Every company says they put the customer first. But for Bradon Rogers, it’s not a slogan, it’s the job.

In this episode, Jamie sits down with Bradon, Chief Customer Officer at Island, to talk about what it really takes to build trust at scale, lead with empathy, and deliver on every promise in a fast-moving tech landscape.

With more than 25 years in cybersecurity, enterprise software, and cloud technology, Bradon has led technical and customer teams at some of the biggest names in the industry. Today, at Island, he’s helping redefine what it means to build technology around people.

Together, they dig into:

• How a Chief Customer Officer bridges the gap between engineering precision and human connection
• Why trust is the real metric of success inside any team or customer relationship
• How Island is rewriting the enterprise browser story for security, simplicity, and productivity
• What government and public institutions could gain by adopting a customer-first mindset, and much more.

If you’re a leader navigating growth, innovation, or just the challenge of building trust in complex systems, this is a masterclass in how to do it right.

About Bradon Rogers

Bradon Rogers is the Chief Customer Officer at Island, where he directs the technical aspects of all customer interactions, leveraging his vast experience in cybersecurity, enterprise software, and cloud technology. Bradon's career in cybersecurity spans over 25 years, during which he has played an executive leadership role for some of the largest firms in the industry.

Guest Quote

“  At the end of the day, the role of chief customer officer is to drive an outcome. Buying a piece of software is not an outcome. Making a piece of software pivot to be used to solve a problem that you stated at the beginning of the journey with a vendor, that to me is the role of the chief customer officer.”

Time Stamps 

00:00 Episode Start

01:22 Bradon Rogers' Career Journey

06:10 Leadership Lessons and Trust Building

19:29 Explaining Island’s Vision

21:44 Role of a Chief Customer Officer

31:22 Building Trust Through Relationships

35:02 The Importance of Compensation Alignment

56:45 Empowering Public Sector Digital Transformation

01:02:56 The Enterprise Browser Debate

01:03:45 AI's Role in Future-Proofing

01:06:30 Balancing Security and Innovation

01:08:25 Bridging Security, Innovation, and Leadership in the Public Sector

01:12:52 The Roundup

Sponsor

Ever To Conquer is brought to you by RedLeif, a digital agency focused on accelerating the modernization and security of public sector data. Visit RedLeif.io to learn more.

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