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Redesigning Healthcare. Unfiltered.

Redesigning Healthcare. Unfiltered.

Di: TopHealth Media
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Where healthcare’s most consequential decisions get made out loud.


The show where healthcare leaders unpack what’s actually driving performance, and where the next billion dollars will be made or lost. Hosted by RaeAnn, a 30-year operator who has built and turned around health plans, provider organizations, and healthcare services companies, this is not theory or trend coverage. It’s direct, on-the-record conversations with the CEOs, CFOs, regulators, operators, and investors responsible for growth, margin, quality, and transformation, this is where healthcare’s most important insights are unpacked in real time.


RaeAnn Grossman is the CEO of HLTHWorks, and she has spent more than 30 years inside the organizations responsible for driving growth, quality, risk, and operational performance across U.S. healthcare.

© 2026 Redesigning Healthcare. Unfiltered.
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  • Surfing the AI Tidal Wave: From Compliance to Culture in Healthcare
    Aug 24 2026

    Welcome to another episode of Redesigning Healthcare Unfiltered. I’m RaeAnn Grossman, CEO of HLTHWORKS, and today I’m joined by Brian Singer, a seasoned Chief Technology Officer with experience spanning health plans, providers, vendors, and healthcare-adjacent services. In this episode, we dive deep into a pressing topic shaking up the industry: the messy tidal wave of artificial intelligence in healthcare.

    Together, we explore the mounting challenges of integrating AI, from regulatory complexity and technology pitfalls to cultural shifts and accountability in day-to-day operations. We tackle the practical realities of ensuring data quality, establishing disciplined processes, and building effective governance amidst relentless regulatory changes at federal, state, and organizational levels.

    You’ll hear candid insights about the dangers of shadow AI, the importance of cross-team collaboration, and how organizations must transform their culture to survive and thrive in the face of unstoppable technological waves. Whether you’re a C-suite leader, operator, or simply navigating the evolving healthcare landscape, this episode will arm you with the perspective and strategies needed to redesign healthcare with rigor, transparency, and resilience.

    00:00 Discussing AI Responsibility and Challenges

    06:11 Risks of AI and automation

    09:36 Improving medical data automation

    11:15 Optimizing backend efficiency in healthcare

    15:31 Challenges with data standardization

    18:52 Updating legacy systems and data governance

    22:24 Addressing organizational culture change

    26:25 Challenges in healthcare AI implementation

    31:19 Balancing compliance in AI development

    34:37 Evaluating company security and AI use

    40:25 Warning about fraud and penalties

    42:10 Combining business and technology

    HLTHworks' Website - hlthworks.com

    RaeAnn's Linkedin - linkedin.com/in/raeann-grossman-299756a

    Podcast's Website - redesigning-healthcare.com

    Podcast Media Partner - tophealth.care

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    40 min
  • Accountability Without Visibility: The Hidden Risks of AI in Healthcare Compliance
    Aug 6 2026

    Welcome back to Redesigning Healthcare. Unfiltered. In this episode, host RaeAnn Grossman, CEO of HealthWorks, is joined by seasoned Chief Compliance Officer and consultant Marie to dive into the burning topics surrounding compliance in today’s rapidly evolving healthcare environment. As new regulations, audits, and AI-driven innovations transform the industry faster than ever, healthcare organizations face mounting risks and uncharted territory. Together, RaeAnn Grossman and Amelia Marie Biehler confront the uncomfortable truths compliance officers are grappling with, from invisible risks and gaps in oversight to the critical need for discipline and cross-functional governance. Get ready for a candid, unfiltered conversation about where healthcare compliance is headed and what it will take to stay ahead of the fire.

    Timestamps:

    00:00 Introduction to Compliance in Healthcare

    06:23 Discussing AI governance gaps

    08:11 AI accountability and inventory gaps

    14:11 Evolving role of compliance officers

    15:18 Adapting compliance to technical expertise

    21:32 Implementing regulatory and AI systems

    25:15 AI and compliance discussion

    26:13 Preview of AI in Healthcare


    HLTHworks' Website - hlthworks.com

    RaeAnn's Linkedin - linkedin.com/in/raeann-grossman-299756a

    Podcast's Website - redesigning-healthcare.com

    Podcast Media Partner - tophealth.care

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    24 min
  • Hard Lessons and Bold Moves: How Execution Defines Healthcare Success
    Aug 6 2026

    Welcome back to Redesigning Healthcare. Unfiltered. In today’s episode, host RaeAnn, a seasoned healthcare leader with over 25 years of experience and six successful builds under her belt. This isn’t a highlight reel, RaeAnn offers a raw look into the moments that defined her career, the tough decisions she made, and the lessons learned from both her wins and her missteps.

    She dives into the real execution challenges facing healthcare today, exploring why the industry’s biggest obstacles aren’t about knowledge, but about putting ideas into action. You’ll hear candid stories of navigating conflict, driving innovation without roadmaps, restructuring culture, and aligning people around a shared, outcome-driven vision.

    Whether you’re a health plan executive, an investor, a clinician, or someone passionate about healthcare transformation, this episode explores the principles, practical experience, and grit it takes to push healthcare forward. Stay tuned as RaeAnn shares the hard-earned wisdom that keeps her motivated to tackle the industry’s toughest problems and help shape the future of care.

    Timestamps:

    00:00 Conflict and Decision-Making in Expansion

    04:31 Navigating workplace dynamics as a woman

    07:00 Building a company with no roadmap

    11:30 Streamlining health system payments

    14:44 Aligning Vision, Trust, and Tech

    19:20 Building trust through kindness in healthcare

    23:12 Aligning roles in healthcare system

    25:55 Discussing Community and Innovation in Healthcare

    27:40 Connecting with RaeAnn and upcoming episodes


    HLTHworks' Website - hlthworks.com

    RaeAnn's Linkedin - linkedin.com/in/raeann-grossman-299756a

    Podcast's Website - redesigning-healthcare.com

    Podcast Media Partner - tophealth.care

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    28 min
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