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How to Work with a Software Development Contractor

A common question we hear from early-stage startups is how to accelerate product development. Working with a software development contractor is often an essential approach for startups with tight budgets who need the ability to turn up and down expenses. The diversity of skillsets needed is often another great reason to go with contractors instead of full-time employees.

But what type of software development contractor is right for your startup? Let’s take a look at a few approaches and explore some best practices.

Types of Software Development Contractors

Independent Contractors

One of the most traditional approaches has always been independent contractors. If you have a strong network consisting of the skillsets you need, this may be one of the best approaches for you.

Getting talent from your network can usually mean you have more of a known commodity and trusted working relationship.

Remote Development

There are a lot of remote development options all over the world. These are companies that specialize in fostering a network of software developers, designers and project managers in order to customize a team for most jobs. But how do you know if this is a good fit for your company?

I like to think about this option when a company or project is ready for a full team of developers to tackle a project quickly. It’s essential that you have a really thought-out product feature set, user experience, mockups and requirements ready to start on. Remote dev teams will likely shine in these scenarios.

If your project is still forming or may have a lot of changes as things develop with your company, I suggest keeping more of your new product development in house to keep the team close to those changes.

Most remote development shops offer competitive rates and a breadth of different skills to put together a small team quickly. Some of the things I like to ask these companies when I speak with them are how long of a commitment for a project do they need and how easily can they scale the team up or down.

Freelance Platforms

Platforms like Upwork are also a solid approach and can be used in a variety of ways to find the right software development contractor for your needs. These platforms have a wide range of skill sets and allow for shorter to longer time frame jobs.

One approach that’s worked well for me on freelance platforms has been testing the waters with smaller jobs until you find a freelancer that provides a high level of communication and quality, then continuing to build a relationship with that freelancer through longer-term projects.

With freelance platforms, you should also look to build trust a little more slowly. These platforms do attract some less reputable folks, so keep an eye for odd requests about getting access to your systems early on in a relationship. Hold the freelancer accountable to prove themselves repeatedly until such access is given.

Contractor Management Best Practices

No matter the type of software development contractor you work with, the most successful relationships will come when you put the same amount of effort and relationship into them as if they were a full-time employee. Here are some best practices that have worked for us:

  • Make sure you have a detail-oriented product or project manager on your team helping organize the backlog with your contract staff. Creating and managing a product backlog is the real art to keeping product development aligned with a vision and shouldn’t be outsourced.
  • Take time to build a relationship. Get to know your contractor just like if they were part of your team. Someday they might be. The more you can communicate the overall vision, the more aligned a freelancer can be.  This will help them to be more excited and passionate and will likely show in their work.
  • Provide detailed scopes of work and success criteria. Same philosophy as measure twice and cut once.
  • I prefer a high frequency of checking in, goal setting and payments. This keeps you very in tune with what work is being done and what’s next. I do this weekly with some of our contractors.
  • Be understanding. Some weeks will be slower than expected, and some will be faster. Overall I look for consistent quality, communication and iteration, and only look to move on if those things aren’t met consistently.

As you can see, there’s a lot to consider when managing software development contractors, but these options can be used in a variety of ways. When done successfully they can really help to scale your product development efforts and keep costs within reason.

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