How to Use a Metaphor Like Rocky to Motivate Your Team | Jason Bressler Evp/CTO of United Wholesale Mortgage, the #1 Wholesale Lender in the U.S. #206

In Episode #206, I talk with Jason Bressler. Jason is the EVP, Chief Technology Officer at United Wholesale Mortgage, the #1 wholesale lender in the nation.

As a CIO and Business IT Leader here are some wins you will get by listening:

·     How to use a metaphor (like Rocky Balboa) to motivate your team. (9:30)

·     When you’re on your heels, how can you shift the culture in the midst of taking a lot of heat (10:30)

·     How to hire in a fast-moving company (From 200-1,100 employees) (6:00)

·     How to be a people leader with a tech background (4:30)

·     How to scale communication- “How can people own your messaging?” (17:30)

·     How to lead a team of over 1,100 IT Professionals. (4:30)

·     The power of mentors. (13:30)

·     The components of servant leadership- (2:00)

o  Creating a safe space

o  Challenging the “Why”

o  Gathering opinions and discerning which is the best

·     Why Jason is so active on LinkedIn as well as about his passion and leadership development. (00:30)

·     Why Jason is a big believer in culture over skill. (1:00)

·     including how to create a “Family Feel.” (6:00)

·     How to get your IT team to work best with business folks. (7:30)

·     The best way to innovate as a Business IT Leader (11:30)

·     Why passion is critically important. (14:30)

·     People burnout because life makes them forget why they do what they do. (15:30)

·     When you have order in something that you can control, it helps you distinguish between order and chaos. (18:30)

·     Leadership best practices. (19:00)

In this role, Jason has taken on the responsibilities of both a CIO and CTO. Jason’s background is exclusively in running IT organizations for mortgage companies. He has spent the last 25 years in this space, starting out in smaller shops and eventually working his way to United Wholesale Mortgage where he leads an ever-expanding team of over 1,100 IT members.

Jason has built a reputation in the industry for his incredible work ethic. He does whatever it takes to accomplish his goals and takes pride in his style of leadership. In our conversation, Jason says what is really important to him is becoming a people leader with now a technology background.

How to connect with Jason Bressler:

·      Jason Bressler’s LinkedIn

People referenced in Podcast:

·     Gary Vaynerchuk (Marketing Expert)


You can go to the show notes to get more information about this interview and what we discussed in this episode. Click Here to download the full transcript.