Episode 3: How Digital Strategy Enables Innovation with Wendy Rinella

We sat down with Wendy Rinella, CEO of the Oakville Community Foundation, to talk about the foundation’s journey from paper-based processes to a digitally mature operating model that enables innovation. 


We talked about:  

  • The importance of building a durable digital strategy that is culturally aligned—and the perils of trying to implement strategy from the top-down. 
  • How digital investments free up time for staff to work on more strategic investments.
  • Some really exciting examples of how investing in digital infrastructure has enabled the foundation to drive meaningful change in their community. 

Learn more at theocf.org

Come see us at PEAK2021! We’re thrilled to be leading a session on May 6th at 3pm, Where Intention Meets Action: Operationalizing Trust Based Philanthropy. Or swing by the exhibitor hall to chat with one of our friendly team members.

Episode Three Transcript: 

Wendy Rinella:

We started at the end of 2017 to begin the transition in the last quarter. And then we did the transition for all of 2018. And so we had no idea we were getting ready for a pandemic. So when the pandemic came, we were in a place where we just left the office and we could work remotely. And we had the blessing that the only thing that we hadn't fully changed was we were in the process of switching to electronic fund transfers. We had planned to do that for 2020, but we did it in a week.

James Law:

In philanthropy, the path from setting strategy to seeing success can be a little difficult. Here we dig into the experiences of grantmakers figuring out this journey for themselves to help us all better understand how to operationalize our mission and our vision. I'm James Law, director of innovation here at Grantbook and this is the More Good Podcast. 

We sat down with Wendy Rinella, CEO of the Oakville Community Foundation to talk about the foundation's journey from paper-based processes to a digitally mature operating model that enables some pretty cool innovation. We talked about the importance of building a durable digital strategy that is culturally aligned, and the perils are trying to implement such a strategy from the top down. We then look over how digital investments freed up time for staff to work on more strategic initiatives and some really exciting examples of how investing in digital infrastructure earlier had enabled some pretty meaningful changes in their community. 

Hello Wendy.

Wendy:

Hi James. How are you?

James:

I'm well, how are you doing?

Wendy:

I am doing great, particularly since I'm talking to you.

James:

You're so sweet. Thank you so much for taking some time today. I know it's towards the end of the year. We're all trying to tie up loose ends, but I really do appreciate you coming on to share a little bit about Oakville Community Foundation and the journey you've been on over the past couple of years.

Wendy:

Very happy to. What would you like to know?

James:

Maybe to get us started, because probably a lot of our listeners will be American, but if you can get us started, maybe talk a little bit about the Oakville Community Foundation and your role there, and then we can keep going.

Wendy:

Sure. So in Canada, there are 191 community foundations, and they're very similar to community foundations in the United States, because actually I think the whole community foundation movement was founded in Cleveland. So the Oakville Community Foundation is 26 years old. We're going to be 27 next year. And we see our focus as building community through philanthropy. And we are about over $100 million in assets and that includes funds that we hold that are endowed and funds that we invest on behalf of other charities. So charities will bring their endowed funds to our investment pool and invest with us. And last year we granted about $3.6 million into our community, which is a small community. We're about 200,000 people and growing and actually becoming more diverse. So Oakville is about one third of our population is what we call a visible minority or racialized community, which also includes Indigenous people.

I myself, I have a background in probably every sector that there is. I started out in government. I moved into the private consulting, not for profit, industry associations, ended up in a for-profit where I was the head of corporate affairs and set up a community foundation, did a bunch of community work. Have sat on about 15 different community boards. And when this job came open, I thought, well, I haven't done that yet. So it looks like fun. So I've been here for five years as the CEO. So does that help? Is there anything else you'd like to know about us?

James:

I think that's incredibly helpful and that history of yours, I think I've always found particularly fascinating. I hear that the job popped up, but maybe in your mind, how did you land there? It wasn't something you had done before, but was there something in particular that really drew you to the position?

Wendy:

Yeah. So one of the volunteer roles that I had was I was chair of the local chamber of commerce. And I was also on boards of various education and youth focused charities. And what I really enjoyed was the community building opportunities that we had. And I realized I liked my community building work more so than I liked my every day to day job. We're a small community. So basically within the private sector, the people that I see at events and within the charitable sector, guess what, they're the same people. And so I pretty much knew, I would say about half the board of directors, when I applied because a lot of them had been on the board of the Oakville Chamber of Commerce with me or their spouses had. So it wasn't an unknown entity. And I was somewhat familiar with the foundation at that time. So I didn't come from a fundraising or direct work-related job like a lot of people in the charitable sector. They become experts in the field and they stay within the sector. I wasn't one of those people.

James:

Got it. And the reason I'm curious about your journey there is because when we first met, Grantbook and Oakville, we started working on the digital strategy for the foundation together. And we're really seeing a lot of the fruits of that come out. But I'm just curious, after your journey there, when you landed in the foundation, what did you see? What brought you on to this journey of digitalization?

Wendy:

Well, when I arrived here, there was a leviathan of paperwork and the organization, they had an electronic or I should say they were using FIMS, which many people might know. So they had a financial management system and that was about it. And then of course we were using things like SurveyMonkey and E-news. And there was no integrated system. They were producing paper statements for our fund holders on an annual basis and their goal was to get them out before the end of February the December 31st statements for the previous year. To have them out and mailed. 

And I mean, for me, one of the biggest things that was a challenge for me because I came from the insurance sector, which is really digitized and electronic, and I walked in, I picked up my phone, it was a landline and I hadn't used it in 10 years. I hadn't used a landline. I hadn't used voicemail. We were always VOIP. And we were getting our messages emailed and I was like I have to call in. My God, I couldn't even remember how to do it. So needless to say, that was one of the very first things I did. And I realized as well when I looked around, I mean, we had a granting program and you know what, people were doing their best and we were running these paper-based granting programs. We had a PDF application that people had to download and fill. And then the day of the closing of the granting round, they'd have to come in and make eight copies of it. And they all rushed in on the last day with their copies. And the maximum amount you could get at the time was $5,000.

And they did this twice a year. And then we'd spend all this time sorting the applications and putting them into an Excel spreadsheet and then having to send them out to reviewers who would review them. And then they'd make a recommendation to a granting team. And I was just phenomenally perplexed as to why we had sunk so much cost into competitively adjudicating what should be a sector that should be collaborative. They all have these professional boards and I knew a lot of people who sat on these boards, CAs and lawyers. And why did we have to review their grant application, to adjudicate whether or not they were doing quality work? Was it really our job to say, yes charity, your work is good or is that the role of someone like the CRA to say you meet the charitable requirements. The CRA, so it's the Canada Revenue Agency. It's like the IRS for your American listeners. So when I say CRA, think IRS. Okay.

James:

Thank you, Wendy.

Wendy:

So that to me was like, I was really perplexed by just how many sunk costs we had in our work.

James:

You had mentioned earlier that everyone's doing their best, everyone, at least in our sector, comes with good intentions and they are trying to sort of live for their values. Maybe from your perspective, looking back a little bit, why do you think some of this is? How do you think maybe some foundations got caught up in a little bit of that bureaucracy or living a little behind still using voicemail and phone lines only, let's say? Yeah, looking back, why do you think some of that happens?

Wendy:

Well, I guess a variety of reasons. Number one, they live hand to mouth, right? And the staff here are here because they're passionate about the work. There are very few charities that have IT people. I mean, they're lucky if they can outsource a chief information officer or even have a group on call to help them with any of their tech if it breaks down or if they have challenges. So I think there's just a lack of technology in the sector. And the other side of it is that we also have had the benefit of having a lot of outside organizations like Benevity and CanadaHelps come in and provide these stop gap measures to offer some digitized platforms for charities and they're great. For those organizations that are small, they can rely on these external groups. I don't know what the equivalent is in the US, so I apologize. But I think it's just lack of resources, lack of time, lack of knowledge. It's a whole trifecta of unsatisfactory situations.

James:

Definitely. I think that story you just told, I think a lot of people probably associate with that and empathize and definitely identify with that. But despite all that and the help that some of those stopgap measures did provide, you've been able to take the foundation rather on a pretty cool and significant journey, let's say over the past three, five years. So what was that like? How did that go? Can you take our listeners maybe through a bit of that journey to become more digital?

Wendy:

Sure. So one of the funnier parts is that our digital journey actually began in San Francisco when I attended the Silicon Valley Community Foundation Conference as a delegate with Community Foundations of Canada. And I think your boss at the time was there. And I had really gone because I wanted a window because I knew how Silicon Valley was in terms of the community foundation. I thought, oh my God, they will probably have some really cool tech. Right. That's what I was thinking.

James:

Yeah.

Wendy:

So if I go there, maybe I'll get a really great window into all these different types of technology. So I had to go all the way to Silicon Valley to meet Anil and to get some exposure to what you did at Grantbook. And I shared with him my challenge of the cost of shifting because we don't have any lines in our budget.

I still have to kill about 20% of what I eat here. We're not a completely self-funded organization yet like a lot of the older ones are. We're still within our first generation. So the reality for us was, how am I going to pay for this and at the same time find the capacity and the time to transition the organization? And at this as well, our director of philanthropy really wanted a CRM solution. And we were looking at adding on another provider, am I allowed to say their name?

James:

Yes, you could. If you want. Yep.

Wendy:

Okay. Blackbaud was providing because they had bought Raiser's Edge I believe it's called. We were hearing that it was supposed to be integrated with FIMS, but it wasn't quite perfect and would take time. So we were hearing it was $50,000 and as I was talking to Anil about it, he said, "Well, how do you know that's what you need?" And I was like, "Well, how do I not know?" And he goes, "Well, have you done a digital strategy?" And I was like, "What the hell is that?"

James:

I hear you.

Wendy:

You might've heard that before. 

James:

Some days even from myself. Even some days from myself, Wendy.

Wendy:

So it was him sharing how there's a need to appreciate the culture of the organization in order to find the right technology. And then I shared with him the story that the team here had told me about how a board member recognizing there was a need for digitization had brought in a consultant without the consent of the CEO at the time. Had done a top down analysis and made some recommendations which the team didn't support. And I thought, I don't want to do that. I want to make sure that the team who's going to use it is enthusiastic about it. And at the same time I also felt we were getting some competition from bank based funds or I guess they're called donor-advised funds.

And I was concerned the banks are just technology companies, right, with numbers when you plunk them in. And I was worried like, how are we ever going to be able to compete with a bank going forward? Our community is a wealthy community filled with financial professionals, so how are we ever going to attract people if we don't have online access? So I was worried about things like scalability, online access for our donors, value to the donors or fund holders. So those were all the things that were in my head. So you probably remember my mantra. I was all about scalability. I kept saying scalability. I think I had one word for two years.

James:

It's incredibly critical. Yeah. I mean the scalability point, it's so critical, Wendy. Please continue soon, but given the growth your community foundation has had since we first interacted, I think your point is very correct. Very few people, I guess, want to make their system more efficient so they can stay the same. There is definitely an angle here that it can help you grow more easily really, and be more impactful more easily.

Wendy:

Yeah. Well, the reality is because we were able to go on that journey and bring in a variety of different granting, CRM, donor portal, it's all integrated. What we ended up doing was freeing up more time for staff to work on more strategic initiatives. And that to me has been the incredible value proposition that the digitization has offered us because without that, I mean, we were a back office, right, for anybody who wanted to start in lieu of a private foundation. We offered you the opportunity to come under our tax filing. We'll assist you with learning about charities. We'll do research about the community through our vital signs reports. And that was our value proposition, which I think the banks have really encroached in with their donor-advised funds. They don't do the community-based work and they don't know the charities very well, but the back office part is there. Right.

And so what's your value proposition in this type of environment where somebody outflanks you? That's all they do is tech, right? So you've got to figure out what space and purpose you have and hold. We adopted the purpose, community building through philanthropy and now, I feel like we're able to do that and able to focus on that because of the process that we went through here when it wasn't. It's never linear. I remember you and Neil talking about the trough of despair through the transition. And we would often have conversations about who is in the trough of despair.

James:

At least you had a name for it? And you knew you could climb out of it. It's really important, but I'm glad the term stuck.

Wendy:

It’s really important to tell people that. That you're not going to turn it on and suddenly the angels are going to sing and you're just going to sit back and relax, the AI is going to do everything for you, right? So there were learning opportunities and we did of course go with Foundant. And I would never have thought about some of the questions that Grantbook asked the technology providers because they weren't my top of mind. And I guess for tech people, they're top of mind, but charity people, they're not. And one of the key things that I thought was really important was it's not just customer service in terms of fixing your program if it's not operating that day, like it's not responding, but it's actually being able to tell the owner of the tech what changes you need so that you can do your job better.

And Foundant provides that to us and we've been able to get some changes and adaptations to the tech that's helped us incredibly. And so I'm forever thankful to Grantbook for helping us understand what the technology is we need, doing the due diligence on the providers and then helping train us really. And I think I've shared with you, James, that we have a number of women who are grandmothers around here and they all wanted to adopt you. And then I got the request, can we hire James? So you were so good at holding everyone's hand and keeping us focused and just reminding us because it took us a year. We started at the end of 2017 to begin the transition in the last quarter. And then we did the transition for all of 2018.

And so we had no idea we were getting ready for a pandemic. So when the pandemic came, we were in a place where we just left the office and we could work remotely. And we had the blessing that the only thing that we hadn't fully changed was we were in the process of switching to electronic fund transfers. We had planned to do that for 2020, but we did it in a week. So we are forever thankful. And the other big thing that we realized and you were very helpful with as well is we didn't load all the platforms at once. Right. So we started with the financial management. We added the CRM. We added the donor portal. We added the granting application. And this year for whatever serendipity there is in the world, we had decided last fall to...

Because I have to admit, I was just shocked when I started looking into it that a lot of the service organizations like the Rotary clubs and we have a group called International Order of the Daughters of the Empire and the Optimist and all these different groups, had scholarships and bursary programs and they were all paper-based. Who has access to that? What kid can find those? We talk about digital citizenship and how it makes things more available, but if you don't know where those applications are, where to find them and how to download them, you're not going to have access to those resources. So at the end of last year, we loaded about, remember we're a 200,000 person community, we loaded $300,000 worth of scholarships and bursaries onto the scholarship fund.

And we gave it away for free. For me, it's a loss leader. There's my business background where I say my main requirement was as long as Oakville students are eligible to apply, anybody can put their application on our base. And we customized the applications for everybody except for the basic information, but they were all customized in terms of questions so that everybody could put their logo on them. And Darren gave me a sweet deal at Foundant because I told him we'd be the showcase. I'm a bit of a wheeler dealer. I take that from my dad. And so he gave us that bump so we could be the showcase. And so the schools in our region closed in March and they didn't open back up, but we had 500 kids on that platform accessing scholarships and bursaries and getting awards.

That is the beauty of the technology, right? The kids had a one window access. They could find all these scholarships. Our reviewers could go into the platform and into their individual applicants and adjudicate them and share it online. Who knew we were going to provide that great service. So, that to me has been one of the things I'm really proud of. And the other is of course, Foundant has a crowdfunding application and we've been using that. So instead of our funds, and as I've often shared with people, I really dislike competitive granting processes although, this one has a bit of competitiveness to it, we took applications from over 50 charities in our community and enabled them to apply for up to $25,000. And we said, you know what, operations are just fine. We don't need you to do any special tricks because what you do is important to our community and you're keeping it resilient.

And we said we've got $250,000 to match, so we're matching $150,000 from our fund holders and $100,000 from our public. We're already at almost $200,000 from our fund holders and $150,000 from the public as we talk and growing. So we've exceeded the match and we've exceeded half the $1.2 million that they were looking for and I couldn't be happier. So it's really enabled us to provide a great service and people love it. I call it a virtual shopping mall for charities. And we have people going on and put giving $25 to 15 different organizations. I didn't even envision this value proposition as we talked about what we could do in the future. I had no idea that this would be an opportunity. So that's been our journey and very thankful to have met Grantbook in San Francisco.

James:

That's awesome, Wendy. And I think you've just highlighted so many important and critical elements of how pursuing a digital journey can enable so much. But I also want to come back just a little bit to how much of this seems to be driven by values and mission and the core value proposition of Oakville? Because sometimes we do have folks coming to us who say, I need to fix my technology, particularly in the community foundation space because they say, hey, banks are becoming more competitive as you've so aptly described. They are nothing if not a back office powerhouse. So we often then turn back and say, that's great, we can give you the tech, but what is the value you're bringing to your community and your donors? Can you talk a little bit more about how you got to that point about community building being your value proposition, how you explored that, how you arrived there? I think that's a really great point.

Wendy:

Yeah. So one of the things I often hear as well, and I'm sure every other community foundation does, which is, what's your role distinguishing you from the United Way, right? So United Way is very focused on human services and they do great work. We are 360 degree grantors. We grant to environment, animal rescue, arts, culture, heritage, education in our communities. I don't know if this is the same for the United States. No offense Americans, but your public and healthcare and education systems are embarrassing. But in Canada we are heavily taxed and we have very good systems, but they're not the mainstay of what we do at community foundations, but we still support them with scholarships and bursaries. And of course we still have to build part of our hospitals in the local communities.

And our hospitals are the biggest fundraisers in the country. So those are the things that we find ourselves very much front and center with and how we approached what our purpose is, was really to say, okay, what are the things that we can do to increase people's belonging in the community? And one of the things that we have done in the past and we continue to do, we built a whole heritage trail system through our community. And we did it 20 years ago and we ended up expanding it. So we began thinking about our role as the glue and being the glue and the convener, how can we think about how we make people in our communities more sustainable? And we've actually adopted the Sustainable Development Goals, but we're not really focused on the basic people needs, one. We're actually focused more along the lines of community education and employment.

So we see our role, and part of it is implicated by the pandemic, but is around community resiliency and community building. And that aligns with, I never remember the SDG numbers, but I think it's 10. We see our role as making sure there's opportunities in our community for education, employment, and social economy. And I can get into that. Those are SDGs, I think it's like four or five and six or something and some one's I'm wrong. And then of course the other one is to reduce inequalities and then create partnerships for sustainable development. So when we started thinking about what is our place and being that facilitator, convener, we have one program that we've extended since I've been here and it started the year I started. I didn't create it, but implemented it, where we take single moms. We work with a variety of partners like government, YMCA, the local community college, which is a local college and we support the moms for four years.

Get them to go back to school. Their kids are supported with aftercare. They're given income assistance and housing through the regional government. And at the end of their course, there's an industry counsel mentoring them and helping them find jobs. And it has an 87% success rate. So that program was there and it's modeled on one in Toronto and it's incredibly successful at removing people from income assistance. And the wonderful thing about it is that from my perspective is that it puts the individual in the center and wraps all supports around them and then has a case worker navigator. And with that model, one of the most challenged groups in our society is kids that are coming out of child welfare systems, foster kids. Kids who are wards of the state. We have taken that model and brought, believe it or not, 20 different groups together to support them. Different charities, government, not for profits, even some businesses.

And right now we had our first 26 students go through it. And we're using an SDG indicator called NEET, which measures how many kids are not in employment, education and training. And for these kids, more than one in four was not in education, employment and training between the ages of 15 and 24. And the rest of our population is five to 10% depending on age and gender. And these kids that are now up to 92% of those kids. The first 26 are satisfied with our education, employment and training. And so when you think about being able to free up your resources that are focused on paperwork and redeploy them to a successful outcome in your community, that is the real value proposition of digitization for me. Right. You can show a bunch of images of people sitting on the side of the curb or homeless, that's not going to inspire people to give.

What inspires people to give is your program that takes someone like that and turns them into a success because as soon as we got our first successful graduate in our single mom program, money doesn't stop coming in and I'm expecting the same with this program once we showcase those successful youths. People love to be associated with success. And so that to me has been the biggest change is where we can take that administrative resource and redeploy it for our community's benefit. So that's my learning curve.

James:

It's an amazing story, Wendy. And I think it's just tying the line between why digitize, with all that wonderful work that has always been waiting to be done. Right. It's not that it wasn't there. It's always been there. It's just been waiting to be harnessed and for people to focus their attention. I want to come back. You talked a lot about centering the individual and this is really fascinating for me because in the tech space, there's a lot around human centered design and in some philanthropy spaces, they're pursuing that as well. And a lot of people are like, well, how do I do this in programming? Can you talk a little bit about how you arrived at centering the services around the individual and putting them at the center? How did you and your team come to that approach?

Wendy:

So I think it's also an outcropping of in Canada the discussions around truth and reconciliation with our Indigenous population and how Indigenous communities have really been the focus of what we call white savior philanthropy. Right. Where the charity rides on their horse over to the First Nations reserve and says, and this is a true story and it's local, "I'm here to put Toastmasters. Let's put a Toastmasters club together. This will help you people learn how to publicly speak and present yourself so that you can get good jobs." Okay. Well intentioned, not the priority of the community and highly offensive. And so it's a need to have an understanding of what the client's needs are, not the donor's needs. And that is a big learning curve in philanthropy right now because our challenge is we have to fundraise from people who've earned these funds. And in order to separate them from these funds and give them the trust, you need to show them that they like to think that they know how somebody's journey should go and your challenge is to show them how success looks like in reality.

And that is a really difficult conversation process and change in the sector. And right now with that youth out of care program, youth coming out of the child welfare system, we call it the care system in Canada. And it was interesting because we had parties sitting at the table and we had one fellow who was with a credit union. And he said, "I know the solution to this. We just need to find housing for these kids." And of course you do need to find housing, but once they're centered with housing, we can wrap all the services around the house. Right. And that seems logical and it would probably work for seniors. It's probably a great solution for seniors, but the youth kind of looked at us and said, well, until I know what I'm doing, I don't want to live somewhere.

I need to know what my purpose is, is what they were saying. Am I in education? Am I in employment, I'm training? What program am I in? Until I know what my purpose is, I'm not willing to settle down. That's the last of my worries. So they wanted a sense of purpose. And that was for me where I took a step back and I thought, whoa, there it is. That is client centered or client led developmental programming because when I was in the private sector, marketing people had focus groups, right? And they're going to ask their customers what they want, just like Darren did with me, what do you want, right? And so I think that is one of the biggest challenges in our sector is centering our charitable work. And everybody has great work, but it's all supply side driven in most cases. Right. It's not demand side driven. And that is what I see is also one of the things that it's a hard nut to crack and we're just going to keep working at it. But it's really a challenge because in the private sector, your money comes from your customers. So it's easy to make it client driven. It doesn't work that way in the charitable sector.

James:

No, there's definitely a business model canvas or impact, or some sort of value canvas that the sector we need to really figure out because you're right. Who's keeping you alive basically is not really who's consuming your impact services. It's a tough nut to crack, but I think demonstrating it via these programs and showing the momentum that you can get by making some folks feel uncomfortable for a little bit, I think is a great place to start. Because it is really fantastic the way you've and Oakville CF has started to build programming. So thanks for sharing that as well.

Wendy:

Hey, my pleasure. Anything else you need to know?

James:

No, I think we can pivot to wrapping up here. So here at the podcast, whenever we wrap up, there's just one or two sort of quick fire questions that we'd like to do. And I think for this one, I'm going to pick this one. If you had a magic wand and you could wave it to fix one challenge in your day to day, what would you fix? What's top of mind, Wendy?

Wendy:

I would stop all the people on LinkedIn who sell technology from emailing me. That's my big ask. Stop mailing me.

James:

That is perfect. It's funny, we usually get like, sometimes we get like, oh, if I could fix the system or if the world could change this way. I think this is great at saying stop the noise, I have other stuff to do.

Wendy:

Yes. But I just wanted to extend my thanks again to Grantbook for making it so easy for us to move forward with our digital strategy and making it so inclusive of the team, which was phenomenally important and flagging for us poor charity types. Really putting us into a space of knowledge around technology. And so I'm forever grateful for you guys and highly recommend you to your audience.

James:

That's perfect. Thank you so much, Wendy. I really appreciate your time today. If folks listened to this and are interested about your work or maybe want to help you out at all, even if they're not from Oakville, do you have any thoughts about where they could go or what they should look at?

Wendy:

They're always welcome to visit our website, which is www.theocf.org.

James:

Perfect. So thank you so much.

Wendy:

My pleasure. All the best.

James:

All right. Have a good one.

Wendy:

You too.

James:

The More Good Podcast is produced by Sara Saddington. Grantbook is a strategic technology consulting firm for grantmakers around the world. Don't forget to subscribe to the More Good Podcasts wherever you get your audio and learn more about our work at grantbook.org.


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Sara Saddington

Content Lead

Content Lead

Sara Saddington is a content marketer with experience crafting compelling messaging for B2B companies at the intersection of technology and service delivery. As a lifelong reader, writer, and editor, Sara brings an innate understanding of narrative structure, a passion for data-driven story-telling, and an eye for clarity and consistency. Sara is excited to support the Grantbook team in their mission to help foundations around the globe plan, design, implement and optimize their digital strategies so they can activate more good in the world.