6 Steps to Choosing the Software Stack for Your Business

on July 19, 2019

There are more tools now days than we’ve ever had access to. Data moves faster and customers expect more than ever before. How do you choose the right tools for your business so you can navigate?

Changing third-party software, tech stacks and apps has been a constant for us since day one. We’re always learning something new about our stack and how can improve it.

The difficult part about choosing the right chat software or the right cloud technology is that you often don’t quite get the full scope until you’re using it. This can be a real nightmare when you have to spend time migrating services instead of building your business and focusing on customers.

We’ve learned a few insights on how to choose the right software for your business and keep your data in check.

1. Hit a feature rich + simplicity balance

You know your business will evolve over the years. The biggest mistake is locking yourself into cheap or free software that only goes part of the way.

Instead of looking for the cheapest or (or any “est”) solution strike a balance between an app that is feature rich and is simple to use. That is, it lets you get everything done, but it doesn’t stand in your way.

A good example of this is Freshdesk. It gives you almost everything a small business needs to handle support but it doesn’t lock you into a specific way of doing things that many competitors do.

If you’re going for a CRM, pick a cloud-based one instead of installing an open source one on your servers. Simple, but not entirely cheap. You can’t beat your own records by being the cheapest run company on the block. Invest in software that doesn’t break the bank and lets you run your company.

2. Go for the safest(er) bet and ignore hype

Building your business on beta or new-kid-on-the-block software might be a big mistake. In our experience, new-but-not-complete or under-supported software has hard limits that you will outgrow.

A good example of this is the scripting language Lua, which we used to re-build the second version of Dedupely. The community was tiny, installing new packages was like pulling teeth, we had to build everything we couldn’t find already written by the community. In the end we needed to re-build again because it was too much of a technical burden.

Ignore the hype–Every industry has its cool niche product that is popular because it did something new and different or because 75% of companies in [insert popular tech hub] uses it. This means nothing if it doesn’t do the job for you and help your people do their job. Going for the software that caters to a wider number of industries, earlier on, is the safer bet.

There was a lot of hype around Ruby on Rails. It’s a great framework, but Ruby is not right for every company nor every dev team. Node.js has now taken over Rails in the hype factor. Tomorrow it will be another technology.

Intercom does just chat, and every chat can be treated like a chat or ticket (because there’s no ticketing). While that’s okay, we needed more than that. So we switched.

Every software company has their own values and matching your values with the software you want to implement is better than getting boxed into someone else’s use case (that has nothing to do with yours).

3. Implement data entry correctly from day one

Adding a new support desk? Make sure your customer profiles and cross-referenced ids are properly coded into your website so you don’t have to hunt them down later.

Most data entry will be automated (that is via an import, Zapier integration, PieSync, lead form, payment or signup form) so you have control over the source of how data moves around your company.

4. Get feedback from employees and contractors

Your staff uses the software every day. So ask them what they need to get the job done right.

No one likes working at a company that forces them to use tools they hate. So you either have to find people who are experts on those tools or listen to your team as a whole and find new tools.

5. Budget based on time/money/resource ROI

Email is something we failed at in the early days. I have nightmare memories of setting up our own email server to send transactional emails. Every OpenSSL upgrade meant a possible break to our email server, meaning suddenly no one (customers and staff) got emails.

We later switched to Mailjet and Google Suite and totally put all those headaches behind us. For what we pay we’ve gotten back our time, sanity and the ability to plug-in to services that we’re not skilled in and don’t make money building, but that we need.

Email is too important for us to get wrong. The same goes for data centers, support software, CMSs, CRMs and all the other apps we use day to day to run our business.

Going cheap, not only hurts your customers, but also the company morale, productivity and overall stability.

6. Remember GDPR and Privacy

GDPR can’t be ignored if you want to serve customers around the globe. There are plenty of IT privacy laws now days but GDPR is by large part the game changer. If you stay on top of GDPR you should be in good standing with other jurisdictions (like Brazil, Argentina and Australian laws).

However, make sure you do your homework. IT privacy is changing every day and you need to keep an eye out and adapt. Also, you need to make sure your subprocessors (the software and apps you buy) are on board and aren’t violating these terms.

This means keeping an keen eye on everyone you buy from.

Your industry compliance and the types of customers you handle make all the difference and may narrow the choices you have when purchasing software.


Running a business in today’s age means taking advantage of existing tools. How to find the right tools requires some unpolarized thinking, a bit of realistic budgeting, listening to your team and making sure it’s all properly implemented from day one so there’s less technical debt later when you may have to migrate.

Also, be aware of new IT privacy laws and how to comply. Your business is too important to risk on other companies who take privacy less seriously than you do.