You need enterprise software. Selecting, buying, and implementing it is a complex nuisance requiring a level of detailed technical knowledge that is rarely part of the “day job” of the people making the decision. And don’t forget: the entire process could take anywhere from six months to a couple years (or more).
But that’s not the problem.
The predatory stereotype surrounding software salespeople is often true. Many of these salespeople, especially those working for large, publicly traded companies or venture-capitalized start-ups, are on quota. This doesn’t make them bad people, but if they miss their quota, they risk being fired; if they close the deal, they make a lot more money. It’s easy to see how this zero-sum game might lead one to gloss over complexity and nuance.
Companies create an intentional veil of confusion around their products, contracts, and pricing for a key reason: they are beholden to revenue estimates for which Wall Street and/or venture capitalists hold them accountable. Failure to meet those estimates can mean lowered stock prices and loss of share-owner trust.
But that’s not the problem either, because—let’s be honest—who trusts salespeople, anyway?
The key issue is nonprofits themselves. You’re too nice. Thousands, millions of organizations deal with punishing sales experiences. And some do wind up happy. How? If your nonprofit wants to make the process of selecting, buying, and implementing enterprise software work, you need to become knowledgeable, demanding, cynical—in short, you need to be a tough customer.
Have staff knowledgeable about the business operations and technology help make the right choice. Free up their time so these people can focus on the process and engage with the details before a decision is made. If you have staff whom can drive the process, you have to make sure that their other responsibilities are reduced so they can give this process their undivided attention. Consider devoting internal staff to the project or working with a consultant familiar with the organization’s needs.
Software can only improve a situation when it is aligned to an organization's strategic plans and goals. How many nonprofits actually get specific goals and expectations from senior leadership before researching and selecting software? The best projects have someone from senior leadership (CEO, COO) as engaged project sponsors, setting direction, removing roadblocks and holding everyone accountable. If the CEO can have an intelligent conversation about what’s going well and what’s not working during the process, her/his level of involvement is about right.
Get buy-in from staff. Dictates from on-high rarely survive conditions on the ground. Project owners or managers need to check with staff to find out if the software will work for them and give them what they need. The result is that staff will actually use the product when the switch flips on.
Boards usually carry the ultimate fiduciary responsibility for an enterprise software decision, but they are almost never involved in the selection process. If the board has to approve the funds, they might consider appointing a member to get involved and stay involved. You don't want to have to ask the board for money twice.
Consider the alignment of the vendor with your market and their track record of happy long-term relationships with other clients that look like you. My personal belief is that smaller, privately held firms are most willing to go the extra mile for their clients.
Hold vendors accountable to terms of contracts, statements of work, and deadlines. If something feels wrong, it probably is. The best time to address a problem is early in the process. If this makes your salesperson or project manager uncomfortable, it might be a reasonable indication that you found something that make your life difficult after go-live. It is okay to push back early—you are the customer, after all.