How to Buy Enterprise Software, According to HubSpot’s Head of Learning and Development


This article is part of Made @ HubSpot, an internal thought leadership series through which we learn from experiences conducted by our own HubSpotters.

As someone who manages HubSpot’s learning technology, I’ve sometimes bought software the wrong way. I pushed forward without the right technical partners, missed an automatic contract renewal deadline, and rolled out changes to my team without empathy as to how this might affect their day-to-day.

From these experiences and working with others at HubSpot who procure and implement software, I learned a parcel. Today, I feel good about the way I manage our technology and purchasing decisions.

I have come to realize that a successful buying decision is less of a question management of suppliers and research (although these are important factors) and more on project management, change management, and get buy-in for new ideas.

Here are some of my biggest lessons for those who are considering buying new software or just curious to learn more.

Lesson # 1: Establish a business reason before applying for membership.

In the past, I hadn’t taken the time to step back and assess the value my proposal would bring to the all organization. Even if the user base of your new software will be only a small part of the employees, reflect on and communicate how it relates to business results.

Here are some examples:

  • A process is currently very manual and you want to automate it. The business reason for this software would be to save time and money.
  • Your team is trying to accomplish something and you don’t have the skills, the time, or the features. The business reason for this software would be to expand the capabilities of the team.
  • Recently our L&D team at HubSpot wanted to be able to track the performance of new hires in their training courses. The business reason for this software was that we could give managers a better idea of ​​how best to spend their time mentoring their new hires as they take on the job.

Once you’ve established the purpose of your business, you’re more likely to gain stakeholder support.

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Another important business factor to consider when joining is the cost-value ratio. Adding more software means another supplier to manage, another contract to be considered, and another system for your colleagues and teammates to adopt.

Make sure you think it through and believe that this new software will deliver enough value to override these considerations. This will help you deal with the initial objections.

Obtaining membership should take place well in advance of when you plan to purchase the software. This process takes time. You need to talk to people outside of your department and often outside of your business to make sure you understand the landscape of what’s already happening, what’s possible, and what it will take to run new software.

Lesson 2: Realize that you are going to need help.

You may be the most experienced software buyer in the world, but you can’t do it all on your own. In my experience, the best help you can get with purchasing and implementing software is the team whose very expertise is software: your IT team.

Loop them at the start of your process, see what they’re already doing to solve the challenge you’ve identified, and ask at least one champion for their opinion. Depending on your business, you may also need to loop through security, legal, and finance so that they can add their expertise and highlight any blind spots you might have.

You will also need two key people: someone to serve as a project manager and someone who has expertise in the type of software you are considering purchasing (which could be you with enough research).

It’s important to remember that you can’t make isolated decisions about software and expect everyone to love and use it. You might think you know what’s best for the team, but you really need feedback, and you need to get it before you dive too deep.

You don’t have to take everyone’s opinion as a requirement, but you should take everything that is mentioned by multiple people into account and capture those comments. The more you document and share how you make your decisions along the way, the less reluctance you’ll face when you’re ready to start finalizing the deal.

It may take a while at first to write everything down and share it, but this process will save you a lot of time in the end.

Lesson # 3 Be vulnerable and empathetic.

Change is difficult for everyone. Even those who are most excited about using new software may be overwhelmed by the prospect of changing what they are used to. It is important to be transparent and empathetic with your project team, colleagues and the organization at large.

For example, if your team members generally like processes and organization, recognize that a project is going to be difficult because there will be a lot of things that start out in disorganized or unfamiliar ways. One proven method of solving this problem as a team is to openly share your emotions and then collectively decide to move on.

Encouraging your teammates to share their concerns can help you better define the direction of your project and create a sense of camaraderie that will come in handy when the going gets tough.

Whatever team you’re on, who your user base will be, or how many vendor demos you’ve watched before, these tips should get you started on the right track. Buying software isn’t easy, but if done right it can add a lot of value, connect you with your colleagues, and help you discover the art of change management.

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