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Member Spotlight | Leon Wilson

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Leon Wilson, Cleveland Foundation

An Interview with Leon Wilson, Chief of Digital Innovation & Chief Information Officer, Cleveland Foundation, and a TAG member since 2015.


How might you describe your role at the Cleveland Foundation?

As Chief of Digital Innovation and CIO of the Cleveland Foundation I technically have two distinct roles.

  1. First, is serving as the Chief Information Officer overseeing the responsibilities and activities of the foundation’s Information & Technology Services department; focusing on strategic and transformational use of technology and data throughout the foundation as a part of the executive committee.
  2. Secondly, as the Chief of Digital Innovation I work with the foundation’s Program team leading and overseeing our “Digital Excellence” grant-making strategy geared toward “building a stronger, more equitable and inclusive digital community”; along with elevating Greater Cleveland’s position as a major regional smart community and technology innovation hub.

Finally, I’d be remiss if I didn’t share my 3rd unofficial hat serving as a technology coach and thought leader to our grantees, as needed. Specifically, I focus on how they can better leverage technology to support the delivery and execution of their social missions. As you can see, I am fortunate to have both internal and external facing sets of responsibilities.


At the Cleveland Foundation, how is technology playing a more strategic role?

While the Cleveland Foundation has historically been viewed as one of the more progressive grantmaking foundations, the same could not be said for how we utilized technology and data within the foundation. This is one of the reasons why the position of the CIO was created. That said, since my arrival at the foundation a little over 2 years ago, I’ve been focused on elevating the use of technology across all areas of the foundation along with improving our core infrastructure and investment in cybersecurity. We’re only now in a position where we can begin building on the additional investments in new & existing technologies, staffing, reorganizing, and cross-department partnership building.

For example, areas such as extensive reduction in paper via electronic workflow management within a number of key business process, and stronger data integration between our marketing and advancements teams pertaining to donors, event attendees and other friends of the foundation are areas we’re heavily focused on. This enables both teams to have greater visibility into our key stakeholders.


How have these shifts altered the skillset you look to build for yourself and/or your team?

We're investing in upskilling existing IT staff on workflow management, agile app development within the Office365 platform, alongside recruiting new talent with strong information management and data analytics skills. We’re trying to move beyond traditional records and data management, towards more impactful information/data analysis and retrieval solutions.


What are you energized about this year?

Beyond what we’re already working on with the greater digitization of processes that still generate paper, my aspirational vision is to align the data needs of the foundation toward collecting and measuring grant outcomes to better evaluate impact for our board, program staff, and grantees.


What are you reading right now that you'd recommend to others?

In my digital innovation role, I’m focused on the equitable and influential role of technology and how this results in both intentional and unintentional consequences for residents. This focus has me reading the following books:

  1. A New Digital Deal, by Bas Boorsma
  2. Technically Wrong, by Sara Wachter-Boettcher
  3. Automating Inequality, by Virginia Eubanks
  4. Algorithms of Oppression, by Safiya Umoja Noble

The Technology Affinity Group (TAG) is a 501(c)(3) non-profit membership organization that promotes the power of technology to advance the goals of the philanthropic sector.