And even if the management (all the way up to the Executive Director) can see through the fog of their daily firefighting to see the potential of expanded an IT

And even if the management (all the way up to the Executive Director) can see through the fog of their daily firefighting to see the potential of expanded an IT budget to make the overall mission more effective & efficient they often can't shake money loose to do so because their donors insist that their dollars go toward costs directly associated with serving the bottom-line mission of the organization (e.g., to pay for meals served at a soup kitchen); not for organizational "overhead." Grants exist for tech-oriented projects, but it's very difficult to be adaptive & iterative because the grant life-cycle is measured in years. Not very "agile." Apply for a grant to make an improvement X using technology Y this year. Next year, receive the grant but realize that improving X is no longer relevant or technology Y is no longer optimal and you risk your grant funding by changing course or stay your course and achieve a non-optimal (or irrelevant) goal. Extremely frustrating. Incentives in the non-profit world (especially for charities & social services) are really skewed because the people paying for the services are not the same people receiving the services, and the demand for services is essentially unlimited.