Ever to Conquer

Why Every State Agency Needs a CCO with Bradon Rogers, Chief Customer Officer at Island

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 [http://redleif.io] to learn more. Connect with Bradon Rogers LinkedIn [https://www.linkedin.com/in/bradon/] Learn more about Island [https://www.island.io/] Connect with Jamie X [https://x.com/JDubyaGrant?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor] LinkedIn [https://www.linkedin.com/in/jdubyagrant/] Learn more about RedLeif [https://redleif.io/] Follow the Show YouTube [https://www.youtube.com/watch?v=HarpE1cygB4] Apple [https://podcasts.apple.com/us/podcast/ever-to-conquer/id1810573654] Spotify [https://open.spotify.com/show/6Ud9gF1XWvhhtJdZXnXsuV] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.

How Florida Built the #1 State University System with Ray Rodrigues, Chancellor of the State University System of Florida

Florida has been ranked the #1 state university system in America for nine years running. But what does it really take to build and keep an education system at the top? In this episode, Jamie sits down with Ray Rodrigues, Chancellor of the State University System of Florida, to talk about how Florida became the nation’s model for affordable, high-quality higher education and what it will take to stay there. Ray brings a uniquely powerful perspective. He started his career at General Electric, spent 17 years at Florida Gulf Coast University, served more than a decade in the Florida Legislature, including as House Majority Leader and State Senator, and now leads a system of 12 institutions and more than 430,000 students. His path through the corporate, academic, and political worlds gives him a rare vantage point on what it takes to reform higher education. Together, they dig into: * How Florida froze tuition for a decade while rising to #1 in national rankings * The story behind performance-based funding and preeminence designations * The debates around intellectual diversity and DEI, and what the data really shows * Where higher ed is heading next, from affordability to microcredentials and three-year degrees, and much more. If you are an educator, policymaker, parent, or just someone who wants to understand where the future of higher education is headed and what it will take to keep it strong, this is the episode you cannot afford to miss. About Ray Rodrigues Ray Rodrigues is Chancellor of the State University System of Florida. In this role, Chancellor Rodrigues is the primary liaison between the Board of Governors, the State Legislature, the Executive Branch, Departments, and Agencies throughout the State of Florida. The State University System has been ranked #1 in the nation by U.S. News and World Report since 2017. Additionally, the Chancellor is CEO of the Board of Governors and provides oversight, guidance, and administration by implementing policies and regulations adopted by the Board, which impacts 12 institutions and more than 430,000 students annually.    Chancellor Rodrigues started his career at a corporate component of General Electric, where he managed their U.S. Import Compliance team. Additionally, Ray Rodrigues then worked for 17 years at  Florida Gulf Coast University, where he held positions of Director of Interagency Partnerships, Director of Community Relations, and Business Manager for the College of Arts and Sciences. In addition to his professional career, Chancellor Rodrigues has an extensive career in public service, where he served as the Florida State Senator for District 27 and four terms in the Florida House of Representatives. During his time in the Legislature, Rodrigues served as the Chair of the Senate Reapportionment Committee, Chair of the Senate Government Operations Committee, Chair of the House Health and Human Services Committee, and the House Majority Leader. His ability to listen, build consensus, and be an agent of change led to his unanimous appointment as Chancellor. Chancellor Rodrigues earned a Bachelor of Arts degree from Berry College in Rome, Georgia, and in 2017 earned his Master in Public Administration (MPA ) from Florida Gulf Coast University. Ray is an avid reader, statesman, and storyteller. Ray, his wife Ruth, and son Rhett call Tallahassee home. Guest Quote “ The American confidence in higher education has declined significantly. The number one reason why it has declined is the American public believes higher education is too focused on having faculty members push their own political agenda, and that indoctrination is harming the value of the degrees. We're armed to show that that's not what's happening in Florida.” Time Stamps  00:00 Episode Start 01:45 Chancellor Ray Rodrigues's Background 04:33 Challenges in Higher Education Funding 07:36 Legislative Experience and Policy Making 17:37 Role as Majority Leader 20:41 Transition to Chancellor 22:58 Navigating the Higher Education Ecosystem 41:05 Intellectual Diversity and Free Speech on Campus 45:16 Legislation for Intellectual Freedom 01:02:24 DEI in Higher Education 01:05:54 Legislation to Eliminate DEI Programs 01:13:24 Performance-Based Funding in Florida 01:21:52 Parental Advice Against College 01:22:51 Florida's Unique Higher Education System 01:24:29 Diversity and Success in Florida's Education 01:27:50 Innovations in Higher Education 01:35:18 Engaging with the Public Sector 01:38:36 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 [http://redleif.io] to learn more. Connect with Ray Rodrigues Learn more about the State University System of Florida [https://www.flbog.edu/] Connect with Jamie X [https://x.com/JDubyaGrant?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor] LinkedIn [https://www.linkedin.com/in/jdubyagrant/] Learn more about RedLeif [https://redleif.io/] Follow the Show YouTube [https://www.youtube.com/watch?v=HarpE1cygB4] Apple [https://podcasts.apple.com/us/podcast/ever-to-conquer/id1810573654] Spotify [https://open.spotify.com/show/6Ud9gF1XWvhhtJdZXnXsuV] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.

How Tech is Raising Our Children Without Consent with Dr. Lisa Strohman, Clinical Psychologist and Founder of Digital Citizen Academy

We talk a lot about protecting our kids’ future, but the real fight is happening in classrooms, living rooms, and phone screens every single day. In this episode, Jamie sits down with Dr. Lisa Strohman, clinical psychologist, former FBI profiler, and founder of Digital Citizen Academy, to talk about the real psychological and societal cost of unchecked technology and what it’s going to take to reverse course. Lisa brings a uniquely powerful perspective. She has been on the ground at Quantico profiling predators, in the halls of Congress crafting policy, and in therapy rooms with the families paying the price. Her work now centers on one mission: to give kids, parents, and educators the tools to fight back against a digital world they never signed up for. Together, they dig into: * Why social media is more dangerous than a gun in your child’s room * What AI literacy in schools needs to look like  * The real neuroscience behind screen time, attention, and identity * Why tech isn’t evil, but intentionality is everything * What Lisa is building to scale truth, empathy, and protection in an era of misinformation and digital harm, and much more. If you’re a parent, educator, policymaker, or just someone who wants to understand how we ended up here and what we can do about it, this is the episode you can’t afford to miss. About Dr. Stohman Dr. Lisa Strohman has widely become known for her advocacy and education around mental wellness as it relates to our digital lives. She has worked with thousands of parents, schools and children around the globe. An attorney, clinical psychologist, and author, Dr. Strohman established the Digital Citizen Academy, a non-profit program offered to schools with an in-home plan that educates, empowers and inspires balance and prosocial use of technology.  She is the founder and director of Digital Citizen Academy, one of the first organizations to address the global issue of technology addiction and overuse. As a licensed clinical psychologist, Dr. Strohman has spent more than a decade working with individual, family and adolescent clients struggling with issues including depression, anxiety, addiction and technology overuse. Recognizing the growing challenges parents now face with their children, and the increasingly serious issues her young patients are dealing with due to our growing dependency on technology,  inspired Dr. Strohman to launched the Technology Wellness Center, which she co-founded with Dr. Melissa Westendorf JD, PhD in 2014. With her work in schools and in the media Dr. Strohman recognized the need for prevention education and diversion programs and founded Digital Citizen Academy for students, educators and parents addressing these issues related to technology. Dr. Strohman attended the University of California, Davis where she received a Bachelor of Science in Psychology, graduating Magna Cum Laude. She then completed a joint, integrated program in law and Psychology at Villanova and Drexel Universities. During her undergraduate career, Dr. Strohman gained experience as a lead program coordinator with Families for Early Autism Treatment (FEAT), as a family reunification therapist and a hospice counselor. While attending graduate school, she performed research in substance abuse, risk communication and child abduction. Her avid interest in public policy earned her the honor of becoming a legislative intern for Congress. She was also selected as an honors intern with the Federal Bureau of Investigation and invited to become a visiting scholar with the FBI’s National Center for the Analysis of Violent Crime division as she completed her dissertation. After earning her Juris Doctorate, Strohman worked at a large law firm, while completing her residency at the Arizona State Hospital in both a clinical and forensic rotation in clinical psychology. She eventually settled back into her counseling practice as the clinical psychologist with Lifescape Medical Associates, where she utilizes her training in cognitive behavior therapy to help patients. In addition to establishing the Technology Wellness Center, Dr. Strohman and Dr. Westendorf developed an assessment test to help parents identify if their child is at risk from technology overuse. The two have also co-authored a book, Unplug: Raising Kids in a Technology Addicted World, published in July 2015. In an effort to educate parents, caregivers and students, Dr. Strohman is a guest speaker to schools, parent organizations and students to help raise awareness and offer preventative tools and resources. She is also frequently featured in the media as an expert source for issues related to technology use and behavior, including a weekly feature on Dr. Drew’s radio show as well as an expert on Dr. Oz’s ShareCare site. Guest Quote “ I don't want to overwhelm people with here’s how it can be really super dangerous. I want to really give that picture of tech as a tool is awesome, tech as a toy, not so much. So let's kind of look at what the good and the bad of it is.” Time Stamps  00:00 Episode Start 01:35 Lisa's Early Life and Background 04:13 Lisa's Professional Journey and Achievements 07:35 Experiences in Law and Psychology 17:01 Challenges and Insights from Government Work 26:48 Impact of Technology on Critical Thinking 34:23 Rethinking the Formative Years 40:34 Digital Citizens Academy: Addressing the Problem 47:39 Challenges in Education and Social Media 54:26 Scaling Solutions for Schools 01:03:44 The Role of AI in Education 01:27:02 Executive Order: AI Training for All 01:32:33 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 [http://redleif.io] to learn more. Connect with Dr. Lisa Strohman LinkedIn [https://www.linkedin.com/in/lisa-strohman-j-d-phd-478a64b] Learn more about DCA [https://digitalcitizenacademy.org/] Connect with Jamie X [https://x.com/JDubyaGrant?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor] LinkedIn [https://www.linkedin.com/in/jdubyagrant/] Learn more about RedLeif [https://redleif.io/] Follow the Show YouTube [https://www.youtube.com/watch?v=HarpE1cygB4] Apple [https://podcasts.apple.com/us/podcast/ever-to-conquer/id1810573654] Spotify [https://open.spotify.com/show/6Ud9gF1XWvhhtJdZXnXsuV] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.

From Transactions to Trust: The Empathy-Driven Public Sector Playbook with Rajeev Bajaj, EVP of Education Solutions at MGT

The public sector doesn’t need more point solutions. It needs partners who can actually help solve the right problems. In this episode, Jamie sits down with Rajeev Bajaj, EVP of Education Solutions at MGT, to talk about what it really takes to modernize public sector go-to-market, from both sides of the table. Rajeev brings a rare perspective, having led in the classroom, at city hall, and in the private sector. That experience fuels his mission: to replace hero selling with real partnerships, grounded in listening, trust, and discovery. For Rajeev, it’s not about closing the deal. It’s about designing solutions that public sector leaders can stand behind and scale. They dive into: * Why the "AE as hero" model fails in complex public ecosystems, * How to build discovery-driven sales teams that lead with empathy, * What public sector leaders can do to shift from passive buyers to empowered change agents, * Why the next wave of innovation needs to be open source, * How to bridge the trust gap between government and big tech, and much more. If you're building, selling, or leading in the public sector, this conversation is a blueprint for making the shift from vendor to true partner. About Rajeev Rajeev Bajaj began his career in education over a decade ago as an elementary school teacher at PS 161 in Harlem. After his time in the classroom, he transitioned to key leadership roles at the New York City Department of Education, including Managing Director in the Office of Accountability. Most recently, Rajeev served as President of Sangari Global Education, an education services provider that delivers inquiry-based science educational materials to over 500,000 students worldwide. Prior to his work in education, Rajeev began his career in technology first at Microsoft and later as part of the core team that launched Jamcracker, a web services provider based in Silicon Valley. Rajeev graduated from Northwestern University with a B.S. in industrial engineering/management sciences and has a master’s degree in education from Hunter College. He is a recipient of a Fulbright Teaching Fellowship through the Fulbright Memorial Fund-Japan and is a 2012 graduate of the Broad Foundation’s Fellowship for Education Leaders. Guest Quote “The ability to listen, to ask good questions, to be a good consultant in that way, and then to co-design what a solution or an architecture for a solution might look like—I think is the path to success.” Time Stamps  00:00 Episode Start 02:40 Developing the Next Public Sector Leaders 05:22 Building Trust and Empathy in Business 09:58 Team-Based Approach vs. Hero Selling 19:18 Public-Private Sector Collaboration 30:31 First-Order Thinking in the Public Sector 43:15 Transitioning from Public to Private Sector 47:50 Bridging the Talent Gap: Public to Private Sector Transitions 53:52 Challenges in Moving from Buy Side to Sell Side 56:08 Rethinking the AE Role as Chief of Discovery 01:01:39 Customer Acquisition and Lifetime Value 01:05:59 AI and Education 01:14:32 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 [http://redleif.io] to learn more. Connect with Rajeev LinkedIn [https://www.linkedin.com/in/bajajr/] Learn more about MGT [https://www.mgt.us/] Connect with Jamie X [https://x.com/JDubyaGrant?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor] LinkedIn [https://www.linkedin.com/in/jdubyagrant/] Learn more about RedLeif [https://redleif.io/] Follow the Show YouTube [https://www.youtube.com/watch?v=HarpE1cygB4] Apple [https://podcasts.apple.com/us/podcast/ever-to-conquer/id1810573654] Spotify [https://open.spotify.com/show/6Ud9gF1XWvhhtJdZXnXsuV] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.

The People Part of Technology is Foundational with Jon Rogers, Director of Strategic Workforce Planning at Indiana Department of Child Services

Government isn’t broken because of bad tech. It’s broken because it was never built for the talent we need now. In this episode, Jamie sits down with Jon Rogers, Director of Strategic Workforce Planning at the Indiana Department of Child Services, to unpack what it really means to build the future of public sector work, from the inside out. Jon shares his unconventional journey from high school teacher to CIA officer to government tech leader, and how that unique perspective fueled a bold new model for hiring and retention in state government. His mission is to replace outdated degree requirements with real skills, real people, and real results. They dive into: * How Indiana’s apprenticeship-style program is transforming future technology leaders, * Why soft skills like communication are actually the hardest to master, * How public sector teams can out-compete on mission and culture, * What legacy IT leaders get wrong about modernization, and much more. If you're rethinking how we recruit, reskill, and retain talent, this episode is a masterclass in what’s possible when you start with people first. About Jon Jon Rogers is the Director of Strategic Workforce Planning, Indiana Department of Child Services. Previously, he was the Director of Strategic Workforce Planning for the Indiana Office of Technology (IOT), which provides consolidated IT services in support of Indiana’s executive branch. Jon joined IOT in 2018 and became the agency’s inaugural Strategic Workforce Planning staffer under former CIO Tracy Barnes. In his current role, he developed and administered a nationally recognized work-based learning program – State Earn and Learn (SEAL) IT – which reskills adults from other jobs and occupations into information technology and security. Since 2020, SEAL IT has graduated forty-eight adults (a graduation rate of over 84 percent) into positions supporting the State of Indiana. While doing so, Jon led the agency’s efforts to move into skills-based hiring, removing degree requirements from job postings, and he was a member of Indiana’s delegation to the National Governors’ Association Community of Practice in Skills-Based Hiring (2024-25). SEAL IT and IOT’s Strategic Workforce Planning team received a State IT Innovation of the Year award from StateScoop in consecutive years (2022-23), an HR Impact award in Talent & Recruitment from the Indianapolis Business Journal, a National Association of State Chief Information Officers State IT Recognition Award for Enterprise IT Management Initiatives (2023), a StateScoop 50 award for state leadership (2024), and the Indiana Chamber of Commerce/Institute for Workforce Excellence Impact Award for Innovative Program of the Year (2024). Before joining IOT, Jon worked in federal positions with the Office of United States Senator John Warner (Ret.) and the Central Intelligence Agency, where he was a finalist for D/CIA mentor of the year. He earned an MBA and M.Public Affairs from the University of Texas at Austin, a BA in Government from The College of William & Mary in Virginia, and a Senior Certified Professional credential from the Society for Human Resource Management. Guest Quote “ When finding the right people in a workplace, don't go for the skills first. Go for the human. Go for the human pick. Pick a good human.” Time Stamps  00:00 Episode Start 02:21 Jon's background and career journey 07:19 Breaking down transferable skills and workforce development 18:35 Why soft skills are the hardest skills in tech 34:56 Entering the golden age of public sector software 51:05 Rethinking recruitment and retention 59:18 Recognizing hidden talents and fostering a strong culture 01:11:10 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 [http://redleif.io] to learn more. Connect with Jon LinkedIn [https://www.linkedin.com/in/jon-rogers-70ba36177/] Learn more about the Indiana Department of Child Services [http://www.in.gov/dcs/] Connect with Jamie X [https://x.com/JDubyaGrant?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor] LinkedIn [https://www.linkedin.com/in/jdubyagrant/] Learn more about RedLeif [https://redleif.io/] Follow the Show YouTube [https://www.youtube.com/watch?v=HarpE1cygB4] Apple [https://podcasts.apple.com/us/podcast/ever-to-conquer/id1810573654] Spotify [https://open.spotify.com/show/6Ud9gF1XWvhhtJdZXnXsuV] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com [https://pcm.adswizz.com] for information about our collection and use of personal data for advertising.