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Jason Webb —Milwaukee-Based Advocate of Racial Reconciliation Shares His Insights on What it Takes to Be a Pastor and Public Speaker

Originally published on

Jason Webb is a Milwaukee-based movement leader, public speaker, advocate for racial reconciliation, and an entrepreneur. His skillset includes networking, fundraising, strategic planning, leadership, merger and acquisition, recruiting, and business expansion. Mr. Webb has mobilized these skills to establish and manage churches and nonprofits and their budgets. He recently obtained a new leadership role for Great Lakes Church in Kenosha, Wisconsin.

Mr. Webb, you are a successful pastor and a public speaker, with extensive domestic and international experience. Why did you decide to pursue your career?

There were a couple of reasons. One, I love people and being in the industry of the church world and in the nonprofit, any chance I can have to influence people and help them really take that next step in their lives to be more fully who they are designed to be, that’s what gets me up in the morning. On a more personal level, I had, what I would consider divine encounter, where I felt strongly that that’s what I was supposed to do and that being in church work is what was really the path my life was supposed to take.

You recently started a new position as a Team Manager and Groups Director for Great Lakes Church. What does your typical day at work look like?

Every day is different. Most days consist of meeting with leaders and staff who I coach. I help equip them so that they can then work with the hundreds of people in the church in volunteer roles. That’s really my job is to help lead the key leaders and to help them be better leaders in their spheres of influence.

In addition to that, I do a lot of writing. I also do some speaking. Preparing for that reading, there’s a lot of that work. Then some of my jobs also include counseling people.

What do you consider your biggest professional accomplishment so far?

I would say my biggest professional accomplishment is the leaders I’ve developed and seen them then flourish in their different places of work. I developed a leader who worked for me several years ago and really coached and mentored him and then challenged him one day to start his own church. I said, “You can stay here and it would be great for me, but really you have gifts that I think exceed the role you’re in.”

So he started a new church, I helped fund it, and I sent him enough, a few people to start it with him, and now it’s going to a few hundred. That church has won Business of the Year in the town in a couple of those years. It’s just crazy the work he’s doing. So when I see that I think, “Okay, that’s probably my greatest accomplishment.” I’ve done other things that you can measure, such as I grew a church from nothing to 1,100 people. I helped engage in racial reconciliation efforts and all that, but really it’s the leaders I’ve developed that I say are my greatest success.

This is awesome. As a public speaker, you talk about faith and racial reconciliation a lot. What is your favorite speaking engagement so far?

My favorite speaking engagement was a couple of years ago, probably two and a half years ago. It was a Martin Luther King Day celebration where churches across Milwaukee that I’d worked with and racial reconciliation came together. I gave a talk called “The Day I Learned I was White.” Just a response to that was really phenomenal but also just the passion I have for that issue, not only because I live in perhaps the most segregated city in America but because I have two black children and that’s a really personal issue for me. There are many speaking engagements that I love, but that, in particular, was my favorite one.

It sounds like a great read for anyone who is white in the current circumstances. What does it take to become successful in your field?

Number one is a love for God. Obviously, if you’re in the church world, that’s non-negotiable and it’s more than just something you say, it has to be deep inside of who you are. You can only lead people as far as you’re going personally so that your own faith’s journey, your own spiritual journey is vital for leadership.

The second thing is you have to have a deep love for people because you’re in the people business. People are messy. They’re complicated. They’ll criticize, they’ll be in tragic moments in their life, and you have to be willing to step into the mess with them.

So those two things. Also, I think you have to just have a deep passion to change the world around you. By that, it sounds like a grand sweeping statement but really what I mean by that is you have to be willing to take risks, you have to be willing to start new things, you have to be willing to do whatever it takes to see change happen in people’s lives around you.

Incremental change is the most powerful. You’ve influenced many leaders throughout your career. But I am curious, who has had the most impact on you professionally?

When I was 18, I knew I wanted to go into pastoral work. My home church — that summer, after I came back from the college of my freshman year, the pastor there was Dan Denyes. He said, “Hey, we need an intern, would you want to be that?” He just took me under his wing and taught me what it meant to enter into church work. I didn’t know anything that I was doing but he watched alongside me and to this day now, 25 years later, he still does that with me. He still connects with me and makes sure that I’m still becoming fully who I was designed to be in this world in the ministry.

As an advocate for racial reconciliation, you, like no other, know that it’s important to speak up about race on a church and personal level as well. How can we all contribute to racial reconciliation in light of current events?

That’s a seven-hour answer. Of course, you need to speak up, engaging in things like the protests are important. Going beyond that, to fight systemic injustice because, in the end, the protests just raise awareness of the issue but you have to engage in a much more practical level. You have to be willing to say, “Okay, how do we get involved in the school where there’s an educational gap?”

In my case, in the Milwaukee area, it is the worst city in America for the education of young black kids. How do we bridge that? How do we help kids who go home to a family where their mom is working three jobs, their dad is not there, and there are little brothers and sisters all around him, and yet they still have to do their homework? How do you help them with that? Those things are all real. Right now that’s a good thing. You have to engage in systemic issues.

Honestly, the thing I think is so vital is friendship. You have to humanize the issue. One of the things about the George Floyd video is that it shows an officer who dehumanized an individual. What we have to do is show the humanity in each other. If it makes it awkward of saying, “Hey, you know what, you’re a person of color and I just need friends of color, and I know this is awkward but I want to be your friend,” then just step into the awkwardness and say, “Okay, tell me what it’s like to be you and I’ll tell you what it’s like to be me, and we’ll engage in a relationship.”

I think so many people say things like, “I have a black friend,” but they really don’t. They just know somebody but they’re never in each other’s homes, they’re never sharing life with each other. Reconciliation always begins with friendship and vulnerability and humanity. As simple as that sounds, I think it’s where we have to begin.

That’s such great advice. Thank you so much for your time, Mr. Webb.

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