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When Is the Best Time to Outsource Custom Software Support?

If you’re a CIO, CFO, or an overworked developer, you’ve probably considered finding more efficient ways to support the custom enterprise applications at the heart of your organization. 

But when is the right time to outsource support for your custom applications? 

I get asked this question often, because custom enterprise applications are often supported in-house (where some or all of the original developers are still employees), there’s a common misconception that it’s an arduous, or even impossible, task to outsource it effectively. 

Yet many organizations find that the right external partner can deliver quality support—and even increase confidence in operational continuity. Those who do, typically engage an outsourced service partner to address three primary challenges they face:

Challenge #1: Keeping developers focused on development and innovation, not maintenance and firefighting

How well do these characteristics describe your current situation?

  • Our top developers—the ones with solid knowledge of the business—have little time to actually create anything new because they’re constantly being pulled back into maintenance and support of current custom applications.
  • Those same developers are feeling simultaneously bored and overworked. Bored because they don’t develop anything new and overworked because of the flow of support issues that need to be resolved.
  • Our team is constantly being forced to switch context because the urgency of support issues. Every context switch spends developer-time just getting back up to speed.
  • We have multiple projects, but struggle to hire new developers to fill roles on those teams.

If those statements ring true for your development team, it may be time to consider outsourcing support. Your developers will thank you for freeing them up to do what they do best—develop. And they’ll be less likely to take that talent elsewhere.

Challenge #2: Reducing the on-going risk of supporting aging or custom applications

Is your team more competent in supporting your custom applications? Is it becoming more difficult to support those applications when a problem arises? Consider whether these descriptions apply to your organization:

  • Our support processes and procedures are often ill-defined and rarely documented.
  • There is a sense that much of our support depends on the implicit and private knowledge of a couple of key developers who could leave at any time.
  • The quality of support is highly variable across our team.
  • Our developers are resolving issues that a Tier 1 or Tier 2 support team could do.
  • We are vulnerable when Tier 3 support issues arise during holidays and vacation times.

Even the process of transferring knowledge to the outsourced team accelerates getting those deferred maintenance and resolution procedures defined and documented.

Challenge #3: Utilizing Your In-House Team’s Resources More Efficiently


Is there unnecessary complexity and overhead with your current support team? Consider the following: 

  • Our dedicated support team is underutilized.
  • We’re often looking for additional tasks to assign to our support team.
  • We need multiple skill sets and end up with a full-time person for each skill, but really we only need each skill part time.
  • Our support team is inefficient because it has become the place we transfer less-skilled developers.

Outsourced support providers can afford to assign more senior engineers to support your applications because you don’t need to pay for all of their time.

If you’ve faced any of the above challenges in your environment, the best time to outsource may be now.

Supporting your custom enterprise application is never easy, but partnering with a set of experts on a fractional basis may help you reduce risks and improve efficiency—all while freeing up developer time to focus on new mission critical projects.

If you’d like to explore if custom support outsourcing is a good fit for your environment, give me a call.


Tim Michalski

Tim Michalski is the founder & CEO of Lighthouse Software, a legacy software support and modernization firm that specializes in the delicate transition from older, reliable software systems to newer, modern technologies.

At the age of 8, Tim resolved to be an entrepreneur. At the age of 13, Tim discovered the creative power of computer programming when he received his first computer and learned his first programming language. For nearly 30 years since that day, Tim has passionately devoted most of his conscious hours towards becoming an expert software engineer and experienced entrepreneur. In that time, Tim built Lighthouse Software from the ground-up and championed the cause of restoring existing technology investments with iterative modernization over time to lower risks and gain a competitive advantage for his clients. Clients include numerous Fortune 500 companies to small technology firms in banking, healthcare, and government.

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