contractors management

Working with contractors

Recently, we’re getting ready to engage with contractors to help us drive a major initiative forward.

Behind the scenes at work, here is a view that happens before contractors write any code.


It starts by figuring out what company you’ll be working with. 

Your company might already have a pre-vetted list of vendors, but we reached out internally for recommendations in our case. After meeting with a few representatives, we settled on a couple of companies we liked.

To decide on one of them, we created a weighted decision matrix. We rated both companies in pricing, availability, expertise, onboarding times, size, and a few other attributes essential to our decision-making criteria. 


It is time to make things official with a company in mind. 

On our end, we have legal counsel to help us draft the needed documents, but you can reach out to the vendor and ask them to send you the first draft instead.

You can expect two documents, a Master Service Agreement (MSA) and a Statement of Work (SOW).

Please think of the MSA as the contract allowing both companies to do business with each other, while the SOW will go into the specifics for each engagement you have with them.

As an example, the MSA could contain non-compete, non-solicitation, or security requirements applying to all contractors. On the other hand, the SOW will have working hours, deliverables, pay rates, and additional job-specific information.

It is common to have one MSA and one or more SOWs.

Selecting contractors

With all the legalities in place, it is time to start figuring out who’ll be doing work for you.

Whether it is a long-term engagement or work with a well-defined deliverable, you will need to determine the technology stack and the level of experience expected.

The vendor typically does some initial candidate vetting and will present a few options for you to select from.

It is on you to further develop a process to validate that candidates meet your expectations.

That means a quick engineering assignment that we then review internally.

Product engagement

With a team ready, they’ll need to know what they will be working on. This is where your product manager comes in.

Just like your team needs guidance on the product and an understanding of priorities, so will your contractors.

Engineering engagement

With good direction, your contractors will now be ready to start work, so we’ll need to get deeper into specifics.

Think about items such as level of access to your repositories, reviewing pull requests, CI/CD checks, release strategies, getting the code working locally.

In reality, this part doesn’t look much different from the engineering onboarding your employees might go through.


Engaging with contractors is an excellent way to augment your workforce and make further progress on your initiatives.

But to ensure a successful engagement, it helps to:

  • have a procurement process to land on a suitable partner
  • understand the standard legal contracts used
  • have a way to examine engineers for your required expertise
  • please provide them with the necessary support to seamlessly work on what is important to you.

Contractor icons created by juicy_fish – Flaticon


Vendor procurement

We’re currently considering bringing contractors to help us with a backlog of work and, in theory, unblock our engineering team to work on more valuable initiatives.

We began by thinking aloud about what it would look like for external contractors to work with us. For context, we rarely work with external contractors since we have a philosophy of hiring worldwide.

we decided on a specific set of criteria that we would like for our contractors to engage in

  • Only well-defined work is assigned
  • Engagement will have an end date
  • Contractors will need to be self-sufficient after onboarding

With the criteria above would begin looking for possible vendors to work with us. This is where the procurement process begins.

We started by gathering information from people within the company who had worked with vendors in the past and were willing to recommend working with them again.

A few companies showed up, and we started speaking to two of them at a high level. 

Both companies had very similar profiles. 

They were both nearshore companies with similar price points, technology experience, and a list of prior engagements providing social validation.

Since they both had similar profiles, we moved on to a more strategic way of comparing them by introducing a weighted vendor comparison matrix.

The matrix has weighted values for each of the attributes we care for, allowing us to measure each vendor critically, considering that we value specific characteristics, such as prior experience and onboarding time, differently than others such as price and payment options.

This simple exercise provided some much-needed clarity and allowed us to select the right vendor for our contractors in the future with a higher level of confidence.

Icons made by Freepik from www.flaticon.com