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The 3 challenges of launching a tech startup in a legacy enterprise

Taylor Veino

Feb 27, 2019 1:00:00 PM

Featuring: Alex Behrens

A legacy enterprise isn’t typically something you associate with startups. I’d venture to say that most of us have a picture in our minds of legacy enterprises being these slow-moving behemoths. On the flip side, we picture startups as agile, sleek and fast.  What you may not realize is that an increasing number of legacy enterprises are launching miniaturized versions of software enterprise startups internally.

These new divisions are intended to do things like introducing Agile to the development process and building new products and services to break into new markets. Alex Behrens, a close friend of The Frontier Podcast and, is not new to building technology or startup culture in different industries. We consulted Alex to identify the three major challenges of launching a startup inside of a legacy enterprise.

Challenge #1 – Making Infrastructure Changes Within a Legacy Company

Legacy enterprises are called that because they have a legacy infrastructure.  They’re running on hardware and software that has been superseded in the marketplace, but it’s incredibly difficult to just rip and replace it due to the sheer scale involved.  So, when an internal software development startup division launches within the company – and when all the engineers want to use the shiny new tools like Kubernetes and AWS – it’s bound to be a steep mountain to summit.

Challenge #2 – Avoiding a Work Silo

That said, any engineers you do bring in should be ready and willing to integrate with the legacy team, while still maintaining the hustle and innovation that comes with a startup team. As you source and vet these engineers, pay close attention to their empathy and flexibility index. Or, even better, scale up your team using a service like, which will professionally vet candidates for those particular soft skills.

Challenge #3 – Choosing the Right Language and Frameworks

This is especially challenging in a legacy environment, because the company was likely built on certain languages and frameworks that are at best no longer particularly relevant and at worst downright hindrances.  At the same time, a balance needs to be struck between using the right tools for the job at hand and not introducing too much complexity and disparity from an Ops perspective.

Air Your Grievances

So, instead of treating your internal startup like it’s a separate entity, treat it as part of the greater whole.  This means being able to have your team work together with the existing departments, especially the enterprise IT team.  A great way to do this is to sit down with them and have a frank conversation about what you’re trying to accomplish and why you need certain infrastructure to do it.  Give them a chance to be frank as well and speak about what they may not like about your choice. Ask them to be your partners in finding a good solution that best fits the company’s needs.

I’ve seen firsthand how having these types of conversations – truly open communication – is so incredibly beneficial.  It builds partnerships and friendships, and, In time, you may find that your biggest “nemesis” in another department will end up becoming your staunchest ally and will help support you in pushing through needed infrastructure changes in the organization.

Launching a startup in any form isn’t an exact science.  Mistakes will be made. But successfully navigating the pitfalls allows for some truly amazing things to be built.

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Written By:

Taylor Veino

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