Table of Contents

How to choose software

Max Dana Updated by Max Dana

ArtsPool relies heavily on software -- particularly web-based "software as a service" (aka SAAS) platforms -- to provide our services to members. You should refer to the article Selection of vendors, consultants, software, and tools for general information on vendor selection, but you can use this guide to help you with the selection and implementation of software systems.

Please be sure to include the Technology Team in your evaluation process so that they can provide a technical and security review before you move forward.

Evaluation process

When selecting software, it's a good practice to evaluate multiple systems side by side so that you can get a clear understanding of the pros and cons of the software you are considering. The Technology Team has created a Software System Comparison Template that you can make a copy of to help with this process.

  1. Follow the processes in the article Selection of vendors, consultants, software, and tools to form a Selection Team.
  2. Make a copy of the Software System Comparison Template, put it in an appropriate folder, and share it with the Selection Team. Feel free to create a new subfolder in the Technology Review: Prospective Vendors folder in Google Drive for this purpose.
  3. Add the names and links to the software under consideration in the Platform column.
  4. Fill out the Price, Users, and Estimated Cost columns based on each system's pricing plans. This generally needs to be calculated manually for each system since pricing plans are structured differently and you may want your team to see different scenario options. The Estimated Cost column can reflect a monthly estimated cost but it's helpful to calculate it as an annual cost so that the ArtsPool Finance team can more easily see the budget impact.
  5. Change the feature headers (Feature 1, Feature 2, Feature 3, etc.) to reflect the features that you want to prioritize in your selection. Add or remove columns as needed. Fill out these columns during your review of each system, leaving notes and comments on cells when clarification is needed.
  6. Use the Other Features and Notes columns to add any other information that you think would be useful to flag (e.g. some cool feature that the system has that isn't mission-critical but sets it apart).
  7. @-mention the ArtsPool Technology Team on the security review column and they will do an analysis of the systems based on ArtsPool's Data Security Policy guidelines for third party services.
  8. Once you have completed the initial evaluation, loop in other impacted stakeholders not on the Selection Team, e.g. the ArtsPool Finance Team or service teams that will be working with the data, so that they have a chance to provide feedback.

Selecting a system

After you have evaluated each system and gathered feedback, it's time to make a decision. The Selection Team (generally the team or teams who will be using the system) should make the final decision, taking into account any feedback provided by the ArtsPool Finance Team, Technology Team, or other stakeholders.

Generally, other teams should not veto software decisions unless they see major issues relating to budget impact, security, or usability. In instances where there is strong disagreement on a system, rely on the Operations Team to mediate.

Below are some things to keep in mind when making your decision.

  • Is the system accessible? Make sure that the system is web-based, has a reasonable uptime/performance guarantee, works well on weak wifi connections or older computers, and doesn't have accessibility issues for people with disabilities. Phone apps are nice, but working from phones isn't our ideal mode of work so consider phone apps to be a bonus feature.
  • Is the system secure? As stewards of our member data, we are charged with keeping them safe, particularly if the data include personally identifiable information. Look for things like SOC 1 or SOC 2 reports, 2-factor authentication, encryption of data in transit (via SSL) and at rest (in the database), permissioned access, and tools for monitoring unusual activity. A quick Google search can also turn up whether the company has experienced any notable data breaches.
  • Is the system sustainable? Make sure that ArtsPool can afford to carry the expense over time and the cost scales in a reasonable way. Per-user and per-send/per-action pricing can be a trap, so be sure to think about how the costs will increase as ArtsPool grows.
  • Is the system usable? Make sure that the system is easy to learn and easy to use. Nothing is worse than clunky software with a confusing or error-prone user interface, so look for systems that use modern idioms for user experience design. This is something you have to feel out, so it's best to try to get a live demo of the system so that you can click around a bit.
  • Is there sufficient tech support? Look for an up-to-date knowledge base or user community and find out what the existing support channels are. Sneaky companies like to make support a paid feature so be sure to ask about that. See if there is a system status page and review their Twitter account to see if it's active as a support channel.
  • Is the company aligned with our values? This can be hard to determine, but try to do a vibe check by reading the company's website, social media accounts, and/or blog. Even better, ask if they have an anti-racism statement, statement of values, or report on diversity, equity, and inclusion that they can share.

Engaging stakeholders

As mentioned above, the Selection Team should be in charge of deciding what system they use as long as they share their documented rationale with ArtsPool's management team and other stakeholders and there are not any red flags relating to affordability, security, or usability. The process of gathering feedback and developing consensus internally is sufficient in terms of internal approvals, though you may want to note specific teams sign-off on your evaluation sheet or team planner so that you have a record.

That said, care should be taken to engage members in the selection of any software that will be used by members so that you can ensure that it will not have an adverse effect on members' operations.

Pool Improvement Proposals

A great way to document your recommendation for review by various stakeholders is to use our Pool Improvement Proposal Template. Just make a copy of the template rename it, and save it in an appropriate folder. Write the proposal using the highlighted text as a guide for the types of information and level of detail to include. Try to anticipate the questions that stakeholders might have and answer them in the proposal.


Once stakeholders have had a chance to review the selection and the decision is made, it's time to implement the new system. Below are some guidelines to help the implementation go smoothly.

  • Assemble an implementation team. This may be the same team that made the software decision, but take the time to define the team and bring in specialists from other teams if necessary.
  • Develop a clear timeline with a go-live date. Define all important steps and milestones and give each a target completion date. Define a final "go live" date when ArtsPool will start using the system and make sure anyone who will be using the system knows about this date. Be conservative in your time estimates so that you have some flexibility if you encounter speed bumps.
  • Assign responsibility. Each task in the implementation process should have one person who is accountable for its completion, even if multiple people help complete the task. This person should be prepared to report on progress at project check-ins
  • Have a system for tracking the project. You can use a project management system such as Trello or Asana for this or copy an existing spreadsheet from prior system implementations. Either way, be sure that you have an agreed-upon way to manage the project and that all people working on the project have access to it.
  • Check-in regularly on progress. If your team meets monthly, its a good idea to schedule short weekly project check-ins. A monthly accountability cycle is just too slow for any kind of meaningful project implementation.
  • Communicate. Be sure to let other ArtsPoolers know if there are updates on the project progress that affect them. You don't need to update them just for the sake of updating them, but always over-communicate around go-live dates or any stage that requires action from people beyond the implementation team.
  • Keep good notes. Things go wrong (and right) and it's a good idea to keep track of them for future generations. Your implementation process might be useful as a model for other teams, and keeping good notes also helps us operate better as an open-location, asynchronous workplace.

How did we do?

Selection of vendors, consultants, software, and tools