Author Archives: Brandi Butler

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.

Weekly Roundup | 🛡️Top Strategies of the Week for IT Business Leaders – January 13, 2021

Finding new ways to add value as a leader is a major key to success. Here are some thought-provoking offense and defense themes from the previous week.

Weekly Summary

IT Business Leadership, Strategy & Innovation

Offense & Defense Innovation

1.    “Find Ways to Add Value as a Business IT Leader”- Sean D. Mack, CIO, and CISO at Wiley, discusses the ways the Business IT Leaders can add value to the organization.

2.    “What are the Highest Risks of MFA?”- Roger Grimes, Data-Driven Defense Evangelist at KnowBe4, advises that CIOs and CISOs should never use Biometrics as a standalone authentication method.

3.    “How to Empower Your Team with Kolbe, Myers-Briggs, and Emergenetics”- Lou Pellicori, Managing Director, Chief Information and Technology Officer at Glenmede Trust Company, N.A., describes his experience using personality testing in team building.

4.    “Practical Security Decisions you can Make Today with Quantum Computing and Data Encryption”- Roger Grimes, Data-Driven Defense Evangelist at KnowBe4, talks about how to prepare for the advances in quantum computing.


Practical Security Decisions You Can Make Today With Quantum Computing and Data Encryption #205

In Episode #205, Bill is joined by Roger Grimes, Data-Driven Defense Evangelist at KnowBe4, to talk about the current state of quantum computing and how best to prepare for the future from a security perspective.

Quantum computing is still relatively young with the first computer being built in 1998 and containing only one qubit. This technology has advanced rapidly, however. There are some who theorize that quantum computing will have thousands of qubits and be able to break cryptography within a couple of years.

It was this rapid increase in development that made NIST issue a warning in 2016 that quantum computing can crack asymmetric encryption soon and encouraged businesses to prepare. Awareness of this issue is still very low as Roger says, “I don’t talk to anyone that even knows this is an issue. It’s like this looming Y2K problem getting ready to come across us.”

Roger also offers several practical security tips for CSOs including to avoid putting critical secrets across your network, to perform a data-protection inventory, and to create policies so that people aren’t buying systems that are bringing in weak crypto.