Being Your Own “Internal Customer”

Here’s another big one. In a corporate environment, you have internal customers—departments or stakeholders with specific goals that align with the overall company mission. For a startup, the only customer you have is you. You don’t have a preexisting feedback loop from various departments, and you don’t have established success metrics. You have to create that from scratch.

Advice: Start by building an internal customer profile based on your target market, then use that to set clear goals and success criteria for your dev team. If you’re focused on, say, usability for early adopters, set KPIs around usability testing and build from there. By acting as your own “internal customer,” you’re setting a clear direction and saving your team from working in a vacuum.

5. Get Ready to Build AND Sell

Corporate software development often has the luxury of a separate, dedicated sales team to deliver the product to the right audience. As a startup founder, you’re both the builder and the seller. That means you’re not just iterating on software—you’re iterating on messaging, product-market fit, pricing, and maybe even distribution models.

Advice: Factor in time for sales-ready iteration in your dev cycle. As you build, keep track of how each release or update affects the user experience. Ask yourself if the changes make your pitch clearer or simpler and how they align with the current market’s needs. Ultimately, this approach will help you bridge the gap between building the product and ensuring it’s market-ready.

Conclusion

Building software as a startup founder requires a whole different toolkit than you may be used to. You’re part-teacher, part-salesperson, part-zen master, and always the chief budget officer. By recognizing the unique mindset shifts and traps of startup software development, you’re positioning yourself—and your team—for the best chance of success. Focus on creating clarity for your team, set ruthless priorities, embrace change, and never lose sight of the fact that the first version is just the beginning. In the startup world, adaptability isn’t just a skill—it’s the entire game.